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Our top choices for Chilmark cottages
1. Charming cottage overlooking the bay in Padanaram Village.
Charming cottage overlooking the bay in Padanaram Village.Dartmouth
10.0 out of 10, Exceptional, (17 reviews)
10/10
Exceptional
(17 reviews)
"Place was very cute, nicely decorated and updated. Views were beautiful from the deck! Mattress in the bedroom was uncomfortable dipping in the center so we kept rolling into the middle."
"Place was very cute, nicely decorated and updated. Views were beautiful from the deck! Mattress in the bedroom was uncomfortable dipping in the center so we kept rolling into the middle."
Gretchen M.
$466 nightly
The price is $521
$521 total
Nov 24 - Nov 25
Total with taxes and fees
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.
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.
Learn more about Chilmark
Menemsha Beach offers spectacular sunsets where locals and visitors gather with picnic dinners to watch the sky change colors. Hike the scenic trails at Waskosim's Rock Reservation or visit nearby Martha's Vineyard for charming shops and restaurants.
Top reviews in Chilmark
The Coonamessett
The CoonamessettFalmouth
10/10 Excellent
Gorgeous property right out of the gate from the area where you enter and check-in merging with the space to sit by the fireplace then the beautiful, rustic tavern and stunning event space in addition to the lovely, updated and spacious room just yards away for our overnight stay! Very friendly and kind staff as well!
Could not be more impressed and pleased with our stay. Perfect balance of rustic, old Cape Cod charm and modern amenities. Superb!
Gorgeous property right out of the gate from the area where you enter and check-in merging with the space to sit by the fireplace then the beautiful, rustic tavern and stunning event space in addition to the lovely, updated and spacious room just yards away for our overnight stay! Very friendly and kind staff as well!
Could not be more impressed and pleased with our stay. Perfect balance of rustic, old Cape Cod charm and modern amenities. Superb!
Holly
Madison Inn
Madison InnOak Bluffs
10/10 Excellent
My boyfriend and I had the best overnight at the Madison Inn. The room that we booked was small, but still so comfortable and cute and it was in a really convenient location in the center of Oak Bluffs. Staff was so friendly and awesome. Amazing amenities. Def recommending this place to all of my friends! Looking forward to staying again.
My boyfriend and I had the best overnight at the Madison Inn. The room that we booked was small, but still so comfortable and cute and it was in a really convenient location in the center of Oak Bluffs. Staff was so friendly and awesome. Amazing amenities. Def recommending this place to all of my friends! Looking forward to staying again.
Anonymous traveler
Shore Haven Inn
Shore Haven InnFalmouth
10/10 Excellent
I had a wonderful stay at the beach breeze inn. I highly recommend this property and will stay here again in the future.
I had a wonderful stay at the beach breeze inn. I highly recommend this property and will stay here again in the future.
Nicole
Frederick William House
Frederick William HouseFalmouth
10/10 Excellent
My friend and I spent 4 nights in this beautiful bed and breakfast. The property is conveniently located on Route 28 in Falmouth. Not only is the house on a bike trail, but you are allowed to use the bikes for free, even to take to the Vinyard, a 40 minute ride by ferry. We went over twice using the Queen Authority first from Falmouth and the Steamship Authority from Woods Hole the next. The Steamship was cheaper and better. But there are really nice beaches nearby. Woods Hole is nearby where...
My friend and I spent 4 nights in this beautiful bed and breakfast. The property is conveniently located on Route 28 in Falmouth. Not only is the house on a bike trail, but you are allowed to use the bikes for free, even to take to the Vinyard, a 40 minute ride by ferry. We went over twice using the Queen Authority first from Falmouth and the Steamship Authority from Woods Hole the next. The Steamship was cheaper and better. But there are really nice beaches nearby. Woods Hole is nearby where...
Elm
Faraway Martha's Vineyard
Faraway Martha's VineyardEdgartown
10/10 Excellent
Easily within walking distance of everything. All staff were very pleasant & helpful.
Easily within walking distance of everything. All staff were very pleasant & helpful.
Cathy
Vineyard Harbor Motel - Private Beach
Vineyard Harbor Motel - Private BeachVineyard Haven
10/10 Excellent
Location, cleanliness, beachfront!
Location, cleanliness, beachfront!
Martina
The Franklin Hotel Martha's Vineyard
The Franklin Hotel Martha's VineyardEdgartown
10/10 Excellent
Fresh, clean, fun, and comfortable! Easy to access- we had two rooms - bathrooms are cute! Bedrooms nice and beds comfy, living area and kitchenette downstairs very charming! Sat outside as well.
Fresh, clean, fun, and comfortable! Easy to access- we had two rooms - bathrooms are cute! Bedrooms nice and beds comfy, living area and kitchenette downstairs very charming! Sat outside as well.
Kathryn
Delano Homestead Bed & Breakfast
Delano Homestead Bed & BreakfastFairhaven
10/10 Excellent
Liz is a fantastic host! The breakfasts were great (ask for her French toast). Neat neighborhood house full of history. I’d go back in a hot heartbeat
Liz is a fantastic host! The breakfasts were great (ask for her French toast). Neat neighborhood house full of history. I’d go back in a hot heartbeat
Bob
The Lightkeepers Inn
The Lightkeepers InnEdgartown
10/10 Excellent
We had a great stay!! The rooms were so cozy and the location is perfect. The lighthouse is so close by! Great dinning near by! Can't wait to go back!!
