Title: Cuttyhunk Vacation Rentals from CA $306: Short-Term Rentals for 2026 | Expedia.ca

[Cuttyhunk Travel Guide](https://expedia.ca/Cuttyhunk.dx3000441000)[Hotels in Cuttyhunk](https://expedia.ca/Cuttyhunk-Hotels.d3000441000.Travel-Guide-Hotels)[Flights to Cuttyhunk](https://expedia.ca/Cheap-Flights-To-Cuttyhunk.d3000441000.Travel-Guide-Flights)[Cuttyhunk Car Rentals](https://expedia.ca/Car-Rentals-In-Cuttyhunk.d3000441000.Car-Rental-Guide)[Cuttyhunk Vacation Packages](https://expedia.ca/Cuttyhunk.d3000441000.Destination-Travel-Guides)

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# Cuttyhunk Vacation Rentals

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## Check prices for these dates

Tonight

[Dec 25 - Dec 26](https://www.expedia.ca/Hotel-Search?regionId=3000441000&startDate=2025-12-25&endDate=2025-12-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 26 - Dec 27](https://www.expedia.ca/Hotel-Search?regionId=3000441000&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)

This weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=3000441000&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=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)

## Our top choices for Cuttyhunk vacation rentals

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

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

![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)

### Cottage in Dartmouth

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

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)

![TV](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)

![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)

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

### Vacation Home in Middletown

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

10/10

Exceptional

(1)

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

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

Dana N.

CA $141

CA $593 total

includes taxes & fees

Jan 20 - Jan 21, 2026

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

![Interior](https://images.trvl-media.com/lodging/105000000/104180000/104171400/104171381/1f987369.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104180000/104171400/104171381/0ccbe487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/105000000/104180000/104171400/104171381/eab754df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/105000000/104180000/104171400/104171381/e282fb3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in New Bedford

[](https://www.expedia.ca/New-Bedford-Hotels-Lovely-4-Bedroom-Apartment-For-Rent.h104171381.Hotel-Information)

9.0/10

Wonderful

(2)

"My friend and I were looking for a place to stay for a last minute day-trip to Nantucket. This property was great for that purpose and Angelino was a very responsive host. One thing to note is that while there is plenty of free street parking, there is no onsite parking even though we were told there was one spot available. I think this might have been due to some confusion regarding which property we had actually booked."

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

Elizabeth C.

CA $172

CA $477 total

includes taxes & fees

Dec 26 - Dec 27

[](https://www.expedia.ca/New-Bedford-Hotels-Lovely-4-Bedroom-Apartment-For-Rent.h104171381.Hotel-Information)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/104000000/103440000/103430400/103430309/f6978f1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/104000000/103440000/103430400/103430309/a91c1c76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103440000/103430400/103430309/6fdf7262.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/104000000/103440000/103430400/103430309/d6b46ec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Middletown

[](https://www.expedia.ca/Middletown-Hotels-Middletown-Modern-Apartment-RIBryan-Property.h103430309.Hotel-Information)

9.6/10

Exceptional

(16)

"Apartment was beautiful in a great location!!!"

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

cathy g.

CA $219

CA $525 total

includes taxes & fees

Dec 26 - Dec 27

[](https://www.expedia.ca/Middletown-Hotels-Middletown-Modern-Apartment-RIBryan-Property.h103430309.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)

![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)

![TV](https://images.trvl-media.com/lodging/93000000/92440000/92431600/92431523/929c0e22.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)

### Vacation Home in Middletown

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

9.6/10

Exceptional

(94)

"My family had an amazing stay at this bungalow. It is very clean and offered everything we needed for our stay in Newport. The beach is very close and there are plenty of restaurants and convenience store within walking distance. "

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

Tamara C.

CA $155

CA $611 total

includes taxes & fees

Jan 20 - Jan 21, 2026

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

![Interior](https://images.trvl-media.com/lodging/116000000/115460000/115457600/115457583/77b4c928.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115460000/115457600/115457583/17274708.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/116000000/115460000/115457600/115457583/d05c9955.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115460000/115457600/115457583/82c20bc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Middletown

[](https://www.expedia.ca/Middletown-Hotels-Ellery-Beach-Bungalow-47-Relaxed-Island-Living.h115457583.Hotel-Information)

10/10

Exceptional

(4)

"Fantastic stay! "

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

Cristin C.

