Oak Bluffs holiday rentals

We found 1,943 holiday rentals — enter your dates for availability
Discover a selection of 271 homes, 34 apartments and other holiday rentals in Oak Bluffs that are perfect for your trip. Holiday homes offer the best amenities for your family, friends or furry companion, such as parking and a hot tub. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Oak Bluffs

Showing deals for:27 Nov - 4 Dec

Exterior
Private kitchen
Interior
Living area
Very good
(42 reviews)

The Cabin on Chappy!

Edgartown

8% off
S$3,219
for 7 nights, 1 cottage
S$460 per night
includes taxes & fees
The Cabin on Chappy!
Spacious wrap around deck with all day sun and shade
Living room  with loft space above
Entering from the driveway
West wing with futon/sleeper
Exceptional
(43 reviews)

Striking 5BR/4BA Chilmark Contemporary with Views of the Sound

Chilmark

7% off
S$7,737
for 7 nights, 1 home
S$1,105 per night
includes taxes & fees
Striking 5BR/4BA Chilmark Contemporary with Views of the Sound
Dining
Living area
Living area
Outdoor dining
Exceptional
(17 reviews)

THE PARK ESTATE! Your Martha's Vineyard Getaway!

Oak Bluffs

9% off
S$71,201
for 7 nights, 1 home
S$10,172 per night
includes taxes & fees
THE PARK ESTATE! Your Martha's Vineyard Getaway!
Private kitchen
Terrace/patio
Interior
Exterior
Exceptional
(7 reviews)

BRAND NEW!

Oak Bluffs

8% off
S$10,053
for 7 nights, 1 home
S$1,436 per night
includes taxes & fees
BRAND NEW!
Outdoor relaxing!
Exterior
Living area
Sun room off the kitchen.
Exceptional
(5 reviews)

WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!

Edgartown

8% off
S$31,971
for 7 nights, 1 home
S$4,567 per night
includes taxes & fees
WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!
Your closest neighbors are a family of Osprey!
This unique home was
carefully renovated to maintain its original character.
Laughter and stories are guaranteed as you
get together on the West Porch.
You will create forever memories in this amazing setting.
Exceptional
(27 reviews)

Oceanfront, Private Dock and Harthaven Private Beach - Walk to Noman's, Inkwell

Oak Bluffs

8% off
S$50,661
for 7 nights, 1 home
S$7,237 per night
includes taxes & fees
Oceanfront, Private Dock and Harthaven Private Beach - Walk to Noman's, Inkwell
Outdoor dining
Interior
Private kitchen
Interior
Exceptional
(51 reviews)

Luxury Loft Historic Center Oak Bluffs

Oak Bluffs

16% off
S$7,154
for 7 nights, 1 home
S$1,022 per night
includes taxes & fees
Luxury Loft Historic Center Oak Bluffs
Living area
Living area
Exterior
Rose covered flower arch next to unit
Exceptional
(39 reviews)

Maushop Village Getaway with Ocean Views, Steps to Private Beach

Mashpee

7% off
S$5,610
for 7 nights, 1 cottage
S$801 per night
includes taxes & fees
Maushop Village Getaway with Ocean Views, Steps to Private Beach
Private kitchen
Living area
Exterior
Interior
Very good
(5 reviews)

Beautiful Custom Home In Oak Bluffs

Oak Bluffs

8% off
S$12,822
for 7 nights, 1 home
S$1,832 per night
includes taxes & fees
Beautiful Custom Home In Oak Bluffs
Family Room with Panoramic View of the Pool and the Patio
Terrace/patio
Living area
Interior
Exceptional
(5 reviews)

Heated Indoor Pool & Spa - Golf Course View

Mashpee

5% off
S$11,303
for 7 nights, 1 villa
S$1,615 per night
includes taxes & fees
Heated Indoor Pool & Spa - Golf Course View
Screened-in porch
Living area
Dining Room
Exterior
Exceptional
(8 reviews)

Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails

Chilmark

8% off
S$12,288
for 7 nights, 1 home
S$1,755 per night
includes taxes & fees
Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails
Pool
Living area
Dining
Room
Exceptional
(26 reviews)

Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.

East Falmouth

7% off
S$8,399
for 7 nights, 1 home
S$1,200 per night
includes taxes & fees
Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.
Kitchen
Kitchen
Kitchen Breakfast Nook
front of house at dusk
Exceptional
(7 reviews)

6bedroom, 4bath, chefs kitchen, central air, ping pong, walking distance to town

Vineyard Haven

8% off
S$16,510
for 7 nights, 1 home
S$2,359 per night
includes taxes & fees
6bedroom, 4bath, chefs kitchen, central air, ping pong, walking distance to town
Living area
Living area
Living area
Property grounds
Excellent
(36 reviews)

A Vineyard Home Perfect For Family Gatherings

Vineyard Haven

7% off
S$6,487
for 7 nights, 1 home
S$927 per night
includes taxes & fees
A Vineyard Home Perfect For Family Gatherings
Dining
Private kitchen
Private kitchen
Pool
Exceptional
(53 reviews)

