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Vacation Rentals in South Orleans, MA

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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    The BoatHouse is unique. Built and furnished in Cape Cod Cottage style, it sits literally right on Pleasant Bay with deck and stairs leading into the water. In the master bedroom look out across Pleasant Bay before you get out of bed. Full bathroom inside and delightful outside shower. Lounge,... View all property information
    Location Information
    South Orleans, Cape Cod 02662
    5 of 5 bubbles Reviewed January 26, 2016
    I stayed here on my honeymoon many years ago, and have returned every year since then. I could roll out of bed, onto the deck, and into the water without walking 5 steps! Pleasant...
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    1 / 28
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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
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    South Orleans, Cape Cod
    1 / 28
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    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
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    South Orleans, Cape Cod 02662
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    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
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    South Orleans, Cape Cod 02662
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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 / 37
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Enjoy Brand New Cape Style Home With All Amenities in Orleans! Peak Summer Weekly Rates:last week of June until the first week in September: $5,000/week. The actual Address is 5 White Cedar but for Google Mapping we are using the lot next door:80Portanimicut​Road Well appointed, Brand New... View all property information
    Location Information
    South Orleans, Cape Cod 02662
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    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 02653
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    6 S. Little Bay Road, South Orleans (ID# 55120) 2017 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
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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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
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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
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    South Orleans, Cape Cod 02653
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Fall in Love with this expansive 4-BR. Bow Roof House located on a country road in desirable Orleans, within walking distance to Pah Wah landing, where you can launch your boat, kayaks or canoes, or sail to the Outer Beach. The Pah Wah Point hiking trails and a sandy beach at Little Pleasant Bay... View all property information
    Location Information
    South Orleans, Cape Cod
    1 / 13
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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
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    South Orleans, Cape Cod
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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 / 18
    4.5 of 5 bubbles (2) Very good
    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    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 / 13
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    9 Woodridge Road (ID# 99912) ~ Bayside 4 Bedroom Home ~ Pleasant Bay Area 2017 Season! Enjoy a Cape Cod vacation. This 4 Bedroom, 2.5 bath home includes a finished basement great for entertaining and access out to the outdoor shower. There are two Bedrooms and a full bathroom on each floor. All 4... View all property information
    Location Information
    South Orleans, Cape Cod 02653
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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
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    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
    Location Information
    South Orleans, Cape Cod
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