Title: Thimble Islands Vacation Home Rentals : Search Top Private Vacation Homes for Rent | 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)[Vacation Rentals in Thimble Islands](https://expedia.ca/Thimble-Islands-Vacation-Rentals.d6341069.Travel-Guide-VacationRentals)[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://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Thimble Islands Vacation Rentals ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [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 three months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Thimble Islands Vacation Homes ![WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120950000/120949800/120949708/5a0a3fb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/121000000/120950000/120949800/120949708/555620ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/121000000/120950000/120949800/120949708/362e0707.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120950000/120949800/120949708/439006bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pleasant apartment with AC in charming New Haven West New Haven CA $140 CA $212 total includes taxes & fees Oct 11 - Oct 12 [](https://www.expedia.ca/New-Haven-Hotels-Pleasant-Apartment-With-AC-In-Charming-New-Haven.h120949708.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/728215df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/ea540de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/a7476bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/38c1ca05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shoreline Oasis Clinton 9.2/10 Wonderful (7) "A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!" CA $250 CA $366 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Clinton-Hotels-Shoreline-Oasis.h113308197.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) ![Dining](https://images.trvl-media.com/lodging/66000000/65400000/65396400/65396309/314c977a.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) ### Once the old Schools house now a newly furnished Apartment Wallingford Center 9.0/10 Wonderful (12) "Excellent option for a short stay near the heart of it all in Wallingford." CA $152 CA $394 total includes taxes & fees Oct 6 - Oct 7 [](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/58000000/57700000/57696800/57696731/04508426.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/58000000/57700000/57696800/57696731/af23948e.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) ![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) ### Newly Remodeled 1-BR Close to Everything yet Very Private Wallingford 10/10 Exceptional (9) "I was very pleased with the accomodations. I had everything I needed and it was comfortable and quiet. I was able to get my research done and enjoyed the peaceful setting, and it was convenient to the friends and family I visited during my stay. I will definitely stay here again. " CA $160 CA $405 total includes taxes & fees Oct 5 - Oct 6 [](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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/af0195f8.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) ![Interior](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/d3b32f3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Jewel of The Cove - Historic Coastal Retreat East Shore 10/10 Exceptional (4) "loved it so much, beautiful property 100 % would stay again " CA $289 CA $716 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/East-Haven-Hotels-The-Jewel-Of-The-Cove-Historic-Coastal-Retreat.h105862474.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/94000000/93150000/93141500/93141440/820d5ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93150000/93141500/93141440/e1407a3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93150000/93141500/93141440/babedb18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/94000000/93150000/93141500/93141440/a978cb80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space! Milford 8.6/10 Excellent (8) "Relaxing stay. Nature walk on beach areas " CA $244 CA $473 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Milford-Hotels-42-Wood-Ave-5-Minute-Walk-To-Beach-Amazing-Backyard-Space.h93141440.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) ![Fridge](https://images.trvl-media.com/lodging/35000000/34470000/34466200/34466156/03481d1f.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) ![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... CA $558 CA $993 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Deep-River-Hotels-Peace-Barn-In-The-Heart-Of-The-CT-River-Valley.h34466156.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) ![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) ![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 Momauguin 10/10 Exceptional (3) "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. " CA $174 CA $228 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/East-Haven-Hotels-Cozy-Home-Near-New-Haven.h118949631.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) ![Dining](https://images.trvl-media.com/lodging/60000000/59630000/59625600/59625523/d1cc68c7.