Title: Thimble Islands Vacation Rentals from CA $182: Short-Term Rentals for 2025 | Expedia.ca

 

[Thimble Islands Travel Guide](https://expedia.ca/Thimble-Islands.dx6341069)[Hotels in Thimble Islands](https://expedia.ca/Thimble-Islands-Hotels.d6341069.Travel-Guide-Hotels)[Flights to Thimble Islands](https://expedia.ca/Cheap-Flights-To-Thimble-Islands.d6341069.Travel-Guide-Flights)[Thimble Islands Car Rentals](https://expedia.ca/Car-Rentals-In-Thimble-Islands.d6341069.Car-Rental-Guide)[Thimble Islands Vacation Packages](https://expedia.ca/Thimble-Islands.d6341069.Destination-Travel-Guides)

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# Thimble Islands Vacation Rentals

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## Check prices for these dates

Tonight

[Nov 9 - Nov 10](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-11-09&endDate=2025-11-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Nov 10 - Nov 11](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-11-10&endDate=2025-11-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Vacation Rentals in Thimble Islands

![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95970000/95964000/95963946/85b73e1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/96000000/95970000/95964000/95963946/019a35cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95970000/95964000/95963946/b0bf0535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Oven, stovetop, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/96000000/95970000/95964000/95963946/ccd93650.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Branford

[](https://www.expedia.ca/Branford-Hotels-Grace-Island-Private-Island-Vacations.h95963946.Hotel-Information)

![Honeymoon Apartment, 3 Bedrooms, Kitchen | In-room dining](https://images.trvl-media.com/lodging/58000000/57250000/57240500/57240415/a842220e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Executive Apartment, 2 Bedrooms, Kitchen | Living area](https://images.trvl-media.com/lodging/58000000/57250000/57240500/57240415/efa198e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Rooftop terrace](https://images.trvl-media.com/lodging/58000000/57250000/57240500/57240415/b4ae858c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Apartment, 2 Bedrooms, Kitchen | Private kitchen](https://images.trvl-media.com/lodging/58000000/57250000/57240500/57240415/236a6b7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Furnished Apartments by Hyatus Downtown at Yale

The Hill

9.6/10

Exceptional

(60)

"Wonderful property- brand new building, nice spacious rooms perfect for family. Instructors for check in and out and everything in between very clear and helpful. "

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

Zhuo

[](https://www.expedia.ca/New-Haven-Hotels-Luxury-Furnished-Apartments-By-Hyatus-Downtown-At-Yale.h57240415.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/8e3d5f6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/3067f697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/14ad38a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/b4ee006e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1-bedroom cottage with Grove Beach 🏖️ access.

Clinton

9.2/10

Wonderful

(36)

"Host was very friendly and accommodating"

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

Monika M.

CA $145

CA $306 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Clinton-Hotels-Shalom-Cottage-With-Private-Beach-Rights.h90991445.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/728215df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/a7476bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/ea540de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/38c1ca05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Shoreline Oasis

Clinton

9.2/10

Wonderful

(7)

"Cute apartment in a house, separate from the hosts space downstairs. Clean and walking distance to some great harbor-front restaurants. 1 bed and 2 couches (no pull-out couch)"

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

Molly H.

CA $251

CA $366 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Clinton-Hotels-Shoreline-Oasis.h113308197.Hotel-Information)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/77000000/76890000/76889000/76888939/1add7dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bowling](https://images.trvl-media.com/lodging/77000000/76890000/76889000/76888939/2f89df04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Apartment, 1 Bedroom, Kitchen | Living area](https://images.trvl-media.com/lodging/77000000/76890000/76889000/76888939/1991850f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Rooftop terrace](https://images.trvl-media.com/lodging/77000000/76890000/76889000/76888939/7babae09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Apartments by Hyatus at Pierpont

The Hill

9.4/10

Exceptional

(21)

"Great. Would prefer to anyone"

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

Bryan

[](https://www.expedia.ca/New-Haven-Hotels-Luxury-Apartments-By-Hyatus-At-Pierpont.h76888939.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/108000000/107560000/107557500/107557460/282f9b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107560000/107557500/107557460/d4937d76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107560000/107557500/107557460/d820b069.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107560000/107557500/107557460/a0e0c5f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Studio| Near Yale| Downtown New Haven

Downtown New Haven

9.0/10

Wonderful

(10)

"Nice location in downtown New Haven. The room itself is nice and convenient. The window near the bed does not close because there is a large tube going through the window with tape around it. On a chilly day/night this is not comfortable and there is nothing one can do since the window does not close. You can also hear everything going on outside because the window does not close. Bedsheets were not clean either. Contacted the host about the window and bedsheets and the host gave me the...

