Title: Thimble Islands Vacation Rentals from CA $247: 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) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Thimble Islands Vacation Rentals - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2026-05-01&endDate=2026-05-03&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) ![Exterior detail](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/b4ee006e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/0c11d8f6.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) ### 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 (34) "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 $117 CA $257 total includes taxes & fees Jan 10 - Jan 11 [](https://www.expedia.ca/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information) ![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/122000000/121400000/121396500/121396426/021898ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/55b895af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beachside Bliss w/ Game Room, Gym & Golf Green [](https://www.expedia.ca/Westbrook-Hotels-Beachside-Bliss-W-Game-Room.h121396426.Hotel-Information) Westbrook 10/10 Exceptional (1) "Perfect house for 6 guests. Loved that it was close to the beach." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shannon G. CA $210 CA $705 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Westbrook-Hotels-Beachside-Bliss-W-Game-Room.h121396426.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/100000000/99410000/99406900/99406822/f55efa2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99410000/99406900/99406822/1c33ad63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99410000/99406900/99406822/9b6d9dce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/100000000/99410000/99406900/99406822/c4e3d4e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Adorable Cottage, 5 min walk to water & town [](https://www.expedia.ca/Westbrook-Hotels-Adorable-Cottage.h99406822.Hotel-Information) Westbrook Center 9.4/10 Exceptional (15) "Very nice small place to stay by the beach and close to great coffee shop. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donovan V. CA $261 CA $602 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Westbrook-Hotels-Adorable-Cottage.h99406822.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/115000000/114610000/114606800/114606760/01311672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114610000/114606800/114606760/fbf67c3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/115000000/114610000/114606800/114606760/9a205457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms](https://images.trvl-media.com/lodging/115000000/114610000/114606800/114606760/723e2839.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Westville Stay • 2BR • Near Yale • Free Parking [](https://www.expedia.ca/New-Haven-Hotels-Westville-Stay-2BR-Near-Yale-Free-Parking.h114606760.Hotel-Information) West New Haven 10/10 Exceptional (3) "We were only here for a short stay, but everything was smooth and comfortable for us! Hotel-like linens and blackout curtains made for a very cozy sleeping experience." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ross f. CA $100 CA $310 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/New-Haven-Hotels-Westville-Stay-2BR-Near-Yale-Free-Parking.h114606760.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) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/a34caa46.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) ![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) ### 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) "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 $193 CA $728 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Clinton-Hotels-The-Cozy-Glass-House.h107779041.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) ![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) ![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) ![Interior](https://images.trvl-media.com/lodging/92000000/91720000/91713800/91713725/8e45a276.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) "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 $173 CA $355 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Higganum-Hotels-Cozy-Comforts-Country-Living-At-Its-Finest-Just-10-Min-To-Downtown-Middletown.h91713725.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) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/121000000/120070000/120065600/120065513/9c9682a1.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) ![Hair dryer](https://images.trvl-media.com/lodging/121000000/120070000/120065600/120065513/a94b7e4c.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 9.4/10 Exceptional (3) "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 $131 CA $286 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/New-Haven-Hotels-One-Bedroom-Apartment-In-United-States-Of-America.h120065513.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) ![Interior](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/89dee084.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) ### 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) "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 $225 CA $467 total includes taxes & fees Jan 10 - Jan 11 [](https://www.expedia.ca/Clinton-Hotels-Stylish-Modern-Stay-Steps-From-The-Ocean.h120150878.