Oak Bluffs holiday rentals

We found 1,882 holiday rentals — enter your dates for availability
Discover a selection of 268 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:18 Dec - 25 Dec

Spacious wrap around deck with all day sun and shade
Living room  with loft space above
West wing with futon/sleeper
Kitchen slider and herb garden
Exceptional
(45 reviews)

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

Chilmark

7% off
S$6,805
for 7 nights, 1 home
S$972 per night
includes taxes & fees
Striking 5BR/4BA Chilmark Contemporary with Views of the Sound
family room going into dining room
Terrace/patio
family room
dining room
Exceptional
(34 reviews)

Cotuit Home with an Inground Pool less One Block from the Beach

Cotuit

8% off
S$16,993
for 7 nights, 1 home
S$2,428 per night
includes taxes & fees
Cotuit Home with an Inground Pool less One Block from the Beach
Screened-in porch
Living area
Chef's kitchen
Exterior
Exceptional
(10 reviews)

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

Chilmark

8% off
S$12,321
for 7 nights, 1 home
S$1,760 per night
includes taxes & fees
Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails
Dining table with view of ocean in the sunroom
Living area
Living area
Rose covered flower arch next to unit
Exceptional
(39 reviews)

Maushop Village Getaway with Ocean Views, Steps to Private Beach

Mashpee

8% off
S$5,484
for 7 nights, 1 cottage
S$783 per night
includes taxes & fees
Maushop Village Getaway with Ocean Views, Steps to Private Beach
Private kitchen
Living area
Pool
Dining
Exceptional
(28 reviews)

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

East Falmouth

8% off
S$8,229
for 7 nights, 1 home
S$1,176 per night
includes taxes & fees
Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.
Family Room with Panoramic View of the Pool and the Patio
Terrace/patio
Interior
Private kitchen
Exceptional
(5 reviews)

Heated Indoor Pool & Spa - Golf Course View

Mashpee

7% off
S$12,400
for 7 nights, 1 villa
S$1,771 per night
includes taxes & fees
Heated Indoor Pool & Spa - Golf Course View
Outdoor relaxing!
Exterior
Living area
Sun room off the kitchen.
Exceptional
(6 reviews)

WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!

Edgartown

8% off
S$31,990
for 7 nights, 1 home
S$4,570 per night
includes taxes & fees
WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!
Deck with outdoor dining & plenty of flowers.
Kayaks to paddle around Waquoit Bay to Washburn Island
Slate kitchen island & granite dining room table.
Seating for 10.
Open floor plan of Living Room/ Dining room & Kitchen.
Wonderful
(67 reviews)

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

East Falmouth

8% off
S$4,026
for 7 nights, 1 home
S$575 per night
includes taxes & fees
Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool.
Spacious and private backyard
Kitchen view into dining room
Spiral staircase leading to the 2 second floor bedrooms
Out door shower
Exceptional
(96 reviews)

Perfect location for your summer vacation! Newly renovated kitchen & bathrooms!!

Falmouth

7% off
S$5,521
for 7 nights, 1 home
S$789 per night
includes taxes & fees
Perfect location for your summer vacation! Newly renovated kitchen & bathrooms!!
Dining
Living area
Outdoor dining
Exterior
Exceptional
(17 reviews)

THE PARK ESTATE! Your Martha's Vineyard Getaway!

Oak Bluffs

8% off
S$72,577
for 7 nights, 1 home
S$10,368 per night
includes taxes & fees
THE PARK ESTATE! Your Martha's Vineyard Getaway!
Large, farmhouse fireplace perfect for chillier seasons.
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.
Exterior
Exceptional
(42 reviews)

Sanctuary House: An ocean-view farmhouse retreat

Vineyard Haven

7% off
S$6,715
for 7 nights, 1 home
S$959 per night
includes taxes & fees
Sanctuary House: An ocean-view farmhouse retreat
Private kitchen
Living area
Interior
Interior
Exceptional
(6 reviews)

Spacious home for entertaining, centrally located to beach, ferry, and airport.

