Top Hotels
Insights
FAQs
Hotels in Oak Bluffs

Vacation rentals in Oak Bluffs, MA

Find deals on 361 vacation rentals in Oak Bluffs, MA

Oak Bluffs, MA
May 7 — May 82

momondo compares 3M+ hotel and accommodation options.

Top rentals in Oak Bluffs

Find the perfect vacation rental for your stay in Oak Bluffs
Price
$147
$4,921
Review Score
0+
6+
7+
8+
9+

Hostels and cheap hotels in Oak Bluffs

These hotels and hostels usually make for a cheap way to stay in Oak Bluffs
Nana's Rear Treehouse Photo

Nana's Rear Treehouse

West Tisbury, MA, United States

6.5
Coastal home with outdoor shower, grill, fireplace, central AC, & W/D Photo

Coastal home with outdoor shower, grill, fireplace, central AC, & W/D

Oak Bluffs, MA, United States

9.3
The Lemonade Stand Photo

The Lemonade Stand

West Tisbury, MA, United States

8.7

Island Getaway

Oak Bluffs, MA, United States

3.5

Sea Glen Cottage

Oak Bluffs, MA, United States

4.7
Cozy Vineyard Haven Cottage Less Than 1 Mi to Beach! Photo

Cozy Vineyard Haven Cottage Less Than 1 Mi to Beach!

Vineyard Haven, MA, United States

Get the best value vacation rental in Oak Bluffs

These Oak Bluffs vacation rentals have the best prices for their ratings
The Lemonade Stand Photo

The Lemonade Stand

West Tisbury, MA, United States

8.7
In-Town Certified National Historic Oak Bluffs Property - Photo

In-Town Certified National Historic Oak Bluffs Property -

Oak Bluffs, MA, United States

10.0
Coastal home with outdoor shower, grill, fireplace, central AC, & W/D Photo

Coastal home with outdoor shower, grill, fireplace, central AC, & W/D

Oak Bluffs, MA, United States

9.3
Martha's Vineyard Vacation Home Photo

Martha's Vineyard Vacation Home

Edgartown, MA, United States

9.4
Make Lasting Memories In This Adorable Vineyard Cottage! Photo

Make Lasting Memories In This Adorable Vineyard Cottage!

Oak Bluffs, MA, United States

9.9
Nana's Rear Treehouse Photo

Nana's Rear Treehouse

West Tisbury, MA, United States

6.5

momondo's favorite vacation rentals in Oak Bluffs

Learn more about these user-preferred vacation rentals in Oak Bluffs
Private Family Home, Heated Pool, Hottub, 5 Br.4.5 Bath, Wifi, Ac Photo

Private Family Home, Heated Pool, Hottub, 5 Br.4.5 Bath, Wifi, Ac

Oak Bluffs, MA, United States

9.6
$4,730
Multiple Ensuites, Central Air, Perfect Location Photo

Multiple Ensuites, Central Air, Perfect Location

Oak Bluffs, MA, United States

10.0
$957
Comfortable Island Home, Easy Access to Beaches and Town Photo

Comfortable Island Home, Easy Access to Beaches and Town

Oak Bluffs, MA, United States

9.8
$521
Make Lasting Memories In This Adorable Vineyard Cottage! Photo

Make Lasting Memories In This Adorable Vineyard Cottage!

Oak Bluffs, MA, United States

9.9
$253
Spacious family house, short walk to the Lagoon & close to Oak Bluffs center Photo

Spacious family house, short walk to the Lagoon & close to Oak Bluffs center

Oak Bluffs, MA, United States

9.4
$437
Beautiful 3 bedroom 2 bath Home / Close to Town & Beach Photo

Beautiful 3 bedroom 2 bath Home / Close to Town & Beach

Oak Bluffs, MA, United States

10.0
$724
In-Town Certified National Historic Oak Bluffs Property - Photo

In-Town Certified National Historic Oak Bluffs Property -

Oak Bluffs, MA, United States

10.0
$311
Light Open Vacation Home, Sweeping Waterviews, Hill Top, Private Photo

Light Open Vacation Home, Sweeping Waterviews, Hill Top, Private

Chilmark, MA, United States

10.0
$2,034
Lovely Vacation Home Within Walking Distance To Oak Bluffs And The Beach Photo

Lovely Vacation Home Within Walking Distance To Oak Bluffs And The Beach

Oak Bluffs, MA, United States

10.0
$690
Original Pratt House built in 1866 with Ocean View of the Inkwell beach. Photo

Original Pratt House built in 1866 with Ocean View of the Inkwell beach.

