Oak Bluffs Vacation Rentals

Our Favorite Vacation Rentals in Oak Bluffs

  • Beachside Retreat - 300 Yards to Surf Drive Shore
     3br Home/Apartment
    RedAwning
    From
    $560
  • Barbara's Place
     Country House
    Booking.com
    From
    $163
  • Downtown apartment w/ ocean view, balcony & central air - walk everywhere!
     2br Home/Apartment
    HolidayLettings
    From
    $231
  • Falmouth Family Getaway
     4br Home/Apartment
    RedAwning
    From
    $468
  • The Oak Estate
     Country House
    Booking.com
    From
    $318
  • Cozy MV Cottage with Charming Romantic Gardens
     2br Home/Apartment
    HolidayLettings
    From
    $815
  • Tranquil 4BR on Bourne’s Pond
     4br Home/Apartment
    RedAwning
    From
    $449
  • Beach Edgartown Center Restaurantes Bar Bike Path
     Home/Apartment
    Booking.com
    From
    $139

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

  • Newly Renovated Home in New Seabury
     3br Home/Apartment
    RedAwning
    From
    $510
  • Beautiful Popponesset Beach Retreat on Deans Pond
     3br Home/Apartment
    RedAwning
    From
    $852
  • Waterfront Retreat w/ Dock & Private Beach
     5br Home/Apartment
    RedAwning
    From
    $920
  • Walk to Beach & Town *NEW* The Oak Bluffs House
    Excellent2br Home/Apartment
    Airbnb
    From
    $437

Oak Bluffs Pet-Friendly Vacation Rentals

  • Charming, dog-friendly home near beaches and marina!
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $297
  • Gorgeous 3BD/2BA Vacation House in the Vineyard
     4br Home/Apartment
    HolidayLettings
    From
    $404
  • Newly built in 2019! Lovely home w/ central AC, deck & gas grill!
     3br Home/Apartment
    HolidayLettings
    From
    $368
  • Spacious East Falmouth House - Walk to Great Pond!
     3br Home/Apartment
    HolidayLettings
    From
    $562

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

  • — 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

    Jaz
    JazThe Life of a Social Butterfly
  • — I love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.

    Alli Sims
    Alli SimsAlli Sims
  • — 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

Vacation Rentals in Oak Bluffs

Find the perfect accommodation for your vacation at AllTheRooms.com. We aggregate Airbnb, Priceline, RedAwning and many more. AllTheRooms has 1,122 rentals, hotels and other great places to stay during your time in Oak Bluffs, with everything from cheap hostels and homestays to extravagant Airbnbs and hotels. A trip to Oak Bluffs can be affordable - our cheapest price vacation rental is available at $29 per night. A typical rental in Oak Bluffs costs on average $456 per night.

If you need an internet connection during your time in Oak Bluffs, then you can choose from over 392 places to stay that have WiFi internet. 22 of our accommodations come with breakfast in the price. Fitness addicts can get a workout in during their stay by choosing from 3 accommodations that have gym facilities. If you're planning on arriving in Oak Bluffs by car, be sure to choose from 381 accommodations that provide parking. 62 accommodations have a a pool or jacuzzi

Those traveling with a cat, dog or some other animal can stay in any of 84 accommodations that are designated as pet-friendly.

677 accommodations in Oak Bluffs have been reviewed; 66% are rated highly. 423 places to stay in are instantly bookable.

Destinations near Oak Bluffs

  • Boston3,434 Properties
  • Nantucket3,200 Properties
  • Provincetown2,232 Properties
  • Eastham1,635 Properties
  • Dennis Port1,612 Properties
  • Chatham1,533 Properties
  • Brewster1,437 Properties
  • Wellfleet1,309 Properties
  • Orleans1,220 Properties
  • Somerville1,024 Properties
  • Edgartown987 Properties
  • West Yarmouth906 Properties
  • Cambridge865 Properties
  • Falmouth861 Properties
  • Mashpee843 Properties
  • Hyannis801 Properties
  • South Yarmouth775 Properties
  • Brookline747 Properties
  • Tisbury704 Properties
  • Plymouth669 Properties
  • Rockport664 Properties
  • East Falmouth661 Properties
  • West Dennis619 Properties
  • North Truro597 Properties
  • Gloucester594 Properties
  • South Chatham589 Properties
  • Lenox535 Properties
  • Harwich522 Properties
  • Worcester486 Properties
  • Dennis464 Properties
  • Salem462 Properties
  • Harwich Port444 Properties
  • East Sandwich439 Properties
  • Centerville434 Properties
  • Hancock430 Properties
  • Great Barrington405 Properties
  • Revere401 Properties
  • Vineyard Haven397 Properties
  • Waltham383 Properties
  • Lee360 Properties
  • Northampton356 Properties
  • Sandwich340 Properties
  • Quincy339 Properties
  • Truro335 Properties
  • Newton329 Properties
  • Medford321 Properties
  • Watertown319 Properties
  • Williamstown312 Properties
  • Newburyport306 Properties
  • Marblehead299 Properties
  • Pittsfield297 Properties
  • South Dennis289 Properties
  • North Falmouth265 Properties
  • Chelsea263 Properties
  • Amherst255 Properties
  • Stockbridge244 Properties
  • Marshfield242 Properties
  • Osterville229 Properties
  • Arlington229 Properties
  • Barnstable228 Properties
  • Wareham204 Properties
  • West Harwich196 Properties
  • Scituate196 Properties
  • Woburn186 Properties
  • Chilmark168 Properties
  • Bourne161 Properties
  • Sturbridge151 Properties
  • Fairhaven137 Properties
  • Winthrop128 Properties
  • Westport116 Properties
  • Ipswich116 Properties
  • West Stockbridge109 Properties
  • Marlborough107 Properties
  • Hull95 Properties
  • New Marlborough87 Properties
  • Sheffield80 Properties
  • Manchester76 Properties
  • Springfield64 Properties
  • Concord63 Properties
  • Sudbury48 Properties
  • Ashburnham33 Properties
  • Cheshire22 Properties
  • Hubbardston8 Properties