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.

Vacation Rentals in 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.
mm/dd/yyyy mm/dd/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
    $302 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    South Orleans is popular with travelers just like you. Don’t let them get your perfect place first—book today!
    1 / 10
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    1 / 22
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    1 / 11
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy this cozy 3 bedroom Cape Cod Cottage in Nauset Village cottage colony! 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... View all property information
    Location Information
    South Orleans, Cape Cod
    1 / 25
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    South Orleans, Cape Cod
    1 / 13
    5 of 5 stars (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    South Orleans, Cape Cod
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    South Orleans, Cape Cod
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • Porch
    • Parking
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    South Orleans, Cape Cod
    1 / 34
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Patio
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    This charming remodeled antique home is only 2/10ths of a mile to a Pleasant Bay beach and a short distance to the five star rated Wequassett Resort. The interior has a brand new kitchen with granite counter tops, stainless steel appliances, wide pine floors and opens up to a dining area with a... View all property information
    Location Information
    South Orleans, Cape Cod
    1 / 4
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Balcony
    • Ocean Views
    • Patio
    • Waterfront
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Six feet of plush lawn separate the MainHouse from the waters of Pleasant Bay. The large garden has plenty of quiet places for reading, relaxing and/or snoozing in the shade or in the sun. Swim or fish from the dock or the nearby beach. Arrangements for a boat mooring are possible. Off-street... View all property information
    Location Information
    South Orleans, Cape Cod
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • DVD Player
    • Air Conditioning
    • Grill
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This 2 bedroom, 2 bathroom home is located on a private dirt road overlooking Pah Wah Pond in South Orleans. It is in walking distance to beautiful Pah Wah Conservation Area on Pleasant Bay, just perfect for hiking. Five minutes in the other direction, a short walk takes you to the town landing and... View all property information
    Location Information
    South Orleans, Cape Cod
    1 / 18
    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Washer
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Porch
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    52 Forest Way, Orleans MA (ID# 18423) 2016 Season! Contemporary home with lots of space, nestled in a quiet wooded area of Orleans. This home is ideal for a casual vacation. 5 Bedrooms (2 Queens, 1 Double, 4 Twins) and 3 Baths. No Pets Accepted. Weekly Rental (7 Night Minimum in Season) _Rent:... View all property information
    Location Information
    South Orleans, Cape Cod
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Washer
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Parking
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    East Egg Associaton Property ID: 52204 Property Name: 2 Ellerslie Road East Egg community. AC units in all bedrooms. Private access to association beach on Pleasant Bay which is less than half mile away (access from Ellersie to Carlton to Little Bay Rd.) Nice open floor plan, large three season... View all property information
    Location Information
    South Orleans, Cape Cod
    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Satellite TV
    • Parking
    • DVD Player
    • Washer
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Wonderful vacation home in very exclusive South Orleans neighborhood with a private path to Little Pleasant Bay private Beach. Home is multi-level with an open floor plan for family entertaining and designed for privacy. Upstairs level includes a living room (with sofa bed), dining room, kitchen... View all property information
    Location Information
    South Orleans, Cape Cod
    1 / 13
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Grill
    • DVD Player
    • Parking
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    9 Woodridge Road, Orleans MA (ID# 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... View all property information
    Location Information
    South Orleans, Cape Cod
    1 / 20
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Patio
    • Washer
    • DVD Player
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    6 S. Little Bay Road, South Orleans (ID# 55120) 2016 Season: Lovely home in East Egg Community of South Orleans with views, beach access, central air conditioning and a beautiful expansive yard. Views of Pleasant Bay from almost every room as well as a great brick patio for everyone to enjoy. This... View all property information
    Location Information
    South Orleans, Cape Cod
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Waterfront
    • Grill
    • Air Conditioning
    • Washer
    • Internet Access
    • Satellite TV
    • DVD Player
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    613 Orleans Rd, South Orleans (ID#41809) Beautiful contemporary home on Pleasant Bay! This wonderful property offers direct access to the beach, boat landing, spectacular views, and all amenities including air conditioning and a beautiful outdoor shower. Perfect for the boating family! 3 Bedrooms... View all property information
    Location Information
    South Orleans, Cape Cod