Title: Book the Best Thimble Islands LUXURY Hotels - Upscale Hotels in Thimble Islands, CT | 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) # Find luxury hotels in Thimble Islands, CT ![](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 availability on Thimble Islands Luxury Hotels Tonight [Oct 22 - Oct 23](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-10-22&endDate=2025-10-23&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Oct 23 - Oct 24](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-10-23&endDate=2025-10-24&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-10-24&endDate=2025-10-26&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-10-31&endDate=2025-11-02&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Thimble Islands Luxury Hotels ## Top Thimble Islands Hotel Reviews ![Red Roof Inn Milford - New Haven](//images.trvl-media.com/lodging/1000000/10000/7200/7188/a7d6f81c_y.jpg) ### Red Roof Inn Milford - New Haven 10/10 Excellent "Stayed here while my apartment was being renovated, staff was fantastic!!!" [](https://expedia.ca/New-Haven-Hotels-Red-Roof-Inn-Milford-New-Haven.h7188.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 "Rooms look old some of the furniture looks well used" [](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![Omni New Haven Hotel at Yale](//images.trvl-media.com/lodging/1000000/50000/50000/49957/7466af25_y.jpg) ### Omni New Haven Hotel at Yale 10/10 Excellent "Perfect overall" [](https://expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.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 "Staff was very helpful and room was nice and clean." [](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 location and the staff was warm and friendly. Stay here. " [](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) ![Hampton Inn by Hilton Shelton](//images.trvl-media.com/lodging/1000000/210000/200400/200381/e6ef0843_y.jpg) ### Hampton Inn by Hilton Shelton 10/10 Excellent "Everything was great all the way around. Just a little fyi the bathtub was extremely slippery. That would worry me for an older crowd. Very very slippery. Be cautious of this. Otherwise great place. " [](https://expedia.ca/New-Haven-Hotels-Hampton-Inn-By-Hilton-Shelton.h200381.Hotel-Information) ![Motel 6 Milford, CT](//images.trvl-media.com/lodging/1000000/10000/300/291/5125a116_y.jpg) ### Motel 6 Milford, CT 10/10 Excellent "Extremely comfortable bed and I just love their pillows! Excellent choices in vending machines convenient parking easy on easy off interstate. Friendly staff and other guests are helpful. Handicap accessible. My favorite place to get away " [](https://expedia.ca/New-Haven-Hotels-Motel-6-Milford.h291.Hotel-Information) ![La Quinta Inn & Suites by Wyndham New Haven](//images.trvl-media.com/lodging/1000000/10000/1300/1241/e8cbddf6_y.jpg) ### La Quinta Inn & Suites by Wyndham New Haven 10/10 Excellent "good" [](https://expedia.ca/New-Haven-Hotels-La-Quinta-Inn-Suites-By-Wyndham-New-Haven.h1241.Hotel-Information) ## 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) - 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