Title: Chilmark Vacation Home Rentals from CA $148: Search Top Private Vacation Homes for Rent | Expedia.ca

  

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Photo by Wen C.

# Chilmark Vacation Rentals

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## Check prices for these dates

In two weeks

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Chilmark Vacation Homes

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/103000000/102910000/102903600/102903531/w1170h1108x0y0-1f9b0efc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/103000000/102910000/102903600/102903531/43c8d00c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102910000/102903600/102903531/c1974577.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/103000000/102910000/102903600/102903531/ac544bb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quaint 1 Bed 1 bath private beach home. Long term renters welcome for winter!

Dartmouth

10/10

Exceptional

(17)

"We had a great stay at Oceans 11! The home is beautiful, it was incredibly clean, and very well stocked! We look forward to staying here again!!"

CA $134

CA $434 total

includes taxes & fees

Oct 8 - Oct 9

[](https://www.expedia.ca/South-Dartmouth-Hotels-Quaint-1-Bed-1-Bath-Private-Beach-Home-Family-Friendly-Sleeps-4-Guests.h102903531.Hotel-Information)

![TV, fireplace, books](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483217/31f34cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483217/60505837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483217/8ca80e40.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)

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

Oak Bluffs

9.0/10

Wonderful

(2)

"The house was lovely. Very clean and orderly. Beautiful back porch that we enjoyed very much. The beds were very comfortable. Our only complaint was the Master bathroom needs some updating. The shower head desperately needs to be changed and the lighting is extremely poor. Also, only 1 half size mirror on the whole first floor. Other than that, it was perfect."

CA $244

CA $935 total

includes taxes & fees

Oct 7 - Oct 8

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

![Exterior detail](https://images.trvl-media.com/lodging/89000000/88110000/88105300/88105289/ba401672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88110000/88105300/88105289/02505418.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/89000000/88110000/88105300/88105289/c351e849.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/89000000/88110000/88105300/88105289/22b905eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

East Falmouth

10/10

Exceptional

(34)

"The location was a perfect fit for our needs. "

CA $188

CA $1,325 total

includes taxes & fees

Oct 13 - Oct 14

[](https://www.expedia.ca/East-Falmouth-Hotels-Waterfront-On-Lake-6-Bd.h88105289.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/120000000/119240000/119235800/119235778/5e706fb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119240000/119235800/119235778/0e0957a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/120000000/119240000/119235800/119235778/4745e616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119240000/119235800/119235778/da0f7ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming studio in tranquil Falmouth with AC

Falmouth

CA $167

CA $263 total

includes taxes & fees

Oct 8 - Oct 9

[](https://www.expedia.ca/East-Falmouth-Hotels-Charming-Studio-In-Tranquil-Falmouth-With-AC.h119235778.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/106000000/105110000/105107700/105107624/d976ba66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105110000/105107700/105107624/d8c88062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/106000000/105110000/105107700/105107624/a0826dd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105110000/105107700/105107624/7e9c9c46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Great Harbors Summer Home

Falmouth

CA $614

CA $1,559 total

includes taxes & fees

Oct 19 - Oct 20

[](https://www.expedia.ca/East-Falmouth-Hotels-Great-Harbors-Summer-Home.h105107624.Hotel-Information)

![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)

![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/88000000/87140000/87138100/87138001/78407270.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/88000000/87140000/87138100/87138001/6ae555bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/88000000/87140000/87138100/87138001/e74f179e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Mashpee

10/10

Exceptional

(7)

"Nice house! Great area. Close to nice beach !"

