Title: Thimble Islands Vacation Rentals from CA $315: Short-Term Rentals for 2026 | 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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## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Thimble Islands vacation rentals

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/2e009ba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/a654b98c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/8e3d5f6a.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.

[](https://www.expedia.ca/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information)

Clinton

9.6/10

Exceptional

(37 reviews)

"Many local restaurants near by. Christy's for breakfast was very good. "

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

Benjamin H.

CA $110

CA $246 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88520000/88510200/88510197/d84925d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/89000000/88520000/88510200/88510197/deffdcef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi](https://images.trvl-media.com/lodging/89000000/88520000/88510200/88510197/a991ed0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88520000/88510200/88510197/62b9e13d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The gardners Cottage 1 mile from long Island Sound - pet friendly

[](https://www.expedia.ca/Clinton-Hotels-The-Gardners-Cottage-1-Mile-From-Long-Island-Sound-Pet-Friendly.h88510197.Hotel-Information)

Clinton

10/10

Exceptional

(21 reviews)

"Enjoyed our stay - Highly recommend!"

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

Mary S.

CA $175

CA $357 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Clinton-Hotels-The-Gardners-Cottage-1-Mile-From-Long-Island-Sound-Pet-Friendly.h88510197.Hotel-Information)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/92000000/91720000/91713800/91713725/65f83363.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91720000/91713800/91713725/8e45a276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/92000000/91720000/91713800/91713725/034a5b48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91720000/91713800/91713725/w750h486x0y3-ef058f17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

[](https://www.expedia.ca/Higganum-Hotels-Cozy-Comforts-Country-Living-At-Its-Finest-Just-10-Min-To-Downtown-Middletown.h91713725.Hotel-Information)

Haddam

10/10

Exceptional

(28 reviews)

"Fantastic experience from beginning to end! Loved every minute of my stay! "

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

Jody U.

CA $171

CA $350 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Higganum-Hotels-Cozy-Comforts-Country-Living-At-Its-Finest-Just-10-Min-To-Downtown-Middletown.h91713725.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105190000/105183900/105183859/e98e2196.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105190000/105183900/105183859/c6f6bbf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105190000/105183900/105183859/efa99c71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105190000/105183900/105183859/b134d0d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature 

[](https://www.expedia.ca/Killingworth-Hotels-Cozy-Cabin-In-The-Woods-Situated-On-6-Private-Acres-Surrounded-By-Nature.h105183859.Hotel-Information)

Killingworth

10/10

Exceptional

(55 reviews)

"Amazing property, we loved everything about it, highly recommended, will stay again "

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

Rick

CA $616

CA $1,124 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Killingworth-Hotels-Cozy-Cabin-In-The-Woods-Situated-On-6-Private-Acres-Surrounded-By-Nature.h105183859.Hotel-Information)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/127000000/126440000/126436600/126436580/fbff432c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126440000/126436600/126436580/3334a4a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/127000000/126440000/126436600/126436580/65332922.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/127000000/126440000/126436600/126436580/2de38756.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

[](https://www.expedia.ca/Westbrook-Hotels-Private-2nd-Floor-Apt-4-Mins-To-Beach-EV-Charger-Parking-Included.h126436580.Hotel-Information)

Westbrook Center

CA $137

CA $403 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Westbrook-Hotels-Private-2nd-Floor-Apt-4-Mins-To-Beach-EV-Charger-Parking-Included.h126436580.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/2db3f072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/bdac0629.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/646c7316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/02f647fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### All New 1BR with tons of Charm

[](https://www.expedia.ca/Wallingford-Hotels-Seasons-Hospitality-Presents-All-New-1BR-With-Tons-Of-Charm.h102008958.Hotel-Information)

Wallingford Center

9.8/10

Exceptional

(8 reviews)

"Charming, unique, and very comfortable. Would surely stay again. "

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

David S.

