Title: Cuttyhunk Vacation Home Rentals : Search Top Private Vacation Homes for Rent | Expedia.ca

  

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# Cuttyhunk 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=3000441000&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 two months

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=3000441000&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=3000441000&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)

In four months

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=3000441000&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Cuttyhunk 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/ac544bb6.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)

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

Dartmouth

10/10

Exceptional

(17)

"I stayed for just one night, and wasn't actually around much as I was visiting a friend, but the house was immaculate and exactly as advertised."

CA $148

CA $451 total

includes taxes & fees

Oct 12 - Oct 13

[](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)

![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)

![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)

### 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 12 - Oct 13

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

![Exterior](https://images.trvl-media.com/lodging/114000000/113940000/113930900/113930804/5c05c011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113940000/113930900/113930804/0f9d440a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/114000000/113940000/113930900/113930804/30c5320d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113940000/113930900/113930804/65b22b42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Seapowet suite

Tiverton

10/10

Exceptional

(1)

"The property is located in a beautiful little setting set back off the road with a huge lawn and outside patio area. Alan, the owner was very accommodating. Inside was two bedrooms, a bathroom and a nice big living room with a table. Also was a mini fridge along with a microwave and a Keurig coffee maker. A great little hiking area about 200 feet down the road. Beds were comfortable and very clean. I would highly recommend this place."

CA $121

CA $222 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/Tiverton-Hotels-Seapowet-Suite.h113930804.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

Falmouth

10/10

Exceptional

(201)

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

CA $252

CA $727 total

includes taxes & fees

Nov 3 - Nov 4

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

![TV, fireplace](https://images.trvl-media.com/lodging/116000000/115160000/115155900/115155816/ec92862e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115160000/115155900/115155816/476b1d9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/116000000/115160000/115155900/115155816/9ca02a6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115160000/115155900/115155816/afac6491.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ellery Beach Bungalow #45- A Refined Island Escape

Middletown

10/10

Exceptional

(1)

"Beautiful area, walking distance to the beach and restaurants, nice clean house"

CA $167

CA $607 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Middletown-Hotels-Ellery-Beach-Bungalow-45-A-Refined-Island-Escape.h115155816.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/93000000/92440000/92431600/92431523/31b29a06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92440000/92431600/92431523/3bfdbef2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/93000000/92440000/92431600/92431523/929c0e22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92440000/92431600/92431523/9054a4ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ellery Bungalow #51- Island Calm Near Newport

Middletown

9.6/10

Exceptional

(94)

"This was the perfect size and location for our group of 5, would definitely stay again! "

CA $182

CA $627 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Middletown-Hotels-Ellery-Bungalow-51-Island-Calm-Near-Newport.h92431523.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107640000/107630500/107630402/5687f6d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107640000/107630500/107630402/66478905.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, video library](https://images.trvl-media.com/lodging/108000000/107640000/107630500/107630402/69327ef3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/108000000/107640000/107630500/107630402/w1216h1624x0y0-66b80400.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!

Dartmouth

CA $165

CA $423 total

includes taxes & fees

Oct 18 - Oct 19

[](https://www.expedia.ca/North-Dartmouth-Hotels-Charming-1-Bedroom-House-With-AC-And-WiFi-In-Dartmouth-Close-To-Buttonwood-Park.h107630402.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/45000000/44790000/44788900/44788859/130dc2ea.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)

![Exterior](https://images.trvl-media.com/lodging/45000000/44790000/44788900/44788859/b39967ae.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 $216

CA $614 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)

![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)

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483278/01b70ed1.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 11 - Oct 12

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76160000/76155400/76155312/9ed34572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/77000000/76160000/76155400/76155312/33cd546b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76160000/76155400/76155312/87ab56ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76160000/76155400/76155312/5462b7b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stunning, Chic Remodel! Beach House Minutes to Newport!

Middletown

9.8/10

Exceptional

(18)

"The house was convientky close to Newport There were 6 adults with us plenty of space for everyone. Host was very responsive And accommodating. "

CA $1,465

CA $2,762 total

includes taxes & fees

Oct 13 - Oct 14

[](https://www.expedia.ca/Middletown-Hotels-Stunning.h76155312.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)

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

![Interior](https://images.trvl-media.com/lodging/105000000/104150000/104141900/104141861/3771ef4a.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

(13)

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

CA $1,115

CA $1,887 total

includes taxes & fees

Oct 15 - Oct 16

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

![Smart TV](https://images.trvl-media.com/lodging/103000000/102860000/102852300/102852293/9218d955.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)

![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

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 $2,548 total

includes taxes & fees

Nov 4 - Nov 5

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

![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!

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 16 - Oct 17

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

![Highchair](https://images.trvl-media.com/lodging/95000000/94870000/94870000/94869907/cf095dcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/95000000/94870000/94870000/94869907/cbacbb68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/95000000/94870000/94870000/94869907/466956bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/95000000/94870000/94870000/94869907/e2259d42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Half mile to beach, Family & Pet Friendly, Newly Renovated Full House

Middletown

10/10

Exceptional

(17)

"Great property in a convenient location. Highly recommend this home. Property manager was great at getting back to us. "

CA $451

CA $1,159 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/Middletown-Hotels-Half-Mile-To-Beach.h94869907.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103440000/103432500/103432449/96bbef47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103440000/103432500/103432449/d035a3b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103440000/103432500/103432449/2d9aa99f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/104000000/103440000/103432500/103432449/10cc10c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Little Creek Retreat - RIBryan Property

Middletown

9.4/10

Exceptional

(13)

"Although my party and I only stayed for 1 night we still had a great time in this lovely house."

