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Vacation Rentals in South Orleans, MA

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    South Orleans is popular with travellers 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
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    1 / 13
    5 of 5 stars (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 28
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Satellite TV
    • Grill
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    About this property
    Exquisite Custom Built 5BR Home in Orleans, tons of stuff for the kids! Peak Summer Weekly Rates: $6,900-$7,200 If you're looking for upscale accommodations yet plenty for the kids to do, this stunning new home is the one for you. Situated on a quiet cul-de-sac near Pleasant Bay, the home offers a... View all property information
    Location Information
    South Orleans, Cape Cod
    1 / 11
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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 / 22
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Internet Access
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    • Child-friendly
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    • x
    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
    Location Information
    South Orleans, Cape Cod
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
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    • Washer
    • Wi-Fi
    • Porch
    • Parking
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    • 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 / 25
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Child-friendly
    • x
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    • 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 / 34
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
    • Wi-Fi
    • Patio
    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
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    • ?
    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
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    1 / 4
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • 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
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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