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/124000000/123640000/123634200/123634189/afd79af7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123640000/123634200/123634189/8330fb1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/124000000/123640000/123634200/123634189/b6eaff49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123640000/123634200/123634189/3a7fb390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quintessential Essex. Steps from the Steam Train! [](https://www.expedia.ca/Essex-Hotels-Quintessential-Essex-Steps-From-The-Steam-Train.h123634189.Hotel-Information) Essex CA $221 CA $428 total includes taxes & fees Jan 10 - Jan 11 [](https://www.expedia.ca/Essex-Hotels-Quintessential-Essex-Steps-From-The-Steam-Train.h123634189.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/119000000/118950000/118949700/118949631/7f5d3999.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) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118950000/118949700/118949631/8e373067.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) ### Cozy East Haven Home • Near Beach & Yale [](https://www.expedia.ca/East-Haven-Hotels-Cozy-Home-Near-New-Haven.h118949631.Hotel-Information) Momauguin 10/10 Exceptional (5) "Beautiful seaside cottage. Updated and well appointed, bidet, fire pit and more. Very close to several beaches. Driving distance to many attractions, statue of liberty, and more. I would stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roberta e. CA $173 CA $227 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/East-Haven-Hotels-Cozy-Home-Near-New-Haven.h118949631.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) ![Interior](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/02f647fe.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/0888acaf.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 (7) "Charming, unique, and very comfortable. Would surely stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David S. CA $159 CA $398 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Wallingford-Hotels-Seasons-Hospitality-Presents-All-New-1BR-With-Tons-Of-Charm.h102008958.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) ![Exterior](https://images.trvl-media.com/lodging/106000000/105190000/105183900/105183859/0f5be429.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) ### 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 (54) "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 $622 CA $1,125 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Killingworth-Hotels-Cozy-Cabin-In-The-Woods-Situated-On-6-Private-Acres-Surrounded-By-Nature.h105183859.Hotel-Information) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/66000000/65400000/65396400/65396309/5733ff3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/66000000/65400000/65396400/65396309/fa52948e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/66000000/65400000/65396400/65396309/2ef4f563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/66000000/65400000/65396400/65396309/314c977a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Once the old Schools house now a newly furnished Apartment [](https://www.expedia.ca/Wallingford-Hotels-Once-The-Old-Schools-House-Now-A-Newly-Furnished-Apartment.h65396309.Hotel-Information) Wallingford Center 9.0/10 Wonderful (13) "Excellent option for a short stay near the heart of it all in Wallingford." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeanette W. CA $159 CA $391 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Wallingford-Hotels-Once-The-Old-Schools-House-Now-A-Newly-Furnished-Apartment.h65396309.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/89f62aee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/f935d452.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/0a69331b.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/a34edd2d.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) "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 $159 CA $398 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Wallingford-Hotels-All-New-Studio-Apartment-In-Center-Of-Town.h103029991.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/96000000/95040000/95032200/95032165/446f217c.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) ### 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 (11) "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 $170 CA $418 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/New-Haven-Hotels-Urban-Oasis-3BR-Parking-Washer-Dryer-Yale-East-Rock.h95032165.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h946x0y0-a3c0ca5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, offices](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1282h963x0y0-3ce0e673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h959x0y0-51b04f4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h956x0y0-f00664d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard [](https://www.expedia.ca/Old-Saybrook-Hotels-Capt-Nathaniel-Clarke-Historic-Homestead.h18762073.Hotel-Information) Saybrook Manor 9.6/10 Exceptional (133) "We loved our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deana L. CA $277 CA $711 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Old-Saybrook-Hotels-Capt-Nathaniel-Clarke-Historic-Homestead.h18762073.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/118000000/117610000/117606200/117606175/b679883f.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/118000000/117610000/117606200/117606175/56acba4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/118000000/117610000/117606200/117606175/bdff1679.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117610000/117606200/117606175/58bd6555.