CA $157

CA $397 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Wallingford-Hotels-Seasons-Hospitality-Presents-All-New-1BR-With-Tons-Of-Charm.h102008958.Hotel-Information)

![Cookware/dishes/utensils](https://images.trvl-media.com/lodging/96000000/95040000/95032200/95032165/0eb76bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, Netflix, streaming services](https://images.trvl-media.com/lodging/96000000/95040000/95032200/95032165/f8e41211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer](https://images.trvl-media.com/lodging/96000000/95040000/95032200/95032165/d9bfd1d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/96000000/95040000/95032200/95032165/a1d7bab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

[](https://www.expedia.ca/New-Haven-Hotels-Urban-Oasis-3BR-Parking-Washer-Dryer-Yale-East-Rock.h95032165.Hotel-Information)

East Rock

9.8/10

Exceptional

(14 reviews)

"Thanks to the detailed information from the host check-in couldn’t have been easier. The home was clean and well-appointed. Great location with access to the Yale tram and local markets and restaurants. "

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

Denyce D.

CA $130

CA $365 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/New-Haven-Hotels-Urban-Oasis-3BR-Parking-Washer-Dryer-Yale-East-Rock.h95032165.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/dad41f01.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/104000000/103030000/103030000/103029991/eacee686.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/ac508f02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/f2a274b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### All New Studio apartment in center of town

[](https://www.expedia.ca/Wallingford-Hotels-All-New-Studio-Apartment-In-Center-Of-Town.h103029991.Hotel-Information)

Wallingford Center

10/10

Exceptional

(2 reviews)

"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."

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

Nadine C.

CA $157

CA $397 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Wallingford-Hotels-All-New-Studio-Apartment-In-Center-Of-Town.h103029991.Hotel-Information)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107010000/107006300/107006244/2e4ae9c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107010000/107006300/107006244/0354b8c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107010000/107006300/107006244/dc1e76d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107010000/107006300/107006244/bb842e1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Downtown New Haven Escape

[](https://www.expedia.ca/New-Haven-Hotels-Downtown-New-Haven-Escape.h107006244.Hotel-Information)

Dwight

8.0/10

Very good

(6 reviews)

"Great place to stay, a little tight for 2 people but good for a single. Well appointed and a great location in the city. Would definitely recommend a stay here."

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

Michael H.

CA $164

CA $315 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/New-Haven-Hotels-Downtown-New-Haven-Escape.h107006244.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)

![Smart TV](https://images.trvl-media.com/lodging/96000000/95040000/95033700/95033642/90f4ffc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/96000000/95040000/95033700/95033642/w905h683x59y0-78a87dbf.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

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

West Haven

10/10

Exceptional

(6 reviews)

"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 $198

CA $478 total

includes taxes & fees

Feb 24 - Feb 25

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

![Dining](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/eea5c652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/e689a456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/95b993b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/a34caa46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

[](https://www.expedia.ca/Clinton-Hotels-The-Cozy-Glass-House.h107779041.Hotel-Information)

Clinton

10/10

Exceptional

(3 reviews)

"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "

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

Elya D.

CA $149

CA $677 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Clinton-Hotels-The-Cozy-Glass-House.h107779041.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120070000/120065600/120065513/02904b89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer](https://images.trvl-media.com/lodging/121000000/120070000/120065600/120065513/a94b7e4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/121000000/120070000/120065600/120065513/43b2916f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/121000000/120070000/120065600/120065513/9dab6fe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### One bedroom apartment in United States of America, New Haven

[](https://www.expedia.ca/New-Haven-Hotels-One-Bedroom-Apartment-In-United-States-Of-America.h120065513.Hotel-Information)

Dwight

8.6/10

Excellent

(4 reviews)

"Apartment was very clean and well supplied, host very responsive. Location is convenient to Yale and restaurants. As noted in the listing, you'll have to carry your luggage up 4 flights of stairs. There is some street noise as is typical for that part of the city. Very happy with it overall and plan to stay again."

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

Philip S.

CA $130

CA $283 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/New-Haven-Hotels-One-Bedroom-Apartment-In-United-States-Of-America.h120065513.Hotel-Information)

![](https://images.trvl-media.com/lodging/91000000/90870000/90867500/90867477/74b8760e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/91000000/90870000/90867500/90867477/5fccfa31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/91000000/90870000/90867500/90867477/b6be5543.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/91000000/90870000/90867500/90867477/0ce4a5f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds

[](https://www.expedia.ca/New-Haven-Hotels-Green-N-Groovy-In-The-Heart-Of-East-Rock-Near-DT-Yale-Quaint-And-Comfortable.h90867477.Hotel-Information)

East Rock

10/10

Exceptional

(4 reviews)

"Great place - wish we had more than one night. "

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

Steri-Clean N.