CA $878

CA $1,594 total

includes taxes & fees

Oct 7 - Oct 8

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

![Game room](https://images.trvl-media.com/lodging/103000000/102450000/102447400/102447329/742d03a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102450000/102447400/102447329/544af88d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/103000000/102450000/102447400/102447329/1c965ef4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102447400/102447329/81d250a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Falmouth

10/10

Exceptional

(9)

"The house is very nice and clean and Brian was extremely communicative and flexible with a late checkout. Would definitely stay again"

CA $402

CA $1,024 total

includes taxes & fees

Oct 8 - Oct 9

[](https://www.expedia.ca/East-Falmouth-Hotels-E-Falmouth-Game-Barn-Fire-Pit-Outdoor-Shower.h102447329.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33940000/33934600/33934525/5384c7f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/34000000/33940000/33934600/33934525/24a10f3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33940000/33934600/33934525/ea4dee86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player](https://images.trvl-media.com/lodging/34000000/33940000/33934600/33934525/cab22aa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Newly Renovated Martha's Vineyard Vacation Rental!

Katama

9.6/10

Exceptional

(46)

"Stay was nice, property is very clean and in close distance to most everything. Just wish they had made the lack of towels and linens more obvious in the listing. "

CA $289

CA $876 total

includes taxes & fees

Oct 9 - Oct 10

[](https://www.expedia.ca/Edgartown-Hotels-Newly-Renovated-Marthas-Vineyard-Vacation-Rental.h33934525.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)

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

![Outdoor dining](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483278/b5bfe5f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483278/01b70ed1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Oak Bluffs

10/10

Exceptional

(7)

"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."

CA $767

CA $1,691 total

includes taxes & fees

Oct 7 - Oct 8

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

![Beach nearby, beach towels](https://images.trvl-media.com/lodging/45000000/44790000/44788900/44788859/2e8c2b33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/45000000/44790000/44788900/44788859/a610c782.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/45000000/44790000/44788900/44788859/130dc2ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/45000000/44790000/44788900/44788859/2e4456f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### ☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village

Westport

9.6/10

Exceptional

(20)

"We enjoyed our stay and recommend It. Delightful back yard and patio area and a very pleasant front porch."

CA $215

CA $611 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Westport-Point-Hotels-Westport-Point-Beach-House-On-12-Acre-Easy-Access-To-Beachhistoric-Village.h44788859.Hotel-Information)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/105000000/104150000/104141900/104141861/135ba2ce.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)

![Exterior](https://images.trvl-media.com/lodging/105000000/104150000/104141900/104141861/w1137h737x0y3-8e7c3a3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104150000/104141900/104141861/4813bd07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Dartmouth

10/10

Exceptional

(12)

"Extremely well designed extremely comfortable and well appointed. Beautiful scenery, and very relaxing."

CA $1,115

CA $1,887 total

includes taxes & fees

Oct 7 - Oct 8

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

![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)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33564900/33564802/c7d101e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33564900/33564802/32ea6769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Falmouth

10/10

Exceptional

(201)

"Loved this spot. So easy to get to downtown and Surf Beach. It was fabulous and clean!"

CA $197

CA $655 total

includes taxes & fees

Oct 7 - Oct 8

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

![Exterior](https://images.trvl-media.com/lodging/103000000/102860000/102852300/102852293/aee30659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/103000000/102860000/102852300/102852293/02ffb52f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/103000000/102860000/102852300/102852293/9218d955.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102860000/102852300/102852293/c8592884.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Beach Estate, Panoramic Ocean Views, 5700 sqft

Mattapoisett

9.8/10

Exceptional

(6)

"This was the perfect getaway for our large family. Everything was immaculate and we had all the comforts of home. We had a great week!"

CA $1,025

CA $2,489 total

includes taxes & fees

Oct 8 - Oct 9

[](https://www.expedia.ca/Mattapoisett-Hotels-The-Beachfront-Estate.h102852293.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/51000000/50890000/50881400/50881359/e4a4a2f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/51000000/50890000/50881400/50881359/4b01bb13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, in-room safe, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/51000000/50890000/50881400/50881359/aef25d53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/51000000/50890000/50881400/50881359/04fb6552.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Seashell Cove - Martha's Vineyard

Katama

9.8/10

Exceptional

(22)

"Property was perfectly kept and very comfortable. "