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) ![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) ### Stocked home close to Yale, in Heart of New Haven Mill River 9.0/10 Wonderful (16) "We loved our stay. It was just as expected and the host is responsive and friendly" CA $207 CA $350 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/New-Haven-Hotels-Stocked-Home-Close-To-Yale.h59625523.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) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/94000000/93400000/93397900/93397831/38eef8d7.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) ![Terrace/patio](https://images.trvl-media.com/lodging/94000000/93400000/93397900/93397831/3625879a.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) "The property had everything needed and was a short distance to so many campus sites. Would definitely stay again." CA $149 CA $292 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/New-Haven-Hotels-The-Santiago-In-Science-Park-At-Yale-New-Haven.h93397831.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) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78180000/78173400/78173305/6dab1099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78180000/78173400/78173305/f3668968.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) ### Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit. Fair Haven 9.6/10 Exceptional (13) "Had a really nice stay, enjoyed this open airy space with comfortable beds and beautiful light with a view of the river. Very nice time, would stay again." CA $265 CA $481 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/New-Haven-Hotels-Gorgeous-Waterfront-3-Bedroom.h78173305.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/116000000/115260000/115259000/115258989/252c46c4.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/116000000/115260000/115259000/115258989/433d0836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/116000000/115260000/115259000/115258989/8a1bcc1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/116000000/115260000/115259000/115258989/3093e15f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic 1-bedroom apartment with WiFi, fitness room in cool New Haven The Hill CA $223 CA $424 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/New-Haven-Hotels-Chic-1-Bedroom-Apartment-With-WiFi.h115258989.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) ![Interior](https://images.trvl-media.com/lodging/101000000/100840000/100834300/100834240/5a216515.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clear LI Sound waterview, Wedding pics, Yale&Beach East Shore 10/10 Exceptional (7) "Attended a wedding close by. This house was a comfortable clean place to rest in between events. Lovely water front. Calm and peaceful" CA $408 CA $855 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/East-Haven-Hotels-Clear-LI-Sound-Waterview.h100834240.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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101950000/101940900/101940832/95857e89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/102000000/101950000/101940900/101940832/59afcbd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### McAngel Haven: 5 mins from Yale West Haven 9.6/10 Exceptional (14) "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." CA $320 CA $718 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/West-Haven-Hotels-McAngel-Haven-5-Mins-From-Yale.h101940832.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119680000/119675600/119675548/w1129h844x110y34-2fc4b8f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Two Bedroom Stay In Downtown New Haven! Dwight 10/10 Exceptional (1) "Exactly as advertised and had nice personal touches. Very close to attractions and very walkable. " CA $188 CA $422 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/New-Haven-Hotels-Cozy-Two-Bedroom-Stay-In-Downtown-New-Haven.h119675548.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) ![Dining](https://images.trvl-media.com/lodging/77000000/76970000/76963400/76963336/2793242f.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) "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!" CA $198 CA $363 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/New-Haven-Hotels-Gorgeous-Waterfront-2-Bedroom-1-Bath-Modern-Home.h76963336.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/b9ec2943.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) ![Interior](https://images.trvl-media.com/lodging/92000000/91570000/91561700/91561648/e0d341a0.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." CA $332 CA $663 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/East-Haven-Hotels-RARE-New-Haven-GetawayPRIVATE-POOLWalk-To-BEACH.h91561648.Hotel-Information) ![Smart TV, fireplace, video games](https://images.trvl-media.com/lodging/101000000/100740000/100730500/100730498/f46f1136.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100740000/100730500/100730498/13c29b17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/101000000/100740000/100730500/100730498/e9dadc3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100740000/100730500/100730498/3b479b0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown. Durham 10/10 Exceptional (19) "I've stayed here multiple times and it was amazing as always. Great communication, clean, and beautiful! " CA $816 CA $1,326 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Durham-Hotels-Brand-New-Modern.h100730498.