Luxurious & Spacious 6 Bed/5 Bath Home with Ocean Views, New Seabury, Cape Cod

Mashpee

5% off
S$11,646
for 7 nights, 1 home
S$1,664 per night
includes taxes & fees
Luxurious & Spacious 6 Bed/5 Bath Home with Ocean Views, New Seabury, Cape Cod
Dining
Property grounds
Pool
Living area
Exceptional
(31 reviews)

Cape Cod New Seabury Family Compound private pool near beach/dining/shopping

Mashpee

6% off
S$9,968
for 7 nights, 1 home
S$1,424 per night
includes taxes & fees
Cape Cod New Seabury Family Compound private pool near beach/dining/shopping
Living area
The garden gate
Dining
Exterior
Exceptional
(39 reviews)

Walk to private beach from beautiful Abels Hill house

Chilmark

7% off
S$6,919
for 7 nights, 1 home
S$988 per night
includes taxes & fees
Walk to private beach from beautiful Abels Hill house
Pet Friendly Cape House.
Kayaks to paddle around Waquoit Bay to Washburn Island
Deck with outdoor dining & plenty of flowers.
Open floor plan of Living Room/ Dining room & Kitchen.
Wonderful
(66 reviews)

Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool.

East Falmouth

7% off
S$4,153
for 7 nights, 1 home
S$593 per night
includes taxes & fees
Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool.
View of sea from pass-thru Oak Bluffs bedroom
Private deck off Primary BR: faces ocean and Farm Pond
Kitchen island, French door fridge with ample storage
Our house is on the corner (in the foreground).  Inkwell & bike path steps away.
Exceptional
(17 reviews)

Oceanfront Home - Walk to Everything

Oak Bluffs

6% off
S$18,503
for 7 nights, 1 home
S$2,643 per night
includes taxes & fees
Oceanfront Home - Walk to Everything
Marina
Marina
Exterior detail
Room
Exceptional
(10 reviews)

Martha’s Vineyard 7 Bedroom Vintage Home! 15 min walk to beaches and Oak Bluffs!

Oak Bluffs

5% off
S$15,295
for 7 nights, 1 home
S$2,185 per night
includes taxes & fees
Martha’s Vineyard 7 Bedroom Vintage Home! 15 min walk to beaches and Oak Bluffs!
Exterior
Meals on the patio are a daily delight- sparkly mornings to ocean dipped sunsets
Dining area can seat 8-10 and looks onto patio and water views.
Newly built cedar and mahogany with rain head shower.
Exceptional
(42 reviews)

Sanctuary House: An ocean-view farmhouse retreat

Vineyard Haven

7% off
S$6,261
for 7 nights, 1 home
S$894 per night
includes taxes & fees
Sanctuary House: An ocean-view farmhouse retreat
Out door seating for 8 & gas grill.
Use of clubhouse heated POOL & tennis courts.
Great kayaking down the street to Washburn Island & Waquoit Bay.
Open dining room, living room, kitchen (brand new) 
 & deck.
Wonderful
(35 reviews)

Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.

East Falmouth

7% off
S$4,153
for 7 nights, 1 home
S$593 per night
includes taxes & fees
Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.
Exterior
Outdoor shower with over-sized rainfall shower head.
Kitchen with new hardwood floors
New chairs for 2023
Exceptional
(94 reviews)

Charming, Clean And Well Maintained Home Walking Distance To Town And Beach

Vineyard Haven

7% off
S$4,320
for 7 nights, 1 home
S$617 per night
includes taxes & fees
Charming, Clean And Well Maintained Home Walking Distance To Town And Beach
Front porch
Kitchen
Dining Room
Kitchen/Living Room area
Exceptional
(30 reviews)

Across the street from Old Silver Beach; New house with hot tub. Sleeps 12.

Falmouth

8% off
S$6,928
for 7 nights, 1 home
S$990 per night
includes taxes & fees
Across the street from Old Silver Beach; New house with hot tub. Sleeps 12.
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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Explore the beachside setting in Oak Bluffs

Enjoy the wineries and other features of Oak Bluffs. This walkable and scenic city is well known for its beaches, shopping and local tours. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Oak Bluffs

Are you hoping to find attractions to visit while you're in town? Venture out of your cosy holiday rental and experience everything that makes Oak Bluffs a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Farm Neck Golf Club (1.2 mi / 2 km)
  • Shining Sea Bikeway (9.2 mi / 14.8 km)
  • Cape Cod Winery (8.6 mi / 13.8 km)
  • Cape Cod Country Club (11.5 mi / 18.5 km)
  • Stand Up & Paddle Cape Cod (15.1 mi / 24.3 km)
  • Fulling Mill Brook Preserve (9.7 mi / 15.6 km)

Exploring the natural landscape of Oak Bluffs

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Oak Bluffs is a great place to get outside. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Ocean Park (0.3 mi / 0.5 km)
  • Oak Bluffs Town Beach (0.4 mi / 0.7 km)
  • Inkwell Beach (0.5 mi / 0.7 km)
  • Edgartown Beach (2.8 mi / 4.5 km)
  • Lambert's Cove Beach (5.6 mi / 9.1 km)
  • Menauhant Beach (6.4 mi / 10.3 km)

Seasonal weather in Oak Bluffs

If warm-weather activities are high on your list, August, July, September and June are the hottest months to visit, when temperatures average 20°C.

