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

 

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# Thimble Islands Vacation Rentals

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## Check prices for these dates

In two weeks

[Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2026-02-06&endDate=2026-02-08&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Thimble Islands Vacation Homes

![Beach](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/891accf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/1c400db4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/623abb73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/a0e54ecb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beachside Bliss w/ Game Room, Gym & Golf Green

Westbrook

CA $139

CA $643 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Westbrook-Hotels-Beachside-Bliss-W-Game-Room.h121396426.Hotel-Information)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/66000000/65400000/65396400/65396309/bf5d2058.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/66000000/65400000/65396400/65396309/94637ed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/66000000/65400000/65396400/65396309/c537ec71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/66000000/65400000/65396400/65396309/4b37fe37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Once the old Schools house now a newly furnished Apartment

Wallingford Center

9.0/10

Wonderful

(13)

"The fact that it was listed with a hot tub and there wasn't one was very disappointing! Clean and cute. Location was convenient. Could use a better bed and pillows. It was a good place to stay,"

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

Robert K.

CA $153

CA $397 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Wallingford-Hotels-Once-The-Old-Schools-House-Now-A-Newly-Furnished-Apartment.h65396309.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/119000000/118950000/118949700/118949631/ce1fc249.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118950000/118949700/118949631/f54053dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/119000000/118950000/118949700/118949631/57c8df73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/119000000/118950000/118949700/118949631/7f5d3999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy East Haven Home • Near Beach & Yale

Momauguin

10/10

Exceptional

(4)

"Such a cute place, loved all the nautical touches. Great space for a weekend getaway, pretty well-stocked kitchen, clean & cozy. Really appreciated the outdoor space & amenities too! And Michael the host is very responsive & helpful! "

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

Amal A.

CA $158

CA $210 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/East-Haven-Hotels-Cozy-Home-Near-New-Haven.h118949631.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76540000/76532900/76532852/w1440h958x0y3-16ec6595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76540000/76532900/76532852/e207012e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76540000/76532900/76532852/bf5bce9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76540000/76532900/76532852/w1024h676x0y3-0bf31286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking

East Rock

9.6/10

Exceptional

(8)

"Property owner takes great care of the place. Instructions were easy to follow and the location was right down the road from the places we were going to. We would rent again if we ever come back to New Haven"

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

Derek L.

CA $162

CA $468 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/New-Haven-Hotels-Cozy-Gem-In-Heart-Of-East-Rock-King-Bed-Near-DT.h76532852.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/f8cef332.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h960x0y0-cce9554c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h953x0y0-69414cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/a2326e66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Saybrook Manor

9.6/10

Exceptional

(133)

"We thoroughly enjoyed our stay...the historic home was a perfect New England getaway for our group of women."

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

Shari M.

CA $281

CA $726 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Old-Saybrook-Hotels-Capt-Nathaniel-Clarke-Historic-Homestead.h18762073.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59630000/59625600/59625523/41e92d5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/60000000/59630000/59625600/59625523/d503d3cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/60000000/59630000/59625600/59625523/8cacb4e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/60000000/59630000/59625600/59625523/d1cc68c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stocked home close to Yale, in Heart of New Haven

Mill River

9.2/10

Wonderful

(18)

"Gary’s unit met our needs perfectly, and we are glad that we found it for our family visit. The unit was clean, spacious, and the location was great."

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

Wataru M.

CA $209

CA $357 total

includes taxes & fees

Nov 13 - Nov 14

[](https://www.expedia.ca/New-Haven-Hotels-Stocked-Home-Close-To-Yale.h59625523.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76520000/76517200/76517198/20e25c4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76520000/76517200/76517198/1ad08d18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/77000000/76520000/76517200/76517198/w1024h677x0y3-3ae856a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/77000000/76520000/76517200/76517198/4c904784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Casa Soleada in East Rock |King Bed| Near DT and Yale SOM | Free parking

East Rock

9.8/10

Exceptional

(10)

"Beautiful and spacious home in lovely neighbourhood. We so enjoyed our brief stay. "

![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg)

Nina

CA $202

CA $534 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/New-Haven-Hotels-Casa-Soleada-In-East-Rock-King-Bed-Near-DT-And-Yale-SOM.h76517198.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/58000000/57700000/57696800/57696731/04508426_edited_1287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/58000000/57700000/57696800/57696731/41a9baa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/58000000/57700000/57696800/57696731/ab91a76d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/58000000/57700000/57696800/57696731/e8f968ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Newly Remodeled 1-BR Close to Everything yet Very Private

Wallingford

10/10

Exceptional

(9)

"We were please with this top floor property which was only 3.5 miles where we were for graduation weekend. The apartment is well-appointed and quiet. Karl was an excellent and highly responsive host. Some reviews mention difficulties accessing the driveway because of the unusual road intersections there, but we did not find that an issue. The parking is ample and behind the building. Nice yard, patio, and grill area. Not fancy but very functional. We would stay there again."