CA $260

CA $539 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/New-Haven-Hotels-Green-N-Groovy-In-The-Heart-Of-East-Rock-Near-DT-Yale-Quaint-And-Comfortable.h90867477.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/9e16b0d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/6f35c24c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/2a31845e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/00ea4ccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish Modern Stay Steps from the Ocean

[](https://www.expedia.ca/Clinton-Hotels-Stylish-Modern-Stay-Steps-From-The-Ocean.h120150878.Hotel-Information)

Clinton

10/10

Exceptional

(1 review)

"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "

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

Kelly Z.

CA $222

CA $461 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Clinton-Hotels-Stylish-Modern-Stay-Steps-From-The-Ocean.h120150878.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/109000000/108430000/108426600/108426521/80f01b71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108430000/108426600/108426521/29cf6475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108430000/108426600/108426521/6cc66b4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108430000/108426600/108426521/w828h1096x0y0-260bbef7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beach Apartment in Woodmont Milford

[](https://www.expedia.ca/Milford-Hotels-Beach-Apt-In-Woodmont-Milford.h108426521.Hotel-Information)

Milford

9.0/10

Wonderful

(2 reviews)

"Had a great stay!"

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

Garry G.

CA $153

CA $460 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Milford-Hotels-Beach-Apt-In-Woodmont-Milford.h108426521.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/92000000/91290000/91280400/91280330/w912h683x56y0-1b804b30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/92000000/91290000/91280400/91280330/w509h683x257y0-63fee154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/92000000/91290000/91280400/91280330/w906h683x60y0-589c021c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91290000/91280400/91280330/w905h683x60y0-ac1558cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious Bohemian Nook

[](https://www.expedia.ca/New-Haven-Hotels-Spacious-Bohemian-Nook.h91280330.Hotel-Information)

West New Haven

8.4/10

Very good

(8 reviews)

"The place was incredibly clean. The instructions were clear for entering and locking up. Great experience! Thanks Dylan. "

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

Andrew P.

CA $154

CA $346 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/New-Haven-Hotels-Spacious-Bohemian-Nook.h91280330.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/60000000/59630000/59625600/59625523/d1cc68c7.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/60000000/59630000/59625600/59625523/3c6f0ef9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/60000000/59630000/59625600/59625523/58d0e4d3.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)

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

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

Mill River

9.2/10

Wonderful

(19 reviews)

"Great value very close to university. "

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

Lawrence

CA $172

CA $310 total

includes taxes & fees

Feb 25 - Feb 26

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

![TV](https://images.trvl-media.com/lodging/120000000/119680000/119675600/119675542/f31b1b95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/120000000/119680000/119675600/119675542/2e811bdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer](https://images.trvl-media.com/lodging/120000000/119680000/119675600/119675542/6b7f737f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119680000/119675600/119675542/a9759b5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.

[](https://www.expedia.ca/New-Haven-Hotels-Modern-Studio-Near-Yale.h119675542.Hotel-Information)

Dwight

8.0/10

Very good

(2 reviews)

"The studio apartment is in a very convenient location. It is a lovely walk to Yale. Many restaurants just outside the door. My friends, who joined me for a meal, found parking easily. It was a plus having use of a parking pass for Dwight Street. We never had a problem getting a parking spot. We also loved being able to bring our two small pups with us. The bottle of wine was a thoughtful touch. "

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

ELIZABETH M S M.

CA $188

CA $320 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/New-Haven-Hotels-Modern-Studio-Near-Yale.h119675542.Hotel-Information)

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

![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)

![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)

![Interior](https://images.trvl-media.com/lodging/77000000/76970000/76963400/76963336/c08fe3a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Fair Haven

7.6/10

Good

(5 reviews)

"Thanks for hosting us! It was clean and nice. For future guests, a long body mirror might be nice but we had a wonderful time and appreciated you bringing us extra towels quickly!"

