A row of colorful, historic houses with a central path.

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Oak Bluffs cottages

Terrace/patio

WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (50 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is NZ$2,783
includes taxes & fees
20 Aug - 21 Aug
WATERFRONT Downtown Cottage w/ Beach
Exterior

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
Tisbury
10.0 out of 10, Exceptional, (60 reviews)
"We loved the location and place was great!"
United States
Eileen M.
The price is NZ$1,963
includes taxes & fees
16 Aug - 17 Aug
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
Property grounds

4 Mi to Bristol Beach! Coastal Retreat w/ Pond

4 Mi to Bristol Beach! Coastal Retreat w/ Pond
East Falmouth
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay at this charming New England home. The house was spotless, beautifully maintained, and full of character. It had all the comforts we needed, inviting spaces to relax in after exploring the area. The location was perfect—close to local shops, scenic spots, and great dining. Our host was friendly, responsive, and made us feel right at home. We honestly couldn’t have asked for a better experience, and we look forward to returning."
United States
Shaun G.
The price is NZ$1,158
includes taxes & fees
14 Aug - 15 Aug
4 Mi to Bristol Beach! Coastal Retreat w/ Pond
Cottage (2 Bedrooms) | Interior

4 Mi to Bristol Beach! Coastal Retreat w/ Pond

4 Mi to Bristol Beach! Coastal Retreat w/ Pond
3.0 star property
East Falmouth
The price is NZ$1,167
includes taxes & fees
14 Aug - 15 Aug
4 Mi to Bristol Beach! Coastal Retreat w/ Pond
Exterior

Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!

Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!
Falmouth
9.4 out of 10, Exceptional, (3 reviews)
"Good location, close to ferry and restaurants. Quiet neighborhood."
United States
Kerry B.
The price is NZ$1,279
includes taxes & fees
17 Aug - 18 Aug
Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!
Outdoor dining

Chappy cottage with private beach

Chappy cottage with private beach
Edgartown
10.0 out of 10, Exceptional, (18 reviews)
"What a gorgeous location, my family and I had a wonderful time on Chappy, will definitely be back!"
United States
Clinton G.
Chappy cottage with private beach
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 Oak Bluffs Hotel Reviews

Pequot Hotel

Pequot Hotel

10/10 Excellent
"Loved it. Perfect location. Very cozy. 10/10 - would stay again!"
Michelle 3-night trip
Posted 9 hours ago
Pequot Hotel

Find out more about Oak Bluffs

Oak Bluffs Cottages information

Number of reviews
Accommodation
247 Cottages
Lowest Price
NZ$1,167
Highest Price
NZ$1,167

Frequently asked questions

How much do cottages in Oak Bluffs cost?
Cottages in Oak Bluffs range between NZ$1,167 and NZ$1,167 per night. These stays offer a chance to get in touch with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Oak Bluffs?
Enjoy reconnecting with nature in one of the 247 cottages available in Oak Bluffs. To help you choose a property that's right for you, take advantage of our filters to search for perks or amenities you need.
What is there to do in Oak Bluffs near my cottage?
Oak Bluffs has enough experiences and sights to keep you busy for weeks, starting with East Chop Light. Farm Neck Golf Club, Oak Bluffs Town Beach and Trinity Park Tabernacle are other impressive attractions. If you have time to spare, Cottage Museum and Inkwell Beach are nice finishing touches to your itinerary.