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

William M.

CA $162

CA $405 total

includes taxes & fees

Nov 13 - Nov 14

[](https://www.expedia.ca/Wallingford-Hotels-Newly-Remodeled-1-BR-Close-To-Everything-Yet-Very-Private.h57696731.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/w1440h957x0y3-6274ae75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/d3b32f3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/fdec6f9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/bbafc8c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Jewel of The Cove - Historic Coastal Retreat

East Shore

10/10

Exceptional

(5)

"loved it so much, beautiful property 100 % would stay again "

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

Leilani R.

CA $291

CA $728 total

includes taxes & fees

Nov 17 - Nov 18

[](https://www.expedia.ca/East-Haven-Hotels-The-Jewel-Of-The-Cove-Historic-Coastal-Retreat.h105862474.Hotel-Information)

![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/77000000/76970000/76963400/76963336/89c597eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/77000000/76970000/76963400/76963336/2c0c3b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76970000/76963400/76963336/64eef4ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/77000000/76970000/76963400/76963336/02effb57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Fair Haven

7.6/10

Good

(5)

"This was a 2 month stay for us and was not equipped for longer term stays. Storage is a challenge. On the plus side, the host is responds quickly and helped with any issues we had. The location was great as we needed to be in a specific area."

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

monica f.

CA $204

CA $372 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/New-Haven-Hotels-Gorgeous-Waterfront-2-Bedroom-1-Bath-Modern-Home.h76963336.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/94000000/93400000/93397900/93397831/8c48c1bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/94000000/93400000/93397900/93397831/ef2c1702.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/94000000/93400000/93397900/93397831/3625879a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, Netflix, Hulu, books](https://images.trvl-media.com/lodging/94000000/93400000/93397900/93397831/498bd184.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Santiago in Science Park at Yale New Haven

Dixwell

8.0/10

Very good

(8)

"On both nights of our stay we dealt with loud noises from the apartment above going past 1:30 AM. This was unsettling and prevented us from getting a good night’s sleep. While the pictures online are accurate as regards the interior – it was clean and updated - they don’t illustrate the unfortunate exterior environment. The “off street parking” is a communal dirt area behind two houses with potholes and a very narrow driveway connecting it to the road. If you have a minivan or a larger car, you...

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

Jen r.

CA $170

CA $341 total

includes taxes & fees

Nov 19 - Nov 20

[](https://www.expedia.ca/New-Haven-Hotels-The-Santiago-In-Science-Park-At-Yale-New-Haven.h93397831.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101950000/101940900/101940832/ac2eb1be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101950000/101940900/101940832/95857e89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/102000000/101950000/101940900/101940832/a059ffe0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/102000000/101950000/101940900/101940832/056a1402.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### McAngel Haven: 5 mins from Yale

West Haven

9.6/10

Exceptional

(17)

"My family and I stayed at the property for a wedding in Milford. The house had plenty of space for our group to say, and the bedrooms were comfortable. The three bathrooms were helpful for our group to efficiently get ready for the wedding, and the kitchen was adequately appointed for us to have meals."

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

Bradley D.

CA $322

CA $740 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/West-Haven-Hotels-McAngel-Haven-5-Mins-From-Yale.h101940832.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/56000000/55580000/55578100/55578046/2eae24fa.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/56000000/55580000/55578100/55578046/c089c103.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/56000000/55580000/55578100/55578046/16d2ef5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/56000000/55580000/55578100/55578046/159aea95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 171 Broadway · Renovated House Steps Away From The Ocean

Milford

8.4/10

Very good

(8)

"\*\*Overall lowest experience of all vacation rental experiences\*\* Pros: - Out-of-season pricing (in-season is total rip-off), - Relatively clean - Safe community - Comfortable beds - Decent bathrooms - Good AC (except for noise - see below) Cons: - Front & Rear door locks both beeped and auto unlocked at the same time at midnight on the last night - Cheap shades in bedrooms didn't fully cover windows - Under-furnished. Despite red flags in reading reviews & owner responses on there not being...

