Title: Chilmark Vacation Rentals from $134: Search Short-Term Rentals | Expedia.com

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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 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=6135676&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6135676&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=6135676&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=6135676&startDate=2026-05-29&endDate=2026-05-31&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/f0ed7d64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach bar](https://images.trvl-media.com/lodging/12000000/11630000/11621700/11621632/d6ee0dce.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)

### The Club at New Seabury

[](https://www.expedia.com/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

$154 nightly

$176 total

Feb 8 - Feb 9

Total with taxes and fees

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

![Property grounds](https://images.trvl-media.com/lodging/28000000/27120000/27117800/27117723/b17fdba7.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)

![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.com/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.

$539 nightly

$617 total

Feb 28 - Mar 1

Total with taxes and fees

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

![Private kitchen](https://images.trvl-media.com/lodging/119000000/118960000/118951300/118951248/e3989985.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)

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

### Falmouth Oasis

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

Falmouth

$390 nightly

$446 total

Feb 8 - Feb 9

Total with taxes and fees

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

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

![Fridge, microwave, coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/76000000/75220000/75212700/75212637/799566b4.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)

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

[](https://www.expedia.com/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.

$175 nightly

$200 total

Feb 28 - Mar 1

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/34000000/33570000/33564900/33564802/7664efea.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)

![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)

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

[](https://www.expedia.com/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.

$433 nightly

$496 total

Feb 8 - Feb 9

Total with taxes and fees

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

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/108000000/107997300/107997278/ad29049f.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)

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

[](https://www.expedia.com/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.

$373 nightly

$416 total

Feb 7 - Feb 8

Total with taxes and fees

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

![Smart TV, foosball, table tennis](https://images.trvl-media.com/lodging/103000000/102450000/102447400/102447329/1bba2858.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/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.

$629 nightly

$720 total

Feb 6 - Feb 7

Total with taxes and fees

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

![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)

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

### Oak Bluffs - Quiet neighborhood

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

Oak Bluffs

9.4/10

Exceptional

(43 reviews)

"Perfectly situated!"

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

Damani B.

$596 nightly

$666 total

Feb 11 - Feb 12

Total with taxes and fees

[](https://www.expedia.com/Oak-Bluffs-Hotels-Oak-Bluffs-Quiet-Neighborhood.h33734316.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.com/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.

$996 nightly

$1,140 total

Feb 6 - Feb 7

Total with taxes and fees

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

![Terrace/patio](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483217/e6152028.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)

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

[](https://www.expedia.com/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.

$792 nightly

$885 total

Feb 6 - Feb 7

Total with taxes and fees

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

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78190000/78183300/78183300/f7474205.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)

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

[](https://www.expedia.com/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.

$971 nightly

$1,085 total

Feb 6 - Feb 7

Total with taxes and fees

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

![1 bedroom, free WiFi](https://images.trvl-media.com/lodging/35000000/34480000/34479600/34479505/641ca26a.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/35000000/34480000/34479600/34479505/98af49e3.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.com/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.

$478 nightly

$534 total

Mar 1 - Mar 2

Total with taxes and fees

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

$1,099 nightly

$1,258 total

Feb 6 - Feb 7

Total with taxes and fees

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

![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)

![Dining](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483278/1925ab75.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.com/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.

$1,085 nightly

$1,212 total

Feb 6 - Feb 7

Total with taxes and fees

[](https://www.expedia.com/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)

![Smart TV, video games, DVD player, music library](https://images.trvl-media.com/lodging/28000000/27140000/27132200/27132184/cb631ceb.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)

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

[](https://www.expedia.com/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

$951 nightly

$1,062 total

Feb 6 - Feb 7

Total with taxes and fees

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

![Dining](https://images.trvl-media.com/lodging/121000000/120700000/120691300/120691227/b7624eeb.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)

![Smart TV, table tennis](https://images.trvl-media.com/lodging/121000000/120700000/120691300/120691227/2a21b056.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cape Cod Escape at Casa de Leo!

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

Falmouth

$1,371 nightly

$1,569 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/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)

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34480000/34479300/34479239/e0d373cf.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.com/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.

$478 nightly

$534 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/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.com/Hotel-Search?startDate=2026-02-19&endDate=2026-02-20&regionId=6135676&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

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Cottages

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Cabins

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Condos

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Apartments

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Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Chilmark%2C+Massachusetts%2C+United+States+of+America&regionId=6135676&latLong=41.34317%2C-70.744751&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=APART_HOTEL)

Villas

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## Top Chilmark Hotel Reviews

![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.com/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.com/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.com/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.com/Falmouth-Hotels-Falmouth-Tides-Motel.h69374512.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

"Professional Courteous Attentive Clean room and good shower"

[](https://expedia.com/Vineyard-Haven-Hotels-Vineyard-Harbor-Motel.h60384563.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.com/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.com/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.com/Vineyard-Haven-Hotels-Mansion-House-Inn-And-Spa.h2182094.Hotel-Information)

![InnSeason Resorts Surfside](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154024/d2448752_y.jpg)

### InnSeason Resorts Surfside

10/10 Excellent

"Room was clean, beautiful view, loved the hot tub in the room, and staff was very friendly and always willing to help. "

[](https://expedia.com/East-Falmouth-Hotels-InnSeason-Resorts-Surfside.h1154024.Hotel-Information)

## Find out more about Chilmark

**Everything you need to know about Chilmark vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chilmark vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chilmark vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Chilmark vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Chilmark. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chilmark in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $134 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Chilmark rentals**

At Expedia, we put the best Chilmark vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chilmark rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chilmark vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chilmark. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

- Trending destinations on Expedia.com
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### Trending destinations on Expedia.com

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- [Siesta Key Vacation Rentals ](https://www.expedia.com/Siesta-Key-Vacation-Rentals.d6881.Travel-Guide-VacationRentals)
- [Galveston Vacation Rentals ](https://www.expedia.com/Galveston-Vacation-Rentals.d1341.Travel-Guide-VacationRentals)
- [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals)
- [Palm Springs Vacation Rentals ](https://www.expedia.com/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals)
- [Florida Keys Vacation Rentals ](https://www.expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)
- [Lake Tahoe Vacation Rentals ](https://www.expedia.com/South-Lake-Tahoe-Vacation-Rentals.d10150.Travel-Guide-VacationRentals)
- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

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

Hotels

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Cars

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Activities

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Packages

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General

- [Visit Manchester-by-the-Sea](https://expedia.com/Manchester-By-The-Sea.dx129363)
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