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Chatham Vacation Homes

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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    ID #LAKE110 Lake front vacation home on Lovers Lake in Chatham in the Great Hill Neighborhood. Heron Haven is a peaceful, spacious home in a beautiful lake front setting with many sought after features. This home sleeps 10 guests and boasts Central A/C and 4 living areas to spread out and relax.... View all property information
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    Chatham, Cape Cod 2633
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Come stay at: Starfish Beach Cottage! Find your Pathway to Peace! Waterfront 3 bedroom, 2 bath vacation rental cottage is located right on the beach in Chatham, the best of Cape Cod. Peak Summer Weekly Rates:  last week of June until the first week in September: $3900-$4,600/week. Perfect for a... View all property information
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    Chatham, Cape Cod 02633
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    169 Lime Hill Road CHATHAM This magnificent and well-appointed home is the epitome of luxury living with added Cape Cod style. Conveniently located less than 3/4 of a mile from Chatham Village, you also have deeded rights to a path to Oyster Pond.. Every amenity is provided, from central air to... View all property information
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    Chatham, Cape Cod 02633
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2017 Rental Rate $3875 per week, including the cleaning fee Off Season, $2725 per week, including the cleaning fee Light and bright, this spacious beach home is located right down the street from family-friendly Hardings Beach. Plenty of room to spread out and relax as you enjoy your Chatham... View all property information
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    Chatham, Cape Cod 02633
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    South Chatham
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    2017 Rental Rate: $3000 per week including the cleaning fee ~~ Weekly rentals from mid-JUNE to mid-SEPT Fabulous Cape Cod beach rental located steps from Nantucket Sound with breathtaking views from the huge deck overlooking the marsh and the ocean. Airy, light and bright decor. Finished walkout... View all property information
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    South Chatham, Chatham 02633
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    5 of 5 bubbles (1) Excellent
    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Beautiful Chatham Get-away! Located on a sandy, dead end lane, this cottage is the perfect Summer get-away. A large screened in porch fronts the cottage and is the perfect place for meals or evening game nights! Beautiful pine floors extend throughout the open floor plan. The living room has a... View all property information
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    South Chatham, Chatham 02659
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    338 Seapine Road CHATHAM, ID# 104736 Waterfront 3 bedroom home overlooking Bassing Harbor and Fox Hill with the outer beach beyond. Located on a cul de sac near Eastward Ho! Country Club in North Chatham, the home is a classic Cape in style. Water access for kayaking in Pleasant Bay and beyond.... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    1 / 30
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
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    Chatham, Cape Cod 02633
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    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2017 Rental Rate: $2775 per week, including the cleaning fee Off-Season: $1175 per week, including the cleaning Weekly rentals from mid-JUNE to mid-SEPT Lovely, updated condo with water-views of the Nantucket Sound. Light and bright with comfy upscale furnishings. Located on a quiet side street in... View all property information
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    South Chatham, Chatham 02659
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    2017 Rental Rate: $6450 per week, including the cleaning fee This recently renovated antique farmhouse is filled with upscale furnishings and is practically in the center of town! Located on large lot, it offers a wonderful mixture of new and old. There is one bedroom on the first floor with a... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2017 Rental Rate: $2375 per week, including the cleaning fee ~~Off-Season: $1675/week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Light and bright cottage just steps to the warm Nantucket Sound waters of Pleasant Street Beach! Tasteful, traditional furnishings throughout.... View all property information
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    Chatham, Cape Cod 02659
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    North Chatham
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Completely renovated condo in North Chatham. Enjoy this lovely condo with all amenities including Central AC mini split, WiFi, and new furnishings. Sleeps 4. Read on to learn more about our Chatham Mass Vacation Rentals Peak Summer Weekly Rates:  last week of June until the first week in September:... View all property information
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    North Chatham, Chatham 02650
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    ON THE WATER ...<BR><BR>* Beautiful water views! <BR>* Back decks open to mesmerizing views of Emery Pond <BR>* Hammock and patio furniture chosen for comfort and relaxation!<BR>* Direct access to pond from backyard. <BR><BR>* Clean swimmable pond.<BR>* Bass fishing plentiful!<BR>* Gas grill.<BR>*... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Why not stay at our Chatham home this summer? Peaceful and inviting, our cape-style home is in a very picturesque area of Chatham. Come relax in our breezy screened porch or enjoy the warm Nantucket Sound waters of Pleasant and Forest Beaches which are a five minute walk (3/10 mi). Leave your car... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    #603 - Lovers Holley Home: Lovely renovated home less than one mile from Chatham's famous downtown shopping and overlooking Lover's Lake - which is a walk around corner in a few minutes. All Chatham beaches are within two miles.  This home, located in the Great Hills Estates, provides a very... View all property information
