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Chilmark Holiday Rentals

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Holiday Rentals in Chilmark

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

10.0 out of 10, Exceptional, (50)
"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.

Water-view home in great location with spacious backyard, grill, kayaks, dogs OK

8.0 out of 10, Very good, (3)
"This small house provided a big relief in our trip. Located steps from the best lobster roll in town and about a block from the water, this is a FANTASTIC spot for getting away."
Water-view home in great location with spacious backyard, grill, kayaks, dogs OK

Cozy efficiency apartment/heated pool

9.8 out of 10, Exceptional, (17)
"This is a great property for an individual or a couple looking to explore the island!"
Cozy efficiency apartment/heated pool

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (324)
"A great unique and quiet place, very close to Boston."
The Club at New Seabury

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (124)
"Great place just had another family staying above our room that was very noisy the last night we were there"
The price is NZ$437
includes taxes & fees
7 July - 8 July
Sea Mist Resort

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (173)
"Excellent location! Close to the Ferry and downtown !"
InnSeason Resorts Captain's Quarters

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (93)
"Wonderful location, nice staff!"
Beachside Village Resort

Charming Seaside Cottage Central to the Beach and New Seabury Resort Community

2.0 star property
9.4 out of 10, Exceptional, (6)
"Perfect cottage"
Charming Seaside Cottage Central to the Beach and New Seabury Resort Community

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

9.6 out of 10, Exceptional, (78)
"Close to buses, restaurants and ferries. 10/10, we would stay again."
The price is NZ$1,154
includes taxes & fees
1 July - 2 July
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Maushop Property - First Time Available

10.0 out of 10, Exceptional, (38)
"We had a great time at this little cottage! It’s perfect for a few days or a week stay! The house was clean, perfect location for beach walks or shopping at the commons!"
Maushop Property - First Time Available

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

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

Spacious colonial home close to town with AC, porches, & W/D

Spacious colonial home close to town with AC, porches, & W/D

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

10.0 out of 10, Exceptional, (85)
"Great stay! "
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Your Oasis Awaits

9.8 out of 10, Exceptional, (38)
"We had a great stay. Nice and close to the beach so my mid 80’s mom could even walk back and forth. and the raw bar on property was the perfect place for an easy meal. Would happily stay again."
Your Oasis Awaits

New Seabury home, spacious deck & outdoor shower

8.8 out of 10, Excellent, (10)
"The house was nestled in a wooded area which lends itself to a peaceful and relaxing stay. Each room was decorated nicely which made it very comfortable and We were centrally located near stores for shopping and good restaurants. The setting and home was a cozy and pleasant two day get away for us "
New Seabury home, spacious deck & outdoor shower

Cozy 1 Queen Bed Escape Near Beach & Fun

10.0 out of 10, Exceptional, (1)
"Great stay!"
The price is NZ$412
includes taxes & fees
9 July - 10 July
Cozy 1 Queen Bed Escape Near Beach & Fun

Historic Oak Bluffs home, short walk to town, beach, and harbor.

9.6 out of 10, Exceptional, (30)
"We enjoy it all. "
Historic Oak Bluffs home, short walk to town, beach, and harbor.

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

9.6 out of 10, Exceptional, (64)
"Clean property, great location"
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace

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

28 Parsons- New Listing! 5-Bedroom home in charming East Falmouth, pet-friendly!

28 Parsons- New Listing! 5-Bedroom home in charming East Falmouth, pet-friendly!
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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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?

Water-view home in great location with spacious backyard, grill, kayaks, dogs OK: This highly rated holiday home rental in Chilmark offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Chilmark?

Choose from 68 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.