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Vacation rentals in Pleasant Bay

Find and book unique accommodations on Airbnb

Popular amenities for Pleasant Bay vacation rentals

Free parking on premises

Air conditioning

Homes with more space

Top guest favorite

A charming antique Cape Cod home is framed by a white picket fence and surrounded by lush greenery. The exterior features a gray wood shingle facade and multiple windows. Two red adirondack chairs are positioned on the front porch, inviting relaxation amidst the serene garden.

Home in Orleans

4.95 out of 5 average rating, 42 reviews

1850 Orleans Antique Home with Path to Arey’s Pond

Top guest favorite

A vibrant garden displays blooming red roses and a variety of colorful flowers. An earthenware pot adds earthy tones, complementing the lush greenery. A rustic shed with wooden shutters serves as a backdrop to this lively scene, offering a glimpse of tranquility.

Home in Brewster

4.99 out of 5 average rating, 80 reviews

“Rooster Cottage and Gardens” Entire Private Home

An aerial view showcases a large estate set against a tranquil bay. The property features a sprawling lawn, with a red building juxtaposed against a neighboring white house and lush trees. The calm waters reflect the clear blue sky, enhancing the serene ambiance of the area.

Home in Orleans

4.85 out of 5 average rating, 41 reviews

Private beach

Top guest favorite

An outdoor gathering area is arranged around a circular fire pit, with several comfortable chairs and accent tables. The surrounding garden is filled with lush greenery and vibrant blue hydrangeas. Soft lighting enhances the cozy ambiance as twilight descends.

Home in Orleans

4.99 out of 5 average rating, 96 reviews

Modern Cape Escape Retreat- Walk to Pilgrim Lake