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South Orleans Holiday Homes

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    South Orleans is popular with travellers just like you. Don’t let them get your perfect place first—book today!
    All 22 Rentals in South Orleans
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • DVD Player
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    • Hot Tub
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    Pet friendly
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    Smoking allowed
    About this property
    Waterfront Home with Large Private Deck and Hot Tub Overlooking Pond (Linens Included) Peak Summer Weekly Rates: $2,950 - $3,800 Rents Saturday - Saturday during peak season If you love nature, privacy and water views this comfortable home is for you. You will wake up each morning to find the water...
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    South Orleans, Cape Cod 02662
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Topside BoatHouse on Pleasant Bay1 / 10
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Grill
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    • Ocean Views
    • Balcony
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    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 January 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...
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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,...
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    South Orleans, Cape Cod 02662
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    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,...
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    South Orleans, Cape Cod 02662
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    $1745-$2495 ($100 less if not bringing pet) Rates include all charges; no hidden fees! As a vacation rental, this exquisite 5 bedroom/3 full bath home in South Orleans hits all the right notes exactly on pitch. It is both elegant and relaxed, with plenty of indoor and outdoor space to comfortably...
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    South Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    52 Forest Way 184231 / 18
    (2)Very good
    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    52 Forest Way, Orleans MA (ID# 18423) 2017 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:...
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    South Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    East Egg Associaton Property ID: 52204 Property Name: 2 Ellerslie Road 2017 Season! East Egg community. Private access to association beach on Pleasant Bay which is less than half mile away (access from Ellersie to Carlton to Little Bay Rd. sorry but no parking.) Nice open floor plan Central A/C,...
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    South Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    South Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Internet Access
    • Air Conditioning
    • Satellite TV
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    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    South Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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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...
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    South Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    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...
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    South Orleans, Cape Cod
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    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...
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    South Orleans, Cape Cod 02662
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    ESCAPE from it all to this stunning contemporary, located in South Orleans on a 2 acre lot surrounded by conservation land, one house away from Pleasant Bay. A two minute walk, along one of two scenic paths, leads one to a private association beach on Pleasant Bay. The updated house is remodeled...
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    South Orleans, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Expansive Home by Orleans Town Landing1 / 36
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    South Orleans, Cape Cod
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    South Orleans, Cape Cod
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    South Orleans, Cape Cod
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    South Orleans, Cape Cod
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    South Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    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...
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    South Orleans, Cape Cod
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Balcony
    • Ocean Views
    • Patio
    • Waterfront
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    South Orleans, Cape Cod 02662
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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