We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Pet Friendly Holiday Rentals in Chatham, MA

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    $0
    $598 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travellers to Chatham are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    Clear All
    1 / 19
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    1 / 19
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    1 / 28
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Porch
    • Washer
    • DVD Player
    • Private Outdoor...
    • Internet Access
    • Hot Tub
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    [~] This beautiful home with central a/c sleeps 8 and has the open and bright spaces of a contemporary classic. The first floor boasts floor-to-ceiling windows facing the deck which overlooks acres of private woods and the heated swimming pool. This gorgeous deck contains a new wicker L-shaped... View all property information
    Location Information
    Chatham, Cape Cod 2633
    1 / 15
    4 of 5 bubbles (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Grill
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Parking
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Our Pleasant Street home is a charming 3 bedroom, 2 bath year-round home which is located at 320 Pleasant Street in South Chatham and it can comfortably accommodate up to 8 people. It is only a 2 minute walk to Nantucket Sound, the warm water side of Cape Cod! There is no beach sticker required... View all property information
    Location Information
    Chatham, Cape Cod 02659
    4 of 5 bubbles Reviewed 2 November 2012
    Our family spent Columbus Day weekend at this property located within walking distance of two beaches and enjoyed it very much. The expanded Cape had comfortable room for eight of...
    3 of 5 bubbles Reviewed 3 July 2012
    I traveled with three friends to Cape Cod for a week. Two of us were pretty happy with the selected property, and the other two were a little disappointed. The house is located...
    See all reviews
    1 / 26
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Renovated Sea Captain's Home by Ryder's Cove, Pet Friendly Peak Summer Weekly Rates: $3,000 - $3,500 This home has 4 bedrooms and classic Cape Cod decor. All of the modern amenities are included: AC units in all bedrooms, WiFi, flat screen TV with digital cable, washer/dryer, and a completely... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 38
    West Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    ​Pet Friendly! Updated 4 Bedroom home sleeps 10-walk to Harding's Beach with Deck-Outdoor shower- A/C units. Wifi too. Peak Summer Weekly Rates:(last week of June until the first week in September) $2,600 Walk to Harding's Beach from this Cape Style home! Enter into the open dining room with... View all property information
    Location Information
    West Chatham, Chatham 02669
    1 / 17
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Spend your vacation in this newer 2+ bedroom, 2.5 bath Chatham rental home situated on a lovely country lane only 3/10ths of a mile to Pleasant Street Beach on Nantucket Sound. The master bedroom with queen bed is located on the first floor. The second floor bedroom has a queen and a twin bed and... View all property information
    Location Information
    Chatham, Cape Cod 02659
    5 of 5 bubbles Reviewed 24 August 2016
    This was a well maintained and modern house, lots of efficient space and amenities. It's not your beach shack right on the water or walkup in town, but if you're a 50 something...
    See all reviews
    1 / 37
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pet Friendly! Nothing beats this luxury 4 bedroom, 4.5 bath Vacation Rental located in the heart of Chatham’s historic village!! Peak Summer Weekly Rates:last week of June until the first week in September: $9,100 - $9,400/week Whether you are soaking in the hot tub on the private patio or enjoying... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 36
    North Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Grill
    • Waterfront
    • Washer
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pet Friendly! Waterfront Cape Cod Vacation Rental home in North Chatham on the beach with tennis court. Peak Summer Weekly Rates:last week of June until the first week in September: $5,200 - $5,500/week Steps onto the large deck lead you to the entryway of this Cape home. Welcome back in time to... View all property information
    Location Information
    North Chatham, Chatham 02650
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Beautiful views of Nantucket Sound abound from this 2 bedroom, 1.5 bath traditional Chatham vacation rental only 4/10ths of a mile to Red River Beach and 6/10ths of a mile to Pleasant Street Beach. There is a sun room off the living room with a full-size sleep sofa and the full bath was recently... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 38
    5 of 5 bubbles (1) Excellent
    9 Bedrooms, 5 Bathrooms, Sleeps 20 | Quick View
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Porch
    • Air Conditioning
    • Outdoor Dining Area
    • Washer
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pet Friendly! The Priscilla House is a lovely vacation rental home nestled on Main Street in the charming town of Chatham, Massachusetts on Cape Cod.Walk to town and Lighthouse beach! Sheets and Towels INCLUDED! Peak Summer Weekly Rates:last week of June until the first week in... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 31 May 2016
    This house was perfect for my group of 6 families with six 13 year old boys and their siblings. Despite the large group, it was incredibly quiet, we didn't get into each other's...
