Title: Chilmark Vacation Rentals from CA $202: Short-Term Rentals for 2026 | Expedia.ca

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![Chilmark Shellfish Department on Martha’s Vineyard](https://images.trvl-media.com/place/6135676/824050a0-a336-4250-9bcd-66c115369156.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6135676/824050a0-a336-4250-9bcd-66c115369156.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chilmark vacation rentals

![Meeting facility](https://images.trvl-media.com/lodging/12000000/11630000/11621700/11621632/d67fc379.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/12000000/11630000/11621700/11621632/481dceb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/12000000/11630000/11621700/11621632/f0ed7d64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/12000000/11630000/11621700/11621632/c3910e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Club at New Seabury

[](https://www.expedia.ca/Mashpee-Hotels-The-Club-At-New-Seabury.h11621632.Hotel-Information)

New Seabury

9.0/10

Wonderful

(349 reviews)

"Everything was superb, accommodations, check in service, check out service!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dianna

CA $190

CA $217 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Mashpee-Hotels-The-Club-At-New-Seabury.h11621632.Hotel-Information)

![On the beach, white sand](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154022/7380dc13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154022/23bd3a84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154022/fcdb2776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154022/fa5d1d1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### InnSeason Resorts Captain's Quarters

[](https://www.expedia.ca/Falmouth-Hotels-InnSeason-Resorts-Captains-Quarters.h1154022.Hotel-Information)

Falmouth Heights

9.8/10

Exceptional

(197 reviews)

"This is my go to hotel when I’m in Falmouth. Always clean and the staff are very friendly. The one bedroom units are very nice!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeff

CA $177

CA $202 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Falmouth-Hotels-InnSeason-Resorts-Captains-Quarters.h1154022.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/76000000/75220000/75212700/75212637/e14f844a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/76000000/75220000/75212700/75212637/980cb8d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/76000000/75220000/75212700/75212637/4de6a35c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/76000000/75220000/75212700/75212637/c41c3a39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette

[](https://www.expedia.ca/North-Falmouth-Hotels-Near-Old-Silver-Beach-Falmouth-Private-Entrance.h75212637.Hotel-Information)

Falmouth

8.2/10

Very good

(24 reviews)

"Wonderful stay, had everything we needed, Joy was very receptive to our messages. Thanks so much!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alex K.

CA $134

CA $271 total

includes taxes & fees

Feb 28 - Mar 1

[](https://www.expedia.ca/North-Falmouth-Hotels-Near-Old-Silver-Beach-Falmouth-Private-Entrance.h75212637.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/28000000/27120000/27117800/27117723/37e0972d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, beach towels](https://images.trvl-media.com/lodging/28000000/27120000/27117800/27117723/1d390dbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/28000000/27120000/27117800/27117723/b17fdba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27120000/27117800/27117723/925f539a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Mashpee-Hotels-Charming-Beach-Cottage.h27117723.Hotel-Information)

New Seabury

8.6/10

Excellent

(91 reviews)

"Property needs a refresh."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Paul B.

CA $410

CA $840 total

includes taxes & fees

Feb 28 - Mar 1

[](https://www.expedia.ca/Mashpee-Hotels-Charming-Beach-Cottage.h27117723.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/108000000/108000000/107997300/107997278/7f904b5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/108000000/108000000/107997300/107997278/da383bf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/108000000/108000000/107997300/107997278/70923cac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/108000000/107997300/107997278/ad29049f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming cottage overlooking the bay in Padanaram Village. 

[](https://www.expedia.ca/South-Dartmouth-Hotels-Charming-Cottage-Overlooking-The-Bay-In-Padanaram-Village.h107997278.Hotel-Information)

Dartmouth

10/10

Exceptional

(11 reviews)

"Beautiful cottage ! Immaculately kept! Sunsets at night were amazing to watch. Very comfortable and inviting home. Definitely recommend a nice stay ! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

ralpjh c.

CA $338

CA $595 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/South-Dartmouth-Hotels-Charming-Cottage-Overlooking-The-Bay-In-Padanaram-Village.h107997278.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/119000000/118960000/118951300/118951248/4dca0890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118960000/118951300/118951248/e304be6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/119000000/118960000/118951300/118951248/w1170h878x0y827-cecc0426.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/119000000/118960000/118951300/118951248/e3989985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Falmouth Oasis

[](https://www.expedia.ca/East-Falmouth-Hotels-Falmouth-Oasis.h118951248.Hotel-Information)

Falmouth

CA $197

CA $614 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/East-Falmouth-Hotels-Falmouth-Oasis.h118951248.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102450000/102447400/102447329/612cae04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102447400/102447329/289f35a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102450000/102447400/102447329/251d715a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102450000/102447400/102447329/c8de4671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spring Escape in Hatchville – Sleeps 6 + Dogs!

