Title: Cuttyhunk Vacation Home Rentals from CA $193: Search Top Private Vacation Homes for Rent | Expedia.ca

[Cuttyhunk Travel Guide](https://expedia.ca/Cuttyhunk.dx3000441000)[Hotels in Cuttyhunk](https://expedia.ca/Cuttyhunk-Hotels.d3000441000.Travel-Guide-Hotels)[Vacation Rentals in Cuttyhunk](https://expedia.ca/Cuttyhunk-Vacation-Rentals.d3000441000.Travel-Guide-VacationRentals)[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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## Check prices for these dates

In two weeks

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=3000441000&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=3000441000&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=3000441000&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=3000441000&startDate=2026-05-15&endDate=2026-05-17&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 homes

![Exterior detail](https://images.trvl-media.com/lodging/116000000/115160000/115155900/115155816/c30c5b95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/116000000/115160000/115155900/115155816/ec92862e.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)

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

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

Middletown

10/10

Exceptional

(1 review)

"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 $143

CA $606 total

includes taxes & fees

Jan 20 - Jan 21

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

![Property grounds](https://images.trvl-media.com/lodging/116000000/115460000/115457600/115457583/36e93354.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/ed3d7332.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/116000000/115460000/115457600/115457583/9c2bd44e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ellery Beach Bungalow #47- Relaxed Island Living

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

Middletown

10/10

Exceptional

(4 reviews)

"Fantastic stay! "

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

Cristin C.

CA $143

CA $606 total

includes taxes & fees

Jan 20 - Jan 21

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

![TV](https://images.trvl-media.com/lodging/123000000/122060000/122059200/122059103/43b6111e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/123000000/122060000/122059200/122059103/9af88744.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122060000/122059200/122059103/18345de5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122060000/122059200/122059103/a29a09a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blue Haven Houseboat

[](https://www.expedia.ca/New-Bedford-Hotels-Blue-Haven-Houseboat.h122059103.Hotel-Information)

New Bedford

CA $145

CA $193 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/New-Bedford-Hotels-Blue-Haven-Houseboat.h122059103.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/79000000/78750000/78741400/78741380/dcdc8712.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)

![Exterior](https://images.trvl-media.com/lodging/79000000/78750000/78741400/78741380/2e3c8b7e.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)

### Beach house walking distance to Second Beach

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

Easton's Point

9.8/10

Exceptional

(26 reviews)

"The house was clean, had every thing you could possibly need. Great location."

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

Sarah S.

CA $137

CA $720 total

includes taxes & fees

Jan 20 - Jan 21

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

![Beach nearby](https://images.trvl-media.com/lodging/114000000/113190000/113186500/113186417/765fc521.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113190000/113186500/113186417/w2543h1673x5y0-a4ce08b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113190000/113186500/113186417/w2464h1651x0y6-df32d8be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113190000/113186500/113186417/w2473h1650x4y1-d0c47eb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk to beach corner lot, 5 bed large yard

[](https://www.expedia.ca/Middletown-Hotels-Walk-To-Beach-Corner-Lot.h113186417.Hotel-Information)

Middletown

CA $2,254

CA $3,980 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Middletown-Hotels-Walk-To-Beach-Corner-Lot.h113186417.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/93000000/92440000/92431600/92431523/3934b730.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)

![Exterior](https://images.trvl-media.com/lodging/93000000/92440000/92431600/92431523/f4fe6d80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Middletown

9.6/10

Exceptional

(94 reviews)

"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 $143

CA $606 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Middletown-Hotels-Ellery-Bungalow-51-Island-Calm-Near-Newport.h92431523.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/w1024h678x0y4-5f41b9db.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)

### Between Beaches

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

Easton's Point

8.0/10

Very good

(1 review)

CA $224

CA $935 total

includes taxes & fees

Jan 20 - Jan 21

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

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

![Interior](https://images.trvl-media.com/lodging/34000000/33570000/33564900/33564802/7664efea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, stereo](https://images.trvl-media.com/lodging/34000000/33570000/33564900/33564802/446ec9da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33564900/33564802/850adf08.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

(212 reviews)

"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 $225

CA $693 total

includes taxes & fees

Jan 20 - Jan 21

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103440000/103432500/103432449/dcb33e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/104000000/103440000/103432500/103432449/6a289d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103440000/103432500/103432449/8ceda461.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/aec4d2f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Little Creek Retreat - RIBryan Property

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

Middletown

9.4/10

Exceptional

(14 reviews)

