Oak Bluffs Vacation Rentals

Our Favorite Vacation Rentals in Oak Bluffs

  • New Listing! Magnificent Retreat on Deans Pond
     3br Home/Apartment
    RedAwning
    From
    $837
  • Summercamp
    Good95br 3-star Home/Apartment
    Booking.com
    From
    $169
  • Lakefront cottage with a deck, close to ferries & beaches!
    Nice2br Home/Apartment
    HolidayLettings
    From
    $390
  • Walkable Falmouth Hts Beach Home
     5br Home/Apartment
    RedAwning
    From
    $741
  • OAK BLUFFS COTTAGE, WALK TO TOWN!
     Country House
    Booking.com
    From
    $170
  • Dog-friendly studio w/ shared pool, on-site tennis courts, & prime location
     -1br Studio
    HolidayLettings
    From
    $256
  • New Listing! Beachside Retreat - 300 Yards to Shore
     3br Home/Apartment
    RedAwning
    From
    $549
  • The Oak Estate
     Country House
    Booking.com
    From
    $458

Check prices for these upcoming dates

Oak Bluffs Vacation Rentals with a Pool

  • Renovated picture perfect cape home on private lot
    Excellent3br Home/Apartment
    Airbnb
    From
    $537
  • Two Ponds Residence
    Excellent8br Home/Apartment
    Airbnb
    From
    $735

Oak Bluffs Vacation Rentals with Wi-Fi

  • Falmouth Family Getaway
     4br Home/Apartment
    RedAwning
    From
    $697
  • Tranquil 4BR on Bourne’s Pond
     4br Home/Apartment
    RedAwning
    From
    $702
  • New Listing! Cape Cod Cottage – 100 Yards to Beach
     2br Cottage
    RedAwning
    From
    $475
  • Newly Renovated Home in New Seabury
     3br Home/Apartment
    RedAwning
    From
    $579

Oak Bluffs Pet-Friendly Vacation Rentals

  • NEW LISTING! Waterfront oasis w/ dock, gazebo, amazing views & patio - 1 dog OK!
     3br Home/Apartment
    HolidayLettings
    From
    $581
  • Heated Pool, Hottub,AC,WiFi,sleep22, 2 mi to beach
    Excellent5br Home/Apartment
    HolidayLettings
    From
    $3,129
  • 3 Bedroom in a great in-town location
     3br Home/Apartment
    HolidayLettings
    From
    $518
  • 4BR Pet-Friendly Cape Cod
     4br Home/Apartment
    RedAwning
    From
    $565

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
88 º43
3
78 º23
6
66 º15
9
58 º13
4
55 º1
4
54 º12
8
63 º13
5
66 º18
4
83 º37
2
86 º36
3
91 º40
2
92 º49
1
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Oak Bluffs. The warmest months in Oak Bluffs are May and June, when temperatures reach 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

  • — When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place

    Whitney Wear
    Whitney WearTravel Better Guide
  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen
  • — 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

Vacation Rentals in Oak Bluffs

Browse places to stay from all your favorite providers including Airbnb, Bed and Breakfast, RedAwning and others at AllTheRooms.com. Oak Bluffs has 1,153 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, extravagant travelers and everything in between. For those trying to save money, the cheapest place to stay in Oak Bluffs comes in at $29 a night. The average price of an accommodation is $435 per night.

If you need an internet connection during your time in Oak Bluffs, then you can choose from over 585 accommodations that have WiFi internet. 29 of our accommodations come with breakfast in the price. Choose from 6 places to stay that provide gym facilities, so you won't miss a single workout. Driving to Oak Bluffs? Then choose one of the 554 places to stay that comes with a parking spot included. 60 places to stay have a a pool or jacuzzi

AllTheRooms has 100 pet-friendly places to stay in Oak Bluffs, so if you're traveling with your cat or dog you won't have any trouble.

723 of the rentals in Oak Bluffs have been rated by previous guests. They rated 61% as excellent or good. 398 accommodations allow instant booking.

Destinations near Oak Bluffs

  • Boston4,334 Properties
  • Nantucket3,133 Properties
  • Provincetown2,336 Properties
  • Eastham1,535 Properties
  • Dennis Port1,501 Properties
  • Brewster1,413 Properties
  • Chatham1,340 Properties
  • Wellfleet1,273 Properties
  • Orleans1,221 Properties
  • Somerville1,114 Properties
  • Edgartown998 Properties
  • Cambridge997 Properties
  • West Yarmouth963 Properties
  • Falmouth927 Properties
  • Hyannis892 Properties
  • Mashpee885 Properties
  • Brookline847 Properties
  • Rockport781 Properties
  • Tisbury758 Properties
  • South Yarmouth752 Properties
  • East Falmouth679 Properties
  • Plymouth675 Properties
  • Gloucester649 Properties
  • South Chatham592 Properties
  • North Truro574 Properties
  • Dennis538 Properties
  • Lenox536 Properties
  • West Dennis522 Properties
  • Harwich518 Properties
  • Worcester505 Properties
  • Centerville496 Properties
  • East Sandwich467 Properties
  • Salem463 Properties
  • Harwich Port444 Properties
  • Waltham438 Properties
  • Great Barrington437 Properties
  • Hancock411 Properties
  • Lee407 Properties
  • Northampton394 Properties
  • Newton387 Properties
  • Vineyard Haven384 Properties
  • Revere354 Properties
  • Sandwich350 Properties
  • Williamstown345 Properties
  • Newburyport342 Properties
  • Quincy341 Properties
  • Medford341 Properties
  • Truro340 Properties
  • North Falmouth338 Properties
  • Watertown322 Properties
  • Pittsfield309 Properties
  • Marblehead307 Properties
  • Amherst265 Properties
  • Chelsea264 Properties
  • Marshfield258 Properties
  • South Dennis255 Properties
  • Stockbridge255 Properties
  • Arlington245 Properties
  • Osterville232 Properties
  • Barnstable231 Properties
  • Woburn224 Properties
  • Scituate212 Properties
  • West Harwich203 Properties
  • Wareham202 Properties
  • Sturbridge190 Properties
  • Bourne180 Properties
  • Chilmark174 Properties
  • Marlborough152 Properties
  • Fairhaven132 Properties
  • Winthrop122 Properties
  • Westport121 Properties
  • Ipswich117 Properties
  • West Stockbridge116 Properties
  • Hull110 Properties
  • Sheffield84 Properties
  • Manchester83 Properties
  • New Marlborough81 Properties
  • Concord80 Properties
  • Springfield67 Properties
  • Sudbury52 Properties
  • Ashburnham34 Properties
  • Cheshire27 Properties
  • Hubbardston8 Properties