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

Tom G.

CA $295

CA $541 total

includes taxes & fees

Nov 13 - Nov 14

[](https://www.expedia.ca/Milford-Hotels-171-Broadway-Renovated-House-Steps-Away-From-The-Ocean.h55578046.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/79000000/78180000/78173400/78173305/c1d5dab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/79000000/78180000/78173400/78173305/8c7a6352.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/79000000/78180000/78173400/78173305/6dab1099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78180000/78173400/78173305/b7acb6c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Fair Haven

9.6/10

Exceptional

(13)

"Spacious clean well maintained water front home with all the amenities. Great communication with the property manager. Absolutely loved our stay and will look forward rent again."

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

Jeevan K.

CA $309

CA $545 total

includes taxes & fees

Nov 13 - Nov 14

[](https://www.expedia.ca/New-Haven-Hotels-Gorgeous-Waterfront-3-Bedroom.h78173305.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122130000/122125300/122125262/f5a66411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/123000000/122130000/122125300/122125262/8d51a0b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/123000000/122130000/122125300/122125262/b3188227.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books](https://images.trvl-media.com/lodging/123000000/122130000/122125300/122125262/a7693e51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Shelton

CA $157

CA $571 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Shelton-Hotels-Luxurious-Modern-Feel-W-Custom-Features-AC.h122125262.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/92000000/91570000/91561700/91561648/0c458b06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball, table tennis, books](https://images.trvl-media.com/lodging/92000000/91570000/91561700/91561648/cb920c33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91570000/91561700/91561648/8cd0f7d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball, table tennis, books](https://images.trvl-media.com/lodging/92000000/91570000/91561700/91561648/b9ec2943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

East Shore

8.0/10

Very good

(1)

"It was a nice place. We were in CT for a wedding. It was very close to the venue. The bathrooms were a good size for 10 people staying there getting ready. I would definitely return for another family event in the area. Thank you to the home owners."

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

Suzanne S.

CA $388

CA $752 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/East-Haven-Hotels-RARE-New-Haven-GetawayPRIVATE-POOLWalk-To-BEACH.h91561648.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/101000000/100840000/100834300/100834240/w776h683x124y0-ae153ead.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/101000000/100840000/100834300/100834240/93b50094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100840000/100834300/100834240/0845eb45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100840000/100834300/100834240/cd224da3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Clear LI Sound waterview, Wedding pics, Yale&Beach

East Shore

10/10

Exceptional

(10)

"Amazing location & views. House was pristine & had all amenities. Great park & dog walking path across the street"

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

Louis R.

CA $411

CA $878 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/East-Haven-Hotels-Clear-LI-Sound-Waterview.h100834240.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34470000/34466200/34466156/dfa32454.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/35000000/34470000/34466200/34466156/c8ee0a22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34470000/34466200/34466156/23f6edbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34470000/34466200/34466156/0c89126b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peace Barn in the heart of the CT River Valley

Deep River Center

8.6/10

Excellent

(4)

"The grounds were beautiful Everything else for me and my family’ was awful and should not be rented as a vrbo. Lots of bugs. The upstairs bathroom had no water pressure or hot water. The upstairs bedroom window and screen were duct taped shut. The kitchen was a mishmash of things that didn’t work. The house did smell of mold. The only thing this property has to offer is the lake and the land the lodging was terrible and not at all comfortable. And the lights were terrible, if you could even...

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

Cindy G.

CA $562

CA $999 total

includes taxes & fees

Nov 13 - Nov 14

[](https://www.expedia.ca/Deep-River-Hotels-Peace-Barn-In-The-Heart-Of-The-CT-River-Valley.h34466156.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/4aaa8de8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/e88adc9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/20bbb653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/83198fbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic New England home ,Reunions Beach pass

Guilford

9.2/10

Wonderful

(90)

"House was perfect for family get together. Enjoyed walking into town for afternoon shopping and dining."

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

Jennifer D.

