Oak Bluffs vacation rentals

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Best Oak Bluffs vacation rentals

Most recommended vacation rentals in Oak Bluffs

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Oak bluffs cottage Fills up quickly, make reservation early! - Oak Bluffs - Outdoors view
Oak bluffs cottage Fills up quickly, make reservation early!
Oak Bluffs, MA
Spa
$462+
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Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View - Oak Bluffs - Balcony
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Oak Bluffs, MA
Free Wi-Fi
$682+
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Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View. - Oak Bluffs - Kitchen
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Oak Bluffs, MA
Free Wi-Fi
$646+
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Cozy getaway in a central location w/ a full kitchen & furnished deck - Oak Bluffs - Balcony
Cozy getaway in a central location w/ a full kitchen & furnished deck
Oak Bluffs, MA
Free Wi-Fi
$559+
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Marsh Walk - Oak Bluffs - Living room
Marsh Walk
Oak Bluffs, MA
6.4Okay(14)
Pet friendly
$307+
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The Pinkletink - Oak Bluffs - Beach
The Pinkletink
Oak Bluffs, MA
9.3Wonderful(4)
$322+
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Oak Bluffs Home with Renovated Screened-in Porch - Short Drive to Beach - Oak Bluffs - Living room
Oak Bluffs Home with Renovated Screened-in Porch - Short Drive to Beach
Oak Bluffs, MA
7.7Good(11)
$842+
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Discover The Magic Of Marthas Vineyard! New ! Build In 2020 ! - Oak Bluffs
Discover The Magic Of Marthas Vineyard! New ! Build In 2020 !
Oak Bluffs, MA
$369+
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Marthas Vineyard Apt about 1 Mile to Inkwell Beach! - Oak Bluffs - Living room
Marthas Vineyard Apt about 1 Mile to Inkwell Beach!
Oak Bluffs, MA
9.1Wonderful(14)
Free Wi-Fi
$579+
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Make Lasting Memories In This Adorable Vineyard Cottage! - Oak Bluffs - Living room
Make Lasting Memories In This Adorable Vineyard Cottage!
Oak Bluffs, MA
9.9Wonderful(40)
$319+
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Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs - Oak Bluffs - Dining room
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Oak Bluffs, MA
$433+
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Capricorn Beach House - Oak Bluffs
Capricorn Beach House
Oak Bluffs, MA
8.6Very good(66)
Free Wi-Fi
$515+
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Home in Oak Bluffs - Oak Bluffs
Home in Oak Bluffs
Oak Bluffs, MA
7.7Good(2)
Parking
Free Wi-Fi
$918+
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Sea Glen Cottage - Oak Bluffs
Sea Glen Cottage
Oak Bluffs, MA
4.7Mediocre(8)
$355+
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Island Getaway - Oak Bluffs
Island Getaway
Oak Bluffs, MA
3.5Poor(18)
$445+
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Coastal condo with pool & tennis courts near golf, beaches & town - Oak Bluffs
Coastal condo with pool & tennis courts near golf, beaches & town
Oak Bluffs, MA
Pool
$261+
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KAYAK’s insights for vacation rentals in Oak Bluffs

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Oak Bluffs with confidence.

Which month has the cheapest vacation rental rates in Oak Bluffs?

Vacation rentals are cheapest in Oak Bluffs in September, with average rates of $299. In comparison, October is the most expensive month, with prices at $1,223.

What is the cheapest day of the week to book a vacation rental in Oak Bluffs?

Thursday offers the lowest rates in Oak Bluffs, with an average nightly price of $379. The highest prices are found on Tuesday, with average rates at $4,827.
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Good to know

Low season

September

High season

October

Average price (weeknight)

$1,522

Average price (weekend night)

$456
Cheapest month to stay with an average 56% drop in price.
Most expensive month to stay with an average 79% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Oak Bluffs vacation rental deals

  • Vacation rentals in Oak Bluffs are around 50% more expensive than hotels on average. Search here to compare prices for all accommodation types in Oak Bluffs.
  • The best vacation rental properties in Oak Bluffs are Make Lasting Memories In This Adorable Vineyard Cottage! (9.9, 40 reviews), Oak bluffs cottage Fills up quickly, make reservation early! (9.9, 39), and Your \'Vineyard Dream\' Vacation - Oak Bluffs -Sunny Open Floor Plan Close To Town (9.8, 25), based on ratings and reviews from real travelers.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Oak Bluffs for 4 days.

FAQs when booking a vacation home in Oak Bluffs

  • How much is a vacation rental for a week in Oak Bluffs?

    The average price for a weekly Oak Bluffs vacation rental found by KAYAK users in the last 2 weeks is $3,843.

  • How much is a vacation rental for a month in Oak Bluffs?

    The average price for a monthly Oak Bluffs vacation rental found by KAYAK users in the last 2 weeks is $16,470.

  • What types of vacation rentals are available in Oak Bluffs?

    There are loads of different property types that you can make your vacation home in Oak Bluffs. You’ll find apartments, condos, cottages, houses and homestays.

  • Are there any pet-friendly vacation rentals in Oak Bluffs?

    There are a number of dog and pet-friendly Oak Bluffs vacation rentals, with around 8% allowing you to bring your pet along with you.

  • How can I find vacation rentals near me in Oak Bluffs?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Oak Bluffs?

Our map will help you find the perfect place to stay in Oak Bluffs by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Oak Bluffs

Oak Bluffs vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Oak Bluffs. Find cheap vacation homes to rent in Oak Bluffs. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Oak Bluffs that suits you best.

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