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Chilmark Holiday Rentals

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Check prices for these dates

Tonight
26 Jul - 27 Jul
Tomorrow
27 Jul - 28 Jul
Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug

Holiday Rentals in Chilmark

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

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
Private beach nearby, beach bar

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
Indoor pool, outdoor pool, pool loungers

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (131)
"The rooms are spacious if somewhat dated. Good value. "
The price is HK$1,564
HK$1,790 total
includes taxes & fees
24 Aug - 25 Aug
Sea Mist Resort
Beachside Village Resort
Seasonal outdoor pool

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (95)
"The room is in excellent and clean condition, with easy access to the beach."
The price is HK$2,426
HK$2,776 total
includes taxes & fees
28 Jul - 29 Jul
Beachside Village Resort
InnSeason Resorts Captain's Quarters
On the beach, white sand

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

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"
Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Exterior

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

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 HK$911
HK$1,762 total
includes taxes & fees
27 Jul - 28 Jul
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
Terrace/patio

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

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

10.0 out of 10, Exceptional, (2)
"Just as described, the location of the property is surrounded by nature and lush with plants and animals. Lots of beautiful birds such as cardinals and blue jays. Perfect amount of space for 2 people. One of the best parts of the stay was the large walk in shower, and the robes provided were a perfect touch. Overall a very cozy and secluded getaway perfect for a long weekend. "
Relax & Unwind at this Adorable and very private 1 bedroom 1 bath studio
Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C
Outdoor dining

Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C

6.2 out of 10, (17)
"This property has not been well cared for or cleaned. Arrived to a very musty/moldy smell, trash outside, the walls were streaked with dead bug guts and then the stove didn't work!! It was a step above camping. You get what you pay for!"
Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C
Charming Seaside Cottage Central to the Beach and New Seabury Resort Community
TV

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

2.0 star property
9.2 out of 10, Wonderful, (7)
"Perfect cottage"
Charming Seaside Cottage Central to the Beach and New Seabury Resort Community
Southcape Resort Mashpee a Ramada by Wyndham
Exterior

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

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
Smart TV

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
Property grounds

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

5.6 out of 10, (22)
"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
Dining

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!
Terrace/patio

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

10.0 out of 10, Exceptional, (52)
"We had a wonderful stay! The place was clean, cute, and very conveniently located. Would definitely return!"
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
Fridge, microwave, oven, stovetop

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

8.8 out of 10, Excellent, (58)
"Location, plenty of towels"
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK
Coastal chic meets French Provençal in this newly renovated oceanfront home.
5 bedrooms, desk, iron/ironing board, travel cot

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.
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

Falmouth Tides

Falmouth Tides

10/10 Excellent
"Staff was amazing hidden gem "
Garth 1-night trip
Posted 16 hours ago
Falmouth Tides

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.