CA $267

CA $611 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Guilford-Hotels-Historic-New-England-Home.h18760693.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)

![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)

![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)

### 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)

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&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true)

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

## 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

## Thimble Islands Vacation Homes information

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

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-   [Hotels with Early Check-in in The Centre](https://www.expedia.ca/The-Centre-East-Haven-Hotels-Hotel-With-Early-Check-In.0-n553248635976469020-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels)
-   [Hotels with Free Airport Shuttle in The Centre](https://www.expedia.ca/The-Centre-East-Haven-Hotels-Hotels-With-Free-Airport-Shuttle.0-n553248635976469020-0-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels)
-   [Hotels with Hot Tubs in The Centre](https://www.expedia.ca/The-Centre-East-Haven-Hotels-Hotels-With-Hot-Tubs.0-n553248635976469020-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels)
-   [Hotels with an Indoor Pool in The Centre](https://www.expedia.ca/The-Centre-East-Haven-Hotels-Hotels-With-Indoor-Pool.0-n553248635976469020-0-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels)
-   [Hotels with Kitchenettes in The Centre](https://www.expedia.ca/The-Centre-East-Haven-Hotels-Hotels-With-Kitchenettes.0-n553248635976469020-0-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels)
-   [Hotels with smoking rooms in The Centre](https://www.expedia.ca/The-Centre-East-Haven-Hotels-Hotels-With-Smoking-Rooms.0-n553248635976469020-0-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels)
-   [Hotels with Tennis Courts in The Centre](https://www.expedia.ca/The-Centre-East-Haven-Hotels-Hotels-With-Tennis-Courts.0-n553248635976469020-0-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels)
-   [Spa Hotels in The Centre](https://www.expedia.ca/The-Centre-East-Haven-Hotels-Spa-Hotel.0-n553248635976469020-0-tSpaHotel.Travel-Guide-Filter-Hotels)
-   [Waterpark Hotels in The Centre](https://www.expedia.ca/The-Centre-East-Haven-Hotels-Waterpark-Hotels.0-n553248635976469020-0-tWaterparkHotels.Travel-Guide-Filter-Hotels)
-   [The Centre Hotels](https://www.expedia.ca/The-Centre-East-Haven-Hotels.0-n553248635976469020-0.Travel-Guide-Filter-Hotels)

-   [Flights to Branford](https://www.expedia.ca/Cheap-Flights-To-Branford.d6243.Travel-Guide-Flights)
-   [Flights to Guilford](https://www.expedia.ca/Cheap-Flights-To-Guilford.d183062.Travel-Guide-Flights)
-   [Flights to North Branford](https://www.expedia.ca/Cheap-Flights-To-North-Branford.d6004522.Travel-Guide-Flights)
-   [Flights from Branford](https://www.expedia.ca/lp/flights/6243/flights-from-branford)

-   [Branford Vacations](https://www.expedia.ca/Branford.d6243.Destination-Travel-Guides)
-   [Visit Branford](https://www.expedia.ca/Branford.dx6243)
-   [Visit Momauguin](https://www.expedia.ca/East-Haven-Momauguin.dx553248635976474871)

-   [Car rental Branford](https://www.expedia.ca/Car-Rentals-In-Branford.d6243.Car-Rental-Guide)
-   [Car rental East Haven](https://www.expedia.ca/Car-Rentals-In-East-Haven.d7792.Car-Rental-Guide)
-   [Car rental Guilford](https://www.expedia.ca/Car-Rentals-In-Guilford.d183062.Car-Rental-Guide)
-   [Enterprise Rental Cars in Branford](https://www.expedia.ca/Enterprise-Car-Rentals-In-Branford.d6243-c15.Car-Rental-Guide-Suppliers)
-   [Sixt Rental Cars in Branford](https://www.expedia.ca/Sixt-Car-Rentals-In-Branford.d6243-c35.Car-Rental-Guide-Suppliers)

-   [Guilford Vacation Rentals](https://www.expedia.ca/Guilford-Vacation-Rentals.d183062.Travel-Guide-VacationRentals)

-   [Things to do in Branford](https://www.expedia.ca/Things-To-Do-In-Branford.d6243.Travel-Guide-Activities)

-   [Book Vacation Homes in Thimble Islands on Expedia.com](https://www.expedia.com/Thimble-Islands-Private-Vacation-Homes.d6341069-aaPrivateVacationHomes.Travel-Guide-Accommodation)