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

Jamie S.

CA $158

CA $311 total

includes taxes & fees

Feb 24 - Feb 25

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

![Interior](https://images.trvl-media.com/lodging/113000000/113000000/112999100/112999076/9fd3ea2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/113000000/112999100/112999076/c48a29ab.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/113000000/113000000/112999100/112999076/d0920f95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/113000000/112999100/112999076/fc0e0fc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

###  The Nest At Elm City Flats.

[](https://www.expedia.ca/New-Haven-Hotels-Overlook-New-Haven-In-This-2-BDR-Peaceful-Carribean-Nest.h112999076.Hotel-Information)

West New Haven

9.6/10

Exceptional

(9 reviews)

"We had a great stay at this apartment. You do have to go up three flight of stairs but thankfully we were able to climb them. "

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

Joan S.

CA $122

CA $325 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/New-Haven-Hotels-Overlook-New-Haven-In-This-2-BDR-Peaceful-Carribean-Nest.h112999076.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=2026-03-09&endDate=2026-03-10&regionId=6341069&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=VR_SPRING_PROMO_6341069)

## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America&regionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=APART_HOTEL)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America&regionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=CABIN)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America&regionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=COTTAGE)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America&regionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=APARTMENT)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America&regionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=CONDO)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America&regionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=VACATION_HOME)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America&regionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=VILLA)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America&regionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=HOUSE_BOAT)

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## Top Thimble Islands Hotel Reviews

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

### Hyatt Place Milford / New Haven

10/10 Excellent

"Excellent place, welcomed by desk staff, smooth and fast check in. Room clean and spacious."

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

![The Blake Hotel](https://images.trvl-media.com/lodging/33000000/32130000/32129700/32129620/95723c61_y.jpg)

### The Blake Hotel

10/10 Excellent

"The hotel itself is beautiful, and everything was beyond clean. Staff was so welcoming and lovely. "

[](https://expedia.ca/New-Haven-Hotels-The-Blake-Hotel.h32129620.Hotel-Information)

![Homewood Suites by Hilton Orange New Haven](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979983/cf46bed4_y.jpg)

### Homewood Suites by Hilton Orange New Haven

10/10 Excellent

"Excellent "

[](https://expedia.ca/New-Haven-Hotels-Homewood-Suites-By-Hilton-Orange-New-Haven.h38979983.Hotel-Information)

![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg)

### Water's Edge Resort & Spa

10/10 Excellent

"The view of the ocean and gazebos were amazing. Everyone was so courteous and it wasn't a madhouse. Quiet and relaxing. The pool was also nice and warm"

[](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information)

![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg)

### New Haven Hotel

10/10 Excellent

"Great stay"

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

![Holiday Inn Express Branford-New Haven by IHG](https://images.trvl-media.com/lodging/1000000/130000/124400/124313/908bc53f_y.jpg)

### Holiday Inn Express Branford-New Haven by IHG

10/10 Excellent

"Clean room and a tasty breakfast "

[](https://expedia.ca/New-Haven-Hotels-Holiday-Inn-Express-Branford-New-Haven.h124313.Hotel-Information)

![Motel 6 Milford, CT](https://images.trvl-media.com/lodging/1000000/10000/300/291/4c692d71_y.jpg)

### Motel 6 Milford, CT

10/10 Excellent

"Nice "

[](https://expedia.ca/New-Haven-Hotels-Motel-6-Milford.h291.Hotel-Information)

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

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

10/10 Excellent

"Nice "

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

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

### Omni New Haven Hotel at Yale

10/10 Excellent

"Great "

