Photo by Wen C.

Holiday Rentals in Chilmark

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Chilmark

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

10.0 out of 10, Exceptional, (51)
"We were in town for a wedding in Chilmark and the property was exactly what we needed!"
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (325)
"Great stay! Didn't notice it being dated or dirty at all like some reviews said. We loved it!"
The Club at New Seabury

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (133)
"Great resort with suites, very cosy with great amenities, close to excellent beach and shopping."
The price is €244
includes taxes & fees
24 Aug - 25 Aug
Sea Mist Resort

Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..

8.6 out of 10, Excellent, (39)
"Great place for a summer vacation"
The price is €723
includes taxes & fees
8 Aug - 9 Aug
Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (174)
"Excellent location! Close to the Ferry and downtown !"
InnSeason Resorts Captain's Quarters

Beachside Village Resort

3.0 star property
9.4 out of 10, Exceptional, (96)
"Great location! Nice property! "
Beachside Village Resort

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

6.0 out of 10, (22)
"There were times when the shower in the master bathroom only emitted cold water. The water spigot in the tubs would not turn completely off in bathroom in the hallway. I had trouble with the lockbox. Maybe add more specific directions. It would have been helpful to know that MV transit bus was available at the intersection of the street and County Road."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Southcape Resort Mashpee a Ramada by Wyndham

3.0 star property
8.6 out of 10, Excellent, (200)
"Enjoyed our stay."
Southcape Resort Mashpee a Ramada by Wyndham

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

8.8 out of 10, Excellent, (33)
"Great spot for a get away. Private with easy access to activities."
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

Coastal chic meets French Provençal in this newly renovated oceanfront home.

10.0 out of 10, Exceptional, (85)
"Great stay! "
The price is €3,890
includes taxes & fees
16 Aug - 17 Aug
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

8.4 out of 10, Very good, (20)
"So turn key and perfect for Month, Joy is an exceptional host and I’d recommend her place anytime"
The price is €199
includes taxes & fees
4 Aug - 5 Aug
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

Renovated 1-bedroom apartment in Downtown Falmouth Located Right on Main Street

2.0 star property
10.0 out of 10, Exceptional, (1)
"I would 100% recommend this apartment! My friends and I had the best experience. The host was so friendly and made himself available for us via text and in person whenever we needed. The listing aligns perfectly with the actual apartment. The apartment was extremely clean and shampoo conditioner etc were provided for us as well as extra bedding. The building is super easy to access with the instructions provided and the location is amazing as it is right on Main Street in Falmouth! Overall we...
Renovated 1-bedroom apartment in Downtown Falmouth Located Right on Main Street

Relax & Unwind at this Adorable and very private 1 bedroom 1 bath studio

10.0 out of 10, Exceptional, (4)
"A very nice stay. Relaxing and quiet - we would highly recommend!"
Relax & Unwind at this Adorable and very private 1 bedroom 1 bath studio

Water Front DREAM vacation, whole house AC, Free wi-fi, linen&towels, fire pit,

9.6 out of 10, Exceptional, (65)
"Nice house in a beautiful peaceful setting."
Water Front DREAM vacation, whole house AC, Free wi-fi, linen&towels, fire pit,

Charming 3-bedroom house with a pool, AC, WiFi in pleasant East Falmouth

9.4 out of 10, Exceptional, (3)
"Really beautiful place with a lot of space and a very helpful host"
Charming 3-bedroom house with a pool, AC, WiFi in pleasant East Falmouth

Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach

5.6 out of 10, (24)
"Great location and private beach access. Charming enclave perfect for our weekend getaway."
Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach

Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace

9.6 out of 10, Exceptional, (68)
"Clean property, great location"
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!

10.0 out of 10, Exceptional, (53)
"This was my boyfriends 45th birthday weekend. We both have never been to Martha's Vineyard and we love taking adventures. Mike was a wonderful host with a beautiful property. The property is close to shops and food. The buses are close and will take you all over. Thank you Mike for being a great host."
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!

Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK

8.8 out of 10, Excellent, (60)
"Location, plenty of towels"
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK

Breathtaking Views with Private Dock & Pool!

9.2 out of 10, Wonderful, (24)
"Great location!! Awesome stay"
Breathtaking Views with Private Dock & Pool!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chilmark Hotel Reviews

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?

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.: This highly rated holiday home rental in Chilmark is located on the waterfront, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Chilmark?

Choose from 74 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.