A dock with boats, a small wooden structure, and a forested shoreline.

Search Resort Hotels in Chilmark from CA $128

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20
No exact matches found, but these alternatives could be just right

Recommended hotels in Chilmark

A bedroom with a bed, bedside tables, a chair, a table, and a view of the outdoors.

1. The Coonamessett

The Coonamessett
3.5 star property
Falmouth
8.8 out of 10, Excellent, (710 reviews)
"LOVE THIS PLACE!!!"
United States
Colleen
The price is CA $140
CA $160 total
includes taxes & fees
Nov 15 - Nov 16
The Coonamessett
A wooden deck with a white railing, a round table with chairs, and a view of the marina and town in the background.

2. Mansion House Inn And Spa

Mansion House Inn And Spa
3.5 star property
Vineyard Haven
9.4 out of 10, Exceptional, (1,000 reviews)
"Lovely place"
United States
Robyn
The price is CA $243
CA $292 total
includes taxes & fees
Nov 2 - Nov 3
Mansion House Inn And Spa
A covered outdoor area with a wooden deck, seating, and a view of the water.

3. Summercamp

Summercamp
3.5 star property
Oak Bluffs
9.4 out of 10, Exceptional, (1,003 reviews)
"Awesome spot. Loved our stay!"
United States
Adam
The price is CA $286
CA $327 total
includes taxes & fees
Oct 29 - Oct 30
Summercamp
A swimming pool with sun loungers and umbrellas, surrounded by large windows and wooden beams.

4. Inn on the Square

Inn on the Square
3.5 star property
Falmouth
8.8 out of 10, Excellent, (1,005 reviews)
"Perfect location"
United States
Molly
The price is CA $175
CA $235 total
includes taxes & fees
Nov 1 - Nov 2
Inn on the Square
A hotel entrance with a brick facade, a white porch, and a bench.

5. Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel
3.0 star property
Edgartown
8.4 out of 10, Very good, (643 reviews)
"Enjoyed our stay, quiet, convenient to everything in Edgartown!"
United States
Lisa
The price is CA $252
CA $284 total
includes taxes & fees
Nov 2 - Nov 3
Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel
A cozy living room with a stone fireplace, leather sofas, and a large window with blinds.

6. Iris Hotel Cape Cod

Iris Hotel Cape Cod
3.0 star property
Falmouth
8.4 out of 10, Very good, (431 reviews)
"Nice stay."
United States
Erin
The price is CA $173
CA $199 total
includes taxes & fees
Nov 23 - Nov 24
Iris Hotel Cape Cod
A patio area with two Adirondack chairs facing a view of the sea, a picnic table, and a tree.

7. Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach
2.5 star property
Vineyard Haven
9.0 out of 10, Wonderful, (833 reviews)
"Clean and had a nice beach access"
United States
Michael
The price is CA $246
CA $275 total
includes taxes & fees
Oct 26 - Oct 27
Vineyard Harbor Motel - Private Beach
A bedroom with a large bed, a view of the outdoors through sliding glass doors, and a balcony with a white railing.

8. Faraway Martha's Vineyard

Faraway Martha's Vineyard
4.0 star property
Edgartown
9.0 out of 10, Wonderful, (1,001 reviews)
"My stay was wonderful. The well-maintained and beautiful hotel had the best staff I’ve ever experienced!"
United States
Krystin
The price is CA $297
CA $348 total
includes taxes & fees
Nov 23 - Nov 24
Faraway Martha's Vineyard
A large, multi-story house with a covered porch and a well-maintained lawn.

9. Shore Haven Inn

Shore Haven Inn
3.0 star property
Falmouth
9.6 out of 10, Exceptional, (264 reviews)
"Beautiful place"
United States
Joseph Kyle
The price is CA $237
CA $278 total
includes taxes & fees
Oct 25 - Oct 26
Shore Haven Inn
A modern living room with a sofa, coffee table, and various decorative items.

10. AutoCamp Cape Cod

AutoCamp Cape Cod
4.0 star property
Falmouth
9.2 out of 10, Wonderful, (414 reviews)
"Great place to stay. Loved it."
United States
John
The price is CA $124
CA $198 total
includes taxes & fees
Oct 29 - Oct 30
AutoCamp Cape Cod
A two-story house with a brick pathway leading to the front door, surrounded by a well-maintained lawn and green Adirondack chairs.

11. The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard
2.0 star property
Edgartown
9.0 out of 10, Wonderful, (219 reviews)
"Great place to stay. Very nice and private room. We stayed in room 19 and it had a private patio with a kitchenette in our room. Place was easy to find and had plenty of parking. Would recommend again"
United States
Alex
The price is CA $255
CA $284 total
includes taxes & fees
Oct 25 - Oct 26
The Franklin Hotel Martha's Vineyard
A two-story house with a stone facade, a balcony, and a well-maintained garden.

12. Frederick William House

Frederick William House
3.5 star property
Falmouth
9.6 out of 10, Exceptional, (330 reviews)
"Loved the property and our room!"
United States
Kathy
The price is CA $222
CA $254 total
includes taxes & fees
Nov 2 - Nov 3
Frederick William House
A cozy living room with a fireplace, bookshelves, a dining area, and a staircase.

13. Madison Inn

Madison Inn
2.5 star property
Oak Bluffs
9.8 out of 10, Exceptional, (84 reviews)
"Good location, friendly staff. More breakfast/drink options would have been good."
United States
Melissa
The price is CA $284
CA $325 total
includes taxes & fees
Nov 4 - Nov 5
Madison Inn
A spacious living area with a dining table, sofas, and a view of the sea.