CA $153

CA $609 total

includes taxes & fees

Jan 21 - Jan 22, 2026

[](https://www.expedia.ca/Middletown-Hotels-Ellery-Beach-Bungalow-47-Relaxed-Island-Living.h115457583.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)

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

### Vacation Home in Oak Bluffs

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

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 26 - Dec 27

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

![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)

### Vacation Home in Oak Bluffs

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

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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90110000/90109100/90109063/74755b8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/91000000/90110000/90109100/90109063/c6e92501.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90110000/90109100/90109063/6993f501.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/91000000/90110000/90109100/90109063/5332507c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in New Bedford

[](https://www.expedia.ca/New-Bedford-Hotels-The-Charming-Gem-Near-The-Water.h90109063.Hotel-Information)

9.6/10

Exceptional

(34)

"I had stayed here last year and it's so close to several of my family members. This is my go to place when I travel to the New Bedford area."

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

Judy C.

CA $123

CA $306 total

includes taxes & fees

Jan 18 - Jan 19, 2026

[](https://www.expedia.ca/New-Bedford-Hotels-The-Charming-Gem-Near-The-Water.h90109063.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122060000/122059100/122059054/ec0a550c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, stovetop](https://images.trvl-media.com/lodging/123000000/122060000/122059100/122059054/d164748c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/123000000/122060000/122059100/122059054/w1440h1648x0y0-55b95c56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122060000/122059100/122059054/aa23d432.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in New Bedford

[](https://www.expedia.ca/New-Bedford-Hotels-Drift-Loft-Houseboat.h122059054.Hotel-Information)

CA $193

CA $246 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/New-Bedford-Hotels-Drift-Loft-Houseboat.h122059054.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)

![Exterior detail](https://images.trvl-media.com/lodging/97000000/96350000/96347500/96347420/e678f734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Dartmouth

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

8.8/10

Excellent

(6)

"Perfect spot for our long weekend visiting local family and we wish we could have stayed longer. Close to the village, kayaks on site/ water view- house clean and decorated thoughtfully. Pet friendly, we brought our small dog. The outdoor shower is a must try! We hope to be back soon! "

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

Lauren G.

CA $486

CA $871 total

includes taxes & fees

Dec 26 - Dec 27

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

![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)

![Exterior](https://images.trvl-media.com/lodging/114000000/113940000/113930900/113930804/b3784d19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Tiverton

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

9.6/10

Exceptional

(5)

"Adequate for one night. Host friendly."

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

Louise

CA $110

CA $151 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![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)

![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69210000/69206600/69206534/c1d04f62.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)

![Dining](https://images.trvl-media.com/lodging/70000000/69210000/69206600/69206534/12b12e6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Chilmark

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

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)

![TV](https://images.trvl-media.com/lodging/116000000/115410000/115400900/115400854/b98393ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/116000000/115410000/115400900/115400854/2c8ca6ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/116000000/115410000/115400900/115400854/8f8fb086.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115410000/115400900/115400854/w1024h679x0y3-1a62f5d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Easton's Point

[](https://www.expedia.ca/Middletown-Hotels-Between-Beaches.h115400854.Hotel-Information)

8.0/10

Very good

(1)

CA $220

CA $913 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Middletown-Hotels-Between-Beaches.h115400854.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)

![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)

![Smart TV, fireplace, DVD player](https://images.trvl-media.com/lodging/79000000/78750000/78741400/78741380/e22d1060.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)

### Vacation Home in Easton's Point

[](https://www.expedia.ca/Middletown-Hotels-Beach-House-Walking-Distance-To-Second-Beach.h78741380.Hotel-Information)

9.8/10

Exceptional

(26)

"What a great location, well appointed home, and a very professional VRBO host. You know that love and care goes into making guests feel welcomed and special. Lots of amenities and space to make your stay memorable. "

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

Victoria L.

CA $196

CA $760 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Middletown-Hotels-Beach-House-Walking-Distance-To-Second-Beach.h78741380.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/104000000/103440000/103431300/103431272/w1280h849x0y4-b48fd2f3.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/104000000/103440000/103431300/103431272/w1280h848x0y5-1d3c956a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103440000/103431300/103431272/w1276h853x4y0-a5cca067.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103440000/103431300/103431272/w1277h848x3y5-3151e9da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Middletown

[](https://www.expedia.ca/Middletown-Hotels-Middletown-Modern-Bungalow-RIBryan-Property.h103431272.Hotel-Information)

9.4/10

Exceptional

(13)

"Wonderful house and great location!! Super responsive host. Great vacation, thank you!!! "

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

Kristen P.

CA $293

CA $783 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Middletown-Hotels-Middletown-Modern-Bungalow-RIBryan-Property.h103431272.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)

![Interior](https://images.trvl-media.com/lodging/104000000/103440000/103432500/103432449/1d87e5db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Middletown

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

9.4/10

Exceptional

(14)

"Great place! So many bedrooms! Nice private yard, great if you have a dog. Had a wonderful stay, would stay again. Close enough to Newport to drive in and out no problem, plus close to beaches. "

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

Todd C.