Transport to and around Oak Bluffs

The nearest airport is in Vineyard Haven, MA (MVY-Martha's Vineyard), located 5.2 mi (8.3 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Hyannis, MA (HYA-Barnstable Municipal), which is 20.5 mi (32.9 km) away.

Frequently asked questions

What is the best area to stay in Oak Bluffs when booking a holiday rental?
Among the most sought-after neighbourhoods to get a holiday property in Oak Bluffs is Lagoon Heights. Find your perfect stay on Vrbo and experience this area just like a local.
What is the most popular type of holiday rental accommodation in Oak Bluffs?
The most desirable types of holiday rentals in Oak Bluffs are houses. After something a little different? Vrbo has a variety of options to match our guests' requirements, so you'll see holiday homes in all shapes and sizes. The ideal fit is waiting for you — snap up yours today.
How much does it cost to rent a holiday rental in Oak Bluffs?
The average price for a holiday rental in Oak Bluffs is determined by a number of factors, like length of stay, property type and season. Whether you're thinking about a sprawling villa with space for extended family or an apartment for just you and the kids, just add your dates of travel to find stays that offer great value.
How much does it cost to rent a beach house in Oak Bluffs?
The average price for a holiday rental near the beach in Oak Bluffs depends on when you're visiting the area and the style and size of property you're looking for. You can find prices easily and quickly on Vrbo by entering your dates of travel. Then use our filters to choose the number of bedrooms and amenities that you require, like WiFi, air conditioning and a pool.
Are there pet-friendly holiday rentals in Oak Bluffs?
With 310 holiday rentals that welcome four-legged guests, your furry buddy can also come along on your Oak Bluffs holiday. Use the filter tool to browse our pet-friendly holiday rentals and find a holiday home that'll set tails wagging on Vrbo.
Can I rent a house with a pool in Oak Bluffs?
Pack your swimwear and inflatable unicorn, because there are 67 houses with a private pool in Oak Bluffs. Unwind at one of these terrific holiday rentals and every day can be a pool day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find the perfect place for a splashing good time!
What are popular rental amenities in Oak Bluffs?
When it comes to rental amenities that guests are looking for in Oak Bluffs, tennis, a firepit and a chef are at the top of the list. With Vrbo holiday homes, you'll find options to fit your style and taste, whether you're going on a holiday with your partner, family members or even pets.
Are there large group holiday rentals in Oak Bluffs?
You'll find 62 holiday rentals in Oak Bluffs that can host 10 or more people. Whether you're organising a get-together with extended family or a celebration like a birthday, there's ample space to get your group together under the same roof.
Are there holiday rentals in Oak Bluffs that welcome kids?
Bring the entire group together for a fun-packed adventure in Oak Bluffs at one of our 310 family-friendly holiday properties. These stays provide conveniences that are just perfect for getaways with children, such as full kitchens, living rooms and patios. Just click on the "Properties good for families" filter box and pick out your favourite.
What are the top attractions for families in Oak Bluffs?
Keeping the kids happy during your Oak Bluffs holiday is child's play with these top family-friendly attractions:
  • Inkwell Beach
  • Oak Bluffs Town Beach
  • Falmouth Heights Beach
Are there one-bedroom holiday rentals in Oak Bluffs?
There are 30 one-bedroom properties in Oak Bluffs to select from. A one-bedroom holiday rental is a great choice if it's only you and your partner or if you're travelling on your own. Add in more convenience, privacy and space compared to a hotel, and you've got the makings of a break to remember.
Can I find two-bedroom holiday rentals in Oak Bluffs?
Gather your loved ones and experience complete comfort and privacy in one of the 59 two-bedroom holiday rentals Oak Bluffs has to offer.
Are there holiday rentals with WiFi in Oak Bluffs?
Whether you want to keep up with the headlines, make a video call or surf social media, there are 89 holiday homes with WiFi in Oak Bluffs. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Oak Bluffs?
There are 280 Vrbo holiday homes with air conditioning in Oak Bluffs providing that gentle, cool breeze and extra bit of comfort. Enter your preferred travel dates and then take advantage of our filters to find stays with air conditioning.
How old do you have to be to rent a holiday rental in Oak Bluffs?
The age limit can differ across properties on Vrbo, so be sure to check the rules of the holiday home in Oak Bluffs you're considering. But normally, it's 16, 18 or 21.
How long can I rent a holiday rental in Oak Bluffs for?
The amount of time you can stay in an Oak Bluffs holiday rental for depends on each property. Just tap in your preferred travel dates to see options that offer long-term stays. They come with everything you need to make your extended trip more comfortable and convenient, such as kitchens and yards. Some holiday homes may also offer discounted weekly or monthly prices, so you can have a longer stay for less.

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