14. Harbor View Hotel

Harbor View Hotel
5.0 star property
Edgartown
8.8 out of 10, Excellent, (1,002 reviews)
"Top notch hotel!"
United States
Eryn
The price is CA $407
CA $491 total
includes taxes & fees
Nov 23 - Nov 24
Harbor View Hotel
A spacious living room with a sofa, chairs, a coffee table, and a staircase.

15. Morgan Hotel

Morgan Hotel
2.5 star property
Oak Bluffs
8.6 out of 10, Excellent, (273 reviews)
"Very well maintained and located close to shops and restaurants."
United States
Valerie
The price is CA $207
CA $236 total
includes taxes & fees
Oct 25 - Oct 26
Morgan Hotel
A compact hotel room with a kitchenette, a dining area with a yellow chair, a gray sofa with a red pillow, and a large mirror above the sink.

16. Hampton Inn by Hilton New Bedford/Fairhaven

Hampton Inn by Hilton New Bedford/Fairhaven
2.5 star property
Fairhaven
9.0 out of 10, Wonderful, (1,000 reviews)
"Great location very clean"
United States
Richard
The price is CA $115
CA $128 total
includes taxes & fees
Nov 22 - Nov 23
Hampton Inn by Hilton New Bedford/Fairhaven
A wooden fence with a 'WELCOME' sign, two blue wicker chairs with cushions, a small table with a potted plant, and flowers.

17. Town & Beach Motel

Town & Beach Motel
2.0 star property
Falmouth
9.0 out of 10, Wonderful, (592 reviews)
"Great location and very cute room!"
United States
Theresa
The price is CA $175
CA $200 total
includes taxes & fees
Oct 25 - Oct 26
Town & Beach Motel
A hotel room with a large bed, a chair, a window with curtains, a wall-mounted picture, and a hanging light fixture.

18. The Sydney, The Edgartown Collection

The Sydney, The Edgartown Collection
3.5 star property
Edgartown
9.6 out of 10, Exceptional, (217 reviews)
"Clean, comfortable and great location! The staff was very nice and breakfast was excellent. We highly recommend this boutique hotel to anyone!"
United States
richard
The price is CA $511
CA $571 total
includes taxes & fees
Oct 24 - Oct 25
The Sydney, The Edgartown Collection
A multi-story hotel with a grand entrance, a flagpole, and a well-lit facade.

19. Vineyard Square Hotel & Suites

Vineyard Square Hotel & Suites
4.0 star property
Edgartown
9.2 out of 10, Wonderful, (335 reviews)
"Incredible stay. Staff was wonderful, very kind."
United States
Austin
The price is CA $385
CA $430 total
includes taxes & fees
Oct 25 - Oct 26
Vineyard Square Hotel & Suites
A dining area with multiple tables and chairs, a kitchen area with appliances, and a television displaying a logo.

20. Admiralty Inn & Suites - a Red Collection Hotel

Admiralty Inn & Suites - a Red Collection Hotel
3.0 star property
East Falmouth
8.6 out of 10, Excellent, (568 reviews)
"Great cheap place to stay. Breakfast was good"
United States
Maryrose
The price is CA $168
CA $209 total
includes taxes & fees
Nov 1 - Nov 2
Admiralty Inn & Suites - a Red Collection 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chilmark Hotel Reviews

Admiralty Inn & Suites - a Red Collection Hotel

Admiralty Inn & Suites - a Red Collection Hotel

8/10 Good
"Could be a little updated. Was mostly clean. Pool was closed. Did have tables outside but in the courtyard so in the evening when people were out there were disturbing the rooms around it. Perhaps there could be another area to hang out at night away from the rooms."
Michele 2-night trip
Posted 3 hours ago
Admiralty Inn & Suites - a Red Collection Hotel

Find out more about Chilmark

Chilmark Resorts information

Number of reviews
4,700
Accommodation
2 Resorts
Lowest Price
CA $128
Highest Price
CA $571

Frequently asked questions

What is Chilmark like for a resort vacation?
You deserve some time off, and a resort is just the place to find all the amenities and services you need for a relaxing stay in Chilmark. One of the comfortable resort hotels in the area might be just what you're looking for, whether you're hoping for great restaurants on site, shopping possibilities, or fun activities to try.
What's a favorite resort for my stay in Chilmark?
Our highest-rated resort near Chilmark: The Island Inn on Martha's Vineyard - Golf resort. 11.8 mi (19 km) from Chilmark. Features a seasonal outdoor pool, 3 outdoor tennis courts, and a beach shuttle.
What can I do in Chilmark?
For some time by the water, you can head to Menemsha Beach and Stonewall Beach. For more to see in the area, you can spend time at Chilmark Town Hall or Chilmark Public Library.
What's the weather like in Chilmark?
The hottest months are usually August and July with an average temp of 68°F, while the coldest months are February and January with an average of 38°F. Average annual precipitation for Chilmark is 50 inches.
What's the best way to get to and around Chilmark?
Fly into Vineyard Haven, MA (MVY-Martha's Vineyard), which is located 7.6 mi (12.2 km) from the city center. Otherwise, you can search for flights to New Bedford, MA (EWB-New Bedford Regional), which is 25.4 mi (40.8 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

Explore a world of travel with Expedia