Holiday Rentals in Vineyard Haven

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan

Holiday Rentals in Vineyard Haven

Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
Exterior

Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

10.0 out of 10, Exceptional, (64)
"The house was well stocked and had everything you could need. "
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
Nana's Backyard Treehouse with deck, electric/gas grills, kitchenette
Terrace/patio

Nana's Backyard Treehouse with deck, electric/gas grills, kitchenette

8.0 out of 10, Very good, (17)
"Well maintained. Very quiet. No TV. Doubt if there is any air conditioning. "
Nana's Backyard Treehouse with deck, electric/gas grills, kitchenette
The Club at New Seabury
Private beach nearby, beach bar

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (336)
"Very relaxing, loved the different clubs available; beach, pool, tennis, playground for the little ones, bars and food. Some shops were closed due to being off season, but still enjoyed our stay. Looking forward to booking again "
The Club at New Seabury
InnSeason Resorts Captain's Quarters
On the beach, white sand

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (186)
"Great location and helpful staff"
InnSeason Resorts Captain's Quarters
Coastal chic meets French Provençal in this newly renovated oceanfront home.
5 bedrooms, desk, iron/ironing board, travel cot

Coastal chic meets French Provençal in this newly renovated oceanfront home.

10.0 out of 10, Exceptional, (86)
"Great stay! "
The price is €1,182
includes taxes & fees
27 Oct - 28 Oct
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Sea Mist Resort
Indoor pool, outdoor pool, pool loungers

Sea Mist Resort

3.0 star property
8.6 out of 10, Excellent, (137)
"Just there for one night but very enjoyable stay."
The price is €173
includes taxes & fees
7 Nov - 8 Nov
Sea Mist Resort
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Exterior

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

6.4 out of 10, (31)
"The weather was perfect and our crew made the best of our trip."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Smart TV

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

9.4 out of 10, Exceptional, (88)
"The location of this property cannot be beat! Our second time staying here."
The price is €473
includes taxes & fees
11 Nov - 12 Nov
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Interior

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

9.4 out of 10, Exceptional, (91)
"Close to buses, restaurants and ferries. 10/10, we would stay again."
The price is €442
includes taxes & fees
12 Oct - 13 Oct
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub
Exterior

Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub

10.0 out of 10, Exceptional, (112)
"The location and amenities were perfect. We are looking forward to returning next year."
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub
By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound
Property grounds

By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound

9.8 out of 10, Exceptional, (23)
"We had a great week staying at this property. It's well maintained and had plenty of room for a family getaway to the Cape. Steps away from the beach, this property is well taken care of and had everything we needed for a comfortable stay. This would be our first choice for any future trips to the Cape."
By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound
Spacious colonial home close to town with AC, porches, & W/D
TV, DVD player, books

Spacious colonial home close to town with AC, porches, & W/D

10.0 out of 10, Exceptional, (5)
"We had such a great stay here. Very clean and super close to town. We would definitely stay here again. Thanks!"
Spacious colonial home close to town with AC, porches, & W/D
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
Fridge, microwave, oven, stovetop

Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!

10.0 out of 10, Exceptional, (71)
"Large home with plenty of room for extended family. Located in quiet neighborhood close to Oak Bluffs, would highly recommend."
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
Southcape Resort Mashpee
Exterior

Southcape Resort Mashpee

3.0 star property
8.6 out of 10, Excellent, (201)
"Enjoyed our stay."
Southcape Resort Mashpee
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Interior

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

10.0 out of 10, Exceptional, (7)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
The price is €1,070
includes taxes & fees
12 Oct - 13 Oct
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Beachside Village Resort
Seasonal outdoor pool

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (99)
"Great location! Nice property! "
Beachside Village Resort
In Ground Pool, A/C, 4+BR, 3BA, Wifi, Game Room. Sleeps 10-12, strong wifi
Outdoor pool

In Ground Pool, A/C, 4+BR, 3BA, Wifi, Game Room. Sleeps 10-12, strong wifi

9.0 out of 10, Wonderful, (57)
"The house was very large with enough space for our entire family. Plenty of bedrooms and bathrooms. The kitchen and living room was spacious and comfortable. The pool was initially dirty, however the 2nd day the pool was cleaned and we enjoyed it for the rest of our stay. "
In Ground Pool, A/C, 4+BR, 3BA, Wifi, Game Room. Sleeps 10-12, strong wifi
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
TV, fireplace, books

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

9.0 out of 10, Wonderful, (2)
"The house was lovely. Very clean and orderly. Beautiful back porch that we enjoyed very much. The beds were very comfortable. Our only complaint was the Master bathroom needs some updating. The shower head desperately needs to be changed and the lighting is extremely poor. Also, only 1 half size mirror on the whole first floor. Other than that, it was perfect."
The price is €592
includes taxes & fees
8 Nov - 9 Nov
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
3 Bed 2 Bath - Fully Renovated SS Granite kitchen walk to beach Falmouth heights
Dining

3 Bed 2 Bath - Fully Renovated SS Granite kitchen walk to beach Falmouth heights

9.2 out of 10, Wonderful, (35)
"Everything was great "
3 Bed 2 Bath - Fully Renovated SS Granite kitchen walk to beach Falmouth heights
Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people
Beach nearby, sun-loungers, beach towels

Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people

8.8 out of 10, Excellent, (28)
"Jim is fantastic to work with."
Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people
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

Iris Hotel Cape Cod

Iris Hotel Cape Cod

10/10 Excellent
"Nice place! "
Tamara L 1-night trip
Posted 19 hours ago
Iris Hotel Cape Cod

Find out more about Vineyard Haven

Everything you need to know about Vineyard Haven holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Vineyard Haven holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Vineyard Haven holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Vineyard Haven holiday rentals we have selected for you start as low as €173 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 holiday 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 holiday.

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 holiday rentals in Vineyard Haven?

Yes, there are holiday rentals in Vineyard Haven close to Island Cove Adventures, or you can select a more 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 holiday rentals that Vineyard Haven has to offer?

Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub: This holiday home rental outside of Vineyard Haven is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Vineyard Haven?

With 211 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Vineyard Haven?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Vineyard Haven. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a family trip.