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    Chatham, Cape Cod 02633
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    South Chatham
    3 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    2017 Rental Rate: $3625 per week, including the cleaning fee No Off-Season Wonderful waterfront home, right on Taylor's Pond! This spacious home is light and bright, filled with upscale furnishings, colorful decor, and offers a private, peaceful setting in South Chatham. The open floor plan... View all property information
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    South Chatham, Chatham 02659
    1 / 8
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    2017 Rental Rate: $5475 per week, including the cleaning fee Off-Season: $3725 per week (4 night minimum) including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Lovely five bedroom home close to town and the beach! It has everything you need: a huge yard for games, central air, updated... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    1 / 11
    North Chatham
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2017 Rental Rate: $1725 per week, including the cleaning fee ~~ Off Season: $1125 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Recently remodeled cottage with central air is close to shopping and restaurants in downtown Chatham, baseball games at Veteran's Field,... View all property information
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    North Chatham, Chatham 02650
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Comfortable 3 bedroom, 2 bath quiet summer retreat only a half mile to downtown Chatham! Peak Summer Weekly Rates:  last week of June until the first week in September: $2,200/week. Offering Central AC & Wifi - like most of our Cape Cod Vacation Home Rentals - with over 1600 sq. ft. of finished... View all property information
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    Chatham, Cape Cod 02633
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    2017 Rental Rate: $2475 per week including the cleaning fee ~~ Off Season: $1775 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming year-round home, with central air conditioning, within walking distance to the warm waters of popular Ridgevale Beach! Recently... View all property information
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    Chatham, Cape Cod 02633
    1 / 17
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    2017 Rental Rate: $3225 including the cleaning fee~~~ Off Season: $2325 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Private, traditional style cape house in the Sears Point area of Chatham. It has a lovely sun porch, a large living room and a large yard with lots of... View all property information
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    Chatham, Cape Cod 02633
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    2017 Rental Rate: $2800 per week including the cleaning fee Off-Season Rate: $1800 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT You will love this 4 bedroom home near Ridgevale Beach! Located at the end of a dirt road with water views of a freshwater pond and... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Enjoy "Summer Remedy" this traditional, updated Cape Cod Vacation Rental home in Chatham is located just a short walk to Ridgevale Beach. Peak Summer Weekly Rates:  last week of June until the first week in September: $2,300/week Wifi and Central air.  Enter the front door into Living Room with... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    2017 Rental Rate ~ $5225 per week, including the cleaning fee ~~ Off-Season: $3725, including the cleaning fee~~Weekly rentals from mid-JUNE to mid-SEPT Gorgeous home located in a secluded yet convenient area of Chatham and overlooking Oyster Pond. The house is almost surrounded by water views!... View all property information
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    Chatham, Cape Cod 02633
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    2017 Rental Rate: $12,400 per week, including the cleaning fee Off-Season $8800 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT This beautiful home on Shore Road is the perfect spot for your Chatham vacation! It offers beautiful furnishings and plenty of space for... View all property information
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    Chatham, Cape Cod 02633
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    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Welcome to The Little Caper. This updated 4 bedroom, 2 bath vacation rental home in Chatham is well maintained and a great spot for making family memories. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,800/week and just $1,900 in Sept and October!! Just under a... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Welcome to Harding's Beach Hills, where you will find Three Cheers, this charming cottage by the sea! Peak Summer Weekly Rates:  last week of June until the first week in September: $2,000/week. This Chatham Cape Cod Vacation Rental offers ranch style living with A/C units in all 3 bedrooms,... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    2017 Rental Rate: $1800 per week, including the cleaning fee ----Off Season: $1000 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Cute 3 bedroom ranch, walking distance to town and Oyster Pond. A great new 2nd family room just finished in the lower level! No deck, but... View all property information
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    Chatham, Cape Cod 02633
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Come stay at: The Cozy Beach Cottage! Chatham Vacation Rental Cottage at the beach! Peak Summer Weekly Rates:  last week of June until the first week in September: $2,000/week. Get away to this 1 bedroom cozy cottage located right at the beach in Chatham, the best of Cape Cod-Sleeps 4. Perfect for... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2017 Rental Rate: $2675 per week, with the cleaning fee ~~September: $1925 per week, including the cleaning fee~~ Take advantage of the quick walk to the Chatham A's Ball Field, the playground and Main Street from this pristine three bedroom ranch! There are two living spaces, great for the kids... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    2017 Rental Rate: $2450 per week including the cleaning fee No off-season rentals Comfortable and airy post & beam home located in a quiet neighborhood near Harding's Beach. Tons of windows and skylights throughout bring in the sunlight! The eat-in kitchen overlooks the backyard gardens and walks... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2017 Rental Rate: $2100, including the cleaning fee Off-Season $1600 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT This is a well maintained property located in a quiet area in W. Chatham. Spacious bedrooms, one with two double beds. Updated kitchen, with a skylight,... View all property information
