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Latest Vacation Rentals in South Orleans MA (8)

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4 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

This property is professionally managed by Pretty Picky PropertiesCaptivating in South Orleans, Spacious, Pristine with Heated Pool7-Night minimum for June, July & AugustLinens Included, Beds...

Created May 19, 2024

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9 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

Chosen by Cape Cod Life magazine as one of the Top Ten places to stay on Cape Cod. Our waterfront estate now has a gorgeous heated pool plus breathtaking views of over 180 ' plus of Pleasant Bay...

Created May 19, 2024

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5 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

Waterfront home with gorgeous views across Pleasant Bay. Watch the boats sail by from your sunny deck & soak in the breathtaking views across Pleasant Bay. Enjoy swimming, kayaking, paddelboarding...

Created May 19, 2024

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3 Br Private Vacation Home Vacation Rental In South Orleans, Massachusetts

This cozy, three bedroom home sits on a hill overlooking a pond, a creek, and Little Pleasant Bay, with water views on three sides. Located at the end of a quaint country road, you're just steps...

Created May 19, 2024

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2 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

New weeks now open for summer 2023! We will provide an additional $250 discount for singles or couples -- please send a message and we'll discuss how to implement. This is a cozy, immaculate,...

Created May 19, 2024

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4 Br Cottage Vacation Rental In Orleans, Massachusetts

This updated 4-bedroom 2-bathroom home has the best view on Pleasant Bay, hands down. The open floor plan is ideal for large family gatherings, and conversations blend easily through two large...

Created May 19, 2024

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4 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

Enjoy all the comforts of home at this 4 bedroom, 2.5 bath pet friendly home! The first level of the home features a living room with 38 TV, kitchen with dining table and full bathroom as well as...

Created May 19, 2024

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1br Cottage Vacation Rental In South Orleans, Massachusetts

Waterfront A-frame attached home overlooking Pleasant Bay, in South Orleans. Two decks provide a beautiful view of the bay (first picture is the view from the deck). The A-frame is just steps away fro

Created Mar 22, 2022

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