COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

- Travelers
- Owners / Managers
Help
Deals
Discover
- Rental type
  Beach rentals
  
  Mountain view rentals
  
  Pet-friendly rentals
  
  Rentals with a hot tub
  
  Rentals with a pool
  
  Waterfront rentals
  
  2-bedroom rentals
  
  3-bedroom rentals
  
  4+ bedroom rentals
- Other suggestions
  Vineyard Haven (2 miles)
  
  Edgartown (5 miles)
  
  West Tisbury (8 miles)
  
  Chilmark (12 miles)
Manage your booking
$ USD

Travelers

Sign in
Join
Manage your booking
$ USD
Help
Deals

Owners

Owner login
List your property
Help

Search 105,200+ Vacation Rentals

Where do you want to go? ✕

Check in

Check out

Sleeps

Adults

Children

Sleeps

Search

All Vacation Rentals

Martha's Vineyard

Oak Bluffs Vacation Rentals

Oak Bluffs 4+ bedroom Vacation Rentals, Cottages & More - 277 Rentals Available.

Min price

Max price

Bedrooms

Adults

Children

More Filters Fewer Filters

Air conditioning (33)
Balcony or terrace (2)
DVD player (30)
Dishwasher (44)
Fireplace (15)
Garden (2)
Grill (45)
High Speed Internet (47)
Private pool (2)
Swimming pool (2)
Washing machine (45)
Wi-Fi available (44)

More

Less

Cottage (1)
House (47)

More

Less

Payment Protection

To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

277 Vacation rentals

Sort by:

Filters applied: 4+ Bedrooms

Distance calculated in a straight line, road distances may differ. Confirm exact location with the property owner/manager.

1 / 17

Ocean, lake, harbor and parkview Vineyard cottage

Oak Bluffs Cottage

6 bedrooms 6
2 bathrooms
sleeps 10 10
min stay varies

Nearest beach 0.2 mi
Child friendly
Car not necessary

Responds fast! Avg. 15 minutes

“Great house and location! If you are looking for something with space, as well as the ability to walk to the bars and restaurants in Oak Bluffs, this is the house for you! Great location and great porch for those nights when you want to hang in....”

- Review left on 07/20/2014

$573.00

Excellent (2 reviews)

from $573.00 / night

Book

1 / 12

Waterfront-Martha's Vineyard

Oak Bluffs House

4 bedrooms 4
3 bathrooms
sleeps 6 6
7 nights min

Beach/lakeside relaxation
Child friendly
Private garden

$315.00

from $315.00 / night

Book

1 / 15

Adorable Cottage Walking Distance to Town and Beach

Oak Bluffs House

4 bedrooms 4
1 bathroom
sleeps 7 7
min stay varies

Ask about children

$215.00

from $215.00 / night

Inquire

1 / 25

WATERFRONT HOME WITH PRIVATE BEACH

Oak Bluffs House

7 bedrooms 7
4 bathrooms
sleeps 12 12
min stay varies

Ask about children

$1,000.00

Excellent (1 reviews)

from $1,000.00 / night

Inquire

1 / 30

Luxury Oak Bluffs Home with 18 X 30' Pool

Oak Bluffs House

4 bedrooms 4
4 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Ask about children
Air conditioning

$1,143.00

from $1,143.00 / night

Inquire

1 / 30

Wonderful Contempory Home in Meadow View Farms

Oak Bluffs House

4 bedrooms 4
4 bathrooms
sleeps 8 8
min stay varies

Ask about children
Air conditioning

$457.00

from $457.00 / night

Inquire

1 / 20

QUINTESSENTIAL VINEYARD SUMMER HOME

Oak Bluffs House

6 bedrooms 6
4 bathrooms
sleeps 12 12
min stay varies

Ask about children

$500.00

from $500.00 / night

Inquire

1 / 15

Cape Style Home near Lagoon Pond- short walk to Lagoon Beach

Oak Bluffs House

4 bedrooms 4
2 bathrooms
sleeps 8 8
min stay varies

Ask about children

$371.00

from $371.00 / night

Inquire

1 / 23

OAK BLUFFS VICTORIAN ONE BLOCK FROM BEACH, TWO BLOCKS FROM TOWN!

Oak Bluffs House

6 bedrooms 6
3 bathrooms
sleeps 12 12
min stay varies

Ask about children
Air conditioning

$1,271.00

Very Good (1 reviews)

from $1,271.00 / night

Inquire

1 / 18

Five bedroom, in-town, Oak Bluffs home with water views!