CA $329

CA $912 total

includes taxes & fees

Dec 29 - Dec 30

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

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

### Vacation Home in Tisbury

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

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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100540000/100530500/100530404/w1020h678x4y4-99fcc28d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/101000000/100540000/100530500/100530404/w1020h678x4y4-3566264e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/101000000/100540000/100530500/100530404/w1024h678x0y4-5f172227.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/101000000/100540000/100530500/100530404/w1017h678x4y4-eecb3f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Middletown

[](https://www.expedia.ca/Middletown-Hotels-Allston-Greens-Summar.h100530404.Hotel-Information)

10/10

Exceptional

(9)

"Great location and perfect layout of the home for our needs"

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

Anna P.

CA $480

CA $1,315 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Middletown-Hotels-Allston-Greens-Summar.h100530404.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)

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

### Vacation Home in Falmouth

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

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)

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.

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## Top Cuttyhunk Hotel Reviews

![Residence Inn by Marriott New Bedford Dartmouth](https://images.trvl-media.com/lodging/1000000/880000/877200/877180/w4000h2664x0y3-73cda9b6_y.jpg)

### Residence Inn by Marriott New Bedford Dartmouth

10/10 Excellent

"Everyone was awesome. Especially the young man working the desk as well as housekeeping. We spent the weekend for my daughter’s bday and she had so much fun. Breakfast was not the greatest. We got there at 745 and it was all cold and hard but everything else was awesome. Thank you for having us. Merry Christmas "

[](https://expedia.ca/North-Dartmouth-Hotels-Residence-Inn-By-Marriott-New-Bedford-Dartmouth.h877180.Hotel-Information)

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

### Hampton Inn by Hilton New Bedford/Fairhaven

10/10 Excellent

"The hot chocolate bar is amazing!"

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

![Baymont by Wyndham North Dartmouth / Fall River](https://images.trvl-media.com/lodging/1000000/20000/13800/13758/f635e897_y.jpg)

### Baymont by Wyndham North Dartmouth / Fall River

10/10 Excellent

"The staff is always welcoming, rooms are clean. "

[](https://expedia.ca/North-Dartmouth-Hotels-Baymont-By-Wyndham-North-Dartmouth.h13758.Hotel-Information)

![Seaport Resort & Marina](https://images.trvl-media.com/lodging/1000000/550000/544000/543980/b06f5566_y.jpg)

### Seaport Resort & Marina

10/10 Excellent

"rooms were clean, bed was comfortable"

[](https://expedia.ca/Fairhaven-Hotels-Seaport-Inn-Marina.h543980.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)

![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)

![New Bedford Harbor Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/24000000/23260000/23251300/23251279/76e173eb_y.jpg)

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

10/10 Excellent

"Clean room and friendly staff"

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

![Fairfield Inn & Suites by Marriott New Bedford](https://images.trvl-media.com/lodging/4000000/3560000/3551400/3551384/eb19fbf7_y.jpg)

### Fairfield Inn & Suites by Marriott New Bedford

10/10 Excellent

"Room was clean and staff very helpful.We enjoyed the indoor pool too"

[](https://expedia.ca/New-Bedford-Hotels-Fairfield-Inn-Suites-By-Marriott-New-Bedford.h3551384.Hotel-Information)

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

### Best Western Dartmouth-New Bedford

10/10 Excellent

"Itt was great "

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

## Find out more about Cuttyhunk

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 Cuttyhunk. 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 Cuttyhunk ](https://expedia.ca/Cuttyhunk-Private-Vacation-Homes.d3000441000-aaPrivateVacationHomes.Travel-Guide-Accommodation)
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- [Apartments in Cuttyhunk ](https://expedia.ca/Cuttyhunk-Apartments.d3000441000-aaApartments.Travel-Guide-Accommodation)
- [B&B in Cuttyhunk ](https://expedia.ca/Cuttyhunk-Bed-And-Breakfast.d3000441000-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Condo Rentals in Cuttyhunk ](https://expedia.ca/Cuttyhunk-Condos.d3000441000-aaCondos.Travel-Guide-Accommodation)
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- [Motels in Cuttyhunk ](https://expedia.ca/Cuttyhunk-Motels.d3000441000-aaMotels.Travel-Guide-Accommodation)
- [Guest Houses in Cuttyhunk ](https://expedia.ca/Cuttyhunk-Guest-Houses.d3000441000-aaGuestHouses.Travel-Guide-Accommodation)
- [Resorts in Cuttyhunk ](https://expedia.ca/Cuttyhunk-Resort-Hotels.d3000441000-aaResortHotels.Travel-Guide-Accommodation)
- [Holiday Park Resorts in Cuttyhunk ](https://expedia.ca/Cuttyhunk-Holiday-Parks.d3000441000-aaHolidayParks.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find a vacation rental in Cuttyhunk?

### What are some of the best vacation home rentals in Cuttyhunk?

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

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

### Expedia's Latest Trends

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