CA $336

CA $931 total

includes taxes & fees

Oct 13 - Oct 14

[](https://www.expedia.ca/Middletown-Hotels-Little-Creek-Retreat-RIBryan-Property.h103432449.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104130000/104126700/104126675/4986cd4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104130000/104126700/104126675/a90df2b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104130000/104126700/104126675/4d3fab92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104130000/104126700/104126675/4744bb3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Entire house minutes from Newport, RI. Near beaches.

Middletown

10/10

Exceptional

(12)

"I stayed over Thanksgiving holiday to celebrate with my daughter attending school in Boston. The house was pristine, has a well stocked kitchen, thoughtfully decorated, conveniently located and Chadd was a terrific host! I will definitely stay here again, highly recommend the home!"

CA $339

CA $677 total

includes taxes & fees

Oct 20 - Oct 21

[](https://www.expedia.ca/Middletown-Hotels-Newly-Remodeled-Retreat-4-Mins-To-Vineyards.h104126675.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)

![Exterior detail](https://images.trvl-media.com/lodging/97000000/96350000/96347500/96347420/e678f734.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 $277

CA $801 total

includes taxes & fees

Oct 19 - Oct 20

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

![Dining](https://images.trvl-media.com/lodging/34000000/33710000/33705200/33705139/fa292aea.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)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/34000000/33710000/33705200/33705139/31b0a8e8.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 $1,332

CA $2,626 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)

![Exterior](https://images.trvl-media.com/lodging/79000000/78750000/78741400/78741380/8b2e390c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/79000000/78750000/78741400/78741380/e2084987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78750000/78741400/78741380/dcdc8712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78750000/78741400/78741380/0f79d69e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beach house walking distance to Second Beach

Easton's Point

9.8/10

Exceptional

(22)

"Great location, nice house. Great for a group of friends."

CA $627

CA $1,203 total

includes taxes & fees

Oct 20 - Oct 21

[](https://www.expedia.ca/Middletown-Hotels-Beach-House-Walking-Distance-To-Second-Beach.h78741380.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 $1,008

CA $2,051 total

includes taxes & fees

Oct 22 - Oct 23

[](https://www.expedia.ca/Falmouth-Hotels-Beautiful-Home-In-Falmouth-Village.h101356607.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=2025-10-24&endDate=2025-10-25&regionId=3000441000&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Top Cuttyhunk Hotel Reviews

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

### Falmouth Tides

10/10 Excellent

"Beach view from the room was outstanding from very calm and beautiful sunset to waking up to a stormy nasty sea... Such a great experience..."

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

![Atlantic Beach Hotel Newport](//images.trvl-media.com/lodging/1000000/330000/327200/327192/f0b3ff3f_y.jpg)

### Atlantic Beach Hotel Newport

10/10 Excellent

"Clean and comfortable room. It would be helpful if there was a grab bar in the tub as there was done and the tub was very slippery. There was also quite a bit of ice buildup in the freezer of the small refrigerator."

[](https://expedia.ca/Newport-Hotels-Atlantic-Beach-Hotel-Newport.h327192.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

"Loved this place! Location and staff were GREAT!! HIGHLY RECOMMEND 😁"

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

"Clean room, friendly staff"

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

"quiet and clean with restaurants within walking distance "

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

![Best Western Dartmouth-New Bedford](//images.trvl-media.com/lodging/2000000/1540000/1535900/1535858/3263a0b3_y.jpg)

### Best Western Dartmouth-New Bedford

10/10 Excellent

"Great place and great price. Will definitely stay here again "

[](https://expedia.ca/North-Dartmouth-Hotels-Best-Western-Dartmouth-New-Bedford.h1535858.Hotel-Information)

![AutoCamp Cape Cod](//images.trvl-media.com/lodging/50000000/49180000/49175900/49175859/3458b4d1_y.jpg)

### AutoCamp Cape Cod

10/10 Excellent

"Airstream trailer was efficient and fun, the grounds and clubhouse excellent "

[](https://expedia.ca/Falmouth-Hotels-AutoCamp-Cape-Cod.h49175859.Hotel-Information)

![New Bedford Harbor Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/24000000/23260000/23251300/23251279/9aa17686_y.jpg)

### New Bedford Harbor Hotel, an Ascend Collection Hotel

10/10 Excellent

"."

[](https://expedia.ca/New-Bedford-Hotels-New-Bedford-Harbor-Hotel.h23251279.Hotel-Information)

![Newport Beach Hotel & Suites](//images.trvl-media.com/lodging/1000000/530000/522600/522571/cfde7429_y.jpg)

### Newport Beach Hotel & Suites

10/10 Excellent

"Our view was beautiful with sunsets over the pond. Great service and perfect location!"

[](https://expedia.ca/Newport-Hotels-Newport-Beach-Hotel-Suites.h522571.Hotel-Information)

## Find out more about Cuttyhunk

## Cuttyhunk Vacation Homes information

| Number of reviews | |
| --- | --- |
| Accommodation | Vacation Homes |
| Lowest Price | |
| Highest Price | |

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-   [Car rental Chilmark](https://www.expedia.ca/Car-Rentals-In-Chilmark.d6135676.Car-Rental-Guide)
-   [Car rental Westport](https://www.expedia.ca/Car-Rentals-In-Westport.d9742.Car-Rental-Guide)

-   [South Dartmouth Vacation Rentals](https://www.expedia.ca/South-Dartmouth-Vacation-Rentals.d159867.Travel-Guide-VacationRentals)

-   [Things to do in Chilmark](https://www.expedia.ca/Things-To-Do-In-Chilmark.d6135676.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 Cuttyhunk on Expedia.com](https://www.expedia.com/Cuttyhunk-Private-Vacation-Homes.d3000441000-aaPrivateVacationHomes.Travel-Guide-Accommodation)