Oak Bluffs Vacation Rentals

Our Favorite Vacation Rentals in Oak Bluffs

62 Crowell Road Home

RedAwningFrom $688
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Narragansett Cottage

Booking.comFrom $229
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Cozy MV Cottage with Charming Romantic Gardens

HolidayLettingsFrom $730
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Kelley House

NextTripFrom $491
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32 Crosby Lane House

RedAwningFrom $920
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Everybody Loves Raymond

Booking.comFrom $456
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Comfortable & convenient Martha's Vineyard condo w/ shared pool, close to beach!

HolidayLettingsFrom $312
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33 Sunset Home

RedAwningFrom $783
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Oak Bluffs Vacation Rentals with a Pool

Waterside Guest House
Good
AirbnbFrom $354
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Beautiful Home a Pool for Family Vineyard Fun!

AirbnbFrom $453
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Cape Code Getaway
Excellent
AirbnbFrom $345
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Golf view townhouse near the beach

AirbnbFrom $440
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Oak Bluffs Vacation Rentals with Wi-Fi

The old goathouse
Excellent
AirbnbFrom $322
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Oak Bluffs/ Walk to Town/ Harbor Views/ Twin Bed
Excellent
AirbnbFrom $174
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Harbor view apartment, a quick walk from the ferry
Excellent
AirbnbFrom $294
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Quaint Vineyard Escape
Excellent
AirbnbFrom $266
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Oak Bluffs Pet-Friendly Vacation Rentals

Heated Pool, Hottub,AC,WiFi,sleep22, 2 mi to beach
Excellent
HolidayLettingsFrom $2927
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46 Paola Dr Home at East Falmouth

RedAwningFrom $657
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Stunning Private Vacation House With SkyLights in the Vineyard

HolidayLettingsFrom $514
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Dog-friendly, lakefront home w/ roof deck - blocks from the beach!

HolidayLettingsFrom $610
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Oak Bluffs Travel Guide

Oak Bluffs is a historic resort town on Martha's Vineyard, home to sandy beaches, great seafood, unique stores and traditional cottages. The place is colorful and bustling in summer, while tranquil in winter.

Things to Do in Oak Bluffs

Top beaches include Inkwell Beach, being walking distance to the ferry port and State Beach -- ideal for a casual stroll or swim due to its gentle current. From this beach you can get to Jaws Bridge the location of the iconic shark horror movie from 1975. You can hurl yourself off into the water here, as many thrill-seeking jumpers do in summer.

In summer, hire a kayak or canoe on the huge Sengekontacket Pond and enjoy the scenic natural beauty. Alternatively, check out one of the most historic and adored attractions in town, the Flying Horses Carousel. Built in 1876, this vintage carousel is the stuff summer memories are made of.

Another must-visit is the gingerbread cottages at the Oak Bluffs Campground. Dating back to the 19th-century, these cottages with their delicate little fences and tiny dimensions are like something from a fairytale.

For something more relaxing, take a scenic drive along East Chop Drive in Oak Bluffs and drink in the beauty of the coast on one side and beautiful homes on the other. At some point, the East Chop Lighthouse will appear before you and further down you will reach Oak Bluffs Harbor.

Best Time to Visit Oak Bluffs

Visit in summer for the real taste of the atmosphere in Martha's Vineyard.

Price and Availability in Oak Bluffs

Most expensive

Most availability

The most expensive month to stay in a vacation rental in Oak Bluffs is in August, while the cheapest month is in November. The most popular time to book a vacation rental in Oak Bluffs is in the high season in August. Oak Bluffs has its low season in February, when less people are visiting and the vacation home occupancy rate drops.

The cheapest day to stay at a vacation rental in Oak Bluffs tends to be Monday, while the most expensive day tends to be Friday. Vacation homes in Oak Bluffs tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.

The Weather in Oak Bluffs

SEE FULL WEATHER FORECAST:

83º 37º

1.72

86º 36º

2.94

91º 40º

1.98

92º 49º

1.25

88º 43º

3.16

78º 23º

6.41

66º 15º

9.01

58º 13º

3.89

55º 1º

4.48

54º 12º

7.88

63º 13º

5.23

66º 18º

4.19

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Jan

Feb

Mar

Apr

Rainy days

SEE FULL WEATHER FORECAST:

This climate histogram shows you the weather patterns in Oak Bluffs. The hottest month in Oak Bluffs is May, when temperatures peak at 92 ˚F. The coolest month is January, when temperatures drop to 1 ˚F. The wettest month in Oak Bluffs is November with 9.01 inches of rain, while the driest month is August with 1.25 inches of rain.

What Expert Travelers Think

— I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time
Jeff CampbellMiddle Class Dad
Middle Class Dad
— Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location
JazThe Life of a Social Butterfly
The Life of a Social Butterfly
— I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips
Kacie MorganThe Rare Welsh Bit
The Rare Welsh Bit

Vacation Rentals in Oak Bluffs

At AllTheRooms.com we have rentals from all of your favorite providers - Airbnb, VRBO, Homeaway and others. AllTheRooms has 992 vacation rentals, hotels and other great places to stay while you enjoy Oak Bluffs, with everything from inexpensive hostels and homestays to luxury Airbnbs and hotels. For those traveling on a budget, the most economical place to stay in Oak Bluffs is available at $29 per night. On average, an accommodation in Oak Bluffs will cost you $444 per night.

If you have to have an internet connection during your stay in Oak Bluffs, then you can choose from over 509 accommodations that provide WiFi internet. 32 places to stay include a morning meal. Choose from 5 accommodations that provide gym facilities, so you don't miss a single workout. If you are driving to Oak Bluffs, you'll want to pick from 484 places to stay that provide parking. 58 accommodations have a a pool or jacuzzi

AllTheRooms has 90 pet-friendly places to stay in Oak Bluffs, so if you're traveling with your cat or dog you won't have any problems.

We combine a wide variety of Oak Bluffs accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 5 providers, including 338 places to stay from Airbnb, 93 accommodations from VRBO and 86 places to stay from Homeaway.

566 accommodations in Oak Bluffs have been reviewed; 59% are rated excellent or good. 353 accommodations allow instant booking.