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Holiday Homes in South Orleans

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    Travellers to South Orleans are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    All 18 Rentals in South Orleans
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Topside BoatHouse on Pleasant Bay1 / 10
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    This very special 3 bedroom, 2 bath home overlooks the Namequoit River and features lovely waterviews, two waterside decks, newly remodeled kitchen and great amenities. The property is very close to Pah Wah Conservation area with hiking trails and a sandy Pleasant Bay beach. Launch your kayak from...
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    South Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 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...
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    South Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    Exquisite Custom Built 5BR Home in Orleans, Tons of Stuff for the Kids! (linens included) Peak Summer Weekly Rates: $6,800 Rents Saturday to Saturday 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...
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    South Orleans, Cape Cod 02662
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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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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    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 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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 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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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    52 Forest Way 184231 / 18
    (2)Very good
    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    52 Forest Way, Orleans MA (ID# 18423) 2018 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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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet 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. There are...
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    South Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    South Orleans, Cape Cod 02645
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
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    9 Woodridge Road (ID# 99912) ~ Bayside 4 Bedroom Home ~ Pleasant Bay Area 2018 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, 2 Bathrooms, Sleeps 8
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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
    Great Vacation Home Near Pleasant Bay in East Harwich! This comfortable and conveniently located home is close to Orleans, Chatham and beaches on Pleasant Bay. Enjoy a morning cup of coffee on the bright and sunny enclosed porch or the private back patio. The first floor master bedroom opens out...
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    South Orleans, Cape Cod 02645
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    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
    Kid friendly
    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 Sunday - Sunday 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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ESCAPE from it all, one house away from Pleasant Bay, to this stunning contemporary, located in South Orleans on a 2 acre lot surrounded by conservation land. 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, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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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