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

Noel

CA $154

CA $324 total

includes taxes & fees

Nov 20 - Nov 21

[](https://www.expedia.ca/New-Haven-Hotels-Charming-Studio-Near-Yale-Downtown-New-Haven.h107557460.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117300000/117295200/117295126/72a61305.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117300000/117295200/117295126/c90a8a7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117300000/117295200/117295126/e0608e24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/118000000/117300000/117295200/117295126/w1080h1449x0y600-da22829a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DIRECT WATERFRONT with awesome views and near Yale

West Haven

10/10

Exceptional

(2)

"Great place to stay! Easy for an overnight for a family wedding!"

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

Phoebe T.

CA $393

CA $645 total

includes taxes & fees

Nov 20 - Nov 21

[](https://www.expedia.ca/West-Haven-Hotels-DIRECT-WATERFRONT-With-Awesome-Views-And-Near-Yale.h117295126.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/20000000/19180000/19176900/19176844/73c68d22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/20000000/19180000/19176900/19176844/w1200h799x0y1-e5cd35a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19180000/19176900/19176844/w1198h799x1y1-8c5b60c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/20000000/19180000/19176900/19176844/4653b8e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Scenic Waterfront Beach Home-Private Beach, Hot Tub & Panoramic Views

Branford

10/10

Exceptional

(71)

"Great family get together where we all were very comfortable. "

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

Leanne B.

[](https://www.expedia.ca/Branford-Hotels-Private-Sandy-Beach-Hot-Tub.h19176844.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107010000/107006300/107006248/30e2063f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107010000/107006300/107006248/3c500b38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107010000/107006300/107006248/39d80e19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/108000000/107010000/107006300/107006248/676e4d97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### New Cozy 2BR Stay New Haven Close to Yale

East Rock

7.4/10

Good

(3)

"Check-in was fine. Once we got in the space was small. The dishes in the kitchen and the bed in the master bedroom were dirty. "

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

Kristin R.

CA $263

CA $397 total

includes taxes & fees

Nov 13 - Nov 14

[](https://www.expedia.ca/New-Haven-Hotels-New-Cozy-2BR-Stay-New-Haven-Close-To-Yale.h107006248.Hotel-Information)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120950000/120949800/120949708/223e1e12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120950000/120949800/120949708/439006bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120950000/120949800/120949708/fd85a046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/121000000/120950000/120949800/120949708/362e0707.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

West New Haven

9.0/10

Wonderful

(2)

"Great communication and easy check in, would recommend "

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

Ethan R.

CA $112

CA $182 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/New-Haven-Hotels-Pleasant-Apartment-With-AC-In-Charming-New-Haven.h120949708.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/96000000/95520000/95516800/95516783/208f86f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95520000/95516800/95516783/w506h683x259y0-c5e2bae2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/96000000/95520000/95516800/95516783/w505h683x260y0-b51ccb27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/96000000/95520000/95516800/95516783/w1170h1560x0y486-aa143b2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beach house in Milford, CT

Milford

10/10

Exceptional

(1)

"Beautiful Home right on the Long Island sound, we had such a great time. Beach was easily accessible, The Host’s were amazing and went above and beyond in accommodating us. Highly recommend!!!"

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

Alex F.

CA $1,011

CA $1,300 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Milford-Hotels-Beach-House-In-Milford.h95516783.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/67000000/66960000/66955300/66955225/0611344e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/67000000/66960000/66955300/66955225/w1024h767x0y0-f48123b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/67000000/66960000/66955300/66955225/d9324980.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66960000/66955300/66955225/e305ffa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Madison

10/10

Exceptional

(36)

"The place was adorable and spotless, the beds were super comfortable it was perfect and a minute from the beach! We will be back. Thanks for a great time!"

