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Holiday Rentals in Chilmark

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Holiday Rentals in Chilmark

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
3.5 star property
9.8 out of 10, Exceptional, (187)
"Great location and helpful staff"
InnSeason Resorts Captain's Quarters
Coastal chic meets French Provençal in this newly renovated oceanfront home.
10.0 out of 10, Exceptional, (86)
"Great stay! "
The price is €1,176
includes taxes & fees
27 Oct - 28 Oct
Coastal chic meets French Provençal in this newly renovated oceanfront home.
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
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
Cozy getaway in a central location w/ a full kitchen & furnished deck
6.8 out of 10, (23)
"The furniture and amenities provided were good"
Cozy getaway in a central location w/ a full kitchen & furnished deck
Beachside Village Resort
3.0 star property
9.2 out of 10, Wonderful, (99)
"Great location! Nice property! "
Beachside Village Resort
Newly Renovated Near Amazing Sunset Beach
9.8 out of 10, Exceptional, (70)
"Amazing property for any trip to North Falmouth. We absolutely loved the location, outdoor shower, layout, and decks. Bill was incredibly responsive and an excellent host. "
Newly Renovated Near Amazing Sunset Beach
2 Acre Waterfront Home Overlooking Waquoit Bay with Spa and Swim Dock
10.0 out of 10, Exceptional, (18)
"Wonderful house, beach, large forested lot, and setting on the bluff just above picturesque Waquoit Bay. House is clean, updated, and very well equipped with many thoughtful amenities for guests. We especially enjoyed using the paddle boards and kayaks, spending time on the property’s beach below the bluff, having dinner on the outside deck overlooking the bay, and great sunsets. A family of osprey hovers nearby on updrafts as they hunt — truly memorable! The nearby area has many great sights...
2 Acre Waterfront Home Overlooking Waquoit Bay with Spa and Swim Dock
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 €440
includes taxes & fees
14 Oct - 15 Oct
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
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!
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
8.8 out of 10, Excellent, (33)
"The peaceful woodland setting is just beautiful! Enjoyed a quiet stay in this spacious one bedroom house. The porch wraps around entire house and gave our morning coffee and breakfast a very special vacation feel."
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
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!
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
14 Oct - 15 Oct
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
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
Classic Cape Cod - Ocean Views - Steps to Falmouth Heights Beach.
10.0 out of 10, Exceptional, (52)
"Beautiful home in a great location! "
Classic Cape Cod - Ocean Views - Steps to Falmouth Heights Beach.
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
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
Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach
2.0 star property
10.0 out of 10, Exceptional, (1)
"The location was great and the pullouts were comfortable. The only downside is the walk through bathroom."
Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach
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
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 Chilmark Hotel Reviews

Find out more about Chilmark

Everything you need to know about Chilmark 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 Chilmark 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 Chilmark holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chilmark holiday 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 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 Chilmark 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 Chilmark 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 Chilmark rentals

At Expedia, we put the best Chilmark 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 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 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 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 holiday rentals in Chilmark?

Yes, there are holiday rentals in Chilmark close to Chilmark Chocolates, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Chilmark has to offer?

Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub: This holiday home rental outside of Chilmark 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 Chilmark?

Choose from 75 Expedia holiday rentals in Chilmark for a memorable holiday.

What’s there to see and do in Chilmark?

Family-friendly attractions include Chilmark Chocolates and Fulling Mill Brook Preserve, whereas Menemsha Beach and Lucy Vincent Beach are a couple of great spots to enjoy the outdoors. While here, Chilmark Town Hall and Chilmark Public Library are other places worth a visit.

What’s a holiday rental in Chilmark like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chilmark. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a small group gathering.