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://a.travel-assets.com/travel-assets-manager/bex-affinities/luxury.jpeg?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 [Dec 21 - Dec 22](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-12-21&endDate=2025-12-22&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Dec 22 - Dec 23](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-12-22&endDate=2025-12-23&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2025-12-26&endDate=2025-12-28&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2026-01-02&endDate=2026-01-04&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for Thimble Islands luxury hotels ![Exterior](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/1ec18076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/f4c87c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/c4093211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner, brunch served; American cuisine, beach views ](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/1ef9d54f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Madison Beach Hotel [](https://www.expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information) Madison Center 9.4/10 Exceptional (341) "The Spa was wonderful and the staff was attentive and helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emma CA $338 CA $389 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information) ![Pub](https://images.trvl-media.com/lodging/38000000/37210000/37200100/37200005/d3190acf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/38000000/37210000/37200100/37200005/8f772244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/38000000/37210000/37200100/37200005/e97c72c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/38000000/37210000/37200100/37200005/f6f7c679.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Graduate by Hilton New Haven [](https://www.expedia.ca/New-Haven-Hotels-Graduate-New-Haven.h37200005.Hotel-Information) Downtown New Haven 9.2/10 Wonderful (927) "Nice stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hans CA $214 CA $246 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/New-Haven-Hotels-Graduate-New-Haven.h37200005.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/72000000/71430000/71427300/71427300/1699c03c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Accessible, Bathtub | Living area](https://images.trvl-media.com/lodging/72000000/71430000/71427300/71427300/6b05d52e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/72000000/71430000/71427300/71427300/4de1fb07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/72000000/71430000/71427300/71427300/fe72aa2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Marcel New Haven, Tapestry Collection By Hilton [](https://www.expedia.ca/New-Haven-Hotels-Hotel-Marcel-New-Haven.h71427300.Hotel-Information) Long Wharf 9.4/10 Exceptional (869) "Great stay! Clean room, staff were friendly, and I loved the amenities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Clark CA $152 CA $174 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/New-Haven-Hotels-Hotel-Marcel-New-Haven.h71427300.Hotel-Information) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/fb2335a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/98c270a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Room, 1 Bedroom, Non Smoking (Room 322)](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/e11ede87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/a99c206a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Copper Beech Inn [](https://www.expedia.ca/Old-Saybrook-Hotels-Copper-Beech-Inn.h1484254.Hotel-Information) Ivoryton 8.6/10 Excellent (506) "Very nice property. Very clean. Staff was very nice - very good breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marilyn CA $385 CA $443 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Old-Saybrook-Hotels-Copper-Beech-Inn.h1484254.Hotel-Information) ![Breakfast and brunch served](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/b7b5473a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/d634e2d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/d9b0e3ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/776a13da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Omni New Haven Hotel at Yale [](https://www.expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information) Downtown New Haven 8.6/10 Excellent (1002) "Great traditional New Haven Hotel. From check in to check out staff was very professional and welcoming. Great job for all of your staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $225 CA $259 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.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=2026-01-04&endDate=2026-01-05®ionId=6341069&adults=2&sort=LUXURY&star=40,50&openPlayBack=true) ## Top Thimble Islands Hotel Reviews ![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg) ### New Haven Hotel 10/10 Excellent "Clean room. Convenient location." [](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) ![Red Roof Inn Milford - New Haven](https://images.trvl-media.com/lodging/1000000/10000/7200/7188/3beb130c_y.jpg) ### Red Roof Inn Milford - New Haven 10/10 Excellent "It’s was good " [](https://expedia.ca/New-Haven-Hotels-Red-Roof-Inn-Milford-New-Haven.h7188.Hotel-Information) ![Hilton Garden Inn Milford](https://images.trvl-media.com/lodging/3000000/2480000/2473700/2473639/268b5ae5_y.jpg) ### Hilton Garden Inn Milford 10/10 Excellent "Very clean room and staff was very helpful and friendly and free parking and you can any where ." [](https://expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-Milford.h2473639.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 "Helpful.Easy check in!" [](https://expedia.ca/East-Haven-Hotels-Home2-Suites-By-Hilton-East-Haven-New-Haven.h1461.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, comfortable room" [](https://expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.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 "The property was well lite and safe. Excellent job with rooms being clean." [](https://expedia.ca/New-Haven-Hotels-Hampton-Inn-By-Hilton-Shelton.h200381.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 "everything was very good." [](https://expedia.ca/New-Haven-Hotels-Motel-6-Milford.h291.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 "Absolutely love the Hyatt! Staff is super friendly! " [](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![La Quinta Inn & Suites by Wyndham New Haven](https://images.trvl-media.com/lodging/1000000/10000/1300/1241/dbc425d9_y.jpg) ### La Quinta Inn & Suites by Wyndham New Haven 10/10 Excellent "Very clean room and an especially kind Front Desk team. 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