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nautical 3BR Sleeps 8 @ Tweed Airport W/ Fire Pit + Smart TVs Near Beach & Yale [](https://www.expedia.ca/East-Haven-Hotels-The-Nauti-Nook-At-Tweed.h117606175.Hotel-Information) East Shore 10/10 Exceptional (1) "Had a Great stay at the nauti nook!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David D. CA $205 CA $624 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/East-Haven-Hotels-The-Nauti-Nook-At-Tweed.h117606175.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/112000000/111830000/111824500/111824460/62b2e5a8_edited_33e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/112000000/111830000/111824500/111824460/a5ee2415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111830000/111824500/111824460/624102e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111830000/111824500/111824460/efeecab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quiet 2bd Townhome apt in the heart of Cheshire. Backyard. [](https://www.expedia.ca/Cheshire-Hotels-Quiet-2-Bedroom-Apartment-In-Wonderful-Cheshire-With-WiFi-And-Beautiful-Views.h111824460.Hotel-Information) Cheshire 9.4/10 Exceptional (14) "Needed a place to sleep for a couple of nights and this worked for us." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James (Jim) L. CA $117 CA $226 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Cheshire-Hotels-Quiet-2-Bedroom-Apartment-In-Wonderful-Cheshire-With-WiFi-And-Beautiful-Views.h111824460.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) ![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) ![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108430000/108426600/108426521/dd253525.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) "Had a great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Garry G. CA $177 CA $532 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Milford-Hotels-Beach-Apt-In-Woodmont-Milford.h108426521.Hotel-Information) ![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122120000/122111200/122111158/09be7b5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122120000/122111200/122111158/c0cd40cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122120000/122111200/122111158/229e8190.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122120000/122111200/122111158/b812e781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Mi to Beach, Shared Yard Space: West Haven Apt! [](https://www.expedia.ca/West-Haven-Hotels-2-Mi-To-Beach.h122111158.Hotel-Information) West Haven CA $189 CA $495 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/West-Haven-Hotels-2-Mi-To-Beach.h122111158.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=2026-01-22&endDate=2026-01-23®ionId=6341069&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [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 ![Hotel Marcel New Haven, Tapestry Collection By Hilton](https://images.trvl-media.com/lodging/72000000/71430000/71427300/71427300/1699c03c_y.jpg) ### Hotel Marcel New Haven, Tapestry Collection By Hilton 10/10 Excellent "Rave reviews from nephew's family, who stayed there during the holidays." [](https://expedia.ca/New-Haven-Hotels-Hotel-Marcel-New-Haven.h71427300.Hotel-Information) ![Hampton Inn by Hilton Shelton](https://images.trvl-media.com/lodging/1000000/210000/200400/200381/e6ef0843_y.jpg) ### Hampton Inn by Hilton Shelton 10/10 Excellent "Clean room could use some extra attention around the trim around the bathroom floor. Staff very friendly and professional." [](https://expedia.ca/New-Haven-Hotels-Hampton-Inn-By-Hilton-Shelton.h200381.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 location! Beautiful hotel. " [](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) ![Homewood Suites by Hilton Stratford](https://images.trvl-media.com/lodging/1000000/880000/873200/873107/fd1eb309_y.jpg) ### Homewood Suites by Hilton Stratford 10/10 Excellent "Room was great " [](https://expedia.ca/New-Haven-Hotels-Homewood-Suites-By-Hilton-Stratford.h873107.Hotel-Information) ![Cambria Hotel New Haven University Area](https://images.trvl-media.com/lodging/79000000/78620000/78614500/78614483/a6a28eee_y.jpg) ### Cambria Hotel New Haven University Area 10/10 Excellent "clean room, helpful staff" [](https://expedia.ca/New-Haven-Hotels-Cambria-Hotel-New-Haven-University-Area.h78614483.Hotel-Information) ![Home2 Suites by Hilton East Haven New Haven](https://images.trvl-media.com/lodging/1000000/10000/1500/1461/b5c018f9_y.jpg) ### Home2 Suites by Hilton East Haven New Haven 10/10 Excellent "Very good " [](https://expedia.ca/East-Haven-Hotels-Home2-Suites-By-Hilton-East-Haven-New-Haven.h1461.Hotel-Information) ![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 "Front desk dude funny" [](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.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 and clean. " [](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 "Clean and nice! Really appreciated the bath robes." [](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. ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in Thimble Islands ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals ](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals ](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals ](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals ](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals ](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals ](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals ](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - 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