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

Search Oak Bluffs Cottage Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Oak Bluffs cottages

Property grounds

1. Make Lasting Memories In This Adorable Vineyard Cottage!

Make Lasting Memories In This Adorable Vineyard Cottage!
Oak Bluffs
9.8 out of 10, Exceptional, (154 reviews)
"Cute, compact, and had everything we needed for ourstay. I'd definitely stay there again."
United States
Karen C.
Make Lasting Memories In This Adorable Vineyard Cottage!
Terrace/patio

2. WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (52 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is ￥153,816
￥222,565 total
includes taxes & fees
Aug 20 - Aug 21
WATERFRONT Downtown Cottage w/ Beach
Property grounds

3. Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Tisbury
10.0 out of 10, Exceptional, (38 reviews)
"Great place, awesome location!"
United States
Connor B.
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Exterior

4. 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 ￥63,104
￥121,696 total
includes taxes & fees
Aug 17 - Aug 18
Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!
Exterior

5. Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people

Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people
Barnstable
8.8 out of 10, Excellent, (29 reviews)
"It was very comfortable with upgraded kitchen and bathroom. It had all we needed. The owner was very responsive . Easy check in process. The location was perfect, just across from a beautiful ocean beach and very near Hyannis and many attractions. "
United States
Helene M.
The price is ￥41,885
￥84,770 total
includes taxes & fees
Aug 19 - Aug 20
Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people
House (3 Bedrooms) | Interior

6. Bike to Beach: Centerville Home w/ Deck!

Bike to Beach: Centerville Home w/ Deck!
3.0 star property
Centerville
The price is ￥39,124
￥99,997 total
includes taxes & fees
Aug 26 - Aug 27
Bike to Beach: Centerville Home w/ Deck!
Exterior

7. Coastal Cottage in Pocasset - 0.5 mile to beach

Coastal Cottage in Pocasset - 0.5 mile to beach
Bourne
10.0 out of 10, Exceptional, (3 reviews)
"Great location for us visiting family who live in Pocasset. Clean home and very comfortable for us."
United States
Kim Z.
Coastal Cottage in Pocasset - 0.5 mile to 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oak Bluffs Hotel Reviews

MV Surfside Hotel

MV Surfside Hotel

10/10 Excellent
"nostalgic and cozy steps from the water"
Kimberly 3-night trip
Posted 3 hours ago
MV Surfside Hotel

Find out more about Oak Bluffs

Oak Bluffs Cottages information

Number of reviews
125
Accommodation
253 Cottages
Lowest Price
￥81,293
Highest Price
￥222,565

Frequently asked questions

How much do cottages in Oak Bluffs cost?
Cottages in Oak Bluffs range between ￥81,293 and ￥222,565 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?
Yes, there are! Reserve a stay at 11 Mashpee - 2 Bedroom Cottage, an excellent base for exploring the great outdoors in Oak Bluffs. This family-friendly cottage has a 3-star rating and comes with useful amenities like a playground and a barbecue grill. After checking in and chilling together in your new digs, it's time to start exploring! Inkwell Beach and Oak Bluffs Town Beach are popular family-friendly attractions in Oak Bluffs.
Why book your cottage in Oak Bluffs with Expedia?
We think that traveling 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.