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Chilmark Vacation Rentals

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Vacation Rentals in Chilmark

View from property
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
8.4 out of 10, Very Good, (18)
"Overall my friends and I have come twice to the Noyes house and are planning to come back next year. As long as you’re comfortable not staying near the main towns, it’s an ideal location - close to the markets and stores of west tisbury, several of the best beaches on the island (Lucy Vincent and Aquinnah in particular), the Chilmark general store, and some of the best farms like beetlebung. The house is something between rustic and luxury, which is deal for a group of friends. It’s not a big...
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Aerial view
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
10.0 out of 10, Exceptional, (31)
"Everything about this house was perfect for our visit with family on MV. It was clean, comfortable, and had all the amenities we needed for a lovely fall week on MV. The location is private and peaceful, with beautiful views. Communication with Christian was easy and accommodating. A little gem!"
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
Outdoor pool, a heated pool
Cozy efficiency apartment/heated pool
10.0 out of 10, Exceptional, (15)
"Very nice apartment, the space was clean and Ronnie the host was very nice."
Cozy efficiency apartment/heated pool
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Fridge, microwave, oven, stovetop
Beautiful dog-friendly home with water view, balcony & washer/dryer
9.4 out of 10, Exceptional, (8)
"Only reason I didn’t give a five for location is that it was sort of far away from most things, but it was a beautiful location out in the woods. The house was lovely and the views were awesome. Would recommend!"
Beautiful dog-friendly home with water view, balcony & washer/dryer
Seasonal outdoor pool, cabanas (surcharge), pool umbrellas
The Club at New Seabury
3.5 star property
9.0 out of 10, Wonderful, (280)
"We loved this place. It was very comfortable and a great value for the money. "
The price is $247
$282 total
includes taxes & fees
May 5 - May 6
The Club at New Seabury
On the beach, white sand
InnSeason Resorts Captain's Quarters
3.5 star property
9.6 out of 10, Exceptional, (141)
"Great location!! We would definitely go back! The one thing we didn’t like was the pull out couch, it was very uncomfortable, my daughter chose to sleep on the sofa the 2nd night and not pull it out. "
InnSeason Resorts Captain's Quarters
Seasonal outdoor pool
Beachside Village Resort by VRI Americas
3.0 star property
9.2 out of 10, Wonderful, (75)
"Wonderful place! Didn’t want to leave, wanted to stay longer! Beautiful view!"
Beachside Village Resort by VRI Americas
Exterior
Charming Cottage Falmouth Cape Cod
3.5 star property
Charming Cottage Falmouth Cape Cod
5 bedrooms, desk, iron/ironing board, travel crib
Coastal chic meets French Provençal in this newly renovated oceanfront home.
10.0 out of 10, Exceptional, (63)
"We very much enjoyed our stay. Scott was a terrific host."
The price is $675
$1,399 total
includes taxes & fees
May 27 - May 28
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Exterior
Quiet duplex by the beach, short walk to Falmouth Village, 2GBps Internet.
9.8 out of 10, Exceptional, (63)
"Property is in a great location, walking distance to the shore and a little longer walk or short drive will get you to town with a pub and a few places to eat. Martha’s Vineyard ferry parking is less than ten minutes away with a free shuttle bus that takes you to the ferry. Regina (owner) is right next door and is very friendly and accommodating!!"
Quiet duplex by the beach, short walk to Falmouth Village, 2GBps Internet.
Property grounds
Adorable waterfront home w/ boat access & a three-season sunroom
9.2 out of 10, Wonderful, (14)
"The house was great aside from a few issues. Owner was quick to respond."
Adorable waterfront home w/ boat access & a three-season sunroom
Private kitchen | Fridge, microwave, oven, stovetop
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK
9.0 out of 10, Wonderful, (37)
"Very clean and updated property! Conveniently located near the water. Comfortable place for us to rest and give my daughter/husband their space. Recommend this place and look forward to hopefully staying again. My only suggestion is to add dimmable lighting. We felt on stage in the living/kitchen area, bedroom. It would be nice to turn down bathroom light during the night."
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK
Outdoor dining
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
10.0 out of 10, Exceptional, (154)
"My best friend and I had an amazing stay!! The house was gorgeous, clean and the view couldn’t be beat. The area had great shops and restaurants. We loved hanging out and the beds were the best of any place I have stayed."
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
Property grounds
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
10.0 out of 10, Exceptional, (11)
"All my wife's children and grandchildren gathered at this lovely home to celebrate her 70th birthday. The home and grounds/neighborhood are simply great and Thomas was a wonderful and responsive host. Since some folks stayed the whole visit and others were only with us for a long weekend, we were thrilled that the dining area accommodated our whole group when necessary, and the kitchen allowed many hands to make light work. The dining table doubled as a spot for the family to gather and...
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Fridge, microwave, oven, stovetop
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
10.0 out of 10, Exceptional, (169)
"This was one of the nicest rentals ive ever stayed in! Everything was spotless and the bed was very comfortable. The kitchen is very well appointed with really nice appliances. Walkable to downtown Falmouth restaurants. Plenty of off street parking too. I definitely recommend this house if youre staying in the area!"
The price is $198
$547 total
includes taxes & fees
May 14 - May 15
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Fridge, microwave, oven, stovetop
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
8.2 out of 10, Very Good, (24)
"Upon entering the property, everything was very clean and welcoming. The rooms were spacious and comfortable. It felt like home. We would definitely book this property again."
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
Property grounds
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!
9.6 out of 10, Exceptional, (74)
"Place was nice. Pool was the key selling point for a winter trip. Tv in every room, but I think something was wrong w the xfinity. Only master bedroom worked with Netflix to watch. That was a huge bummer. If it was warmer weather wouldn’t have been as much of an issue. They had lots of things to do for nice weather but wasn’t the time of year. House was over all nice and relaxing."
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!
3 bedrooms, WiFi, bed sheets
Escape on conservation land with furnished deck, pond views, sunroom, & AC
8.8 out of 10, Excellent, (9)
"Very nice property. Excellent location!"
Escape on conservation land with furnished deck, pond views, sunroom, & AC
Property grounds
Last minute deal - walk to the beach - 4 bedroom - super cute!
9.6 out of 10, Exceptional, (72)
"Such an easy walk to Falmouth Heights Beach and a 5 min drive to downtown, we loved the location of this house! The house itself was large and we comfortably fit 8 adults and 2 babies. Thank you!"
Last minute deal - walk to the beach - 4 bedroom - super cute!
Iron/ironing board, WiFi, bed sheets
Romantic seaside getaway with pool & tennis courts - dog-friendly
9.8 out of 10, Exceptional, (36)
"Great location, lots of amenities - pool, fire pits, tennis courts, nearby restaurant. Communication for checking was excellent."
Romantic seaside getaway with pool & tennis courts - dog-friendly
Don't see what you're looking for?
See all available properties in Chilmark
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 Vacation Rental Travel Info