Oak Bluffs House

5 bedrooms 5
2 bathrooms
sleeps 10 10
7 nights min

Ask about children

$1,315.00

from $1,315.00 / night

Inquire

1 / 24

CLASSIC, VINTAGE,GINGERBREAD

Oak Bluffs House

7 bedrooms 7
3 bathrooms
sleeps 14 14
min stay varies

Ask about children

$543.00

from $543.00 / night

Inquire

1 / 32

Beautiful Oak Bluffs Home with Wonderful Waterviews

Oak Bluffs House

5 bedrooms 5
5 bathrooms
sleeps 10 10
min stay varies

Ask about children
Air conditioning

$1,438.00

from $1,438.00 / night

Inquire

1 / 20

Gracious five bedroom in-town Oak Bluffs victorian

Oak Bluffs House

5 bedrooms 5
2 bathrooms
sleeps 9 9
min stay varies

Ask about children
Air conditioning

$357.00

from $357.00 / night

Inquire

1 / 33

Beautiful Main & Guest house short walk to Lagoon Pond

Oak Bluffs House

5 bedrooms 5
3 bathrooms
sleeps 10 10
min stay varies

Ask about children
Air conditioning

$500.00

from $500.00 / night

Inquire

1 / 27

Beautiful Four Bedroom Home Walking Distance to Downtown Oak Bluffs

Oak Bluffs House

4 bedrooms 4
3 bathrooms
sleeps 9 9
min stay varies

Ask about children
Air conditioning

$525.00

from $525.00 / night

Inquire

1 / 24

Ocean Park Victorian Carousel House

Oak Bluffs House

6 bedrooms 6
3 bathrooms
sleeps 12 12
min stay varies

Ask about children
Air conditioning

$1,071.00

from $1,071.00 / night

Inquire

1 / 19

ENJOY WATERVIEWS OF SENGENKONTACKET POND FROM THE WONDERFUL DECK

Oak Bluffs House

4 bedrooms 4
2 bathrooms
sleeps 8 8
min stay varies

Ask about children

$257.00

from $257.00 / night

Inquire

1 / 19

Charming East Chop Home

Oak Bluffs House

7 bedrooms 7
3 bathrooms
sleeps 12 12
min stay varies

Ask about children

$357.00

from $357.00 / night

Inquire

1 / 21

Beautiful four bedroom house in the Farm Neck area of Oak Bluffs

Oak Bluffs House

4 bedrooms 4
2 bathrooms
sleeps 8 8
min stay varies

Ask about children
Air conditioning

$643.00

from $643.00 / night

Inquire

1 / 21

Four bedroom Oak Bluffs Home

Oak Bluffs House

4 bedrooms 4
3 bathrooms
sleeps 8 8
min stay varies

Ask about children

$414.00

from $414.00 / night

Inquire

1 / 16

Charming Oak Bluffs Cottage within Walking Distance to Town

Oak Bluffs House

6 bedrooms 6
3 bathrooms
sleeps 12 12
min stay varies

Ask about children
Air conditioning

$500.00

from $500.00 / night

Inquire

1 / 20

Beautiful Four Bedroom Home with Central Air Conditioning

Oak Bluffs House

4 bedrooms 4
3 bathrooms
sleeps 8 8
min stay varies

Ask about children
Air conditioning

$400.00

from $400.00 / night

Inquire

1 / 35

Beautiful Oak Bluffs home on Lagoon Pond with Pool!

Oak Bluffs House

4 bedrooms 4
4 bathrooms
sleeps 10 10
min stay varies

Swimming pool
Ask about children
Air conditioning

$571.00

from $571.00 / night

Inquire

1 / 22

Spacious Oak Bluffs Five Bedroom Home Close to Town

Oak Bluffs House

5 bedrooms 5
3 bathrooms
sleeps 10 10
min stay varies

Ask about children
Air conditioning

$591.00

from $591.00 / night

Inquire

1 / 19

Beautiful four bedroom home in-town Oak Bluffs

Oak Bluffs House

4 bedrooms 4
2 bathrooms
sleeps 8 8
min stay varies

Ask about children

$429.00

from $429.00 / night

Inquire

1 / 27

Victorian jewel on sought after Ocean Park in Oak Bluffs

Oak Bluffs House

4 bedrooms 4
5 bathrooms
sleeps 10 10
min stay varies

Ask about children
Air conditioning

$714.00

from $714.00 / night

Inquire

1 / 22

Lovely water views of Sengekontacket Pond

Oak Bluffs House

4 bedrooms 4
3 bathrooms
sleeps 8 8
min stay varies

Ask about children
Air conditioning

$571.00

from $571.00 / night

Inquire

1 / 20

Great Four Bedroom Home in Meadow View Farms

Oak Bluffs House

4 bedrooms 4
2 bathrooms
sleeps 7 7
min stay varies

Ask about children

$286.00

from $286.00 / night

Inquire

1 / 19

CLASSIC AND CHARMING COTTAGE WALKING DISTANCE TO THE BEACH AND TOWN

Oak Bluffs House

5 bedrooms 5
2 bathrooms
sleeps 10 10
min stay varies

Ask about children

$200.00

Excellent (3 reviews)

