Title: Chilmark Vacation Rentals from CA $203: Short-Term Rentals for 2026 | Expedia.ca

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![In the fishing village of Menemsha in Marthas Vineyard.  Delicious lobster rolls, clam chowder, lobster bisque etc. they'll boil your fresh  lobster for you if you don't want to do it yourself. Some benches outside if you want to 'eat in' but best bet is to take your food down to the beach for a picnic. ](https://images.trvl-media.com/place/6135676/25271101-6fdf-4e1c-9afc-551d4a7f6b53.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Shobha George

# Chilmark Vacation Rentals

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## Check prices for these dates

Tonight

[Dec 26 - Dec 27](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-12-26&endDate=2025-12-27&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-12-27&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[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)

## Our top choices for Chilmark vacation rentals

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/70000000/69210000/69206600/69206534/a7337fcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/70000000/69210000/69206600/69206534/74a2ccfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69210000/69206600/69206534/c1d04f62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels, soap, toilet paper](https://images.trvl-media.com/lodging/70000000/69210000/69206600/69206534/892c50c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy efficiency apartment/heated pool

[](https://www.expedia.ca/Chilmark-Hotels-Cozy-Efficiency-Apartmentheated-Pool.h69206534.Hotel-Information)

Chilmark

9.6/10

Exceptional

(21)

"We loved this property and would love to return!"

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

Clifford L.

CA $363

CA $577 total

includes taxes & fees

Dec 31 - Jan 1, 2026

[](https://www.expedia.ca/Chilmark-Hotels-Cozy-Efficiency-Apartmentheated-Pool.h69206534.Hotel-Information)

![Private beach nearby, beach bar](https://images.trvl-media.com/lodging/12000000/11630000/11621700/11621632/4270e26b.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)

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

![Reception](https://images.trvl-media.com/lodging/12000000/11630000/11621700/11621632/36a1f0b0.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

(341)

"Very relaxing, loved the different clubs available; beach, pool, tennis, playground for the little ones, bars and food. Some shops were closed due to being off season, but still enjoyed our stay. Looking forward to booking again "

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

Jose O.

[](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/2000000/1160000/1154100/1154022/7f1dbbf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154022/910c8a68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154022/a3da66ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154022/65350001.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

(192)

"Great property! Would definitely stay again."

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

Brad

CA $177

CA $203 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

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

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

![Smart TV](https://images.trvl-media.com/lodging/108000000/108000000/107997300/107997278/e5963f7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/108000000/107997300/107997278/324c2c1f.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)

"Super location, very nice accommodations, very clean, modern and comfortable "

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

Cathie K.

CA $295

CA $536 total

includes taxes & fees

Jan 2 - Jan 3, 2026

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

![Indoor pool, outdoor pool, sun loungers](https://images.trvl-media.com/lodging/14000000/13580000/13577900/13577889/b0dea528.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/14000000/13580000/13577900/13577889/b5640baf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Townhome, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/14000000/13580000/13577900/13577889/eecd76a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Mini-golf](https://images.trvl-media.com/lodging/14000000/13580000/13577900/13577889/4c89f12c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sea Mist Resort

[](https://www.expedia.ca/Mashpee-Hotels-Sea-Mist-Resort.h13577889.Hotel-Information)

Mashpee

8.6/10

Excellent

(144)

"Just there for one night but very enjoyable stay."

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

Shawna

CA $188

CA $216 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Mashpee-Hotels-Sea-Mist-Resort.h13577889.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/103000000/102530000/102521300/102521259/b93c0278.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102530000/102521300/102521259/cdcbb115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/103000000/102530000/102521300/102521259/f7fbe09e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102530000/102521300/102521259/acb87624.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

[](https://www.expedia.ca/East-Falmouth-Hotels-Contemporary-Coastal-Retreat-Nearby-Falmouth-Beaches-W-Spacious-Living-Area.h102521259.Hotel-Information)

Falmouth

10/10

Exceptional

(8)

"This property was beautiful! The hosts were excellent and were always available to message. I would recommend a stay at this home."

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

Lisa Mason D.

CA $260

CA $778 total

includes taxes & fees

Jan 16 - Jan 17, 2026

[](https://www.expedia.ca/East-Falmouth-Hotels-Contemporary-Coastal-Retreat-Nearby-Falmouth-Beaches-W-Spacious-Living-Area.h102521259.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)

![Dining](https://images.trvl-media.com/lodging/34000000/33940000/33934600/33934525/30d83c1e.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!

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

Katama

9.6/10

Exceptional

(47)

"We really enjoyed our stay. The house was conveniently located near Edgartown and South Beach in a quiet neighborhood. The house had everything we needed and more and was in great shape. Would definitely stay here again. "

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

Patrick S.

CA $277

CA $852 total

includes taxes & fees

Dec 30 - Dec 31

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

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

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33570000/33564900/33564802/7d2038e5.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

(211)

"Nicely furnished and very comfortable. Very private, yet convenient location. "

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

John H.

CA $222

CA $676 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](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/36000000/35760000/35757500/35757434/bb4a3d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/36000000/35760000/35757500/35757434/65053d4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/36000000/35760000/35757500/35757434/7be8da50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/36000000/35760000/35757500/35757434/daf65f80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!

[](https://www.expedia.ca/Mashpee-Hotels-Sleeps-6-New-Seabury-W-Pool-All-Season-Modern-Condo.h35757434.Hotel-Information)

New Seabury

10/10

Exceptional

(79)

"We were extremely happy with our stay. The condo was beautiful, had everything we needed. Looking forward to coming back again next year for a longer stay"

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

Beth H.