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

Edward

CA $348

CA $445 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Madison-Hotels-Newly-Renovated-Carriage-House-Near-Town-Beaches.h66955225.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/67000000/66540000/66538600/66538514/57c462f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66540000/66538600/66538514/2c06ae03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/67000000/66540000/66538600/66538514/d9ebdb03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/67000000/66540000/66538600/66538514/2625ae8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stunning Apt W/ Parking and Gym | Downtown at Yale

The Hill

10/10

Exceptional

(46)

"High quality experience, walking distance to all we needed, clean and spacious. Excellent support and communication from the hosts, would stay again."

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

Coco N.

[](https://www.expedia.ca/New-Haven-Hotels-Stunning-Apt-W-Parking-And-Gym-Downtown-At-Yale.h66538514.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/68000000/67410000/67408600/67408597/8db1b1e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/68000000/67410000/67408600/67408597/9db89f13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67410000/67408600/67408597/7ec9e71f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/68000000/67410000/67408600/67408597/59786c41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Old Saybrook

10/10

Exceptional

(34)

"Enjoyed our stay"

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

Nicole L.

CA $1,004

CA $1,660 total

includes taxes & fees

Nov 27 - Nov 28

[](https://www.expedia.ca/Old-Saybrook-Hotels-Oceanfront-Oasis-Spacious-3-Bedroom.h67408597.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/96000000/95040000/95033700/95033642/abc38fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/96000000/95040000/95033700/95033642/w506h683x259y0-6679e80a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/96000000/95040000/95033700/95033642/w507h683x259y0-8652ce53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/96000000/95040000/95033700/95033642/cc285c9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Angelica’s safe haven @ west haven

West Haven

10/10

Exceptional

(5)

"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."

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

Veronica

CA $192

CA $474 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/West-Haven-Hotels-Angelicas-Safe-Haven-West-Haven.h95033642.Hotel-Information)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/91000000/90860000/90854400/90854342/28f7af55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90860000/90854400/90854342/6a49c7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90860000/90854400/90854342/2a04bf6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90860000/90854400/90854342/87078ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large Charming Historic House close to Beaches

Clinton

9.8/10

Exceptional

(34)

"This old colonial home was very charming. We enjoyed our stay. The only thing to be aware of is there is only air conditioning in 4 of the bedrooms and it was quite hot while we were there. The location is great, and it's a short walk in to town."

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

LauraLee E.

[](https://www.expedia.ca/Clinton-Hotels-Large-Charming-Historic-House-Close-To-Beaches.h90854342.Hotel-Information)

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33510000/33507900/33507839/142f4b2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33507900/33507839/166c2314.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33510000/33507900/33507839/28a14f36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33510000/33507900/33507839/f3dd647a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Cottage in Branford

branford

10/10

Exceptional

(97)

"Host was wonderful to work with. House is amazing. Very spacious, beds were 5 Star hotel worthy!The location and view were spectacular. This was a perfect location and checked off ALL the boxes. "

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

Kelly C.

[](https://www.expedia.ca/Branford-Hotels-Waterfront-Cottage-In-Branford.h33507839.Hotel-Information)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33700000/33694400/33694344/182d5c2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/34000000/33700000/33694400/33694344/484d2f10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33700000/33694400/33694344/aee04e62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33700000/33694400/33694344/598f7463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Milford

10/10

Exceptional

(131)

"Fantastic large rambling house perfect for having a family reunion. The location is fantastic as it is right across the street from the beach. Our host Debbie was very responsive and gracious. We would definitely stay here again!"

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

Sion H.

[](https://www.expedia.ca/Milford-Hotels-Beach-Front-Arts-Crafts-House-With-Gorgeous-Views-Of-The-Sound.h33694344.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/71000000/70110000/70101200/70101127/d31ec06c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/71000000/70110000/70101200/70101127/358a7fae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/71000000/70110000/70101200/70101127/66e0afe2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/71000000/70110000/70101200/70101127/ef304302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

Westbrook Center

10/10

Exceptional

(9)

"We had a great stay at the beach house! Luanne was a super-responsive host and communication with her throughout the stay through the app was a breeze. "

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

Virgil C.

[](https://www.expedia.ca/Westbrook-Hotels-Perfect-Shoreline-Stay-Walk-To-Beach.h70101127.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106820000/106813500/106813451/932e64bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106820000/106813500/106813451/w1290h773x0y1-0b864d2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106820000/106813500/106813451/w1290h774x0y0-5b834682.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106820000/106813500/106813451/63d2600e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3 Bedroom Beach Front Cottage

Milford

10/10

Exceptional

(4)

"Stayed here while attending the Soundside Fest. Perfect location to be away from the busy Bridgeport area. The water is right there and it’s the perfect space for a weekend get away."

