Oak Bluffs Vacation Rentals

Our Favorite Vacation Rentals in Oak Bluffs

  • Downtown Delight
     Country House
    Booking.com
    From
    $207
  • Newly built home w/ gourmet kitchen, furnished patio & grill - 1 dog OK!
     5br Home/Apartment
    HolidayLettings
    From
    $687
  • The Oak Estate
     Country House
    Booking.com
    From
    $406
  • Cozy MV Cottage with Charming Romantic Gardens
     2br Home/Apartment
    HolidayLettings
    From
    $815
  • The Bluffs Estate
     Country House
    Booking.com
    From
    $406
  • Updated Martha's Vineyard home w/jet tub, fireplace- close to ferry terminal!
     4br Home/Apartment
    HolidayLettings
    From
    $543
  • Sea Glen Cottage
     Country House
    Booking.com
    From
    $191
  • Beautiful, Updated, Well-Appointed Home ~ 3bdrm, 4bth in Ideal Private Location
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $553

Check prices for these upcoming dates

Oak Bluffs Vacation Rentals with a Pool

  • Two Ponds Residence
    Excellent8br Home/Apartment
    Airbnb
    From
    $735

Oak Bluffs Vacation Rentals with Wi-Fi

  • Walk to beach and all Oak Bluffs has to offer!111F
    ExcellentHome/Apartment
    Airbnb
    From
    $280
  • Charming water-front cottage on Martha's Vineyard!
    ExcellentHome/Apartment
    Airbnb
    From
    $331
  • 1.5 Miles to Town and Beach! 2BR/2BA Sleeps 4.
    Excellent2br Home/Apartment
    Airbnb
    From
    $545
  • Martha's Vineyard Getaway Cottage
    Excellent2br Home/Apartment
    Airbnb
    From
    $240

Oak Bluffs Pet-Friendly Vacation Rentals

  • Cozy cottage w/ remodeled kitchen - less than a mile from Woods Hole Ferry
     Cottage
    HolidayLettings
    From
    $276
  • Picturesque home w/ back patio & gas grill - 2 blocks to Main Street!
     3br Home/Apartment
    HolidayLettings
    From
    $297
  • New Cape House Steps to the Beach in East Falmouth
    Excellent3br Home/Apartment
    Flipkey
    From
    $657
  • Stunning Spacious House with Water Views
    Excellent6br Home/Apartment
    HolidayLettings
    From
    $982

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
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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 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 Weather in Oak Bluffs

Rainy days
66° 15°
9
58° 13°
4
55°
4
54° 12°
8
63° 13°
5
66° 18°
4
83° 37°
2
86° 36°
3
91° 40°
2
92° 49°
1
88° 43°
3
78° 23°
6
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

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 December, when temperatures drop to 1 ˚F. The wettest month in Oak Bluffs is February with 9.01 inches of rain, while the driest month is May with 1.25 inches of rain.

What Expert Travelers Think

  • — Site is easy to use; clean, laid out well, good colors and branding, fun logo and title that connects to the purpose of the brand. The blog, vacation destinations, and rental destinations is a great feature and really make the brand stand apart from other sites!

    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker
  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum
  • — When I first opened up the AllTheRooms.com site, I was impressed right away... When I’m traveling, I don’t like to waste time searching multiple engines for accommodations, it gets overwhelming and frustrating fast. I want a unique, comfortable stay for the best deal

    Kaelin
    KaelinKindly Kae

Vacation Rentals in Oak Bluffs

At AllTheRooms.com we have rentals from all of the leading providers - Airbnb, Bed and Breakfast, RedAwning and more. We have 1,194 vacation rentals, hotels and other accommodation types in Oak Bluffs ranging from low-cost options to extravagant places to stay. When traveling on a budget, the most economical place to stay in Oak Bluffs is available at $29 per night. The average price of a vacation rental is around $442 per night.

Those needing to get some work done during their trip to Oak Bluffs can pick from 438 places to stay that provide WiFi. We have 29 accommodations that include a breakfast included. You can keep up with your workout regime by staying at one of 3 accommodations that provide gym facilities. Driving to Oak Bluffs? Then choose one of the 410 places to stay that comes with a parking spot included. 60 places to stay have a a pool or jacuzzi

AllTheRooms has 87 pet-friendly places to stay in Oak Bluffs, so if you're traveling with your cat or dog you won't have any problems.

725 of the places to stay in Oak Bluffs have been rated by previous guests. They rated 66% as great. 421 places to stay in are instantly bookable.

Destinations near Oak Bluffs

  • Boston4,371 Properties
  • Nantucket3,367 Properties
  • Provincetown2,404 Properties
  • Eastham1,561 Properties
  • Dennis Port1,535 Properties
  • Brewster1,461 Properties
  • Chatham1,376 Properties
  • Wellfleet1,291 Properties
  • Orleans1,238 Properties
  • Somerville1,167 Properties
  • Edgartown1,023 Properties
  • Cambridge1,011 Properties
  • West Yarmouth1,001 Properties
  • Falmouth965 Properties
  • Mashpee919 Properties
  • Hyannis913 Properties
  • Brookline896 Properties
  • Rockport804 Properties
  • South Yarmouth788 Properties
  • Tisbury774 Properties
  • Plymouth719 Properties
  • East Falmouth702 Properties
  • Gloucester670 Properties
  • South Chatham598 Properties
  • North Truro592 Properties
  • Lenox563 Properties
  • Dennis544 Properties
  • Harwich538 Properties
  • West Dennis532 Properties
  • Worcester531 Properties
  • Salem506 Properties
  • Centerville504 Properties
  • East Sandwich478 Properties
  • Harwich Port465 Properties
  • Waltham453 Properties
  • Great Barrington450 Properties
  • Hancock441 Properties
  • Lee423 Properties
  • Newton403 Properties
  • Northampton397 Properties
  • Vineyard Haven393 Properties
  • Revere390 Properties
  • Sandwich370 Properties
  • Medford368 Properties
  • Quincy366 Properties
  • Newburyport355 Properties
  • Williamstown353 Properties
  • Truro346 Properties
  • Watertown342 Properties
  • North Falmouth339 Properties
  • Pittsfield332 Properties
  • Marblehead320 Properties
  • Chelsea294 Properties
  • Stockbridge272 Properties
  • Amherst272 Properties
  • Marshfield266 Properties
  • South Dennis263 Properties
  • Arlington253 Properties
  • Barnstable240 Properties
  • Osterville238 Properties
  • Woburn228 Properties
  • Scituate218 Properties
  • West Harwich208 Properties
  • Wareham206 Properties
  • Sturbridge196 Properties
  • Bourne183 Properties
  • Chilmark179 Properties
  • Marlborough158 Properties
  • Fairhaven142 Properties
  • Winthrop135 Properties
  • Ipswich125 Properties
  • Westport123 Properties
  • West Stockbridge119 Properties
  • Hull117 Properties
  • Manchester88 Properties
  • Sheffield86 Properties
  • New Marlborough85 Properties
  • Concord82 Properties
  • Springfield67 Properties
  • Sudbury56 Properties
  • Ashburnham36 Properties
  • Cheshire27 Properties
  • Hubbardston8 Properties