CA $202

CA $545 total

includes taxes & fees

Dec 31 - Jan 1, 2026

[](https://www.expedia.ca/Mashpee-Hotels-Sleeps-6-New-Seabury-W-Pool-All-Season-Modern-Condo.h35757434.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)

![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)

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

![Exterior](https://images.trvl-media.com/lodging/67000000/66700000/66698300/66698285/7b1afadb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

East Falmouth

10/10

Exceptional

(88)

"This is an excellent home well-kept great location, and the Host is easy to communicate with. "

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

Gary B.

CA $400

CA $1,222 total

includes taxes & fees

Jan 3 - Jan 4, 2026

[](https://www.expedia.ca/East-Falmouth-Hotels-Coastal-Chic-Meets-French-Provencal-In-This-Newly-Renovated-Oceanfront-Home.h66698285.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/119000000/118960000/118951300/118951248/6d9e4743.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)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118960000/118951300/118951248/ad1e409d.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 $595 total

includes taxes & fees

Dec 30 - Dec 31

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

![Smart TV, DVD player](https://images.trvl-media.com/lodging/51000000/50890000/50881400/50881359/8a6bd89f.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)

![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

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

Katama

9.8/10

Exceptional

(24)

"Property was perfectly kept and very comfortable. "

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

Steve D.

CA $342

CA $785 total

includes taxes & fees

Jan 5 - Jan 6, 2026

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

![Exterior](https://images.trvl-media.com/lodging/103000000/102860000/102852300/102852293/c8592884.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102860000/102852300/102852293/2f243bf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Mattapoisett

9.8/10

Exceptional

(8)

"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!"

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

Catherine T.

CA $966

CA $2,471 total

includes taxes & fees

Jan 6 - Jan 7, 2026

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

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

### 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)

"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 $1,210 total

includes taxes & fees

Dec 27 - Dec 28

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

![Smart TV](https://images.trvl-media.com/lodging/35000000/34480000/34479300/34479239/b1725b94.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)

![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)

### 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)

"Very happy. Thank you for the stay."

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

Gillian S.

CA $369

CA $681 total

includes taxes & fees

Dec 27 - Dec 28

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

![Exterior](https://images.trvl-media.com/lodging/79000000/78190000/78183300/78183300/f462c27f.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)

"The house is clean, peaceful and perfectly appointed with everything you need for a great week on the Vineyard."

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

Celeste P.

CA $684

CA $1,483 total

includes taxes & fees

Dec 30 - Dec 31

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

![Outdoor dining](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483278/b5bfe5f0.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.ca/Oak-Bluffs-Hotels-MOST-CHIC-SPOT-Your-Marthas-Vineyard-Getaway.h48483278.Hotel-Information)

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."

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

Swathanthra M.

CA $752

CA $1,657 total

includes taxes & fees

Dec 27 - Dec 28

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

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120700000/120691300/120691227/325144b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120700000/120691300/120691227/daa1d873.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 $855

CA $2,009 total

includes taxes & fees

Dec 28 - Dec 29

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

![Dining](https://images.trvl-media.com/lodging/88000000/87140000/87138100/87138001/e74f179e.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)

![Exterior](https://images.trvl-media.com/lodging/88000000/87140000/87138100/87138001/6ae555bd.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)

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

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

Cally G.

CA $860

CA $1,562 total

includes taxes & fees

Dec 27 - Dec 28

[](https://www.expedia.ca/Mashpee-Hotels-Spacious-Coastal-New-Seabury-Home-Kayak-Launch-Across-Street-Walk-To-Beach.h87138001.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=2026-01-09&endDate=2026-01-10&regionId=6135676&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

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Apartments

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Cottages

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Private vacation homes

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Condos

[](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=2026-03-26&d1=2026-03-26&endDate=2026-03-29&d2=2026-03-29&lodging=CONDO)

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=2026-03-26&d1=2026-03-26&endDate=2026-03-29&d2=2026-03-29&lodging=VILLA)

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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

"The hot chocolate bar is amazing!"

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

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

### The Coonamessett

10/10 Excellent

"Very friendly staff. Clean quiet and comfortable room. Loved the breakfast options"

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

"Everything was great "

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

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

### Faraway Martha's Vineyard

10/10 Excellent

"Very cozy comfortable hotel!!"

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

![Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/12200/12163/d9e8dd7b_y.jpg)

### Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

10/10 Excellent

"Convenient location. Clean room and helpful staff! "

[](https://expedia.ca/Edgartown-Hotels-Edgar-Hotel-Marthas-Vineyard.h12163.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

"The Mansion House was a lovely stay. Style, class, cleanlines…The Mansion House almost was perfect. 2 things not so much but minor. The thermostat in the room was strange. Very drafty in the room. The continental breakfast for the Mansion House was very stingy. I would have loved plain oatmeal with fresh blueberries but all they had was the sugar filled kids oatmeal. The eggs were cold hard boiled served over ice. Not so much. Other than that, the Mansion House was wonderful. "

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

![Admiralty Inn & Suites - a Red Collection Hotel](https://images.trvl-media.com/lodging/2000000/1280000/1279900/1279850/64d1c0e2_y.jpg)

### Admiralty Inn & Suites - a Red Collection Hotel

10/10 Excellent

"Location breakfast"

[](https://expedia.ca/Falmouth-Hotels-Admiralty-Inn-Suites.h1279850.Hotel-Information)

![The Franklin Hotel Martha's Vineyard](https://images.trvl-media.com/lodging/77000000/76640000/76637400/76637391/0e2e74e1_y.jpg)

### The Franklin Hotel Martha's Vineyard

10/10 Excellent

"Everything. The location, decor, warmth of the design elements, quiet, comfort. It’s one to return to over and over."

[](https://expedia.ca/Edgartown-Hotels-The-Franklin-Hotel-Marthas-Vineyard.h76637391.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

"Great time in Falmouth "

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

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

### Expedia's Latest Trends

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