Vineyard Haven Vacations from $1,385

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Your Vineyard Haven Vacation

Spend less time planning and more time having memorable adventures with a Vineyard Haven vacation package. The neighborhood of Falmouth Heights, which is good for views and coastal beaches, makes a wonderful base for your city break. Love to start exploring your surroundings? Inkwell Beach, Oak Bluffs Town Beach and Oak Bluffs Harbor are among the leading places to visit during a trip to Vineyard Haven. No matter your travel plans or the size of your budget, organizing your ultimate tailored Vineyard Haven vacation is a piece of cake with Expedia.

The Latest Vineyard Haven vacation packages

Price found within the past 48 hours. Click for updated prices.
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
Price was $1,507, price is now $1,385 per person
$1,385
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Vineyard Haven (MVY)
9/10 Wonderful! (832 reviews)
The room was freezing and there was no heater. The lights didn't work. The man at the front desk was not helpful and was never there. If you needed help, it said to call a number but the mail box was full and could not receive messages. It was a terrible experience. Don't stay here

Reviewed on Oct 27, 2026

Harbor View Hotel

Harbor View Hotel

5 out of 5
Price was $1,668, price is now $1,622 per person
$1,622
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
Loved the heated saltwater pool. Was disappointed there was not comfortable sitting in the room, esp on a rainy day or not feeling well, and watching a movie. Was surprised no elevator and we were on the third floor. The “grab and go” breakfast option was no more than a few pastries. That was disappointing. For early departure to catch ferry at 0530, no coffee was available.

Reviewed on Oct 22, 2026

Faraway Martha's Vineyard

Faraway Martha's Vineyard

4 out of 5
Price was $1,602, price is now $1,561 per person
$1,561
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Vineyard Haven (MVY)
9/10 Wonderful! (1,000 reviews)
Lovely property , it seemed it was the end of the season when we visited, so it was very quiet, and maintenance had started in the hotel, not that it bothered us at all . Loved the record player and the hot tub and bikes . The pub/restaurant was very good , with very helpful barmaid (Sophia) who on top of great service in the bar helped us plan the next part of our trip in Boston .

Reviewed on Oct 26, 2026

The Island Inn on Martha's Vineyard

The Island Inn on Martha's Vineyard

2.5 out of 5
Price was $1,531, price is now $1,495 per person
$1,495
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Vineyard Haven (MVY)
8.2/10 Very Good! (58 reviews)

Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

3 out of 5
Price was $1,524, price is now $1,492 per person
$1,492
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Vineyard Haven (MVY)
8.4/10 Very Good! (643 reviews)

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Stay near popular Vineyard Haven attractions

Lambert's Cove Beach

9.2/10 (27 reviews)
This secluded Martha's Vineyard treasure offers pristine white sands and crystal-clear waters away from tourist crowds. Arrive after 5PM during summer to experience its tranquil beauty without a resident pass.
See properties

What to do in Vineyard Haven

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)

$50
per adult
Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)
Edgartown Martha’s Vineyard Self-Guided

Edgartown Martha’s Vineyard Self-Guided (GPS) Audio Walking Tour

$10
per adult
Edgartown Martha’s Vineyard Self-Guided (GPS) Audio Walking Tour
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

$50
per traveler
Massachusetts: Smartphone-Based Audio Tour Bundle
See all activities in Vineyard Haven

Vineyard Haven Hotel Deals

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
60 Beach Road Vineyard Haven MA
$177 nightly
The price is $198 total per night from Oct 28 to Oct 29
$198 total
Oct 28 - Oct 29
Total with taxes and fees
9/10 Wonderful! (837 reviews)
"The room was freezing and there was no heater. The lights didn't work. The man at the front desk was not helpful and was never there. If you needed help, it said to call a number but the mail box was full and could not receive messages. It was a terrible experience. Don't stay here"

Reviewed on Oct 27, 2026

Vineyard Harbor Motel - Private Beach
Mansion House Inn And Spa

Mansion House Inn And Spa

3.5 out of 5
9 Main Street Vineyard Haven MA
$187 nightly
The price is $209 total per night from Nov 2 to Nov 3
$209 total
Nov 2 - Nov 3
Total with taxes and fees
Mansion House Inn And Spa
Harbor Landing Resort

Harbor Landing Resort

2 out of 5
15 Beach St Vineyard Haven MA
Get rates
Harbor Landing Resort
See all 3,059 properties in Vineyard Haven
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.

