Best Resorts in Osterville

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Resorts in Osterville

Margaritaville Resort Cape Cod
Relax by the resort's central pool surrounded by lounge chairs and umbrellas.

Margaritaville Resort Cape Cod

4.0 star property
8.8 out of 10, Excellent, (249)
"Great location, spacious rooms, good size pools and a lazy river. It is a restful oasis to retreat to, once you have explored the towns of the cape, including Hyannis, Chatham and Falmouth Great fun and friendly staff. "
$233 nightly
The price is $267
Aug 24 - Aug 25
Total includes taxes and fees
Margaritaville Resort Cape Cod
Blue Water Resort
Relax by the ocean with a clear view, lounge under shaded umbrellas and enjoy refreshments at the poolside.

Blue Water Resort

3.0 star property
8.2 out of 10, Very Good, (1004)
"Clean, harmonious indoor and outdoor areas, everything perfect and easy for a family vacation with small children."
$199 nightly
The price is $228
Sep 1 - Sep 2
Total includes taxes and fees
Blue Water Resort
The Villages at Ocean Edge
Relax by the pool surrounded by shaded seating areas and lifeguard supervision.

The Villages at Ocean Edge

3.5 star property
8.4 out of 10, Very Good, (1004)
"There was lots to do and see. "
$245 nightly
The price is $280
Sep 1 - Sep 2
Total includes taxes and fees
The Villages at Ocean Edge
Cape Cod Irish Village
Relax by the rooftop pool surrounded by lounge chairs and umbrellas, with a spacious area for gatherings under a large tent.

Cape Cod Irish Village

3.5 star property
6.4 out of 10, (1009)
"Great place "
$126 nightly
The price is $145
Aug 6 - Aug 7
Total includes taxes and fees
Cape Cod Irish Village
The Island Inn on Martha's Vineyard
Two single beds with white linens and wooden headboards, a desk and chair, and a large window with beige curtains.

The Island Inn on Martha's Vineyard

2.5 star property
8.4 out of 10, Very Good, (8)
"The property was very family oriented."
$442 nightly
The price is $494
Sep 3 - Sep 4
Total includes taxes and fees
The Island Inn on Martha's Vineyard
Cozy History Resort Located in the center of the city
Harbor Landing offers outdoor seating areas with umbrellas and a welcoming entrance.

Cozy History Resort Located in the center of the city

4.8 out of 10, (3)
"Lovely community. No restaurant onsite but the location is in the center of plenty of shopping and places to dine. Excellent staff."
Cozy History Resort Located in the center of the city
Captain's Quarters Resort Oceanfront suite, beautiful ocean view, swimming pool
Relax by the pool surrounded by lounge chairs and umbrellas.

Captain's Quarters Resort Oceanfront suite, beautiful ocean view, swimming pool

10.0 out of 10, Exceptional, (1)
"The Inn was beautiful and very accommodating. The staff was great and the location perfect."
Captain's Quarters Resort Oceanfront suite, beautiful ocean view, swimming pool
Spacious waterfront townhouse at Cove at Yarmouth
Relax by the hotel's central pool surrounded by sun loungers and umbrellas.

Spacious waterfront townhouse at Cove at Yarmouth

Spacious waterfront townhouse at Cove at Yarmouth
Deluxe suite at the oceanfront Surfside Resort
Relax by the pool with a view of the surrounding buildings through large windows.

Deluxe suite at the oceanfront Surfside Resort

Deluxe suite at the oceanfront Surfside Resort
Brewster Green Resort
Enjoy cooking in this well-equipped kitchen with a central island, stove, oven, microwave, and sink.

Brewster Green Resort

2.5 star property
Brewster Green Resort
FABULOUS CAPE COD RESORT !
Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

FABULOUS CAPE COD RESORT !

FABULOUS CAPE COD RESORT !
Brewster Green Resort 3-bedroom unit w/2 pools-one indoor, hot tub, fitness room
Relax by the pool surrounded by comfortable seating and lush views.

Brewster Green Resort 3-bedroom unit w/2 pools-one indoor, hot tub, fitness room

Brewster Green Resort 3-bedroom unit w/2 pools-one indoor, hot tub, fitness room
Charming 2-bedroom resort with AC, WiFi in tranquil Falmouth
Relax by the pool surrounded by lounge chairs and umbrellas, with a lifeguard station nearby.

Charming 2-bedroom resort with AC, WiFi in tranquil Falmouth

Charming 2-bedroom resort with AC, WiFi in tranquil Falmouth
Studio Villa directly across from beach. Sleeps 4
Wade into the calm waters of this serene beach, where a natural breakwater invites exploration.

Studio Villa directly across from beach. Sleeps 4

Studio Villa directly across from beach. Sleeps 4
Coastal Family Haven: Spacious Retreat Near Old Silver Beach
Enjoy dining or socializing on this deck with a glass-top table and comfortable seating.

Coastal Family Haven: Spacious Retreat Near Old Silver Beach

Coastal Family Haven: Spacious Retreat Near Old Silver Beach
Martha’s Vineyard Waterfront 1 Bedroom King Bed - Available October 9-16
Stunning marina surrounded by diverse homes with easy access to boating activities.

Martha’s Vineyard Waterfront 1 Bedroom King Bed - Available October 9-16

Martha’s Vineyard Waterfront 1 Bedroom King Bed - Available October 9-16
Cape Cod Not spot
Kids can play on the swing set and slide in this backyard play area surrounded by lush greenery.

Cape Cod Not spot

Cape Cod Not spot
Spacious one bedroom getaway resort on Falmouth Harbor. Sleeps 4 comfortably.
Situated at the waterfront marina, this bench offers serene views of the calm water.

Spacious one bedroom getaway resort on Falmouth Harbor. Sleeps 4 comfortably.

Spacious one bedroom getaway resort on Falmouth Harbor. Sleeps 4 comfortably.
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 13 hours ago
Vineyard Harbor Motel - Private Beach