[](https://www.expedia.ca/East-Falmouth-Hotels-Spring-Escape-In-Hatchville-Sleeps-6-Dogs.h102447329.Hotel-Information)

Falmouth

10/10

Exceptional

(11 reviews)

"Enjoyed our stay. Everything was clean and well kept. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lynn S.

CA $394

CA $1,006 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/East-Falmouth-Hotels-Spring-Escape-In-Hatchville-Sleeps-6-Dogs.h102447329.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/34000000/33570000/33564900/33564802/dc424ea5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33570000/33564900/33564802/f9259183.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, stereo](https://images.trvl-media.com/lodging/34000000/33570000/33564900/33564802/446ec9da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33564900/33564802/850adf08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

[](https://www.expedia.ca/Falmouth-Hotels-Located-Steps-Away-To-Main-Street-And-7-Miles-From-Surf-Drive-Beach.h33564802.Hotel-Information)

Falmouth

10/10

Exceptional

(212 reviews)

"This beautiful well-appointed home was the perfect spot for a girlfriend’s getaway. Walkable to the shops and restaurants, nice big rooms for chats, and a great kitchen island to congregate around for breakfast. We loved our time here!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Annemarie G.

CA $222

CA $681 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Falmouth-Hotels-Located-Steps-Away-To-Main-Street-And-7-Miles-From-Surf-Drive-Beach.h33564802.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33740000/33734400/33734316/8ce14f0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33740000/33734400/33734316/60b17756.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/34000000/33740000/33734400/33734316/60d02931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/34000000/33740000/33734400/33734316/de1fe591.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oak Bluffs - Quiet neighborhood

[](https://www.expedia.ca/Oak-Bluffs-Hotels-Oak-Bluffs-Quiet-Neighborhood.h33734316.Hotel-Information)

Oak Bluffs

9.4/10

Exceptional

(43 reviews)

"perfect for our needs"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ed V.

CA $410

CA $904 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Oak-Bluffs-Hotels-Oak-Bluffs-Quiet-Neighborhood.h33734316.Hotel-Information)

![TV, fireplace, books](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483217/c76c5bcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483217/f9457118.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483217/b46dfa50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483217/e6152028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

[](https://www.expedia.ca/Oak-Bluffs-Hotels-A-NOSTALGIC-SPACE-Your-Marthas-Vineyard-Getaway.h48483217.Hotel-Information)

Oak Bluffs

9.4/10

Exceptional

(3 reviews)

"This house was perfect for our getaway. Rebecca, the host, was extremely responsive and helpful during our trip. The house was as advertised. It was clean, well equipped, and the location was perfect as well "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Louis R.

CA $479

CA $1,222 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Oak-Bluffs-Hotels-A-NOSTALGIC-SPACE-Your-Marthas-Vineyard-Getaway.h48483217.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/88000000/87140000/87138100/87138001/2886fe6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, sun loungers](https://images.trvl-media.com/lodging/88000000/87140000/87138100/87138001/65746ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/88000000/87140000/87138100/87138001/0bccb78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87140000/87138100/87138001/w1006h683x0y0-5fe89fed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

[](https://www.expedia.ca/Mashpee-Hotels-Spacious-Coastal-New-Seabury-Home-Kayak-Launch-Across-Street-Walk-To-Beach.h87138001.Hotel-Information)

New Seabury

10/10

Exceptional

(8 reviews)

"Great place"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Aaron Q.

CA $860

CA $1,572 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Mashpee-Hotels-Spacious-Coastal-New-Seabury-Home-Kayak-Launch-Across-Street-Walk-To-Beach.h87138001.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/102000000/101360000/101356700/101356607/efa5fe91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/102000000/101360000/101356700/101356607/50e10559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101360000/101356700/101356607/8068e640.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101360000/101356700/101356607/83c06ca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Home in Falmouth Village

[](https://www.expedia.ca/Falmouth-Hotels-Beautiful-Home-In-Falmouth-Village.h101356607.Hotel-Information)

Falmouth

10/10

Exceptional

(10 reviews)

"Great house and good location. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeannie E.