    See all reviews
    1 / 47
    5 of 5 bubbles (1) Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Private Outdoor...
    • Grill
    • DVD Player
    • Satellite TV
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pet Friendly! Relax and enjoy this Chatham, Cape Cod Vacation Rental Home offering 6 bedroom 6.5 bathrooms. Peak Summer Weekly Rates:last week of June until the first week in September: $16,525/week. This luxury home is pet friendly with a private pool, central a/c, linens,wifiand more. In historic... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 27 May 2015
    This house is great. Has all the appliances you could want. Different coffee options, 2 sets of large washers and dryers, 3 dishwashers, pool table, big screen TV, pool with...
    See all reviews
    1 / 10
    6 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Satellite TV
    • DVD Player
    • Porch
    • Parking
    • Air Conditioning
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    209 Champlain Rd Chatham MA DOG FRIENDLY Great, rambling home with an old-Cape Cod feel located on the "loop" just around the bend from Stage Harbor. Wonderful area to enjoy while here on the Cape! A tennis court is available to tenants during daytime hours from 10 am to 5 pm. The huge, grassy... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 7
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Air Conditioning
    • Patio
    • Internet Access
    • DVD Player
    • Washer
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    16 ELLIS Pet friendly home in Chatham sleeps 4. Two bedrooms one with a queen and bedroom two has a queen and a single bed. Outdoor seating on the deck is spacious. Enclosed outside shower. One and a half baths. WiFi. A/C in the bedrooms. A short drive to Harding beach. FRIDAY arrival and... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 20
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Panoramic views of Nantucket Sound and a pristine salt marsh await you from this 3 bedroom, 2.5 bathroom South Chatham home. The back deck offers a commanding view of the estuary and wildlife including osprey and egrets while a winding path leads to a secluded beach with warm water and exposed sand... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 29
    5 Bedrooms, 4 Bathrooms, Sleeps 13 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Air Conditioning
    • DVD Player
    • Grill
    • Satellite TV
    • Balcony
    • Internet Access
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Water Views Near Chatham Light, Guest Apartment, Sleeps 11 (Linens Included) Pets Considered Peak Summer Weekly Rates: $7,500 - $8,700 This classic home is perched in the dunes of Chatham, just to the south of Chatham Light. This large home is ideal for larger groups looking for a perfect Chatham... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 33
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Views-Views-Views! Pet Friendly Cape Cod Vacation Rental home with rooftop deck is just .2 to Ridgevale Beach. Peak Summer Weekly Rates:(last week of June until the first week in September) $4,050/week Pet friendly! Enjoy water views from the main floor living areas and the upstairs master bedroom... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 23
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This ideally situated, spacious 5 bedroom, 4 bathroom classic antique home is just steps away from gorgeous Lighthouse Beach and just a short distance to downtown Chatham as well as the famous Mitchell River bridge where fishing is bountiful. Outside, you can enjoy the deck overlooking your own... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 20
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Outdoor Dining Area
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pet Friendly! Classic Cape Cod Vacation Home Rental in Chatham near Schoolhouse Pond for freshwater swimming. Peak Summer Weekly Rates:last week of June until the first week in September:$2,000- $2,100/week Located in a residential area and convenient to the Cape Cod Bike trail, and the Chatham... View all property information
    Location Information
    Chatham, Cape Cod 02633
    Get the List
    1 / 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Parking
    • Internet Access
    • DVD Player
    • Satellite TV
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    241 Training Field Road PET FRIENDLY Charming and updated 3 bedroom air conditioned ranch style home, just 1 mile from beautiful Pleasant Bay at Jacknife Point Beach. $1900 per week in season * $160 Cleaning Fee * $100 Handling Fee * $55 Damage Insurance OR $500 Security Deposit Please contact... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 40
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Grill
    • Air Conditioning
    • Waterfront
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Waterfront & Dog friendly! Sleeps 8! This newer Cape Cod Vacation Rental home in Chatham offers panoramic views and backyard access to beautiful Blue Pond, perfect for kayaking, canoeing and fishing. Peak Summer Weekly Rates:last week of June until the first week in September: $3,500 - $4,200/week... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    ID #MARSH4 Dog Friendly and Now with A/C and WIFI Internet! [~]This 3.5 bedroom and 2 full bath vacation home in Chatham with beautiful marsh views is just a half mile from HARDINGS BEACH and Oyster Pond River/ The Chatham Kayak Co. This home offers such amenities as a washer/dryer, 3 A/C units,... View all property information
    Location Information
