Oak Bluffs holiday rentals

We found 1,940 holiday rentals — enter your dates for availability
Discover a selection of 278 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:20 Nov - 27 Nov

Outdoor dining
Living area
Living area
Exterior
Exceptional
(17 reviews)

THE PARK ESTATE! Your Martha's Vineyard Getaway!

Oak Bluffs

9% off
AU$79,065
for 7 nights, 1 home
AU$11,295 per night
includes taxes & fees
THE PARK ESTATE! Your Martha's Vineyard Getaway!
Room
Living area
Pool
Dining
Exceptional
(25 reviews)

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

East Falmouth

8% off
AU$8,946
for 7 nights, 1 home
AU$1,278 per night
includes taxes & fees
Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.
Sun room off the kitchen.
Exterior
Double sinks for busy kitchens.
Outdoor relaxing!
Exceptional
(5 reviews)

WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!

Edgartown

9% off
AU$34,868
for 7 nights, 1 home
AU$4,981 per night
includes taxes & fees
WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!
Interior
Spacious great room and kitchen
Brand new landscaping
Interior
Exceptional
(16 reviews)

New 4-bedroom House with Swimming Pool–Just a 10-minute Walk to Town

Edgartown

5% off
AU$13,625
for 7 nights, 1 home
AU$1,946 per night
includes taxes & fees
New 4-bedroom House with Swimming Pool–Just a 10-minute Walk to Town
West wing with futon/sleeper
Living room  with loft space above
Kitchen slider and herb garden
Spacious wrap around deck with all day sun and shade
Exceptional
(43 reviews)

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

Chilmark

8% off
AU$10,689
for 7 nights, 1 home
AU$1,527 per night
includes taxes & fees
Striking 5BR/4BA Chilmark Contemporary with Views of the Sound
Rose covered flower arch next to unit
Living area
Exterior
Dining table with view of ocean in the sunroom
Exceptional
(39 reviews)

Maushop Village Getaway with Ocean Views, Steps to Private Beach

Mashpee

8% off
AU$5,920
for 7 nights, 1 cottage
AU$846 per night
includes taxes & fees
Maushop Village Getaway with Ocean Views, Steps to Private Beach
Entryway and custom staircase
Open concept living space on the second floor with custom octagonal ceiling
Kitchen with panoramic west-facing window
Back of house
Exceptional
(30 reviews)

Luxury Chappaquiddick Getaway with Oceanviews

Edgartown

8% off
AU$7,486
for 7 nights, 1 home
AU$1,069 per night
includes taxes & fees
Luxury Chappaquiddick Getaway with Oceanviews
Private kitchen
Room
Interior
Exterior
Excellent
(39 reviews)

The Cabin on Chappy!

Edgartown

8% off
AU$3,493
for 7 nights, 1 cottage
AU$499 per night
includes taxes & fees
The Cabin on Chappy!
Family Room with Panoramic View of the Pool and the Patio
Terrace/patio
Private kitchen
Interior
Exceptional
(5 reviews)

Heated Indoor Pool & Spa - Golf Course View

Mashpee

5% off
AU$12,451
for 7 nights, 1 villa
AU$1,779 per night
includes taxes & fees
Heated Indoor Pool & Spa - Golf Course View
Interior
Terrace/patio
Private kitchen
Dining
Exceptional
(7 reviews)

BRAND NEW!

Oak Bluffs

8% off
AU$11,079
for 7 nights, 1 home
AU$1,583 per night
includes taxes & fees
BRAND NEW!
Exterior
Living area
Interior
Room
Very good
(5 reviews)

Beautiful Custom Home In Oak Bluffs

Oak Bluffs

8% off
AU$10,651
for 7 nights, 1 home
AU$1,522 per night
includes taxes & fees
Beautiful Custom Home In Oak Bluffs
Slate kitchen island & granite dining room table.
Seating for 10.
Kayaks to paddle around Waquoit Bay to Washburn Island
Open floor plan of Living Room/ Dining room & Kitchen.
Pet Friendly Cape House.
Wonderful
(64 reviews)

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

East Falmouth

8% off
AU$4,407
for 7 nights, 1 home
AU$630 per night
includes taxes & fees
Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool.
Dining Room
Living area
Exterior
Chef's kitchen
Exceptional
(8 reviews)

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

Chilmark

8% off
AU$13,564
for 7 nights, 1 home
AU$1,938 per night
includes taxes & fees
Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails
Great kayaking down the street to Washburn Island & Waquoit Bay.
Use of clubhouse heated POOL & tennis courts.
Brand new kitchen with stainless & quartz.
Open dining room, living room, kitchen (brand new) 
 & deck.
Wonderful
(35 reviews)

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

East Falmouth

8% off
AU$4,407
for 7 nights, 1 home
AU$630 per night
includes taxes & fees
Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.
Outdoor dining
Interior
Interior
Private kitchen
Exceptional
(50 reviews)

Luxury Loft Historic Center Oak Bluffs

Oak Bluffs

16% off
AU$8,570
for 7 nights, 1 home
AU$1,224 per night
includes taxes & fees
Luxury Loft Historic Center Oak Bluffs
Kitchen
Front of main house at 47 Cooke St Edgartown MA
Entryway
Hot tub and heated pool
Exceptional
(55 reviews)

