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Oak Bluffs Vacation Rentals

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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
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Oak Bluffs Vacation Rentals with a Pool

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

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Price and Availability in Oak Bluffs

Most expensive
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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.
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The Weather in Oak Bluffs

Rainy days
66° 15°
9
58° 13°
4
55° 1°
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.

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What Expert Travelers Think

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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.

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