[](https://www.expedia.ca/Falmouth-Hotels-Beautiful-Home-In-Falmouth-Village.h101356607.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/35000000/34480000/34479600/34479505/e7497b4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34480000/34479600/34479505/c82ec2ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/35000000/34480000/34479600/34479505/d0394b21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/35000000/34480000/34479600/34479505/98af49e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Oak-Bluffs-Hotels-Walking-Distance-From-Oak-Bluffs-Ferry-Terminal-With-180-Degree-Ocean-View.h34479505.Hotel-Information)

Oak Bluffs

9.4/10

Exceptional

(91 reviews)

"Great place to stay in Oak Bluffs"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephen S.

CA $410

CA $730 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Oak-Bluffs-Hotels-Walking-Distance-From-Oak-Bluffs-Ferry-Terminal-With-180-Degree-Ocean-View.h34479505.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483278/acf9512c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483278/1925ab75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483278/f4a7a012.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483278/76fe1a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### MOST CHIC SPOT! Your Martha's Vineyard Getaway!

[](https://www.expedia.ca/Oak-Bluffs-Hotels-MOST-CHIC-SPOT-Your-Marthas-Vineyard-Getaway.h48483278.Hotel-Information)

Oak Bluffs

10/10

Exceptional

(7 reviews)

"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Swathanthra M.

CA $752

CA $1,657 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Oak-Bluffs-Hotels-MOST-CHIC-SPOT-Your-Marthas-Vineyard-Getaway.h48483278.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27140000/27132200/27132184/w799h599x1y1-63997eab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27140000/27132200/27132184/b9468b21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27140000/27132200/27132184/w799h599x1y1-f17bd4a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sun loungers](https://images.trvl-media.com/lodging/28000000/27140000/27132200/27132184/71bb7218.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!

[](https://www.expedia.ca/Edgartown-Hotels-Charming-Chappaquiddick-Retreat-Steps-From-Private-Beach-Edgartowns-Best.h27132184.Hotel-Information)

Edgartown

9.8/10

Exceptional

(16 reviews)

"The hosts are excellent people, great communicators who want VBRO guests to have an outstanding experience. Chappy is a wonderful retreat from the rest of the world. That is my only word of caution, it requires a ferry to eat out or shop. Otherwise this is a great place to read write meditate beach and let go of everyday worries. It has a higher price tag because your paying for a premium location, guest service experience and higher quality accomodation."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

SparkleCappy

CA $966

CA $1,452 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Edgartown-Hotels-Charming-Chappaquiddick-Retreat-Steps-From-Private-Beach-Edgartowns-Best.h27132184.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/79000000/78190000/78183300/78183300/f462c27f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/79000000/78190000/78183300/78183300/9c21b73d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78190000/78183300/78183300/dbe99d9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78190000/78183300/78183300/f7474205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

[](https://www.expedia.ca/Vineyard-Haven-Hotels-NEW-Renovated-Family-Friendly-Vineyard-Haven-Home.h78183300.Hotel-Information)

Tisbury

10/10

Exceptional

(16 reviews)

"We had an amazing time at this beautiful home. Great, clean space to spend an evening visit with friends and family. Great location with easy access around the island. Would highly recommend! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer T.

CA $684

CA $1,483 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Vineyard-Haven-Hotels-NEW-Renovated-Family-Friendly-Vineyard-Haven-Home.h78183300.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/105000000/104150000/104141900/104141861/3015598e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/105000000/104150000/104141900/104141861/fe6ff6da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104150000/104141900/104141861/6792f460.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/105000000/104150000/104141900/104141861/3771ef4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

[](https://www.expedia.ca/South-Dartmouth-Hotels-Cozy.h104141861.Hotel-Information)

Dartmouth

10/10

Exceptional

(14 reviews)

"Beautiful home, well maintained, incredibly hospitable and responsive host. Kitchen is well equipped and amply stocked with cooking essential and extras for feeding your guests. Wonderful spacious yard great for outdoor fun."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nick R.

CA $1,111

CA $1,937 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/South-Dartmouth-Hotels-Cozy.h104141861.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/121000000/120700000/120691300/120691227/ea86c777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120700000/120691300/120691227/35769b74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/121000000/120700000/120691300/120691227/b7624eeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120700000/120691300/120691227/764a70c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cape Cod Escape at Casa de Leo!