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114610000/114606800/114606760/9a205457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![2 bedrooms, iron/ironing board, internet, bed sheets](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 West New Haven CA $228 CA $422 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/New-Haven-Hotels-Westville-Stay-2BR-Near-Yale-Free-Parking.h114606760.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/120000000/119950000/119949400/119949322/747070d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119950000/119949400/119949322/42426773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119950000/119949400/119949322/8b89a5a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119950000/119949400/119949322/0a474243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern & Spacious 2BR Apartment w/ Gym & Parking and central AC Dwight 10/10 Exceptional (1) "Great stay in a great location, with highly responsive hosts. Very thoughtful touches with baskets of items you may have forgotten as well as beverages /snacks. Rooftop outdoor area is unique as well. Excellent stay!" CA $244 CA $354 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/New-Haven-Hotels-Modern-Spacious-2BR-Apartment-W-Gym-Parking-And-Central-AC.h119949322.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=2025-10-18&endDate=2025-10-19®ionId=6341069&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&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-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 ![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 "the rooms were very clean the people were very friendly " [](https://expedia.ca/New-Haven-Hotels-Hampton-Inn-By-Hilton-Shelton.h200381.Hotel-Information) ![Motel 6 New Haven - Branford, CT](//images.trvl-media.com/lodging/1000000/60000/50400/50320/c15293e5_y.jpg) ### Motel 6 New Haven - Branford, CT 10/10 Excellent "It’s a good " [](https://expedia.ca/New-Haven-Hotels-Motel-6-New-Haven-Branford.h50320.Hotel-Information) ![Pier Blue Inn Old Saybrook - Essex](//images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg) ### Pier Blue Inn Old Saybrook - Essex 10/10 Excellent "Only issue....the refrigerator makes an annoying sound which is amlpified wearing hearing aids" [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![New Haven Hotel](//images.trvl-media.com/lodging/1000000/40000/36800/36721/dd69cbb4_y.jpg) ### New Haven Hotel 10/10 Excellent "Great hotel Lobby!" [](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.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 "Room service was great made sure we had everything we needed daily. Front desk very helpful. Was quiet until last night party on 2nd floor people running up and down hallway child kicked our door very hard around 2am. I believe mother worked for hotel and had family party out of control my husband got up and went out they quieted down after that.Overall the place was great though." [](https://expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information) ![Holiday Inn Express & Suites Milford by IHG](//images.trvl-media.com/lodging/1000000/10000/3900/3900/f87dad0a_y.jpg) ### Holiday Inn Express & Suites Milford by IHG 10/10 Excellent "Only thing—-lights not working in the room—room clean ——staff great—\_cleaner than I expected—-but we could not get lights to work" [](https://expedia.ca/New-Haven-Hotels-Holiday-Inn-Express-Suites-Milford.h3900.Hotel-Information) ![Motel 6 Milford, CT](//images.trvl-media.com/lodging/1000000/10000/300/291/03aae393_y.jpg) ### Motel 6 Milford, CT 10/10 Excellent "Both great " [](https://expedia.ca/New-Haven-Hotels-Motel-6-Milford.h291.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 "Clean room" [](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![Hilton Garden Inn Shelton](//images.trvl-media.com/lodging/1000000/290000/287700/287687/18ff21f4_y.jpg) ### Hilton Garden Inn Shelton 10/10 Excellent "The property was well maintained and the staff was friendly. I had plenty of options for meals around which was convenient. " [](https://expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-Shelton.h287687.Hotel-Information) ## Find out more about Thimble Islands ## Thimble Islands Vacation Homes information | Number of reviews | | | --- | --- | | Accommodation | Vacation Homes | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in Guilford](https://www.expedia.ca/4Star-Guilford-Hotels.s40-0-d183062.Travel-Guide-Filter-Hotels) - [Hotels near Bill Miller’s Castle](https://www.expedia.ca/Bill-Millers-Castle-Hotels.0-l553248621563220905-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Branford](https://www.expedia.ca/Branford-Apart-Hotels.d6243-aaApartHotels.Travel-Guide-Accommodation) - [Apartments in Branford](https://www.expedia.ca/Branford-Apartments.d6243-aaApartments.Travel-Guide-Accommodation) - [B&B in Branford](https://www.expedia.ca/Branford-Bed-And-Breakfast.d6243-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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