CA $534

CA $1,037 total

includes taxes & fees

Oct 7 - Oct 8

[](https://www.expedia.ca/Edgartown-Hotels-The-Seashell-Cove.h50881359.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96350000/96347500/96347420/b1abb2c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/97000000/96350000/96347500/96347420/c234b091.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/97000000/96350000/96347500/96347420/w1090h718x0y0-94558ab4.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/97000000/96350000/96347500/96347420/0dba2924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stones Throw Waterfront

Dartmouth

8.8/10

Excellent

(6)

"We've selected this place for two main reasons - 1) Kayaks included, and 2) pets are welcome (at least, a dog - check the rules). Apart from the two kayaks, three standup boards (SUB) were also available. The property is located near a small cove, so it's perfect for SUB beginners, as there are no waves due to power motorboats, jet skis, etc. Note that launching the boats ISN'T a walk in the park. You'll have to deal with a narrow and relatively steep path, dealing with shrubs, rocks, and...

CA $276

CA $797 total

includes taxes & fees

Oct 17 - Oct 18

[](https://www.expedia.ca/South-Dartmouth-Hotels-Stones-Throw-Waterfront.h96347420.Hotel-Information)

![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)

![Smart TV](https://images.trvl-media.com/lodging/79000000/78190000/78183300/78183300/c6b79c2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/79000000/78190000/78183300/78183300/cf83a268.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78190000/78183300/78183300/5218f616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Tisbury

10/10

Exceptional

(15)

"The house is beautiful and conveniently located. The host, Melissa, was accessible and super helpful. We thoroughly enjoyed our time here and hope to be back in the future."

CA $653

CA $1,457 total

includes taxes & fees

Oct 14 - Oct 15

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

![6 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/102000000/101360000/101356700/101356607/daa0cfd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101360000/101356700/101356607/2b379b98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101360000/101356700/101356607/c1bafd24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/101360000/101356700/101356607/85cca476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Home in Falmouth Village

Falmouth

10/10

Exceptional

(9)

"Great house and good location. "

CA $1,004

CA $2,041 total

includes taxes & fees

Oct 22 - Oct 23

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

![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/67000000/66700000/66698300/66698285/ee45a1b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/67000000/66700000/66698300/66698285/f1b62103.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66700000/66698300/66698285/ae2b4579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/67000000/66700000/66698300/66698285/6e27b7a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Coastal chic meets French Provençal in this newly renovated oceanfront home.

East Falmouth

10/10

Exceptional

(85)

"Great stay! "

CA $872

CA $1,860 total

includes taxes & fees

Oct 27 - Oct 28

[](https://www.expedia.ca/East-Falmouth-Hotels-Coastal-Chic-Meets-French-Provencal-In-This-Newly-Renovated-Oceanfront-Home.h66698285.Hotel-Information)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33710000/33705200/33705139/f87fa2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33710000/33705200/33705139/022a5a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33710000/33705200/33705139/cd443f18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/34000000/33710000/33705200/33705139/fa292aea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Captains House - Newly Renovated Primary Bathroom and Upgraded Kitchen

West Tisbury

10/10

Exceptional

(56)

"Lovely home in quiet up island area. Short drive to beaches."

CA $1,325

CA $2,614 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Vineyard-Haven-Hotels-Historic-Captains-House-Newly-Renovated-Primary-Bathroom-And-Upgraded-Kitchen.h33705139.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/55000000/54940000/54935300/54935241/w2388h1514x0y77-1097f3b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/55000000/54940000/54935300/54935241/b25bc447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Video games, books, video library](https://images.trvl-media.com/lodging/55000000/54940000/54935300/54935241/w2323h1742x204y153-3585a9ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/55000000/54940000/54935300/54935241/0fb3af2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Beautiful Estate with salt water pool & pond with kayaks

Oak Bluffs

CA $3,488

CA $5,456 total

includes taxes & fees

Oct 7 - Oct 8

[](https://www.expedia.ca/Oak-Bluffs-Hotels-Beautiful-Estate-With-Salt-Water-Pool-Pond-With-Kayaks.h54935241.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=2025-10-20&endDate=2025-10-21&regionId=6135676&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