    Chatham, Cape Cod 2633
    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Grill
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pet Friendly! Enjoy this Cape Cod Vacation Rental cottage in Chatham offering 3 bedrooms and 2 baths at the end of a small lane across from the ocean. Wifi and A/C included. A complete Renovation is taking place over the Winter- Everything will be "All New". Peak Summer Weekly Rates:last week of... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 34
    5 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Classic Chatham Charm -- Walk to Beach & Town! (Linens included) Peak Summer Weekly Rates: $5,900 - $6,750(Pets Considered) Located in a premier Chatham Village location, this classic antique home has everything to experience an idyllic Chatham vacation. Park your car in the driveway and leave it... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 42
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Terrace
    • Balcony
    • Washer
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pet Friendly! Welcome to this English Garden inspired 3 bedroom 3.5 bath Chatham Vacation home with lovely coastal touches. Peak Summer Weekly Rates:last week of June until the first week in September: $4,000 - $4,400/week. Offering Central air, Wifi and an open, airy floor plan~ you are sure to... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 37
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Satellite TV
    • Grill
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pet Friendly! Charming, fully renovated Sea Captain's home, located in downtown Chatham. Peak Summer Weekly Rates:last week of June until the first week in September: $5,000/week Enter through the sun porch offering extra dining- directly into the gourmet kitchen with a granite counter breakfast... View all property information
    Location Information
    Chatham, Cape Cod 02633
    4 of 5 bubbles Reviewed 2 October 2014
    Our family of four (parents with our 20-something daughters) rented this nicely renovated historic home in a downtown location... just blocks from the ocean. We went to Chatham...
    See all reviews
    1 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Grill
    • Satellite TV
    • Porch
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    On the Water! With Central Air and Wireless Internet-Pet Friendly too. Peak Summer Weekly Rates:last week of June until the first week in September: $6,500/week Pet friendly for Dogs only-ask your rental specialist for details. This Cape Cod Vacation Rental home in North Chatham has expansive views... View all property information
    Location Information
    Chatham, Cape Cod 02650
    1 / 27
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Chatham Village Classic, Behind Lighthouse(Pets Considered) Peak Summer Rates: $4,600 - $5,300 This grand Chatham Village family home is located in Chatham, right near the Lighthouse.This vintage antique house has 5 bedrooms, and a premier village location. Walk 3-5 minutes down the road to... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 25
    North Chatham
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    You will fall in love with this bright and cheery Cape! Wide planked Pine Hardwood floors in Living room and Dining room. Wide Galley Kitchen, fully equipped, including dishwasher, large side by side fridge and gas stove. New Furniture and Flat Screen TV in Living Room (not photographed yet). Wood... View all property information
    Location Information
    North Chatham, Chatham 02650
    1 / 31
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pet Friendly. Relax in this 3 bedroom, 2 bath Cape Cod Vacation home in Chatham that is convenient to downtown Chatham and beaches. Peak Summer Weekly Rates:last week of June until the first week in September: $3,500/week. Privacy abounds just off Main Street and the home even overlooks a working... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Parking
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Well maintained two bedroom home that sleeps 4.One queen and 2 twins with a pullout in the den. Located in scenic North Chatham. A five minute drive from downtown Chatham, Chatham Bars Inn, the Lighthouse, Chatham Seaside Links golf course and the baseball field which hosts the Cape Cod Baseball... View all property information
    Location Information
    Chatham, Cape Cod 02650
    1 / 23
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Patio
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pet Friendly! Spend Lazy summer days at this Cape Cod Vacation rental in Chatham. Peak Summer Weekly Rates:last week of June until the first week in September: $3,400/week. With the shade from the pines, the spray of sea salt from the Nantucket Sound and the warm summer sun, you are sure to have a... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 35
    4.5 of 5 bubbles (4) Very good
    6 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Wi-Fi
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pet Friendly!! High atop Sears Point in Chatham sits a Classic, Quintessential, New England Bluff house from yesteryear overlooking the sparkling, blue sea. Peak Summer Weekly Rates:last week of June until the first week in September: $6,500/week. This spot is a boater’s paradise! From kayaking to... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 1 week ago
    Our family rented the Bluff House the last week of July and had a lovely time.As boat owners we took advantage of the mooring and dingy that comes with the house. Days were spent...
