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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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
10.0 out of 10, Exceptional, (32 reviews)
"This property is quiet yet close enough to the business areas. Very clean, well maintained lovely unit with balcony. The host Joziane commutated with us from minutes after the booking to the end of stay, very helpful."
United States
Unspecified U.
The price is CA $327
CA $696 total
includes taxes & fees
Oct 9 - Oct 10
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, (10 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 $413
CA $743 total
includes taxes & fees
Oct 20 - Oct 21
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
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.

3. 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, (97 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
The price is CA $428
CA $761 total
includes taxes & fees
Oct 13 - Oct 14
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

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

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
7.8 out of 10, Good, (12 reviews)
"The unit was clean and sufficient for 2 people. Outside could use some attention."
United States
Donna R.
The price is CA $469
CA $890 total
includes taxes & fees
Oct 8 - Oct 9
Walk to Beach & Lighthouse: Oak Bluffs Studio!
A coastal hotel with multiple beachside rooms, a large covered area, and a beach with umbrellas.

5. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (371 reviews)
"The New Seabury resort is beautiful & has excellent customer service. The 4/5 stars is because the unit we stayed in needs some updating. However, the layout, cleanliness, & location is good."
United States
Kathleen
The price is CA $210
CA $240 total
includes taxes & fees
Nov 1 - Nov 2
The Club at New Seabury
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

6. Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs 4BR • 5 Min Drive to Downtown
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"This place was just what we needed! Would definitely stay again. Cozy and feels very homey! Thanks!"
United States
Chris S.
The price is CA $512
CA $1,199 total
includes taxes & fees
Oct 8 - Oct 9
Oak Bluffs 4BR • 5 Min Drive to Downtown
A circular stone patio with Adirondack chairs and a small table in a forested area.

7. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
7.0 out of 10, Good, (12 reviews)
"Loved this spot. Perfect central island location. Fantastic owner with an incredible response time. Would recommend this property to all5 stars"
United States
Eli R.
The price is CA $450
CA $1,019 total
includes taxes & fees
Oct 8 - Oct 9
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.

8. 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, (10 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is CA $567
CA $1,948 total
includes taxes & fees
Oct 8 - Oct 9
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A backyard with a seating area, a white fence, and a variety of plants.

9. Delightful 3-bedroom house with AC in Oak Bluffs

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
The price is CA $639
CA $1,638 total
includes taxes & fees
Oct 30 - Oct 31
Delightful 3-bedroom house with AC in Oak Bluffs
A spacious living room with a wooden staircase, a fireplace, and a leather sofa.

10. < 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 CA $623
CA $1,339 total
includes taxes & fees
Oct 9 - Oct 10
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
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, (10 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is CA $705
CA $1,511 total
includes taxes & fees
Oct 8 - Oct 9
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A room with a view of the sea through large windows, a wooden deck, and a pier with structures.

12. 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, (98 reviews)
"Danny was a great host. Unit clean. Walking distance to everything"
United States
Alvin
The price is CA $385
CA $707 total
includes taxes & fees
Oct 7 - Oct 8
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

13. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is CA $554
CA $1,331 total
includes taxes & fees
Oct 8 - Oct 9
Walk to Beach! Oak Bluffs Home & Studio
A modern interior with a wooden staircase, a kitchen area, and a living space with a sofa and coffee table.

14. 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)
"This was an excellent stay at a beautiful property in Oak Bluffs! Rebecca was a great host who provided clear instructions and helped answer questions in a timely manner. Rooms were spacious, most tastefully decorated and we had everything that we needed. I definitely recommend staying here to have an unparalleled experience of the Vineyard."
United States
Priyanka D.
The price is CA $1,924
CA $3,093 total
includes taxes & fees
Oct 8 - Oct 9
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
A two-story house with a stone facade, a covered patio, and a well-maintained garden.

15. 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, (3 reviews)
"Brenda and Derek were amazing hosts. They have a beautifully landscaped property with all the amenities needed for a relaxing family vacation. They are super responsive and take a lot of pride in giving their guests a top-notch experience. We will definitely consider staying at their properties again."
United States
Lamar A.
The price is CA $3,563
CA $5,299 total
includes taxes & fees
Oct 12 - Oct 13
Beautiful Estate with salt water pool & pond with kayaks
A residential area with a well-maintained lawn, a stone retaining wall, and a two-story house with a blue door.

16. New 4 BR house near center and beaches with bikes

New 4 BR house near center and beaches with bikes
Katama
9.8 out of 10, Exceptional, (12 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is CA $755
CA $2,373 total
includes taxes & fees
Oct 11 - Oct 12
New 4 BR house near center and beaches with bikes
A deck with a fire pit, outdoor seating, and a blue umbrella.

17. 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 CA $335
CA $1,171 total
includes taxes & fees
Oct 8 - Oct 9
Cozy Cottage walk to Menauhant Beach
A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

18. Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (224 reviews)
"Great location "
United States
Stephanie B.
The price is CA $257
CA $737 total
includes taxes & fees
Nov 1 - Nov 2
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Exterior

19. Charming Guesthouse | Walk to Beach | Downtown

Charming Guesthouse | Walk to Beach | Downtown
Falmouth
10.0 out of 10, Exceptional, (1 review)
"The house was very convenient to the beach, Aldi’s, Walmart, and local restaurants & shops. I wasn’t sure how private it was being a guest house, but I never felt that we didn’t have privacy. Our dogs enjoyed the little fenced in yard. We appreciated the updated bathroom and kitchen. The weather was so pleasant a small outdoor area would have been nice, and we missed not having a washer & dryer and dishwasher, but overall it was clean and cozy. We would stay there again! We loved the Cape,...
United States
Kandy W.
The price is CA $280
CA $920 total
includes taxes & fees
Oct 8 - Oct 9
Charming Guesthouse | Walk to Beach | Downtown
A modern living room with a grey sofa, a wooden coffee table, and a television mounted on the wall.

20. LUX on Main | Downtown | Parking | Sleeps 6, #201

LUX on Main | Downtown | Parking | Sleeps 6, #201
Falmouth
10.0 out of 10, Exceptional, (6 reviews)
"This was the perfect location for our Cape Cod getaway. It was very central to everything we were doing while down there, very effortless to get to Martha’s Vineyard as well! The location was perfect with a bunch of different restaurants, shops and other stores all in walking distance. We will definitely consider staying here again in the future!"
United States
Zack D.
The price is CA $299
CA $1,072 total
includes taxes & fees
Oct 7 - Oct 8
LUX on Main | Downtown | Parking | Sleeps 6, #201
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

Seaport Resort & Marina

Seaport Resort & Marina

8/10 Good
"Room was fine. Bed was pretty stiff, but we slept just fine."
Anthony 1-night trip
Posted 2 hours ago
Seaport Resort & Marina

Find out more about Vineyard Haven

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Vineyard Haven. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel: This vacation home rental outside of Vineyard Haven is located near the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Vineyard Haven?

With 207 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 Museum and Martha's Vineyard Film Center. 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.