Oak Bluffs Vacation Rentals

Check prices for these upcoming dates

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
80° 30°
7
69° 13°
3
59° 10°
7
56°
5
62°
2
59°
4
70° 14°
4
77° 31°
4
83° 39°
6
92° 50°
3
86° 44°
3
80° 36°
3
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Rainy days

This climate histogram shows you the weather patterns in Oak Bluffs. The warmest months in Oak Bluffs are June and May, when temperatures reach 92 ˚F. The coolest month is November, when temperatures drop to 2 ˚F. The wettest month in Oak Bluffs is January with 7.37 inches of rain, while the driest month is November with 2.36 inches of rain.

What Expert Travelers Think

  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School
  • — 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
  • — 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 Campbell
    Jeff CampbellMiddle Class Dad

Vacation Rentals in Oak Bluffs

Browse rentals from all the best providers including Airbnb, Priceline, RedAwning and many more at AllTheRooms.com. AllTheRooms has 1,137 vacation rentals, hotels and other great places to stay during your time in Oak Bluffs, with everything from budget hostels and homestays to extravagant Airbnbs and hotels. When traveling on a budget, the most economical place to stay in Oak Bluffs is available at $28 per night. In general, a place to stay in Oak Bluffs will cost you $458 per night.

Those needing to get some work finished during their trip to Oak Bluffs can pick from 402 places to stay that include WiFi. 24 places to stay include a morning meal. You can maintain your workout regime by staying at one of 4 accommodations that provide gym facilities. If you are driving to Oak Bluffs, you'll want to pick from 391 places to stay that provide parking. We track 63 accommodations that have a pool or jacuzzi.

AllTheRooms has 85 pet-friendly places to stay in Oak Bluffs, so if you're traveling with your pet you won't have any problems.

676 accommodations in Oak Bluffs have been reviewed; 65% are rated highly. You can instantly book any of 432 places to stay right now.

Destinations near Oak Bluffs

  • Boston3,441 Properties
  • Nantucket3,241 Properties
  • Provincetown2,272 Properties
  • Eastham1,663 Properties
  • Dennis Port1,632 Properties
  • Chatham1,575 Properties
  • Brewster1,460 Properties
  • Wellfleet1,323 Properties
  • Orleans1,230 Properties
  • Somerville1,045 Properties
  • Edgartown1,004 Properties
  • West Yarmouth913 Properties
  • Cambridge870 Properties
  • Falmouth869 Properties
  • Mashpee859 Properties
  • Hyannis808 Properties
  • South Yarmouth791 Properties
  • Brookline765 Properties
  • Tisbury714 Properties
  • Plymouth678 Properties
  • Rockport673 Properties
  • East Falmouth670 Properties
  • West Dennis627 Properties
  • North Truro612 Properties
  • Gloucester608 Properties
  • South Chatham599 Properties
  • Lenox539 Properties
  • Harwich533 Properties
  • Worcester492 Properties
  • Salem474 Properties
  • Dennis472 Properties
  • Harwich Port463 Properties
  • East Sandwich442 Properties
  • Centerville441 Properties
  • Hancock430 Properties
  • Revere415 Properties
  • Great Barrington411 Properties
  • Vineyard Haven401 Properties
  • Waltham389 Properties
  • Lee368 Properties
  • Northampton357 Properties
  • Quincy357 Properties
  • Sandwich352 Properties
  • Newton341 Properties
  • Truro339 Properties
  • Medford326 Properties
  • Watertown323 Properties
  • Williamstown315 Properties
  • Newburyport312 Properties
  • Marblehead304 Properties
  • Pittsfield300 Properties
  • South Dennis290 Properties
  • North Falmouth267 Properties
  • Chelsea266 Properties
  • Amherst257 Properties
  • Stockbridge246 Properties
  • Marshfield242 Properties
  • Osterville232 Properties
  • Barnstable232 Properties
  • Arlington231 Properties
  • Wareham207 Properties
  • Scituate200 Properties
  • West Harwich198 Properties
  • Woburn186 Properties
  • Chilmark172 Properties
  • Bourne164 Properties
  • Sturbridge155 Properties
  • Fairhaven138 Properties
  • Winthrop130 Properties
  • Ipswich120 Properties
  • Westport117 Properties
  • West Stockbridge109 Properties
  • Marlborough108 Properties
  • Hull97 Properties
  • New Marlborough89 Properties
  • Sheffield81 Properties
  • Manchester76 Properties
  • Springfield65 Properties
  • Concord65 Properties
  • Sudbury48 Properties
  • Ashburnham33 Properties
  • Cheshire22 Properties
  • Hubbardston8 Properties