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

Sarah W.

[](https://www.expedia.ca/Milford-Hotels-Charming-3-Bedroom-Beach-Front-Cottage.h106813451.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=2025-11-24&endDate=2025-11-25&regionId=6341069&adults=2&sort=RECOMMENDED&openPlayBack=true)

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[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FThimble-Islands-Vacation-Rentals.d6341069.Travel-Guide-VacationRentals)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FThimble-Islands-Vacation-Rentals.d6341069.Travel-Guide-VacationRentals)

## Top Thimble Islands Hotel Reviews

![Red Roof Inn Meriden](//images.trvl-media.com/lodging/1000000/10000/2900/2831/05873179_y.jpg)

### Red Roof Inn Meriden

10/10 Excellent

"Yes"

[](https://expedia.ca/Hartford-Hotels-Red-Roof-Inn-Meriden.h2831.Hotel-Information)

![New Haven Hotel](//images.trvl-media.com/lodging/1000000/40000/36800/36721/dd69cbb4_y.jpg)

### New Haven Hotel

10/10 Excellent

"Always happy to be there! Great staff and convenient location, perfect for a short stay on campus."

[](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information)

![Clarion Inn](//images.trvl-media.com/lodging/1000000/10000/7600/7519/36377da0_y.jpg)

### Clarion Inn

10/10 Excellent

"Nice place. "

[](https://expedia.ca/North-Haven-Hotels-Clarion-Inn.h7519.Hotel-Information)

![Hyatt Place Milford / New Haven](//images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/0336d577_y.jpg)

### Hyatt Place Milford / New Haven

10/10 Excellent

"TJ was awesome. Very nice, professional and courteous. Great check in process and genuinely nice person. Thanks TJ!"

[](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information)

![Hampton Inn by Hilton Shelton](//images.trvl-media.com/lodging/1000000/210000/200400/200381/e6ef0843_y.jpg)

### Hampton Inn by Hilton Shelton

10/10 Excellent

"Convenient to Yale New Haven hospital. Nice room layout. Red Barn restaurant nearby great food and cocktails. Great breakfast at hotel"

[](https://expedia.ca/New-Haven-Hotels-Hampton-Inn-By-Hilton-Shelton.h200381.Hotel-Information)

![Home2 Suites by Hilton East Haven New Haven](//images.trvl-media.com/lodging/1000000/10000/1500/1461/b5c018f9_y.jpg)

### Home2 Suites by Hilton East Haven New Haven

10/10 Excellent

"Huge, clean, modern room"

[](https://expedia.ca/East-Haven-Hotels-Home2-Suites-By-Hilton-East-Haven-New-Haven.h1461.Hotel-Information)

![Cambria Hotel New Haven University Area](//images.trvl-media.com/lodging/79000000/78620000/78614500/78614483/a6a28eee_y.jpg)

### Cambria Hotel New Haven University Area

10/10 Excellent

"Great hotel. The WiFi didn’t work well but all else was great. "

[](https://expedia.ca/New-Haven-Hotels-Cambria-Hotel-New-Haven-University-Area.h78614483.Hotel-Information)

![Omni New Haven Hotel at Yale](//images.trvl-media.com/lodging/1000000/50000/50000/49957/7466af25_y.jpg)

### Omni New Haven Hotel at Yale

10/10 Excellent

"Very comfortable room, cheerful helpful and polite staff"

[](https://expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information)

![Best Western Executive Hotel Of New Haven - West Haven](//images.trvl-media.com/lodging/1000000/30000/23300/23217/b63e42e2_y.jpg)

### Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent

"."