    5 of 5 bubbles Reviewed 19 September 2016
    My family has rented The Bluff House for the past ten years and we can’t imagine summer anywhere else! The rooms are airy and light, with amazing views across Oyster Pond River...
    See all reviews
    1 / 31
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Wi-Fi
    • DVD Player
    • Grill
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pet Friendly! Located in a prime in-town location. Peak Summer Weekly Rates:last week of June until the first week in September: $3,875-$3,975/week. This Cape Cod Vacation Rental Cottage complex is just steps to the Mill Pond (a saltwater inlet of Nantucket Sound) in Chatham's Old Village and a few... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 37
    North Chatham
    8 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Porch
    • Outdoor Dining Area
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Chatham Family Compound Sleeps 16 Walk to Beach – Linens Included Peak Summer Weekly Rates: $13,500 - $13,900 Located just 0.2 miles from the beach, this is an ideal estate for multi-generational families or other large groups to spend time together with plenty of space on nearly three acres to... View all property information
    Location Information
    North Chatham, Chatham 02650
    1 / 24
    North Chatham
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Light & Bright Chatham Home, Walking Distance to Beach Linens Included, Pets Considered Peak Weeks: $2,000 Please note: This property is part of a larger estate, and is only available to rent individually in the months outside of July and August Located in historic North Chatham and just 0.2 miles... View all property information
    Location Information
    North Chatham, Chatham 02650
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Wi-Fi
    • Washer
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pet Friendly! Private, Family Ranch Style Riverbay home in Chatham for your Cape Cod Vacation located on a peaceful residential dead end road. Peak Summer Weekly Rates:last week of June until the first week in September: $1,800-$1900 per week $1250 off season As you enter the through the front door... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 31
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    $12,400/week Peak Season (July 2nd - September 3) $8,400/wk for the weeks of (6/25 and 9/3) $7,700/week Shoulder Season (6/18 and 9/10) $6,100/week Shoulder Season (6/11 and 9/17) $5,500/wk (before 6/11 and After 9/24) This beautifully refurbished Chatham rental house has a path that leads to a... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Grill
    • Internet Access
    • Washer
    • Parking
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Charming cape-style pet friendly home close to all that the village has to offer. PET FRIENDLY charming cape-style home close to all that the village has to offer. Close to town, Oyster Pond, Chatham Anglers games, golf, and tennis courts. Enclosed outdoor shower and patio with outdoor dining- 4... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 11
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • DVD Player
    • Grill
    • Washer
    • Satellite TV
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Pet friendly home with central air Comfortable 4 bedroom cape on a quiet street in Riverbay Estates. Convenient to Schoolhouse Pond and Jackknife Cove beach on Pleasant Bay. This home has central air conditioning, an enclosed outside shower, and is PET FRIENDLY. This property rents for $1400 -... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 19
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    About this property
    Lounge on our beautiful beaches, experience great fishing or spoil yourself in our unique shops all while staying in this charming, remodeled and finely decorated home close to Red River and Pleasant Street Beaches. This home has 4 bedrooms and 3 full baths. There is an en-suite master bedroom with... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 35
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Waterfront
    • Patio
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Experience a glimpse of Cape Cod waterfront living at this three-bedroom Chatham home, a dog-friendly property with a wrap-around deck, panoramic views of the Oyster River, and nearby access to Harding's Beach. This quaint two-level home is scenically situated between Nantucket Sound and Oyster... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 20
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Waterfront
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pet Friendly! Oceanfront, updated Cape Cod Vacation Rental home in Chatham. Peak Summer Weekly Rates:last week of June until the first week in September: $3,700/week. Picture yourself at this quaint beach cottage with ocean views and casual living for your summer getaway. Kayak for your use-... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Porch
    • Grill
    • Washer
    • Air Conditioning
    • Internet Access
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This newly renovated, quaint and charming home is set in the heart of Chatham village. Enjoy the full benefit of being steps away from Main Street, the scenic beaches, and the ocean. There are 3 bedrooms/2 baths and plenty of private outdoor space including an outdoor shower and a fire pit.... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Grill
    • Satellite TV
    • Parking
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This charming Cape Cod style cottage is a delight! It is a 2 bedroom, 2 bath home (one large new one) on a large lot with much privacy. It has A/C, hi-speed wireless internet,a new wide-screen HD TV, new carpeting throughout the house, is on a no-outlet street so it is safe for children and is... View all property information
    Location Information
    Chatham, Cape Cod 02659