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.

Holiday Homes and Apartments South Orleans, 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}
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    All 28 Rentals in South Orleans
    loading...
    Sort by
    From
    $1,784
    / Week
    View Details
    1 / 18
    4.5 of 5 stars (2) Very good
    5 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Enquiry
    From
    $2,549
    / Week
    View Details
    1 / 15
    4 of 5 stars (1) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    From
    $7,391
    / Week
    View Details
    1 / 20
    5 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Enquiry
    From
    $471
    / Night
    Payment Protection
    View Details
    1 / 19
    3 Bedrooms / 2 Bathrooms / Sleeps 5
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Lovely, quaint self-catered cottage directly across from Pleasant Bay with spectacular views. Walk across the street to small, sandy Pleasant Bay beach. Three small bedrooms -- one room with double bed, one room with twin beds and one room with a single bed. Full kitchen outfitted with pots, pans,... View all property information
    Make Enquiry
    From
    $2,294
    / Week
    Payment Protection
    View Details
    1 / 12
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Internet Access
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Enjoy the pleasures of a waterfront property -- Wake up to views of a peaceful Pleasant Bay inlet from this sun-filled, modern 3-bedroom cottage in the woods. Launch your kayak or canoe to explore beautiful Pleasant Bay; fish from the dock. Use of the dock for a large boat is also possible. The... View all property information
    Make Enquiry
    From
    $1,274
    / Week
    View Details
    1 / 13
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    9 Woodridge Road (99912) Plesant Bay Enjoy a Cape Cod vacation with the whole family. This 4 Bedroom, 2.5 bath home includes a finished basement great for entertaining and access out to recently finished outdoor shower. There are two Bedrooms and a full bathroom on each floor. All 4 bedrooms have... View all property information
    Make Enquiry
    From
    $2,549
    / Week
    View Details
    1 / 17
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Waterviews on Pleasant Bay in South Orleans with shared private beach! Enjoy the views from the open and warm living/dining area with sliders to full deck. Home offers central A/C, wireless internet, washer/dryer and enclosed outside shower, 3 bedrooms, 2.5 bath contemporary style home with open... View all property information
    Make Enquiry
    From
    $1,274
    / Week
    View Details
    1 / 9
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This cozy, lower level apartment offers beautiful views of Pleasant Bay and comfortable sleeping for 4. It is an apartment under the main house where the owner lives but has its own parking spot and private access to the unit. There is a nice patio area with furniture and a barbeque grill as well... View all property information
    Make Enquiry
    From
    $2,039
    / Week
    View Details
    1 / 9
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This is a nicely furnished home in a quiet area of South Orleans. It is located near a town landing and is convenient to Orleans beaches and Chatham for shopping. With three bedrooms and 2.5 baths, it sleeps 7 comfortably. The first floor features a spacious kitchen with dining table and beautiful,... View all property information
    Make Enquiry
    From
    $2,294
    / Week
    View Details
    1 / 16
    5 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This Brewster rental house has lots of room and an inground pool. It's located on a quiet cul de sac in a neighborhood just under a mile to Pleasant Bay. This spacious, post and beam house has a big front yard and a fenced in patio area around the pool (not heated). The interior has 5 bedrooms and... View all property information
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    From
    $1,274
    / Week
    View Details
    1 / 17
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This is a cute 3 bedroom 2 bath in the center of South Orleans. The location offers easy access via Rt 39 or Rt 28 to Chatham or Orleans for shopping, restaurants and beautiful beaches. The house is nicely furnished with comfy couches and a flat screen in the living room. The dining and kitchen are... View all property information
    Make Enquiry
    From
    $2,549
    / Week
    View Details
    1 / 23
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    You will love this expansive 4-bedroom Bow Roof House located on a country road in desirable Orleans, within walking distance to Pah Wah Landing, where you can launch your boat, kayak or canoe or charter the Helen B fishing tour. Near the Pah Wah Conservation area hiking trails and a sandy beach on... View all property information
    Make Enquiry
    From
    $3,186
    / Week
    View Details
    1 / 23
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This roomy and attractively appointed 4 bedroom, 3 bath home offers comfort and privacy in a quiet South Orleans setting. A private dock with boat slip for a dinghy is available at the end of the cul-de-sac. The property has a boat mooring as well and is a great location for kayaking. Other extras... View all property information
    Make Enquiry
    From
    $2,294
    / Week
    View Details
    1 / 16
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This beautiful 4 bedroom, 3 bath South Orleans home is located in a quiet neighborhood, just a short drive to Pleasant Bay. The first level of the home features a spacious kitchen and dining area, large living area with a/c unit, and a Master Suite with a king sized bed and private bath with shower... View all property information
    Make Enquiry
    From
    $2,549
    / Week
    View Details
    1 / 16
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Located on beautiful Pleasant Bay and situated next to a town public boat landing, this 3 bedroom, 2 bath home offers convenient access to activities in both Orleans and Chatham. With it's own private beach, it's a great spot for swimming, kayaking and canoeing on Pleasant Bay! The property is a 3... View all property information