Oak Bluffs, MA, United States

10.0
$1,509
Quiet/ Wooded/ Walk to town: Shared home w/ 1 other guest room. Photo

Quiet/ Wooded/ Walk to town: Shared home w/ 1 other guest room.

Vineyard Haven, MA, United States

9.4
$240
Cozy getaway in a central location w/ a full kitchen & furnished deck Photo

Cozy getaway in a central location w/ a full kitchen & furnished deck

Oak Bluffs, MA, United States

6.5
$313
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard Photo

Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

Oak Bluffs, MA, United States

8.0
$293
Newly Renovated! Walk to Town Oak Bluffs, 4 Bedroom/3 Bath A/C Photo

Newly Renovated! Walk to Town Oak Bluffs, 4 Bedroom/3 Bath A/C

Oak Bluffs, MA, United States

9.7
$902

Vineyard Charm

Edgartown, MA, United States

7.0
$338
Oak Bluffs Home with Renovated Screened-in Porch - Short Drive to Beach Photo

Oak Bluffs Home with Renovated Screened-in Porch - Short Drive to Beach

Oak Bluffs, MA, United States

7.7
$690

Vineyard Haven

Oak Bluffs, MA, United States

8.0
$465

Winthrop Cottage

Oak Bluffs, MA, United States

8.0
$237

Sea Glen Cottage

Oak Bluffs, MA, United States

4.7
$191

Renovated picture perfect home with new decor on beautiful private lot by beach

Edgartown, MA, United States

9.0
$907

Useful insights on Oak Bluffs vacation rentals

Get a quick overview on price and accommodation trends for your visit in Oak Bluffs

Lowest Vacation Rental Price

$147

Average Length of Stay

2 days
The cheapest price for a room in Oak Bluffs found in the last 7 days is $147/night. This rate is available with The Lemonade Stand.
On average, people stay for 2 days when lodging at vacation rentals in Oak Bluffs. The average accommodation price for 2 days in Oak Bluffs in the past week is $1,098.

When to book a vacation rental in Oak Bluffs

Check out the information below to find the best deal on a vacation rental in Oak Bluffs
Low SeasonSeptembercheapest month to stay
High SeasonOctobermost expensive time to stay
54%expected price decrease
47%expected price increase

Price

$299 - $1,223

Cheapest day of weekThursdayis the cheapest day of the week to book
Highest day of weekTuesdayis the most expensive day of the week to book
$379
$4,827

Information about staying in Oak Bluffs

Read these important travel tips before booking a vacation rental in Oak Bluffs

How long do people typically book vacation apartments for in Oak Bluffs?

On average, people book vacation rentals in Oak Bluffs for stays of around 2 nights.

When is the best time to book a vacation rental in Oak Bluffs?

Oak Bluffs vacation rentals are at their cheapest in September. Rental prices can be around 54% lower per night than in the high season.

How many operators does momondo search for hotels in Oak Bluffs?

As of April 2025, there are 382 operators available to choose from for hotels in Oak Bluffs.

When did momondo last update prices for hotels in Oak Bluffs?

Prices for hotels in Oak Bluffs are updated daily.

Save money when you book vacation rentals with momondo

Best deals on hotels

Best deals on hotels

See deals from 3M+ hotels and accommodations in one place.

Free cancellation

Free cancellation

Use our filter to find stays with free cancellation.

Millions of reviews

Millions of reviews

Check ratings based on millions of real guest reviews.

Price Alerts

Price Alerts

Not ready to book? to track prices.

An easier way to manage your Oak Bluffs trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
Wed 5/7
Thu 5/8
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your stay in Oak Bluffs