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 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Vineyard Haven vacation rentals

A wooden deck with wicker furniture, a table with a vase of flowers, and a view of a marina with boats.

1. WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (53 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is CA $1,365
CA $1,992 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.

2. 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, (40 reviews)
"Great place, awesome location!"
United States
Connor B.
The price is CA $1,172
CA $1,496 total
includes taxes & fees
Sep 6 - Sep 7
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
A modern kitchen with a marble countertop, a central island, and a hanging light fixture.

3. 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 CA $276
CA $623 total
includes taxes & fees
Aug 27 - Aug 28
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.

4. 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, (7 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 CA $517
CA $867 total
includes taxes & fees
Sep 1 - Sep 2
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
A dining area with a view of the sea, a wooden table set with plates and glasses, and a coffee maker on the counter.

5. A View Fit for Royalty! Top Compliments: so clean! fab hot tub! best view!

A View Fit for Royalty! Top Compliments: so clean! fab hot tub! best view!
Tisbury
10.0 out of 10, Exceptional, (31 reviews)
"Host was very informative before the arrival, house was spotless and everything was easy to find "
United States
Anonymous traveller
The price is CA $1,172
CA $2,066 total
includes taxes & fees
Aug 24 - Aug 25
A View Fit for Royalty! Top Compliments: so clean! fab hot tub! best view!
A two-story house with a brick chimney, a wooden deck, and a wooden fence.

6. 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 CA $482
CA $1,144 total
includes taxes & fees
Sep 12 - Sep 13
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

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

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
8.4 out of 10, Very good, (9 reviews)
"Very accommodating early check in and great communication "
United States
Katelyn K.
The price is CA $453
CA $861 total
includes taxes & fees
Sep 1 - Sep 2
Walk to Beach & Lighthouse: Oak Bluffs Studio!
A modern interior with a wooden staircase, a kitchen area, and a living space with a sofa and coffee table.

8. MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.8 out of 10, Exceptional, (12 reviews)
"TLDR: House is nice,"
United States
Rachel
The price is CA $1,861
CA $3,078 total
includes taxes & fees
Sep 20 - Sep 21
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
A coastal hotel with multiple beachside rooms, a large covered area, and a beach with umbrellas.

9. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (366 reviews)
"Overall, very good. Pool and beach area were not the most convenient to access. Short drive required."
United States
Grayson
The price is CA $349
CA $399 total
includes taxes & fees
Sep 7 - Sep 8
The Club at New Seabury
A gravel driveway leading to a house surrounded by trees and a garden.

10. Lovely two bedroom apartment with indoor fireplace

Lovely two bedroom apartment with indoor fireplace
Oak Bluffs
10.0 out of 10, Exceptional, (7 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 CA $275
CA $1,030 total
includes taxes & fees
Sep 7 - Sep 8
Lovely two bedroom apartment with indoor fireplace
A room with a view of the sea through large windows, a wooden deck, and a pier with structures.

11. 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, (96 reviews)
"Danny was a great host. Unit clean. Walking distance to everything"
United States
Alvin
The price is CA $586
CA $950 total
includes taxes & fees
Sep 8 - Sep 9
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
A modern kitchen with white cabinets, a central island with blue drawers, and stainless steel appliances.

12. 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 CA $565
CA $1,407 total
includes taxes & fees
Sep 9 - Sep 10
Brand New Guest house
A circular stone patio with Adirondack chairs and a small table in a forested area.

13. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.8 out of 10, (9 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 CA $436
CA $985 total
includes taxes & fees
Sep 1 - Sep 2
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

14. 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 CA $600
CA $1,937 total
includes taxes & fees
Sep 8 - Sep 9
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A wooden deck with a white railing, two chairs, and a small table.

15. Make Lasting Memories In This Adorable Vineyard Cottage!

Make Lasting Memories In This Adorable Vineyard Cottage!
Oak Bluffs
9.8 out of 10, Exceptional, (155 reviews)
"Cute, compact, and had everything we needed for ourstay. I'd definitely stay there again."
United States
Karen C.
The price is CA $345
CA $701 total
includes taxes & fees
Sep 2 - Sep 3
Make Lasting Memories In This Adorable Vineyard Cottage!
A spacious living area with a high ceiling, a dining table, and a kitchen area.

16. 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 CA $434
CA $1,152 total
includes taxes & fees
Sep 11 - Sep 12
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

17. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is CA $688
CA $1,318 total
includes taxes & fees
Sep 8 - Sep 9
Charming Vacation Home in Oak Bluffs.
A two-story house with a stone facade, a covered patio, and a well-maintained garden.

18. Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"I can’t say enough about this beautiful property. pictures don’t do any justice for this piece of heaven. The flowers were everywhere , it’s so apparent that the property owners take such pride in this beautiful property. The place was spotless when we walked in the door. We met the owners on arrival , they surprised us with a beautiful ballon to celebrate my 50th birthday. My family enjoyed the pool and the fun Tiki. The outdoor fireplace was inviting after the sun went down. I was a little...
United States
Miriam D.
The price is CA $3,377
CA $5,172 total
includes taxes & fees
Sep 20 - Sep 21
Beautiful Estate with salt water pool & pond with kayaks
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.

19. 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, (92 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
The price is CA $414
CA $722 total
includes taxes & fees
Sep 20 - Sep 21
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
A modern living room with a grey sofa, a coffee table, and a fireplace.

20. LUX on Main | Downtown | Parking | Sleeps 6, #203

LUX on Main | Downtown | Parking | Sleeps 6, #203
Falmouth
10.0 out of 10, Exceptional, (5 reviews)
The price is CA $550
CA $1,355 total
includes taxes & fees
Aug 26 - Aug 27
LUX on Main | Downtown | Parking | Sleeps 6, #203
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

Admiralty Inn & Suites - a Red Collection Hotel

Admiralty Inn & Suites - a Red Collection Hotel

10/10 Excellent
"I have a great experience with this hotel. This is third time staying here. The staff is kind and allows me to check-in early. I plan to stay here next year, August 2027"
Markia 3-night trip
Posted 6 hours ago
Admiralty Inn & Suites - a Red Collection Hotel

Find out more about Vineyard Haven

Everything you need to know about Vineyard Haven vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Vineyard Haven vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Vineyard Haven vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Vineyard Haven vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Vineyard Haven. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Vineyard Haven vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Vineyard Haven vacation rentals we have selected for you start as low as CA $399 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Vineyard Haven rentals

At Expedia, we put the best Vineyard Haven vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Vineyard Haven rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Vineyard Haven vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Vineyard Haven. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 3-bedroom house close to Willowbend, New Seabury in charming Mashpee: This vacation home rental outside of Vineyard Haven offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Vineyard Haven?

With 213 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.