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 £1,048
includes taxes & fees
31 Jul - 1 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 £858
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 £519
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 £510
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 £589
includes taxes & fees
9 Aug - 10 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.
The price is £1,207
includes taxes & fees
30 Jul - 31 Jul
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

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

10/10 Excellent
"great place to stay!"
Margaret L. 4-night trip
Posted 1 hour ago
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Find out more about Oak Bluffs

Oak Bluffs Cottages information

Number of reviews
114
Accommodation
253 Cottages
Lowest Price
£510
Highest Price
£1,207

Frequently asked questions

How much do cottages in Oak Bluffs cost?
Cottages in Oak Bluffs range between £510 and £1,207 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 253 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.
Are there any family-friendly cottages in Oak Bluffs?
If you're searching for a slower pace in Oak Bluffs, make a booking for the crew at 11 Mashpee - 2 Bedroom Cottage. With a 3-star rating and handy amenities like a playground and WiFi, you'll find it easy to relax at this family-friendly cottage. Once you've checked in, there's no shortage of family-friendly attractions to see in and around Oak Bluffs. Farm Neck Golf Club and East Chop Light guarantee a good time for young and old.
Why book your cottage in Oak Bluffs with Expedia?
We think that travelling should be easy, so if you're after cottages in Oak Bluffs at a nice price, Expedia delivers. Stick to the budget and pick a thrifty option far from the rush of the city, or book an upscale cottage to pamper your loved ones.
How can I find cheap cottages in Oak Bluffs?
Expedia is here to help you track down cheap cottages in Oak Bluffs. To book your special stay in a couple of clicks, simply use the filter tool to refine your search by star rating, budget and amenities.
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.