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    Chatham, Cape Cod 02633
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    South Chatham
    4 Bedrooms, 6 Bathrooms, Sleeps 9 | Quick View
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    Brand new custom built beauty in South Chatham with water views (linens included) NEW Listing for 2017! (More photos to come soon!) Peak Summer Weekly Rates: $6,400 - $7,300 (Rents Saturday to Saturday during peak season) Be among the first to vacation at this wonderful custom-built home in South... View all property information
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    South Chatham, Chatham 02659
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    2017 Rental Rate: $1500 per week, including the cleaning fee~~Off-Season: $1225 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT A true cottage nestled in the pines! Nicely decorated with nautical theme, with air conditioning to keep you cool. Comfy & Cozy! Lots of... View all property information
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    Chatham, Cape Cod 02633
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Experience "Chatham Coastal Charm". Popular Contemporary Cape Cod Vacation Rental home in Chatham with heated salt water gunite pool that is just a short walk to Hardings Beach (.3). Sleeps 10! Peak Summer Weekly Rates:  last week of June until the first week in September: $7,000/week. Don't miss... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Welcome to: Salty Paws! 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 AC included. A Complete renovation is taking place over the winter. Everything will be "all new"! Peak Summer... View all property information
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    Chatham, Cape Cod 02633
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    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... View all property information
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    Chatham, Cape Cod 02650
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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
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    Chatham, Cape Cod 02633
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Located outside of downtown Chatham sits this charming four bedroom home, known as Stones Throw. This property features great amenities such as central air conditioning, high speed wireless internet, and flat screen TVs in every bedroom. Enjoy an outdoor dinner in your central courtyard accessed... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    2017 Rental Rate: $2100 per week, with the cleaning fee ~~No Off-Season~~ Welcome!! This roomy Cape sits up on a hill located just off of Cockle Cove Road on a quiet one way drive. Just .4 mi to Cockle Cove Beach. There are three bedrooms and 2 full and one half baths. The master BR is en-suite... View all property information
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    Chatham, Cape Cod 02633
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    North Chatham
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    2017 rental Rate: $7850 including the cleaning fee~~ Off-Season: $3900 per week, including the cleaning fee ~ For 10 people only, lower level not available for Off-Season rentals~~ A large recently renovated 6 bedroom home located in the exclusive Cannon Hill Estates of North Chatham. This location... View all property information
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    North Chatham, Chatham 02650
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2017 Rental Rate: $1950 per week including the cleaning fee FRIDAY TO FRIDAY RENTAL! ~~ Off-Season: $1400 per week including the cleaning fee !!! Weekly rentals from mid-JUNE to mid-SEPT Charming cottage just steps to Ridgevale Beach. Upstairs addition is fabulous. It has a separate bathroom and... View all property information
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    Chatham, Cape Cod 02633
    1 / 24
    North Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    #601 - The Salty Seashell: Great Holiday Deal! Beautiful private Chatham home in great location with a deck, patio, grill & yard!  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... View all property information
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    North Chatham, Chatham 02650
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    2017 Rental Rate ~ $4200 per week, including the cleaning fee ~ Off-Season ~ $2000 per week, including the cleaning fee ~ Charming, antique, 5 BR home located on Chatham's "loop", steps to the water and Stage Harbor Yacht Club. Enjoy the breathtaking views of Stage Harbor and Stage Harbor... View all property information
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    Chatham, Cape Cod 02633
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2017 Rental Rate: $2300 per week, including the cleaning fee ~Off-Season: $1200 per week, including the cleaning Weekly rentals from mid-JUNE to mid-SEPT Light and bright 4 BR home, in a great central location! This recently updated home is across from the school tennis courts and playing fields,... View all property information
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    Chatham, Cape Cod 02650
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Welcome to: Seaside Stroll! Beachfront Condo! 3 Bedrooms, sleeps 6! Enjoy water views from both upstairs and main level decks. Walk down the path to the Outermost Harbor, Little Beach, or bike up to the village of Chatham. Easy bike ride to Lighthouse Beach and Monomoy Wildlife Refuge!  Central AC... View all property information
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    Chatham, Cape Cod 02633
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    4.5 of 5 bubbles (4) Very good
    6 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    Come Stay at: The Bluff House! 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... View all property information
    Location Information
    Chatham, Cape Cod 02633