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Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Inns in Osterville

The Coonamessett
Relax on the spacious deck with comfortable seating and umbrellas for shade, overlooking a lush landscape.

The Coonamessett

3.5 star property
8.8 out of 10, Excellent, (562)
"Great place to stay. Staff are amazing and we had the best cheeseburgers! "
$232 nightly
The price is $266
Sep 1 - Sep 2
Total includes taxes and fees
The Coonamessett
The Inn on Onset Bay
Overlooking a serene lake, this charming home offers a peaceful retreat with a bridge view.

The Inn on Onset Bay

2.5 star property
8.4 out of 10, Very Good, (156)
"Second time staying here and the location can't be beat. The inn is clean and comfortable. We really enjoyed our stay"
$133 nightly
The price is $149
Sep 3 - Sep 4
Total includes taxes and fees
The Inn on Onset Bay
Chapter House
Classic two-story house with a symmetrical facade, central entrance, and welcoming front porch, set amidst well-maintained landscaping.

Chapter House

3.5 star property
9.2 out of 10, Wonderful, (155)
"Really enjoyed the bar, which was a great spot for a late afternoon drink before dinner"
$298 nightly
The price is $341
Aug 10 - Aug 11
Total includes taxes and fees
Chapter House
The Coco, The Edgartown Collection
Relax in style on the spacious porch, surrounded by lush gardens and Adirondack chairs.

The Coco, The Edgartown Collection

3.0 star property
9.8 out of 10, Exceptional, (53)
"Staff was very accomodating..Breakfast was excellent..room was beautiful. Close to lots of restaurants and shops..i loved it all."
$573 nightly
The price is $640
Aug 26 - Aug 27
Total includes taxes and fees
The Coco, The Edgartown Collection
Mooncussers Tavern and Inn
Stunning two-story home with a central entrance and beautifully maintained gardens.

Mooncussers Tavern and Inn

2.5 star property
8.8 out of 10, Excellent, (128)
"We had a lovely time "
Mooncussers Tavern and Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Osterville Hotel Reviews

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

10/10 Excellent
"Good location. Enjoyed private beach"
Endia 1-night trip
Posted 12 hours ago
Vineyard Harbor Motel - Private Beach