Search results showing properties in South Orleans, Massachusetts, United States of America

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Photo gallery for Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly

Best view of Pleasant Bay, hands down.

Premier Host

Cottage · On the beach

Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly

Sleeps 8 · 4 bedrooms · 2 bathrooms

9.49.4 out of 10

Exceptionalexceptional

31 reviews(31 reviews)

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Photo gallery for Waterfront Cottage - Adorable & Private

We've added a wall of windows, and love it!

Cottage · Eastham, 6.19 mi from South Orleans

Waterfront Cottage - Adorable & Private

Sleeps 2 · 1 bedroom · 1 bathroom

Private host

1010 out of 10

Exceptionalexceptional

65 reviews(65 reviews)

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Photo gallery for Perfect Location, Private, Immaculate, Affordable, East Dennis Cape Cod

Almost There! Just a short drive to the Outback

Cottage · 7.91 mi from South Orleans

Perfect Location, Private, Immaculate, Affordable, East Dennis Cape Cod

Sleeps 2 · 2 bedrooms · 1+ bathroom

Private host

1010 out of 10

Exceptionalexceptional

46 reviews(46 reviews)

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Cottage · Eastham, 4.06 mi from South Orleans

Cozy Cottage

Sleeps 2 · 1 bedroom · 1 bathroom

Private host

9.69.6 out of 10

Exceptionalexceptional

9 reviews(9 reviews)

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Cottage · 3.58 mi from South Orleans

Charming Brewster Cottage

Sleeps 4 · 1 bedroom · 1 bathroom

Private host

1010 out of 10

Exceptionalexceptional

42 reviews(42 reviews)

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Cottage · Eastham, 3.9 mi from South Orleans

On Town Cove with salt water access! Kayak and paddle board available for use!

Sleeps 6 · 2 bedrooms · 1 bathroom

Private host

9.89.8 out of 10

Exceptionalexceptional

41 reviews(41 reviews)

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Cottage · Eastham, 6.4 mi from South Orleans

Newly renovated, near Cape Cod National Seashore Visitors Center

Sleeps 3 · 1 bedroom · 1 bathroom

1010 out of 10

Exceptionalexceptional

140 reviews(140 reviews)

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Cottage · 8.94 mi from South Orleans

Swan Pond Cottage, Waterfront Central A/C, Open Floor Plan

Sleeps 5 · 2 bedrooms · 1 bathroom

Private host

1010 out of 10

Exceptionalexceptional

196 reviews(196 reviews)

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Cottage · Eastham, 4.01 mi from South Orleans

Comfy cottage in perfect location, quiet setting

Sleeps 4 · 2 bedrooms

Private host

9.89.8 out of 10

Exceptionalexceptional

34 reviews(34 reviews)

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Cottage · 5.9 mi from South Orleans

Cozy Cape Cottage with Beach Access

Sleeps 4 · 2 bedrooms · 1 bathroom

Private host

1010 out of 10

Exceptionalexceptional

2 reviews(2 reviews)

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