Edgartown

8% off
S$29,509
for 7 nights, 1 home
S$4,216 per night
includes taxes & fees
Spacious home for entertaining, centrally located to beach, ferry, and airport.
Upstairs Master Bed with Salt Pond View
Property grounds
Summer Front Garden
Living Room Access to Patio
Exceptional
(58 reviews)

Enjoy the Sunset Over Salt Pond. Walk to Beach. Pets welcome. Kayaks/SUP/Bikes

Falmouth

7% off
S$5,590
for 7 nights, 1 home
S$799 per night
includes taxes & fees
Enjoy the Sunset Over Salt Pond. Walk to Beach. Pets welcome. Kayaks/SUP/Bikes
Back of house
Open concept living space on the second floor with custom octagonal ceiling
Kitchen with panoramic west-facing window
Entryway and custom staircase
Exceptional
(30 reviews)

Luxury Chappaquiddick Getaway with Oceanviews

Edgartown

8% off
S$6,984
for 7 nights, 1 home
S$998 per night
includes taxes & fees
Luxury Chappaquiddick Getaway with Oceanviews
Brand new kitchen with stainless & quartz.
Use of clubhouse heated POOL & tennis courts.
Open dining room, living room, kitchen (brand new) 
 & deck.
Great kayaking down the street to Washburn Island & Waquoit Bay.
Wonderful
(35 reviews)

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

East Falmouth

8% off
S$4,026
for 7 nights, 1 home
S$575 per night
includes taxes & fees
Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.
Laughter and stories are guaranteed as you
get together on the West Porch.
This unique home was
carefully renovated to maintain its original character.
Your closest neighbors are a family of Osprey!
Choose from a variety of seating areas
overlooking the ocean and harbor.
Exceptional
(28 reviews)

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

Oak Bluffs

8% off
S$44,901
for 7 nights, 1 home
S$6,414 per night
includes taxes & fees
Oceanfront, Private Dock and Harthaven Private Beach - Walk to Noman's, Inkwell
Front porch
Kitchen
Kitchen/Living Room area
Dining Room
Exceptional
(33 reviews)

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

Falmouth

8% off
S$6,106
for 7 nights, 1 home
S$872 per night
includes taxes & fees
Across the street from Old Silver Beach; New house with hot tub. Sleeps 12.
Interior
Terrace/patio
Private kitchen
Exterior
Exceptional
(7 reviews)

BRAND NEW!

Oak Bluffs

8% off
S$10,049
for 7 nights, 1 home
S$1,436 per night
includes taxes & fees
BRAND NEW!
Interior
Interior
Outdoor dining
Interior
Exceptional
(51 reviews)

Luxury Loft Historic Center Oak Bluffs

Oak Bluffs

19% off
S$5,883
for 7 nights, 1 home
S$840 per night
includes taxes & fees
Luxury Loft Historic Center Oak Bluffs
Property grounds
Outdoor dining
Living area
Interior
Exceptional
(11 reviews)

Lovely West Falmouth Escape with Sunset and Harbor Views, Bike Path Access

Falmouth

8% off
S$8,493
for 7 nights, 1 home
S$1,213 per night
includes taxes & fees
Lovely West Falmouth Escape with Sunset and Harbor Views, Bike Path Access
Living area
Living area
Private kitchen
Property grounds
Excellent
(36 reviews)

A Vineyard Home Perfect For Family Gatherings

Vineyard Haven

8% off
S$6,350
for 7 nights, 1 home
S$907 per night
includes taxes & fees
A Vineyard Home Perfect For Family Gatherings
Exterior
The garden gate
Terrace/patio
Dining
Exceptional
(41 reviews)

Walk to private beach from beautiful Abels Hill house

Chilmark

7% off
S$6,879
for 7 nights, 1 home
S$983 per night
includes taxes & fees
Walk to private beach from beautiful Abels Hill house
Dining
Terrace/patio
Living area
Exterior
Exceptional
(14 reviews)

Charming Katama Home in Prime Edgartown Location!

Edgartown

16% off
S$8,158
for 7 nights, 1 home
S$1,165 per night
includes taxes & fees
Charming Katama Home in Prime Edgartown Location!
Rear deck with 6 seats and table
lounge chair
Large open area with island kitchen
opposite view from gathering area to stairs
Private kitchen
Exceptional
(8 reviews)

Close to BEACH! Falmouth / Falmouth Heights 4Bdr-2Ba. 2025 Renovation Large Deck

Falmouth

7% off
S$5,813
for 7 nights, 1 home
S$830 per night
includes taxes & fees
Close to BEACH! Falmouth / Falmouth Heights 4Bdr-2Ba. 2025 Renovation Large Deck
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  • More quality time

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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:

  • Shining Sea Bikeway (9.2 mi / 14.8 km)
  • Farm Neck Golf Club (1.2 mi / 2 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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