"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 $335

CA $935 total

includes taxes & fees

Jan 20 - Jan 21

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

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

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

![Interior](https://images.trvl-media.com/lodging/104000000/103440000/103431300/103431272/w1280h849x0y4-0a85db64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, computer monitors](https://images.trvl-media.com/lodging/104000000/103440000/103431300/103431272/e27a6574.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Middletown Bungalow - RIBryan Property

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

Middletown

9.4/10

Exceptional

(14 reviews)

"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 $298

CA $802 total

includes taxes & fees

Jan 20 - Jan 21

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100540000/100530500/100530404/w1024h678x0y4-4b77f22c.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)

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

![TV](https://images.trvl-media.com/lodging/101000000/100540000/100530500/100530404/w1020h678x4y4-16f3aa2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Allston Greens

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

Middletown

10/10

Exceptional

(9 reviews)

"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 $488

CA $1,345 total

includes taxes & fees

Jan 20 - Jan 21

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

![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33740000/33734400/33734316/8ce14f0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Miscellaneous](https://images.trvl-media.com/lodging/34000000/33740000/33734400/33734316/60d02931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/34000000/33740000/33734400/33734316/3532a4f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oak Bluffs - Quiet neighborhood

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

Oak Bluffs

9.4/10

Exceptional

(43 reviews)

"perfect for our needs"

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

Ed V.

CA $376

CA $875 total

includes taxes & fees

Jan 23 - Jan 24

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

![Exterior detail](https://images.trvl-media.com/lodging/113000000/112100000/112096600/112096519/9d8b0d9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/113000000/112100000/112096600/112096519/9c2705c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112100000/112096600/112096519/24695554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112100000/112096600/112096519/9965dee4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spectacular View from Rooftop Deck | Sleeps 12

[](https://www.expedia.ca/Middletown-Hotels-Spectacular-View-From-Rooftop-Deck-Sleeps-12.h112096519.Hotel-Information)

Easton's Point

10/10

Exceptional

(1 review)

"After finding out we had booked hotel rooms with the wrong hotel there were no rooms available last minute for a group of six. Stay Newport was able to get us in last minute and the lodging was wonderful. Very responsive communication. Great location. Very clean and well taken care of property. We wish we could have stayed for a few more days!"

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

Devon D.

CA $977

CA $2,337 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Middletown-Hotels-Spectacular-View-From-Rooftop-Deck-Sleeps-12.h112096519.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/79000000/78190000/78183300/78183300/f462c27f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/79000000/78190000/78183300/78183300/9c21b73d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78190000/78183300/78183300/f7474205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78190000/78183300/78183300/dbe99d9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Tisbury

10/10

Exceptional

(16 reviews)

"We had an amazing time at this beautiful home. Great, clean space to spend an evening visit with friends and family. Great location with easy access around the island. Would highly recommend! "

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

Jennifer T.

CA $696

CA $1,509 total

includes taxes & fees

Jan 21 - Jan 22

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

![TV, fireplace, books](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483217/c76c5bcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483217/b46dfa50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

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

"This house was perfect for our getaway. Rebecca, the host, was extremely responsive and helpful during our trip. The house was as advertised. It was clean, well equipped, and the location was perfect as well "

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

Louis R.

CA $487

CA $1,243 total

includes taxes & fees

Jan 20 - Jan 21

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

![TV, fireplace](https://images.trvl-media.com/lodging/102000000/101860000/101856900/101856830/cb94a1eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/102000000/101860000/101856900/101856830/29afd0a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101860000/101856900/101856830/38ebf860.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101860000/101856900/101856830/w1199h764x0y0-6d83ea91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Solo Fish - Family home, walk to beach and pool!

[](https://www.expedia.ca/Middletown-Hotels-Solo-Fish-Family-Home.h101856830.Hotel-Information)

Middletown

9.0/10

Wonderful

(2 reviews)

"Everything about our stay was perfect. The house was extremely clean and very spacious! We were there celebrating my wedding and hosting many people. All the girls got ready there in the morning and we had so much room! Taking pictures in the home that will last us a lifetime made is super easy due to how clean and modern the home was. We all felt so comfortable there and really enjoyed the backyard as well. We will definitely be coming back!Lastly, the management team was 10/10\. They answered...

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

Jenna M.

CA $789

CA $1,846 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Middletown-Hotels-Solo-Fish-Family-Home.h101856830.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/108000000/107900000/107894800/107894734/db3090a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107900000/107894800/107894734/a28498fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107900000/107894800/107894734/121fe1af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/108000000/107900000/107894800/107894734/1f5ea70a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Third Beach Road

[](https://www.expedia.ca/Middletown-Hotels-Third-Beach-Road-Summ.h107894734.Hotel-Information)

Middletown

6.0/10

(1 review)

"Renovated house, very cute. Kitchen was definitely a highlight as it was a good space for cooking and gathering together. Some amenities of house were not exactly as listed in description. Location of house was nice-close to beach and park with pickleball courts, easy access to Newport wharves and restaurants "

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

Janet S.

