Book Holiday Homes in Vineyard Haven

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Featured Holiday Homes in Vineyard Haven

Cozy getaway in a central location w/ a full kitchen & furnished deck

Cozy getaway in a central location w/ a full kitchen & furnished deck

Oak Bluffs
Stay at this vacation home in Oak Bluffs. Enjoy a garden, laundry facilities, and patios. Popular attractions Inkwell Beach and Island Cove Adventures are located ...
Opens in a new windowCozy getaway in a central location w/ a full kitchen & furnished deck
Moon Compass Escape – Spacious Cape Cod Retreat

Moon Compass Escape – Spacious Cape Cod Retreat

Sandwich
Stay at this vacation home in Sandwich. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Mashpee Wampanoag Indian Museum and Cotuit Center ...
Opens in a new windowMoon Compass Escape – Spacious Cape Cod Retreat
Newly Renovated Near Amazing Sunset Beach

Newly Renovated Near Amazing Sunset Beach

Falmouth
Stay at this vacation home in North Falmouth. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Cataumet Arts Center and Handy Point are ...
Opens in a new windowNewly Renovated Near Amazing Sunset Beach
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Last minute deal - walk to the beach - 4 bedroom - super cute!

Last minute deal - walk to the beach - 4 bedroom - super cute!

Teaticket
Stay at this vacation home in East Falmouth. Enjoy a garden, laundry facilities, and patios. Popular attractions Woods Hole Ferry Terminal and Menauhant Beach ...
Opens in a new windowLast minute deal - walk to the beach - 4 bedroom - super cute!
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!

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

Oak Bluffs
Book a stay at this family-friendly vacation home in Oak Bluffs. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Inkwell Beach and Oak ...
Opens in a new windowModern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

West Tisbury
Stay at this vacation home in Vineyard Haven. Enjoy laundry facilities, patios, and an in-room coffeemaker. Popular attractions Long Point Wildlife Refuge and ...
Opens in a new windowUniquely designed island retreat with fast WiFi & private W/D - dogs welcome
2 Acre Waterfront Home Overlooking Waquoit Bay with Spa and Swim Dock

2 Acre Waterfront Home Overlooking Waquoit Bay with Spa and Swim Dock

Falmouth
Book a stay at this beach vacation home in East Falmouth. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Waquoit Bay National Estuarine Research ...
Opens in a new window2 Acre Waterfront Home Overlooking Waquoit Bay with Spa and Swim Dock
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry

Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry

Falmouth
Stay at this vacation home in Falmouth. Enjoy a garden, laundry facilities, and patios. Popular attractions Woods Hole Ferry Terminal and Island Queen Ferry ...
Opens in a new windowCharming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
Luxury Loft Historic Center Oak Bluffs

Luxury Loft Historic Center Oak Bluffs

Oak Bluffs
Stay at this vacation home in Oak Bluffs. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Inkwell Beach and Trinity Park Tabernacle ...
Opens in a new windowLuxury Loft Historic Center Oak Bluffs
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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.

Vineyard Haven Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Vineyard Haven vacation homes are the perfect way for you to wing it.

Holiday houses in Vineyard Haven let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Vineyard Haven in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Vineyard Haven adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Vineyard Haven with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Vineyard Haven vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Vineyard Haven Holiday Homes essential information

Accommodation
1316 Holiday Homes
Lowest Price
NZ$345
Highest Price
NZ$370
Popular accommodation
Cozy getaway in a central location w/ a full kitchen & furnished deck, Moon Compass Escape – Spacious Cape Cod Retreat, Newly Renovated Near Amazing Sunset Beach, Last minute deal - walk to the beach - 4 bedroom - super cute!, Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!, Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome, 2 Acre Waterfront Home Overlooking Waquoit Bay with Spa and Swim Dock , Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry, Luxury Loft Historic Center Oak Bluffs

Top trending hotels in Vineyard Haven

Mansion House Inn And Spa

Mansion House Inn And Spa

3.5 out of 5
9 Main Street, Vineyard Haven, MA
The price is NZ$370 per night from 1 Dec to 2 Dec
NZ$370
1 Dec - 2 Dec
includes taxes & fees
Stay at this 3.5-star spa hotel in Vineyard Haven. Enjoy a full-service spa, a rooftop terrace, and a health club. Our guests praise the helpful staff in our ...
Opens in a new windowMansion House Inn And Spa
Harbor Landing Resort

Harbor Landing Resort

2 out of 5
15 Beach St, Vineyard Haven, MA
Stay at this hotel in Vineyard Haven. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Inkwell Beach and Woods Hole Ferry Terminal ...
Opens in a new windowHarbor Landing Resort
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
60 Beach Road, Vineyard Haven, MA
The price is NZ$345 per night from 11 Nov to 12 Nov
NZ$345
11 Nov - 12 Nov
includes taxes & fees
Book a stay at this beach motel in Vineyard Haven. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowVineyard Harbor Motel - Private Beach
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Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

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

Tisbury
Book a stay at this family-friendly vacation home in Vineyard Haven. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Inkwell Beach ...
Opens in a new windowDowntown Captain's Mansion- The Dexter- Family, pet, and event friendly
Don't see what you're looking for?
See all available properties in Vineyard Haven
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.