    Make Enquiry
    From
    $2,676
    / Week
    View Details
    1 / 13
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Situated in peaceful serenity on a small South Orleans pond, this well-appointed home offers gracious vacation living, privacy and easy access to Nauset and Skaket Beaches, as well as to Orleans and Chatham activities. With 4 bedrooms and 2.5 baths, it sleeps up to 8 very comfortably. The first... View all property information
    Make Enquiry
    From
    $2,485
    / Week
    View Details
    1 / 28
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This beautifully renovated home features wonderful views of Pleasant Bay. Modern, tastefully furnished, and updated throughout, it offers 3 bedrooms and 2 full baths with room to sleep 8. The kitchen is clean and fresh with marble countertops, newer appliances, and an open dining area. The bedroom... View all property information
    Make Enquiry
    From
    $3,186
    / Week
    View Details
    1 / 26
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Enjoy this beautiful South Orleans home with its own private beach. The interior of the home boasts an open floor plan including a kitchen with granite countertops and center island, spacious dining area, livingroom and a first floor Master Suite with a queen and twin sized bed as well as a private... View all property information
    Make Enquiry
    From
    $1,911
    / Week
    View Details
    1 / 13
    5 of 5 stars (1) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This spacious and comfortable 2-story home sits on a wooded lot within a short distance to a boat ramp and just minutes away from Nauset, Skaket and Pleasant Bay beaches. With four bedrooms and 2.5 baths, it sleeps up to 8 comfortably. The first level features a living room, family room, fully... View all property information
    Make Enquiry
    From
    $7,391
    / Week
    View Details
    1 / 26
    5 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Savor soothing views of Pleasant Bay, Nauset Bar and the Ocean beyond! Gorgeous sun and moon rises too! Swim, fish, shell or relax from private beach and dock - 3 minutes - door to dock. A large, sunny & beautifully maintained home in lovely East Egg affords the space and amenities to insure a... View all property information
    Make Enquiry
    Get the List
    From
    $9,430
    / Week
    View Details
    1 / 30
    4 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This beautiful, newly listed South Orleans home features three levels of living - all with beautiful views of Pleasant Bay and the ocean beyond! Enjoy the shared, private dock and sandy beach just a short walk from the front door of this lovely, contemporary home. The property features a stunning... View all property information
    Make Enquiry
    From
    $2,357
    / Week
    View Details
    1 / 21
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This home sits on a bluff overlooking Pleasant Bay with panoramic views from almost every room. With 4 bedrooms and 3 baths, it sleeps 8 comfortably. The property offers one level living with all four bedrooms on the main level. Off the back of the home is a deck area as well as a large yard... View all property information
    Make Enquiry
    From
    $1,274
    / Week
    View Details
    1 / 17
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Enjoy all the comforts of home at this 4 bedroom, 2.5 bath pet friendly home! The first level of the home features a living room, kitchen with dining table and full bathroom as well as two bedrooms, one with two twins and one with a queen sized bed. Each bedroom has an A/C unit and new hardwood... View all property information
    Make Enquiry
    From
    $1,115
    / Week
    View Details
    1 / 11
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Enjoy this cozy 3 bedroom Cape Cod Cottage in Nauset Village! Each bedroom has a full sized bed and the living room provides TV, a DVD player, and plenty of seating for the whole family! The fantastic deck area leads right to the enclosed outdoor shower, great for rinsing off after a day at the... View all property information
    Make Enquiry
    From
    $1,402
    / Week
    View Details
    1 / 16
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This comfortable 3 bedroom ranch is within close proximity to Little Pleasant Bay. A private walking path brings you to a sandy beach just minutes from your doorstep. The property features three bedrooms and one bath and sleeps up to 6. The first bedroom features a queen sized bed, while the other... View all property information
    Make Enquiry
    From
    $2,421
    / Week
    View Details
    1 / 19
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This very special 3 bedroom, 2 bath home overlooks the Namequoit River and features lovely waterviews, two waterside decks, newly remodeled kitchen and great amenities. The property is very close to Pah Wah Conservation area with hiking trails and a sandy Pleasant Bay beach. Launch your kayak from... View all property information
    Make Enquiry
    From
    $1,402
    / Week
    View Details
    1 / 9
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This well appointed Cape is located in a quiet residential neighborhood in South Orleans. Perfect for the smaller family, it has a private backyard with deck and patio. It’s central location makes it convenient to take in the sights and activities of Orleans, Chatham and Harwich. **NOTE:... View all property information
    Make Enquiry
    From
    $2,549
    / Week
    View Details
    1 / 25
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This 4 bedroom, 3 bath home sits on Namequoit River in Orleans and offers a private dock off the backyard area. The first level of the home offers one bedroom with a king sized bed and the second level features three additional bedrooms, two with a queen sized bed and one with two twins. The... View all property information
    Make Enquiry