CA $744

CA $2,107 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Middletown-Hotels-Third-Beach-Road-Summ.h107894734.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)

![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)

![Outdoor dining](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483278/b5bfe5f0.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 reviews)

"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."

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

Swathanthra M.

CA $765

CA $1,686 total

includes taxes & fees

Jan 20 - Jan 21

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

![Smart TV, books](https://images.trvl-media.com/lodging/105000000/104150000/104141900/104141861/3015598e.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)

![Dining](https://images.trvl-media.com/lodging/105000000/104150000/104141900/104141861/c00f7dc6.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)

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

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

Dartmouth

10/10

Exceptional

(14 reviews)

"Beautiful home, well maintained, incredibly hospitable and responsive host. Kitchen is well equipped and amply stocked with cooking essential and extras for feeding your guests. Wonderful spacious yard great for outdoor fun."

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

Nick R.

CA $1,089

CA $1,919 total

includes taxes & fees

Jan 20 - Jan 21

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

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

![2 bedrooms, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/123000000/122060000/122059100/122059054/17221387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/123000000/122060000/122059100/122059054/21f7b0be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Drift Loft Houseboat

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

New Bedford

CA $196

CA $250 total

includes taxes & fees

Jan 21 - Jan 22

[](https://www.expedia.ca/New-Bedford-Hotels-Drift-Loft-Houseboat.h122059054.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=2026-02-02&endDate=2026-02-03&regionId=3000441000&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

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Cottages

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Apartments

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Condos

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## Top Cuttyhunk Hotel Reviews

![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

"My favorite place to stay on the Island! "

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

"Joy, the receptionist, greeted me with a genuine smile and made me feel so welcome right away! She went out of her way to help with my requests, which was amazing. She was very efficient and pleasant during check-in/out, making a busy process smooth."

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

![Whaler Inn and Suites](https://images.trvl-media.com/lodging/1000000/30000/27500/27418/d818de32_y.jpg)

### Whaler Inn and Suites

10/10 Excellent

"Yes"

[](https://expedia.ca/New-Bedford-Hotels-Whaler-Inn-And-Suites.h27418.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

"Great, comfortable hotel right in the heart of the historic district. Staff was very helpful. "

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

![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

"Heidi at the front desk was helpful in adjusting my schedule and the kitchen staff put out a great breakfast everyday"

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

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

### Falmouth Tides 

10/10 Excellent

"The girl who works at from desck is amazing! The hotel is very good, clean, new and the landscape is gorgeous!"

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

"Friendly staff Clean rooms"

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

"Friendly staff and clean room "

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

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

### Seaport Resort & Marina

10/10 Excellent

"Nice place great venue Staff excellent"

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

## Find out more about Cuttyhunk

## Cuttyhunk Vacation Homes information

| Number of reviews | 427                |
| ----------------- | ------------------ |
| Accommodation     | 468 Vacation Homes |
| Lowest Price      | CA $193            |
| Highest Price     | CA $3,980          |

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- [Flights to South Dartmouth ](https://www.expedia.ca/Cheap-Flights-To-South-Dartmouth.d159867.Travel-Guide-Flights)
- [Flights from Aquinnah ](https://www.expedia.ca/lp/flights/553248634998599060/flights-from-aquinnah)
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- [Aquinnah Cliffs ](https://www.expedia.ca/Aquinnah-Cliffs-Aquinnah.d6091789.Vacation-Attraction)
- [Visit Aquinnah ](https://www.expedia.ca/Aquinnah.dx553248634998599060)
- [Gay Head Lighthouse ](https://www.expedia.ca/Gay-Head-Lighthouse-Aquinnah.d6091787.Vacation-Attraction)
- [Horseneck State Beach ](https://www.expedia.ca/Horseneck-State-Beach-Westport.d553248621532666193.Vacation-Attraction)
- [Lambert's Cove Beach ](https://www.expedia.ca/Lamberts-Cove-Beach-Vineyard-Haven.d6091805.Vacation-Attraction)
- [Martha's Vineyard Vacations ](https://www.expedia.ca/Marthas-Vineyard.d6047691.Destination-Travel-Guides)
- [New Bedford Seastreak Ferry Terminal ](https://www.expedia.ca/New-Bedford-Seastreak-Ferry-Terminal-New-Bedford.d553248635976705931.Vacation-Attraction)
- [Visit South Dartmouth ](https://www.expedia.ca/South-Dartmouth.dx159867)

- [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)