from $200.00 / night

Inquire

1 / 18

WONDERFUL,SPACIOUS, LOVINGLY MAINTAINED HOME IN SENGEKONTACKET AREA

Oak Bluffs House

4 bedrooms 4
2 bathrooms
sleeps 8 8
min stay varies

Ask about children
Air conditioning

$314.00

from $314.00 / night

Inquire

1 / 21

Restored Ginger Bread Home Steps from the Inkwell Beach

Oak Bluffs House

4 bedrooms 4
4 bathrooms
sleeps 10 10
min stay varies

Ask about children

$857.00

from $857.00 / night

Inquire

1 / 20

LUXURY WATERFRONT HOME- BEACH,DEEPWATER DOCK & MOORING

Oak Bluffs House

4 bedrooms 4
2 bathrooms
sleeps 8 8
min stay varies

Ask about children
Air conditioning

$987.00

from $987.00 / night

Inquire

1 / 20

WONDERFUL VIEWS OF SENGEKONTACKET POND FROM THIS LOVELY VINEYARD HOME

Oak Bluffs House

4 bedrooms 4
3 bathrooms
sleeps 8 8
min stay varies

Ask about children
Air conditioning

$571.00

from $571.00 / night

Inquire

1 / 22

Four bedroom steps from Ink Well Beach!

Oak Bluffs House

4 bedrooms 4
1 bathroom
sleeps 8 8
min stay varies

Ask about children
Air conditioning

$429.00

from $429.00 / night

Inquire

1 / 18

Beautiful Home in Farm Neck with Central Airconditioning

Oak Bluffs House

4 bedrooms 4
3 bathrooms
sleeps 8 8
min stay varies

Ask about children
Air conditioning

$714.00

from $714.00 / night

Inquire

1 / 28

Beautiful New Colonial in Oak Bluffs

Oak Bluffs House

5 bedrooms 5
4 bathrooms
sleeps 10 10
min stay varies

Ask about children
Air conditioning

$930.00

from $930.00 / night

Inquire

1 / 19

Walk to Lagoon from this Cute Cottage

Oak Bluffs House

4 bedrooms 4
2 bathrooms
sleeps 8 8
7 nights min

Ask about children
Air conditioning

$422.00

from $422.00 / night

Inquire

1 / 19

CHARMING WATERFRONT HOME

Oak Bluffs House

4 bedrooms 4
2 bathrooms
sleeps 8 8
min stay varies

Ask about children

$457.00

from $457.00 / night

Inquire

1 / 15

Wonderful Four Bedroom Home in Oak Bluffs

Oak Bluffs House

4 bedrooms 4
2 bathrooms
sleeps 8 8
min stay varies

Ask about children
Air conditioning

$500.00

from $500.00 / night

Inquire

1 / 22

Renovated Oak Bluffs cottage steps from Ink Well Beach

Oak Bluffs House

4 bedrooms 4
2 bathrooms
sleeps 10 10
min stay varies

Ask about children
Air conditioning

$357.00

from $357.00 / night

Inquire

Page 1 of 7

1 2 3 4 5 6 Next Last

Martha's Vineyard

This is the estimated nightly price based on a weekly stay. Contact the advertiser to confirm the price - it varies depending on when you stay and how long for.

This is the estimated nightly price based on a weekly stay.

Estimated price per night based on a weekly stay. Owner fees of {FEE} per stay may apply.

This is the total cost of the stay for the dates and number of guests that you entered.

This price is an estimate based on the latest rate information available to us. Contact the advertiser to ask for the exact price, including any additional fees.

Rates for this rental are unknown, please contact the homeowner to confirm the rate.

What is Travelers’ Choice award?

Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travellers and are ranked within the top 10% of properties on Tripadvisor.

Looking for vacation inspiration?

Get the best deals and personalised recommendations, straight to your inbox (you can unsubscribe at any time).

The field must contain a valid email address.

Terms of use | Privacy policy

Discover

Rental type
Other suggestions

Find a Rental
About Us
Terms

Copyright© 2020 Vacation Home Rentals. All rights reserved

See the details for this home, contact the owner, pay for your trip and more!

Go to manage your vacation booking

1

Need to think it over?

Send yourself an email so you can come back to book this property.

Enter your email address

The Enter your email address field is required. The "Enter your email address" field must contain a valid email address.

Privacy Policy

To get help making a booking, call our dedicated Reservations team at:

+1-857-504-6968

+1-857-504-6968

Monday to Sunday - 3:30am to 1:30am UTC