[](https://www.expedia.ca/East-Falmouth-Hotels-Cape-Cod-Escape-At-Casa-De-Leo.h120691227.Hotel-Information)

Falmouth

CA $1,032

CA $2,218 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/East-Falmouth-Hotels-Cape-Cod-Escape-At-Casa-De-Leo.h120691227.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/35000000/34480000/34479300/34479239/2b41432d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/35000000/34480000/34479300/34479239/b1725b94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34480000/34479300/34479239/9c410f43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/35000000/34480000/34479300/34479239/737400ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

[](https://www.expedia.ca/Oak-Bluffs-Hotels-Walking-Distance-From-Oak-Bluffs-Ferry-Terminal-With-180-Degree-Ocean-View.h34479239.Hotel-Information)

Oak Bluffs

9.4/10

Exceptional

(88 reviews)

"The location of this property cannot be beat! Our second time staying here."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ashley S.

CA $410

CA $730 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Oak-Bluffs-Hotels-Walking-Distance-From-Oak-Bluffs-Ferry-Terminal-With-180-Degree-Ocean-View.h34479239.Hotel-Information)

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](https://expedia.ca/Hotel-Search?startDate=2026-02-23&endDate=2026-02-24&regionId=6135676&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cottages

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Private vacation homes

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Apartments

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Condos

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Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Chilmark%2C+Massachusetts%2C+United+States+of+America&regionId=6135676&latLong=41.34317%2C-70.744751&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=APART_HOTEL)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Chilmark%2C+Massachusetts%2C+United+States+of+America&regionId=6135676&latLong=41.34317%2C-70.744751&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=VILLA)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Chilmark%2C+Massachusetts%2C+United+States+of+America&regionId=6135676&latLong=41.34317%2C-70.744751&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=CABIN)

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## Top Chilmark Hotel Reviews

![Iris Hotel Cape Cod ](https://images.trvl-media.com/lodging/1000000/20000/12000/11989/63513190_y.jpg)

### Iris Hotel Cape Cod 

10/10 Excellent

"The bed was so comfortable. Towels thick and luxurious! Had an E station for my electric car."

[](https://expedia.ca/Falmouth-Hotels-Hotel-Cape-Cod.h11989.Hotel-Information)

![Vineyard Harbor Motel - Private Beach](https://images.trvl-media.com/lodging/61000000/60390000/60384600/60384563/6bd7fc20_y.jpg)

### Vineyard Harbor Motel - Private Beach

10/10 Excellent

"Friendly staff, nice clean room"

[](https://expedia.ca/Vineyard-Haven-Hotels-Vineyard-Harbor-Motel.h60384563.Hotel-Information)

![Hampton Inn by Hilton New Bedford/Fairhaven](https://images.trvl-media.com/lodging/1000000/60000/55000/54948/647c4f15_y.jpg)

### Hampton Inn by Hilton New Bedford/Fairhaven

10/10 Excellent

"Clean room. Comfortable bed.Great coffee! Friendly staff workers."

[](https://expedia.ca/Fairhaven-Hotels-Hampton-Inn-By-Hilton-New-BedfordFairhaven.h54948.Hotel-Information)

![The Club at New Seabury](https://images.trvl-media.com/lodging/12000000/11630000/11621700/11621632/4270e26b_y.jpg)

### The Club at New Seabury

10/10 Excellent

"Everything was superb, accommodations, check in service, check out service!!"

[](https://expedia.ca/Mashpee-Hotels-The-Club-At-New-Seabury.h11621632.Hotel-Information)

![Falmouth Inn](https://images.trvl-media.com/lodging/1000000/900000/893200/893142/a26689a2_y.jpg)

### Falmouth Inn

10/10 Excellent

"I stay here alot"

[](https://expedia.ca/Falmouth-Hotels-Falmouth-Inn.h893142.Hotel-Information)

![Falmouth Tides ](https://images.trvl-media.com/lodging/70000000/69380000/69374600/69374512/3742adf6_y.jpg)

### Falmouth Tides 

10/10 Excellent

"Everything was great except we wish we had a little table in the room. "

[](https://expedia.ca/Falmouth-Hotels-Falmouth-Tides-Motel.h69374512.Hotel-Information)

