Book Holiday Homes in Chilmark

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Featured Holiday Homes in Chilmark

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
With a stay at this vacation home in Oak Bluffs, you'll be by the sea, within a 10-minute drive of Inkwell Beach and Martha's Vineyard Chamber of Commerce.
Opens in a new windowCozy getaway in a central location w/ a full kitchen & furnished deck
Newly Renovated Near Amazing Sunset Beach

Newly Renovated Near Amazing Sunset Beach

Falmouth
With a stay at this vacation home in North Falmouth, you'll be within a 5-minute drive of Cape Cod Beaches and Francis A. Crane Wildlife Management Area.
Opens in a new windowNewly Renovated Near Amazing Sunset Beach
☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village

☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village

Westport
The price is AU$660 per night from 6 Nov to 7 Nov
AU$660
6 Nov - 7 Nov
includes taxes & fees
When you stay at this vacation home in Westport Point, you'll be by the sea, within a 5-minute drive of Horseneck Beach State Reservation and Horseneck State ...
Opens in a new window☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village
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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
With a stay at this vacation home, you'll be centrally located in East Falmouth, a 1-minute drive from Cape Cod Beaches and 13 minutes from Woods Hole Ferry ...
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
With a stay at this vacation home in Oak Bluffs, you'll be within a 10-minute drive of Inkwell Beach and Martha's Vineyard Hospital Development.
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
A stay at this vacation home places you in the heart of Vineyard Haven, a 1-minute drive from Long Point Wildlife Refuge and 6 minutes from Martha's Vineyard ...
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
With a stay at this vacation home, you'll be centrally located in East Falmouth, within a 5-minute drive of Cape Cod Beaches and Waquoit Bay National Estuarine ...
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
With a stay at this vacation home in Falmouth (Falmouth Heights), you'll be within a 15-minute drive of Cape Cod Beaches and Woods Hole Ferry Terminal.
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
A stay at this vacation home places you in the heart of Oak Bluffs, within a 10-minute walk of Inkwell Beach and Circuit Avenue.
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.

Chilmark 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 Chilmark vacation homes are the perfect way for you to wing it.

Holiday houses in Chilmark 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 Chilmark 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 Chilmark adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chilmark 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 Chilmark 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.

Chilmark Holiday Homes essential information

Accommodation
909 Holiday Homes
Lowest Price
AU$219
Highest Price
AU$660
Popular accommodation
Cozy getaway in a central location w/ a full kitchen & furnished deck, Newly Renovated Near Amazing Sunset Beach, ☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village, 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 Chilmark

Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
291 Jones Rd, Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is AU$219 per night from 4 Dec to 5 Dec
AU$219
4 Dec - 5 Dec
includes taxes & fees
When you stay at Iris Hotel Cape Cod in Falmouth, you'll be on a lake, within a 5-minute drive of Island Queen Ferry and Shining Sea Bikeway.
Opens in a new windowIris Hotel Cape Cod
Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street, Route 28, Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is AU$272 per night from 6 Nov to 7 Nov
AU$272
6 Nov - 7 Nov
includes taxes & fees
With a stay at Falmouth Inn, you'll be centrally located in Falmouth, a 2-minute drive from Cape Cod Beaches and 10 minutes from Woods Hole Ferry Terminal.
Opens in a new windowFalmouth Inn
Faraway Martha's Vineyard

Faraway Martha's Vineyard

3.5 out of 5
23 Kelly Street, Martha's Vineyard, Edgartown, MA
Centrally located in Edgartown, Faraway Martha's Vineyard is within a 15-minute walk of Edgartown Lighthouse and Lighthouse Beach.
Opens in a new windowFaraway Martha's Vineyard
Save an average of 15% on thousands of hotels when you're signed in
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
350 Quaker Rd, North Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is AU$256 per night from 19 Nov to 20 Nov
AU$256
19 Nov - 20 Nov
includes taxes & fees
When you stay at Sea Crest Beach Resort in North Falmouth, you'll be near the bay, just steps from Cape Cod Beaches and Old Silver Beach.
Opens in a new windowSea Crest Beach Resort
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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.

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^Subject to availability and chosen travel dates.