[](https://expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information)

## Find out more about Thimble Islands

**Everything you need to know about** **Thimble Islands** **vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Thimble Islands vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Thimble Islands vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Thimble Islands vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Thimble Islands. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Thimble Islands vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Thimble Islands vacation rentals we have selected for you start as low as CA $182 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Thimble Islands rentals**

At Expedia, we put the best Thimble Islands vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Thimble Islands rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Thimble Islands vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Thimble Islands. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

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-   [Vacation Homes in Thimble Islands](https://expedia.ca/Thimble-Islands-Private-Vacation-Homes.d6341069-aaPrivateVacationHomes.Travel-Guide-Accommodation)
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Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAyAAAAMgAQAAAADzCzvFAAAFKUlEQVR4Xu3aPXIbORCGYagYMPQR5ig6Gng0HoVHcMhAJaz6Q+NnxqCWvVXegHrfRFQPgGcymLZT+R9Kx8HfCCQUSCiQUCChQEKBhAIJBRIKJBRIKJBQIKFAQoGEAgkFEgokFEgokFAgoUBCgYQCCQUSCiQUSCiQUCChJuQjHdpslOvDazrbj5vNc/ldF3yNfGkfjXyjBaJA5kDaqAeiQOZA2qj3qkgevxVDvrp8rX8z5CtHUvpVl9zr6GSff9uq3v4sEAUyAlEgIAUExB/Mt/dm0xmZaif6r7ZxrNpA6rwHAmKBgCQQkLZofFwg8yjZhe6r1HV6lQICAgLigRQQEPXfkWJ3/K/y6aO+SgnZf8UGAQEZqxQISAEBeQIZOeLNJ16Sf+vWqyh7u7dpOQhIAQE5PgCpgYCUI7Jvq2u13U/8bnQoj5NBFqNDeZwMshgdyuNkkMXoUB4ngyxGh/I4GWQxOpTHySCL0aE8Tp6QR40TLb2KvnW/l3s97rRf/2cgII8CGYGAPApk9LqIn6g2OzEX3d5+okbee91xM+SS5v9xrVfJdWCBgCgQEBD7AQJSdog/aLe3j6zm2ompuuuR6m/XA1mPFMjyxMVIgSxPXIwUyPLExUiBLE9cjBTI8sTFSP0bktpVbU/qWq+7yk+825O+Su7ZNqrcV4OAgIDUJyC+I/fVICAP01fsZNtLufkJHdkvfdATq0BGT6wCGT2xCmT0xCqQ0ROrQEZPrAIZTas+6r2sr9j2JOn2tpG629l+oesfmOXaj5M91rV/nV6lbwQBAQEBAQF5iJT+78S+Vq73XhGdeEm644+r3uzz3a79m/2a60MLBKSAgICA1EDUhMxr7Uk90W9v365V+TAaXW0TiP0AKSAgILtAQJ5AxvZLHWl7SltbrC/i9zr0V0k2WgYCAgIC8t4e7wMBGfmJ2u7fut29tRP/cMe1b6OPR3f8CKSuArFACgjIHEhd9bOQT1t2tk860ZA28u1p56pLGn84AAHxQBQICAjIt4ge7G9vnajt88hX1f1fo1JfpVVXgrQRiAViP0BAQED6ZHwc6cT9Hf9u8/2Jvkpdkr/K2Qe7QMYqBQKyCGSsUiAgi14V8bX1STvRO/eRJfdu875KG+/17dI3dzwICAgISA8ExGvbbe3JBuP7tKVv3ePa9xOthnh57AEB8UBAQEB6IN5HffDZl202vbTfzvabu55O1Cp/lWv9k4DKYx2IAgEBAfH1eawDUT8aKfVErU39jr8k/XW2srEQP9HzVZ/7az/3bSAg1iWBgICAeH4iiKU73rfrqt5s6ts9jSydeLdX0cY5f7spEBAQEBAF0g/QyAJZ5Nvf7PPdPm3tVdS5r8r109Udy0cWiALZB2L5yAJRIPtALB9ZL4n4iaPNpnbHt3zUu9cLPVX3DQREox6IApnbbAoCAnJA8vhNJ2rk288T8viO/2NkgYCAgFggh5EFAuIntu0d8RYX+jixp9E3f8MNAgICkttjkAICskRK/4p9baecbKS/9Naob1Tu3uyJjywQEBAQEBCQ5xHfrv/MpXz7WGUjueN/gfWzeiAgICAgILmA1B3WERkZUmy7X+hy1bxq77630Wm3BGQEokA0AgEpIHM/GNm31fl+u9K3bv2lt5eL/iQwZyMPRIHMbXUOUtdYIApkbqtzkLrGeknk7wUSCiQUSCiQUCChQEKBhAIJBRIKJBRIKJBQIKFAQoGEAgkFEgokFEgokFAgoUBCgYQCCQUSCiQUSCiQUK+D/ANmtFo2LYzWuAAAAABJRU5ErkJggg==)