Find the Best Vineyard Haven Vacation Packages

Vineyard Haven Beach Vacation

Relax by the water and feel the fresh salt air on your skin during your Vineyard Haven vacation. If you're visiting for the first time, why not search for some pretty seashells as a souvenir of your trip to Vineyard Haven? Stay near Long Point Beach, a popular stretch of coast just 8 miles from the downtown area. We also offer superb Vineyard Haven vacation packages closer to Tisbury Town Beach, another wonderful nearby option.

Things You Should Know About Vineyard Haven

  • If fresh ocean breezes and strolls along the shore are your idea of a dream vacation, why not choose one of our Vineyard Haven beach hotels? Staying by the water is the perfect antidote to life's daily stresses.
  • Have a look at Lamberts Cove Inn and Mansion House Inn And Spa. These popular private vacation homes might just be ideal for your vacation in Vineyard Haven.
  • There are plenty of activities that keep the 2,100 or so residents of Vineyard Haven entertained. Browsing our Vineyard Haven things to do page will let you in on everything this place has to offer.
  • Martha's Vineyard Chamber of Commerce, Long Point Beach and Long Point Beach are some great sights that should be on your sightseeing list. With our Vineyard Haven vacation deals, you'll have more money in your pocket to explore.

Vineyard Haven Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Martha's Vineyard Airport (MVY)
Population
2,100
Max Temp Winter
40ºF
Max Temp Summer
70ºF
Top Sights
Inkwell Beach, Old Silver Beach and Falmouth Heights Beach

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Frequently asked questions

How much does a Vineyard Haven vacation package cost?
You can snap up a vacation package to this popular destination from $1,385 on Expedia. But how much your vacation to Vineyard Haven costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Vineyard Haven?
If you're looking to book a cheap Vineyard Haven vacation package, consider planning a trip in August, September and October. You'll typically find better prices on hotels and flights during these months — perfect for budget-conscious travelers.
How many days is enough for Vineyard Haven?
We recommend booking a Vineyard Haven vacation for at least 3 days. This gives you plenty of time to check off top sights including Lambert's Cove Beach and Tisbury Town Beach, and explore neighborhoods like Lagoon Heights and East Chop. You could even fit in one or two day trips outside of Vineyard Haven.
Is it worth booking a vacation package to Vineyard Haven?
Vineyard Haven offers everything you need for an amazing escape. Get your Vineyard Haven vacation off to a flying start by visiting popular attractions like Martha's Vineyard Museum.
How to find the best Vineyard Haven package deals?
Landing a cheap Vineyard Haven package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, apply some filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most pocket-friendly Vineyard Haven package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Vineyard Haven vacation as a package?
You can enjoy significant savings on your Vineyard Haven getaway by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to see some great flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Vineyard Haven?
Score incredible bargains by reserving your flights early with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Vineyard Haven escape.
How to plan a trip to Vineyard Haven?

  1. Choose when to get away: Check your schedule and get packing. Your favorite season and the activities available will also help you decide when to escape to Vineyard Haven.
  2. Calculate your budget: Make sure you have enough money to cover everything from meals and transportation to activities and flights. Your hotel will likely be the biggest expense during your trip to Vineyard Haven.
  3. Organize your Vineyard Haven getaway with our trip planning tool: Search for and book hotels and things to do all in one place. You can also collaborate with your group to plan an unforgettable trip to Vineyard Haven together.
  4. Set the duration of your trip: Start by compiling a list of the attractions you'd like to get to in Vineyard Haven. Then, estimate how long you'll need at each, along with any travel time.
  5. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a tailored Vineyard Haven vacation package.
  6. Book experiences or activities in advance: Whether it's entrance to a big attraction or a day trip in nature, you won't have to worry about missing out on the best Vineyard Haven has to offer. Find all the fun things to do in Vineyard Haven with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Vineyard Haven vacation packages?
Set off on your perfect escape to Vineyard Haven with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait for the next payday — we've teamed up with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no hidden or late payment fees, you can easily stick to your budget and snag great deals while they last.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.