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Holiday Rentals and Villas in South Orleans, MA

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    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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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 22
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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 6 | Quick View
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    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
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    South Orleans, Cape Cod 02653
    1 / 23
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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
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    South Orleans, Cape Cod
    1 / 13
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
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    South Orleans, Cape Cod
    1 / 20
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    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 02653
    1 / 25
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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
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    South Orleans, Cape Cod
    1 / 16
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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
    Location Information
    South Orleans, Cape Cod
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    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    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
    Location Information
    South Orleans, Cape Cod
    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    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
    Location Information
    South Orleans, Cape Cod 02662
    1 / 18
    4.5 of 5 stars (2) Very good
    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Porch
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    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 02653
    1 / 34
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    NEW TO RENTAL MARKET 2016! 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... 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 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    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 02662
    1 / 15
    4 of 5 stars (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • 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 02653
    1 / 16
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
    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
    Location Information
    South Orleans, Cape Cod
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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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 02662
    1 / 34
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
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    • Patio
    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    NEW TO RENTAL MARKET 2016! 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... View all property information
    Location Information
    South Orleans, Cape Cod
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    1 / 13
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • 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 02653
    1 / 22
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This comfortable, updated South Orleans home offers 4 bedrooms and 3 baths with plenty of room to stretch out on your vacation! It features an open layout living/dining area, with a cute sunroom right off the main living space. The first floor boasts an updated, fully equipped kitchen, as well as a... View all property information
    Location Information
    South Orleans, Cape Cod 02653
    1 / 4
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Balcony
    • Ocean Views
    • Patio
    • Waterfront
    • Terrace
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    • x
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    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 02662
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • 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 02662