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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

Compare Cottages in Chilmark with updated reviews, rates, and availability.

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Property grounds

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

8.6 out of 10, Excellent, (79)
"Great location but the place was dirty. Need a better cleaning service. "
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Oceanside Cottage with Private Beach
Terrace/patio

Oceanside Cottage with Private Beach

10.0 out of 10, Exceptional, (3)
"Excellent sea view and very quiet place"
Oceanside Cottage with Private Beach
Cape Cod Cottage steps from Private Beach
TV

Cape Cod Cottage steps from Private Beach

10.0 out of 10, Exceptional, (32)
"Property was great. Small but we were out a lot. Great location and ownner was very helpful and responsive"
Cape Cod Cottage steps from Private Beach
Fully renovated 4-bedroom in private community with pool & close to beach
Pool

Fully renovated 4-bedroom in private community with pool & close to beach

10.0 out of 10, Exceptional, (4)
"What a house and what a recent remodel. Kristen and the accommodations were exceptional. "
Fully renovated 4-bedroom in private community with pool & close to beach
Cozy Beach Cottage
Beach nearby, sun loungers, beach towels

Cozy Beach Cottage

10.0 out of 10, Exceptional, (41)
"We (a party of 3 lifelong friends!) loved this little tucked away cottage. Despite the bad weather cards we were dealt with, (a lot of rain and wind) we easily walked to the Campground and marvelled at the uniqueness of the gingerbread cottages and found some good rainy day hang-out's that I wasn't aware of (especially loved Behind The Bookstore & ventured out on a little bit on a rainy night to listen to live music at Nonan's) The check-in was super easy and we took advantage of the outdoor...
Cozy Beach Cottage
Tranquil Island Retreat, Cozy Seclusion, Beach Access Nearby!
Sun loungers, beach towels

Tranquil Island Retreat, Cozy Seclusion, Beach Access Nearby!

9.8 out of 10, Exceptional, (17)
"We had a nice stay at the cottage. The cottage itself was a little bit more rustic than we had anticipated based on photos and description, but worked for us. It’s in a nice setting in the woods that offers a decent amount of privacy, the trade off being it’s at least a 15 min drive to most places of interest. The lofted bedroom area was nice but may be difficult for those with little ones as the sound carries from the downstairs and there is no door to close. There was also no curtain on the...
Tranquil Island Retreat, Cozy Seclusion, Beach Access Nearby!
Martha's Vineyard 3BR, Pets Ok, 10 Min Walk to Beach or Shops!

Martha's Vineyard 3BR, Pets Ok, 10 Min Walk to Beach or Shops!

9.6 out of 10, Exceptional, (68)
"Was exactly what I expected for our stay on the Island. I grew up on Cape Cod and looking forward to a cozy cottage on the island. The property mgr also lives on the property but I only saw her once when I communicated that the coffee maker broke and was promptly replaced with a new one. Short drive or pleasant walk to downtown Edgartown with its restaurants and shops. Love the outside shower. Was there in September so the beaches are everywhere. Great farms on the island so it's easy and fun...
Martha's Vineyard 3BR, Pets Ok, 10 Min Walk to Beach or Shops!
Chappy cottage with private beach
Fridge, microwave, oven, stovetop

Chappy cottage with private beach

10.0 out of 10, Exceptional, (14)
"This cottage was the perfect little getaway for our family to base our first visit on Chappy. We loved being able to walk to the beach and appreciated the cleanliness of the cottage as well as its charm. "
Chappy cottage with private beach
12 VINEYARD VIEW - FULLY RENOVATED
Property grounds

12 VINEYARD VIEW - FULLY RENOVATED

9.6 out of 10, Exceptional, (40)
"We had such an amazing time staying here! The location is perfect and has amazing ocean views right from the house. Everything was super clean and well maintained. We will definitely be coming back! "
12 VINEYARD VIEW - FULLY RENOVATED
One Bedroom Private Cottage on Large Quiet Property.
TV

One Bedroom Private Cottage on Large Quiet Property.

9.6 out of 10, Exceptional, (4)
"I kind of don't want to leave a good review because it will likely result in this property becoming too hard to book. jk. Seriously, everything about my experience was beyond excellent from the booking process to meeting the owners. The pictures honestly do not do it justice. It is a beautiful cottage that is far enough away from the main house to give you all the privacy one may need/want. It is in walking distance to the Vineyard Haven ferry dock and the retail in that area. The owners were...
One Bedroom Private Cottage on Large Quiet Property.
Cozy Family Cottage Circuit Ave OB Walk to Everything
Terrace/patio

Cozy Family Cottage Circuit Ave OB Walk to Everything

2.0 star property
Cozy Family Cottage Circuit Ave OB Walk to Everything
Cozy New TimberFrame Vineyard Haven!
Exterior

Cozy New TimberFrame Vineyard Haven!