Number of vacation rentals
18
Popular accommodation
Chilmark private vacation homes
Known landmarks
Menemsha Beach, Lambert's Cove Beach and Lucy Vincent Beach
International airport
Vineyard Haven, MA (MVY-Martha's Vineyard)

Other types of properties in Chilmark you may be interested in

View from property
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
8.4 out of 10, Very Good, (18)
"Overall my friends and I have come twice to the Noyes house and are planning to come back next year. As long as you’re comfortable not staying near the main towns, it’s an ideal location - close to the markets and stores of west tisbury, several of the best beaches on the island (Lucy Vincent and Aquinnah in particular), the Chilmark general store, and some of the best farms like beetlebung. The house is something between rustic and luxury, which is deal for a group of friends. It’s not a big...
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Exterior
Sea Crest Beach Hotel
3.5 star property
7.8 out of 10, Good, (1000)
"Loved you front desk stafff"
The price is $118
$187 total
includes taxes & fees
May 2 - May 3
Sea Crest Beach Hotel
Shower, designer toiletries, hair dryer, bathrobes
Harbor View Hotel
5.0 star property
8.8 out of 10, Excellent, (942)
"We had a beautiful room in the old house with amazing views over the ocean. Very special."
The price is $395
$455 total
includes taxes & fees
May 2 - May 3
Harbor View Hotel
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.

Everything you need to know about Chilmark vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chilmark vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Chilmark vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chilmark vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chilmark. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chilmark in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $198 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chilmark rentals

At Expedia, we put the best Chilmark vacation 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 Chilmark 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 Chilmark vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chilmark. 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 vacation rentals in Chilmark?

Yes, there are vacation rentals in Chilmark near Chilmark Chocolates, or you can select a more secluded option if you're looking for extra privacy while you relax. Chilmark is known for its beaches and wineries. Make sure you have time to check out the festivals and local tours during your trip.

What are some of the best vacation rentals that Chilmark has to offer?

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks: This highly rated vacation home rental in Chilmark is located near the beach and has a patio, a selection of games, 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 Chilmark?

Choose from 70 Expedia vacation rentals in Chilmark for a memorable vacation.

What’s there to see and do in Chilmark?

Family-friendly attractions include Chilmark Chocolates and Menemsha Blues Charters, whereas Lucy Vincent Beach and Menemsha Beach are a couple of great spots to enjoy the outdoors. While here, Waskosim's Rock Reservation and Fulling Mill Brook Preserve are other places worth a visit.

What’s a vacation rental in Chilmark like?

A vacation rental is a private property where you can stay for a long or short time in Chilmark. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family getaway.

Recent reviews of Chilmark properties
Expedia verified reviews

Falmouth Tides

Falmouth Tides

5/5 Excellent
"Charming little hotel. The view is amazing and the rooms are nicely updated. Amazing bed also!"
A verified traveler from Manson stayed at Falmouth Tides
Posted 2 days ago
Falmouth Tides