Edgartown close to beach and town 6BD with Pool and Hot Tub

Edgartown

8% off
AU$22,145
for 7 nights, 1 home
AU$3,164 per night
includes taxes & fees
Edgartown close to beach and town 6BD with Pool and Hot Tub
Private kitchen
Living area
Living area
Living area
Excellent
(35 reviews)

A Vineyard Home Perfect For Family Gatherings

Vineyard Haven

8% off
AU$6,887
for 7 nights, 1 home
AU$984 per night
includes taxes & fees
A Vineyard Home Perfect For Family Gatherings
Living area
The garden gate
Dining
Exterior
Exceptional
(39 reviews)

Walk to private beach from beautiful Abels Hill house

Chilmark

8% off
AU$7,340
for 7 nights, 1 home
AU$1,049 per night
includes taxes & fees
Walk to private beach from beautiful Abels Hill house
Living area
Outdoor dining
Interior
Exterior
Exceptional
(14 reviews)

Guest House In Edgartown

Edgartown

8% off
AU$4,076
for 7 nights, 1 home
AU$582 per night
includes taxes & fees
Guest House In Edgartown
Choose from a variety of seating areas
overlooking the ocean and harbor.
This unique home was
carefully renovated to maintain its original character.
Your closest neighbors are a family of Osprey!
Laughter and stories are guaranteed as you
get together on the West Porch.
Exceptional
(26 reviews)

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

Oak Bluffs

9% off
AU$55,946
for 7 nights, 1 home
AU$7,992 per night
includes taxes & fees
Oceanfront, Private Dock and Harthaven Private Beach - Walk to Noman's, Inkwell
View from upper deck
View from kitchen
Toasty Fireplace for fall and winter getaways
Kitchen
Exceptional
(76 reviews)

Beach Front on Beautiful Jenkins Pond, Quiet Area, Discounted off season rates!

East Falmouth

7% off
AU$4,347
for 7 nights, 1 home
AU$621 per night
includes taxes & fees
Beach Front on Beautiful Jenkins Pond, Quiet Area, Discounted off season rates!
front of house at dusk
Kitchen
Kitchen
Kitchen
Exceptional
(7 reviews)

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

Vineyard Haven

8% off
AU$18,045
for 7 nights, 1 home
AU$2,578 per night
includes taxes & fees
6bedroom, 4bath, chefs kitchen, central air, ping pong, walking distance to town
Exterior
Meals on the patio are a daily delight- sparkly mornings to ocean dipped sunsets
Large, farmhouse fireplace perfect for chillier seasons.
Dining area can seat 8-10 and looks onto patio and water views.
Exceptional
(41 reviews)

Sanctuary House: An ocean-view farmhouse retreat

Vineyard Haven

8% off
AU$6,649
for 7 nights, 1 home
AU$950 per night
includes taxes & fees
Sanctuary House: An ocean-view farmhouse retreat
Property grounds
Property grounds
Summer Front Garden
Upstairs Master Bed with Salt Pond View
Exceptional
(57 reviews)

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

Falmouth

8% off
AU$6,477
for 7 nights, 1 home
AU$925 per night
includes taxes & fees
Enjoy the Sunset Over Salt Pond. Walk to Beach. Pets welcome. Kayaks/SUP/Bikes
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    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • 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)
  • Lighthouse Beach (4.8 mi / 7.7 km)
  • Lambert's Cove Beach (5.6 mi / 9.1 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 home?
Among the most sought-after neighbourhoods to get a holiday property in Oak Bluffs is Lagoon Heights. Find your perfect stay on Stayz and experience this area just like a local.
What is the most popular type of holiday home accommodation in Oak Bluffs?
The most desirable types of holiday homes in Oak Bluffs are houses. After something a little different? Stayz 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 home in Oak Bluffs?
The average price for a holiday home 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 home 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 Stayz 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 homes in Oak Bluffs?
With 310 holiday homes 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 homes and find a holiday home that'll set tails wagging on Stayz.
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 homes and every day can be a pool day. Simply enter your travel dates into Stayz, then use the "pool" filter to find the perfect place for a splashing good time!
What are popular home amenities in Oak Bluffs?
When it comes to home amenities that guests are looking for in Oak Bluffs, tennis, a firepit and a chef are at the top of the list. With Stayz 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 homes in Oak Bluffs?
You'll find 62 holiday homes 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 homes 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 homes in Oak Bluffs?
There are 30 one-bedroom properties in Oak Bluffs to select from. A one-bedroom holiday home 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 homes in Oak Bluffs?
Gather your loved ones and experience complete comfort and privacy in one of the 59 two-bedroom holiday homes Oak Bluffs has to offer.
Are there holiday homes 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 Stayz and stay connected on your holiday.
How can I find holiday homes with air conditioning in Oak Bluffs?
There are 280 Stayz 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 home in Oak Bluffs?
The age limit can differ across properties on Stayz, 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 home in Oak Bluffs for?
The amount of time you can stay in an Oak Bluffs holiday home 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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