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

## Find out more about Thimble Islands

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Thimble Islands. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Thimble Islands ](https://expedia.ca/Thimble-Islands-Private-Vacation-Homes.d6341069-aaPrivateVacationHomes.Travel-Guide-Accommodation)
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- [Hotels in East Rock](https://expedia.ca/East-Rock-New-Haven-Hotels.0-n6349501-0.Travel-Guide-Filter-Hotels)
- [Mohegan Sun Casino hotels](https://expedia.ca/Mohegan-Sun-Casino-Hotels.0-l6170930-0.Travel-Guide-Filter-Hotels)
- [Harry A. Gampel Pavilion hotels](https://expedia.ca/Harry-A-Gampel-Pavilion-Hotels.0-l6089821-0.Travel-Guide-Filter-Hotels)
- [Hotchkiss-Fyler House Museum hotels](https://expedia.ca/Hotchkiss-Fyler-House-Museum-Hotels.0-l553248621532665870-0.Travel-Guide-Filter-Hotels)
- [Downtown New Haven Cheap Hotels](https://expedia.ca/Downtown-New-Haven-New-Haven-Hotels-Cheap-Hotels.0-n553248635976008334-0-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Mystic - New London Hotels with Hot Tubs](https://expedia.ca/Mystic-New-London-Hotels-Hotels-With-Hot-Tubs.0-0-d602994-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels)
- [Gold Coast Hotels with Childcare](https://expedia.ca/Gold-Coast-Hotels-Hotels-With-Childcare.0-0-d6233751-tHotelswithChildcare.Travel-Guide-Filter-Hotels)
- [Connecticut Trolley Museum hotels](https://expedia.ca/Connecticut-Trolley-Museum-Hotels.0-l501158-0.Travel-Guide-Filter-Hotels)
- [Foxwoods Resort Casino hotels](https://expedia.ca/Foxwoods-Resort-Casino-Hotels.0-l6170926-0.Travel-Guide-Filter-Hotels)
- [Coastal Connecticut Cheap Hotels](https://expedia.ca/Coastal-Connecticut-Hotels-Cheap-Hotels.0-0-d6233741-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Bill Miller’s Castle hotels](https://expedia.ca/Bill-Millers-Castle-Hotels.0-l553248621563220905-0.Travel-Guide-Filter-Hotels)
- [Coastal Connecticut Casino Hotels](https://expedia.ca/Coastal-Connecticut-Hotels-Casino-Hotel.0-0-d6233741-tCasinoHotel.Travel-Guide-Filter-Hotels)
- [Mystic - New London Family Hotels](https://expedia.ca/Mystic-New-London-Hotels-Family-Hotel.0-0-d602994-tFamilyHotel.Travel-Guide-Filter-Hotels)
- [Ridgefield Playhouse hotels](https://expedia.ca/Ridgefield-Playhouse-Hotels.0-l6182187-0.Travel-Guide-Filter-Hotels)
- [Best Hotels in Essex Village](https://expedia.ca/Essex-Village-Hotels.d553248635976469812.Travel-Guide-Hotels)
- [Downtown New Haven All Inclusive Resorts and Hotels](https://expedia.ca/Downtown-New-Haven-New-Haven-Hotels-All-Inclusive-Hotel.0-n553248635976008334-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels)
- [Best Hotels in Uncasville](https://expedia.ca/Uncasville-Hotels.d602502.Travel-Guide-Hotels)
- [Coastal Connecticut Hotels with Free Breakfast](https://expedia.ca/Coastal-Connecticut-Hotels-Hotels-With-Free-Breakfast.0-0-d6233741-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels)
- [Mohegan Sun Arena hotels](https://expedia.ca/Mohegan-Sun-Arena-Hotels.0-l6089825-0.Travel-Guide-Filter-Hotels)

Flights

- [Flights to Uncasville](https://expedia.ca/Cheap-Flights-To-Uncasville.d602502.Travel-Guide-Flights)

Cars

- [Car rental Windsor Locks Airport (BDL)](https://expedia.ca/Car-Rentals-In-Bradley-Intl.d4998210.Car-Rental-Guide)
- [Discount Quebec Car Rentals In Mystic New London](https://expedia.ca/Discount-Quebec-Car-Rentals-In-Mystic-New-London.d602994-c1137.Car-Rental-Guide-Suppliers)

Packages

- [Foxwoods Resort Casino](https://expedia.ca/Foxwoods-Resort-Casino-Mashantucket.d6170926.Vacation-Attraction)
- [Ocean Beach Park](https://expedia.ca/Ocean-Beach-Park-New-London.d6071449.Vacation-Attraction)
- [Olde Mistick Village](https://expedia.ca/Olde-Mistick-Village-Mystic.d6127201.Vacation-Attraction)

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