10.0 out of 10, Exceptional, (19)
"As advertised. Photos are accurate, as is description. Short walk to town/supermarket, cafes and more. Accommodations are clean, well-kept, and basically brand new. Thanks! Brett Star"
Cozy New TimberFrame Vineyard Haven!
Charming/CozyBeachCottage-Please note rental details prior to booking. Thank You
Beach nearby, sun loungers

Charming/CozyBeachCottage-Please note rental details prior to booking. Thank You

9.8 out of 10, Exceptional, (19)
"Cozy little cottage on the beach lots of memories from my husband’s childhood. Lovely stay."
Charming/CozyBeachCottage-Please note rental details prior to booking. Thank You
Chappy Summer Cabin!
Interior

Chappy Summer Cabin!

8.2 out of 10, Very Good, (33)
"Great host , amazing property "
Chappy Summer Cabin!
2-bdrm Cottage | Close to Everything | Pet Friendly
Exterior

2-bdrm Cottage | Close to Everything | Pet Friendly

9.8 out of 10, Exceptional, (9)
"Beautiful cottage, very clean and comfortable. Very peaceful and quiet! Weather wasn't the best for sitting outside to enjoy nature, but it was beautiful nonetheless. Bonnie is an excellent host! We definitely will return!"
2-bdrm Cottage | Close to Everything | Pet Friendly
3 Bedroom Cottage just steps to Private Beach! Pet Friendly!
Beach nearby, sun loungers, beach umbrellas, beach towels

3 Bedroom Cottage just steps to Private Beach! Pet Friendly!

9.6 out of 10, Exceptional, (38)
"We had an awesome time at the cottage. It’s a quick walk to the neighborhood beach that is very clean. Beautiful area and the neighbors always smiled and waved as we went by. The house was fully equipped and had everything we needed and more and was clean. We only had to buy food- all soaps and supplies were provided which was nice. The owners Matt and Carly were very responsive and friendly and gave us some great recommendations for food (Turk’s is a must!) and activities. "
3 Bedroom Cottage just steps to Private Beach! Pet Friendly!
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Terrace/patio

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

10.0 out of 10, Exceptional, (16)
"Warm and inviting property. Everything was perfect, from the solar lights on the patio to the fireplace in the living area. We enjoyed a walk to dinner. Walked to Carboat for coffee in the morning. Fun visit to Martha’s Vineyard and a pleasant stay in this house !"
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
★The Islander | Steps From Water, Fire Pit, AC★
Terrace/patio

★The Islander | Steps From Water, Fire Pit, AC★

10.0 out of 10, Exceptional, (44)
"I was travelling with my 3 sisters from Canada heading towards Martha's Vineyard for a sister's reunion. We all appreciated the cleanliness and the attention to detail. The space was well appointed. The fridge ice maker did not work well so having some ice cube trays would have been helpful. I highly recommend The Islander."
★The Islander | Steps From Water, Fire Pit, AC★
Cozy, clean, relaxing beach cottage awaits you!!
On the beach, sun loungers, beach towels

Cozy, clean, relaxing beach cottage awaits you!!

10.0 out of 10, Exceptional, (34)
"Dominant house in photo is not rental. House obsequred by tree is the rental. Not enough hanging space. Single room in left house is part of rental."
Cozy, clean, relaxing beach cottage awaits you!!
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

6.2 out of 10, (17)
"We did not stay. Place was a dump No one has called us We are not paying It is illegal not to have carbon / smoke detectors We went to condos at new seabury"
Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach
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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Other property types in Chilmark

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
2 bedrooms, iron/ironing board, internet, bed sheets

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

8.8 out of 10, Excellent, (9)
"We had such a lovely time staying at this house. It was absolutely immaculate inside and appointed with everything we could need and more. The house is light and airy inside, which helped when we had a few days of rain. The location is secluded in the woods (be careful, we did find ticks on us) but a short drive away from the beaches. We will definitely be back "
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
The Club at New Seabury
Seasonal outdoor pool, cabanas (surcharge), pool umbrellas

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (313)
"accommodation was good but cleanliness could have been better. Not bad but some areas needed more attention. Good restaurant and bar service on Thursday. No restaurant available on Saturday."
The price is AED 590
AED 675 total
includes taxes & fees
12 Mar - 13 Mar
The Club at New Seabury
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, (160)
"The rooms where very clean and well taken care of."
The price is AED 431
AED 493 total
includes taxes & fees
9 Mar - 10 Mar
InnSeason Resorts Captain's Quarters
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.

Frequently asked questions

How much do cottages in Chilmark cost?
You can expect to pay between and per night for cottages in Chilmark. No matter your budget, a fantastic stay is just a click or two away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Chilmark with Expedia?
We think that vacations should be a walk in the park, so if you’re searching for cottages in Chilmark at an affordable price, Expedia can help. Keep the budget under control and pick a low-cost option far away from the city rush, or book a 5-star cottage to treat your loved ones.
How can I find cheap cottages in Chilmark?
With Expedia’s filter tool, sourcing cheap cottages in Chilmark is a snap. To find properties that’ll make your wallet smile, narrow down your search by star rating, budget and amenities.