Save an average of 15% on thousands of hotels when you're signed in

[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChilmark-Private-Vacation-Homes.d6135676-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChilmark-Private-Vacation-Homes.d6135676-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Top Chilmark Hotel Reviews

![Faraway Martha's Vineyard](//images.trvl-media.com/lodging/1000000/70000/65700/65623/10e4fb42_y.jpg)

### Faraway Martha's Vineyard

10/10 Excellent

"Just a neat place to stay, very nice place. "

[](https://expedia.ca/Edgartown-Hotels-Faraway-Marthas-Vineyard.h65623.Hotel-Information)

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

### Falmouth Tides

10/10 Excellent

"We were very "

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

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

### The Club at New Seabury

10/10 Excellent

"Fantastic and perfect! Roomy, clean and comfortable "

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

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

### Iris Hotel Cape Cod

10/10 Excellent

"Floor needs cleaning"

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

![Summercamp](//images.trvl-media.com/lodging/11000000/10060000/10058600/10058501/4ff1c19a_y.jpg)

### Summercamp

10/10 Excellent

"Everything was wonderful!"

[](https://expedia.ca/Oak-Bluffs-Hotels-Summercamp.h10058501.Hotel-Information)

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

### Falmouth Inn

10/10 Excellent

"We attened an event very close ny at a marina. We were able to park and walk. Hotel has a restaurant and bar, but lots of options withinn walking distsnce. Close to main street shopping with lots of shops and restaurants. Not a big deal, but we arrivrd at 1pm, check in is at 3pm. Our room was ready but they said $20 extra to check in early, we just left our truck and went out and came back later for our keys. Room was clean. Bed was comfortable. Its a basic hotel, we would stay again "

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

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

### Vineyard Harbor Motel - Private Beach

10/10 Excellent

"Rooms were clean and comfortable a quick walk to the center of town PLUS there was a cute little beach!"

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

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

### Inn on the Square

10/10 Excellent

"The staff were "

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

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

### The Coonamessett

10/10 Excellent

"N/a"

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

## Find out more about Chilmark

## Chilmark Vacation Homes information

| Number of reviews | 10,785 |
| --- | --- |
| Accommodation | 909 Vacation Homes |
| Lowest Price | CA $148 |
| Highest Price | CA $332 |

## Explore a world of travel with Expedia

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-   [National Car Rental Rental Cars in Martha's Vineyard](https://www.expedia.ca/National-Car-Rental-Car-Rentals-In-Marthas-Vineyard.d6047691-c42.Car-Rental-Guide-Suppliers)
-   [Pickup Car Rentals in Martha's Vineyard](https://www.expedia.ca/Pickup-Car-Rentals-In-Marthas-Vineyard.d6047691-tPickup.Car-Rental-Guide-Class)
-   [Rent A Wreck Rental Cars in Martha's Vineyard](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-Marthas-Vineyard.d6047691-c33.Car-Rental-Guide-Suppliers)
-   [Standard Car Rentals in Martha's Vineyard](https://www.expedia.ca/Standard-Car-Rentals-In-Marthas-Vineyard.d6047691-tStandard.Car-Rental-Guide-Class)

-   [Martha's Vineyard Vacation Rentals](https://www.expedia.ca/Marthas-Vineyard-Vacation-Rentals.d6047691.Travel-Guide-VacationRentals)

-   [Things to do in Martha's Vineyard](https://www.expedia.ca/Things-To-Do-In-Marthas-Vineyard.d6047691.Travel-Guide-Activities)
-   [Things to do in Menemsha](https://www.expedia.ca/Things-To-Do-In-Menemsha.d6060685.Travel-Guide-Activities)

-   [Book Vacation Homes in Chilmark on Expedia.com](https://www.expedia.com/Chilmark-Private-Vacation-Homes.d6135676-aaPrivateVacationHomes.Travel-Guide-Accommodation)