![Inn on the Square](https://images.trvl-media.com/lodging/1000000/10000/10000/9953/27ed2889_y.jpg)

### Inn on the Square

10/10 Excellent

"Familiar hotel "

[](https://expedia.ca/Falmouth-Hotels-Inn-On-The-Square.h9953.Hotel-Information)

![The Coonamessett](https://images.trvl-media.com/lodging/7000000/6600000/6591200/6591194/4add9b13_y.jpg)

### The Coonamessett

10/10 Excellent

"The room was spacious and lovely. The room was extremely clean. The staff was friendly. The breakfast had a lovely variety including healthy options. The woman who was serving breakfast was friendly and helpful. The grounds were pretty. Our only disappointment was the noise from several trucks nearby (it sounded like the parking lot and behind us) that sounded like they were unloading things extremely early (around 4 am)."

[](https://expedia.ca/Falmouth-Hotels-The-Coonamessett.h6591194.Hotel-Information)

![Mansion House Inn And Spa](https://images.trvl-media.com/lodging/3000000/2190000/2182100/2182094/e86ce24b_y.jpg)

### Mansion House Inn And Spa

10/10 Excellent

"Spotless, beautiful room with comfortable bed, and welcoming staff through the inn. Also, very close to the ferry and shops/restaurants; ideal location. Would definitely stay here again (and again)!"

[](https://expedia.ca/Vineyard-Haven-Hotels-Mansion-House-Inn-And-Spa.h2182094.Hotel-Information)

## Find out more about Chilmark

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chilmark. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Vacation Homes in Chilmark ](https://expedia.ca/Chilmark-Private-Vacation-Homes.d6135676-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Chilmark ](https://expedia.ca/Chilmark-Cottages.d6135676-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Chilmark ](https://expedia.ca/Chilmark-Apartments.d6135676-aaApartments.Travel-Guide-Accommodation)
- [Condo Rentals in Chilmark ](https://expedia.ca/Chilmark-Condos.d6135676-aaCondos.Travel-Guide-Accommodation)
- [B&B in Chilmark ](https://expedia.ca/Chilmark-Bed-And-Breakfast.d6135676-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Resorts in Chilmark ](https://expedia.ca/Chilmark-Resort-Hotels.d6135676-aaResortHotels.Travel-Guide-Accommodation)
- [Motels in Chilmark ](https://expedia.ca/Chilmark-Motels.d6135676-aaMotels.Travel-Guide-Accommodation)
- [Guest Houses in Chilmark ](https://expedia.ca/Chilmark-Guest-Houses.d6135676-aaGuestHouses.Travel-Guide-Accommodation)
- [Aparthotels in Chilmark ](https://expedia.ca/Chilmark-Apart-Hotels.d6135676-aaApartHotels.Travel-Guide-Accommodation)
- [Farmstay in Chilmark ](https://expedia.ca/Chilmark-Agritourism.d6135676-aaAgritourism.Travel-Guide-Accommodation)
- [Inns in Chilmark ](https://expedia.ca/Chilmark-Inns.d6135676-aaInns.Travel-Guide-Accommodation)
- [Cabin Rentals in Chilmark ](https://expedia.ca/Chilmark-Cabins.d6135676-aaCabins.Travel-Guide-Accommodation)
- [Villas in Chilmark ](https://expedia.ca/Chilmark-Villas.d6135676-aaVillas.Travel-Guide-Accommodation)
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- [Holiday Park Resorts in Chilmark ](https://expedia.ca/Chilmark-Holiday-Parks.d6135676-aaHolidayParks.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Chilmark?

### What are some of the best vacation rentals that Chilmark has to offer?

### How many vacation rentals are there in Chilmark?

### What’s there to see and do in Chilmark?

### What’s a vacation rental in Chilmark like?

### Expedia's Latest Trends

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Flights

- [Cheap Flights to Springfield](https://expedia.ca/Cheap-Flights-To-Springfield.d6047669.Travel-Guide-Flights)

Cars

- [Car rentals in Halifax](https://expedia.ca/Car-Rentals-In-Halifax.d6139204.Car-Rental-Guide)

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- [Things to do in Nantucket](https://expedia.ca/Things-To-Do-In-Nantucket.d285.Travel-Guide-Activities)
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- [Halifax Vacations](https://expedia.ca/Halifax.d6139204.Destination-Travel-Guides)
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General

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