An aerial view of a coastal area with a sandy beach, a small island with buildings, and numerous boats in the water.

Vineyard Haven Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Vineyard Haven vacation rentals

A modern kitchen with a marble countertop, a central island, and a hanging light fixture.

1. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
9.8 out of 10, Exceptional, (30 reviews)
"Lovely and all brand new accommodation's that are clean and comfy! A quiet location too! "
United States
Nancy K.
The price is ￥28,127
￥66,851 total
includes taxes & fees
Sep 8 - Sep 9
Brand new! Lovely apartment-Vineyard Haven
A view through a window with a wooden frame, overlooking a garden with various plants and a body of water in the background.

2. Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Tisbury
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful view of the lagoon; ideal place for a couple or single. Leisurely walk to town and close to public transportation."
United States
Adrienne W.
The price is ￥48,441
￥85,875 total
includes taxes & fees
Sep 20 - Sep 21
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
A wooden deck with wicker furniture, a table with a vase of flowers, and a view of a marina with boats.

3. WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (54 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is ￥107,663
￥167,386 total
includes taxes & fees
Sep 8 - Sep 9
WATERFRONT Downtown Cottage w/ Beach
A modern kitchen with white cabinetry, a central island with stools, a blue sofa, and a round coffee table.

4. Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Tisbury
10.0 out of 10, Exceptional, (41 reviews)
"Great place, awesome location!"
United States
Connor B.
The price is ￥81,099
￥103,504 total
includes taxes & fees
Sep 9 - Sep 10
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
A two-story house with a brick chimney, a wooden deck, and a wooden fence.

5. serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
West Tisbury
The price is ￥49,222
￥122,705 total
includes taxes & fees
Sep 12 - Sep 13
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
A living room with a flat-screen TV on a stand, a black leather chair, and a sofa. There are two windows with curtains, one of which offers a view of the sea.

6. Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Oak Bluffs
9.4 out of 10, Exceptional, (95 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
The price is ￥46,878
￥83,780 total
includes taxes & fees
Sep 10 - Sep 11
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
A gravel driveway leading to a house surrounded by trees and a garden.

7. Lovely two bedroom apartment with indoor fireplace

Lovely two bedroom apartment with indoor fireplace
Oak Bluffs
10.0 out of 10, Exceptional, (8 reviews)
"Great stay, flexible and responsive host. Difficult location, however, as it was not centrally located or easy to access transportation, etc."
United States
Aviva M.
The price is ￥30,785
￥117,120 total
includes taxes & fees
Sep 8 - Sep 9
Lovely two bedroom apartment with indoor fireplace
A modern kitchen with white cabinets, a central island with blue drawers, and stainless steel appliances.

8. Brand New Guest house

Brand New Guest house
Oak Bluffs
10.0 out of 10, Exceptional, (6 reviews)
"This is a new, beautiful and tastefully decorated 2 bedroom one bathroom house with a really nice big yard. Owner was very responsive and We had everything we needed for an enjoyable stay!"
United States
Elizabeth O.
The price is ￥56,254
￥149,583 total
includes taxes & fees
Oct 1 - Oct 2
Brand New Guest house
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

9. Walk to Beach & Lighthouse: Oak Bluffs Studio!

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
8.4 out of 10, Very Good, (10 reviews)
"Very good experience Very clean owner very helpful My second time here"
United States
Diana
The price is ￥51,410
￥97,919 total
includes taxes & fees
Sep 13 - Sep 14
Walk to Beach & Lighthouse: Oak Bluffs Studio!
A coastal hotel with multiple beachside rooms, a large covered area, and a beach with umbrellas.

10. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (367 reviews)
"Overall, very good. Pool and beach area were not the most convenient to access. Short drive required."
United States
Grayson
The price is ￥33,566
￥38,416 total
includes taxes & fees
Sep 8 - Sep 9
The Club at New Seabury
A spacious living area with a high ceiling, a dining table, and a kitchen area.

11. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (9 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is ￥49,222
￥132,654 total
includes taxes & fees
Sep 11 - Sep 12
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

12. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Oak Bluffs
9.8 out of 10, Exceptional, (8 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is ￥62,191
￥206,135 total
includes taxes & fees
Oct 1 - Oct 2
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

13. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is ￥62,348
￥129,510 total
includes taxes & fees
Sep 27 - Sep 28
Charming Vacation Home in Oak Bluffs.
A modern living room with a sofa, chairs, a coffee table, and a dining area.

14. New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (89 reviews)
"Great condo, great location. Fully equipped kitchen and awesome patio. "
United States
Jeff V.
The price is ￥15,315
￥51,866 total
includes taxes & fees
Sep 13 - Sep 14
New Seabury Cape Condo + Pool & Beach Escape
A circular stone patio with Adirondack chairs and a small table in a forested area.

15. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.6 out of 10, (11 reviews)
"We had a perfect pre-/off-season stay with plenty of sleeping space. The location is fantastic—right between Vineyard Haven and Edgartown—making it easy to bike to both, plus there’s a beach across the street. The WiFi wasn’t working when we first arrived, but the owner was incredibly responsive and went above and beyond to fix it quickly. We’ll definitely be back!"
United States
Bethann N.
The price is ￥49,378
￥111,707 total
includes taxes & fees
Sep 13 - Sep 14
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
A cozy living room with a wooden ceiling, a stone fireplace, a leather sofa, and a dining area with a table and chairs.

16. < 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
Oak Bluffs
7.4 out of 10, Good, (3 reviews)
"House was neat architectural wise and family history of home ownership was very cool. However, listing noted there was a washer/dryer and there was not. House also noted that there was a fire pit and it was rusted through. Screen door handles were broken, windows need repair, and house has animals living in the downstairs bathroom wall. House needs updates to charge what was being charged a night. In addition, there was a Nor’easter that hit the island and we attempted to contact the host to let...
United States
Kate K.
The price is ￥51,253
￥125,147 total
includes taxes & fees
Sep 9 - Sep 10
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
A beach with large rocks and waves.

17. Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!

Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!
Oak Bluffs
9.8 out of 10, Exceptional, (60 reviews)
"We had the best girls weekend here! The space was perfect size for us. Great spaces for sitting and chatting, both inside and on the balcony. The location was perfect, right across from the ocean waves and shells on the beach. Walking distance to town and easy access to biking. It had everything we needed."
United States
Rachael C.
The price is ￥77,489
￥143,804 total
includes taxes & fees
Sep 24 - Sep 25
Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!
A deck with a fire pit, outdoor seating, and a blue umbrella.

18. Cozy Cottage walk to Menauhant Beach

Cozy Cottage walk to Menauhant Beach
East Falmouth
8.8 out of 10, Excellent, (8 reviews)
"It was a great weekend spot. Had everything we needed, nicely decorated, and in a great and private location"
United States
Grace P.
The price is ￥29,921
￥118,475 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Cottage walk to Menauhant Beach
A spacious living area with a fireplace, a kitchen with bar stools, and a dining area with a table and chairs.

19. 4 Mi to Bristol Beach! Coastal Retreat w/ Pond

4 Mi to Bristol Beach! Coastal Retreat w/ Pond
East Falmouth
9.4 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay at this charming New England home. The house was spotless, beautifully maintained, and full of character. It had all the comforts we needed, inviting spaces to relax in after exploring the area. The location was perfect—close to local shops, scenic spots, and great dining. Our host was friendly, responsive, and made us feel right at home. We honestly couldn’t have asked for a better experience, and we look forward to returning."
United States
Shaun G.
The price is ￥20,626
￥99,256 total
includes taxes & fees
Oct 5 - Oct 6
4 Mi to Bristol Beach! Coastal Retreat w/ Pond
A boat docked at a concrete pier with a sandy shore in the background.

20. Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
Seconsett Island
10.0 out of 10, Exceptional, (42 reviews)
"Great stay!"
United States
Kian S.
The price is ￥27,346
￥64,562 total
includes taxes & fees
Sep 17 - Sep 18
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Vineyard Haven Hotel Reviews

New Bedford Harbor Hotel

New Bedford Harbor Hotel

10/10 Excellent
"Excellent"
Ethan 1-night trip
Posted 2 hours ago
New Bedford Harbor Hotel

Find out more about Vineyard Haven

Search for holiday rentals in Vineyard Haven on Expedia! You can easily find your home rentals, villas, holiday apartments in Vineyard Haven using one of the methods below:

  • View our selection of featured holiday rentals in Vineyard Haven
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Look no further and take a look at our great range of rental properties in Vineyard Haven!

Frequently asked questions

Can I find vacation rentals in Vineyard Haven?

Yes, there are vacation rentals in Vineyard Haven close to Island Cove Adventures, or you can choose a secluded option if you're looking for a relaxing stay. Visitors like the wineries and beaches in Vineyard Haven. Leave some time to check out the shops and waterfront during your trip.

What are some of the best vacation home rentals that Vineyard Haven has to offer?

Gorgeous Spacious Victorian Cape Cod Beach View Retreat: This vacation home rental outside of Vineyard Haven is located near the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Vineyard Haven?

With 216 Expedia vacation rentals, you're sure to find just the right place for your Vineyard Haven stay.

What can I see and do in Vineyard Haven?

Enjoy the outdoors at Lambert's Cove Beach and Tisbury Town Beach, or simply take in cultural attractions like Martha's Vineyard Film Center and Martha's Vineyard Museum. While here, Martha's Vineyard Chamber of Commerce and Vineyard Haven Terminal are other places worth a visit.

What are vacation rentals like in Vineyard Haven?

Vacation rentals are private properties you can reserve for several days or longer in Vineyard Haven. Vacation rentals offer amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a small group gathering.