We had a great stay!! The rooms were so cozy and the location is perfect. The lighthouse is so close by! Great dinning near by! Can't wait to go back!!
Anonymous traveler
The Palmer House Inn
The Palmer House InnFalmouth
10/10 Excellent
My husband and I loved our stay at the antiques-filled Palmer House Inn. We were able to easily walk to the active Main Street and had our choice of excellent restaurants and gift shops to browse. We also walked to the beach (mostly sandy, but with many sharp rocks as you enter the water), rented bikes and rode to a lighthouse, and enjoyed the delicious breakfasts while sitting on the porch in the cooler weather. I would definitely recommend this property to anyone heading to Cape Cod.
My husband and I loved our stay at the antiques-filled Palmer House Inn. We were able to easily walk to the active Main Street and had our choice of excellent restaurants and gift shops to browse. We also walked to the beach (mostly sandy, but with many sharp rocks as you enter the water), rented bikes and rode to a lighthouse, and enjoyed the delicious breakfasts while sitting on the porch in the cooler weather. I would definitely recommend this property to anyone heading to Cape Cod.
Lori
Falmouth Tides
Falmouth TidesFalmouth Heights
10/10 Excellent
Place was amazing, downstairs rooms very close to the water, everything looks brand new, bathroom was kind of small but again, so many great things compensate all.
Place was amazing, downstairs rooms very close to the water, everything looks brand new, bathroom was kind of small but again, so many great things compensate all.
Luiz
Red Horse Inn
Red Horse InnFalmouth Heights
10/10 Excellent
What the large chains are taking away is just what this Inn does in spades - lots of thoughtful little extras that make your stay enjoyable - A warm welcome from owner's who care - not just complimentary toiletries, but cloth napkins at a generous breakfast display even fresh homemade muffins!! Very clean, pleasantly decorated room and comfortable bed. We will definitely book here again.
What the large chains are taking away is just what this Inn does in spades - lots of thoughtful little extras that make your stay enjoyable - A warm welcome from owner's who care - not just complimentary toiletries, but cloth napkins at a generous breakfast display even fresh homemade muffins!! Very clean, pleasantly decorated room and comfortable bed. We will definitely book here again.
Meredith
Inn on the Square
Inn on the SquareFalmouth
10/10 Excellent
Hotel was good overall and staff was excellent. However, I was disappointed that I had to pay $48 at checki-in for water, parking and WIFI when parking was all I wanted.
Hotel was good overall and staff was excellent. However, I was disappointed that I had to pay $48 at checki-in for water, parking and WIFI when parking was all I wanted.
Andrew
Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel
Edgar Hotel Martha's Vineyard, an Ascend Collection HotelEdgartown
10/10 Excellent
Asked for an early check-in . . . .Got it!!
A varied selection for breakfast . . . Got it!! It was wonderful. It had everything anyone would want, including yogurt and nutrition bars and pancakes for the kids.
Comfortablle beds .... Got it!!
Clean, well lighted bathrooms . . . Got it!!!
Reasonable prices . . . Got it!!!
Friendly staff . . . Got it!!!!
Asked for an early check-in . . . .Got it!!
A varied selection for breakfast . . . Got it!! It was wonderful. It had everything anyone would want, including yogurt and nutrition bars and pancakes for the kids.
Comfortablle beds .... Got it!!
Clean, well lighted bathrooms . . . Got it!!!
Reasonable prices . . . Got it!!!
Friendly staff . . . Got it!!!!
"M"
The Club at New Seabury
The Club at New SeaburyNew Seabury
10/10 Excellent
Perfect little cottage!
Perfect little cottage!
Elizabeth
Inn on the Sound
Inn on the SoundFalmouth Heights
10/10 Excellent
Wonderful stay everything was perfect! Room with all the little touch’s . Lovely made to order breakfast in the morning, delicious cupcakes for an afternoon treat and cookies for a late night snack. Very quiet peaceful Inn overlooking looking the water. Attentive host highly enjoyed or stay!
Wonderful stay everything was perfect! Room with all the little touch’s . Lovely made to order breakfast in the morning, delicious cupcakes for an afternoon treat and cookies for a late night snack. Very quiet peaceful Inn overlooking looking the water. Attentive host highly enjoyed or stay!
Lisa
Frequently Asked Questions
How much do cottages in Chilmark cost?
You can expect to pay between $520 and $520 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?
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What is there to do in Chilmark near my cottage?
Whatever you're interested in, Chilmark has lots of things to keep you entertained. Menemsha Beach, Lucy Vincent Beach and The Yard are on many visitors' trip plans. Don't forget about Chilmark Chocolates, Waskosim's Rock Reservation and Fulling Mill Brook Preserve either. With Expedia's hotel deals in Chilmark, you'll be able to discover more neat attractions like these with the money you save.