Title: Thimble Islands Vacation Rentals from $248: Search Short-Term Rentals | Expedia.com [Thimble Islands Travel Guide](https://expedia.com/Thimble-Islands.dx6341069)[Hotels in Thimble Islands](https://expedia.com/Thimble-Islands-Hotels.d6341069.Travel-Guide-Hotels)[Flights to Thimble Islands](https://expedia.com/Cheap-Flights-To-Thimble-Islands.d6341069.Travel-Guide-Flights)[Car Rentals in Thimble Islands](https://expedia.com/Car-Rentals-In-Thimble-Islands.d6341069.Car-Rental-Guide)[Thimble Islands Vacation Packages](https://expedia.com/Thimble-Islands.d6341069.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=6341069&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=6341069&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=6341069&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=6341069&startDate=2026-06-05&endDate=2026-06-07&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 ![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/bf86c795.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) ![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) ### Luxe Living! Apt 1 Mi to West Haven Medical Center [](https://www.expedia.com/West-Haven-Hotels-2-Mi-To-Beach.h122111158.Hotel-Information) West Haven $311 nightly $358 total Feb 11 - Feb 12 Total with taxes and fees [](https://www.expedia.com/West-Haven-Hotels-2-Mi-To-Beach.h122111158.Hotel-Information) ![Apartment (1 Bedroom) | Private kitchen | Fridge, coffee/tea maker](https://images.trvl-media.com/lodging/126000000/125160000/125152000/125151932/a618c812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, individually decorated, individually furnished](https://images.trvl-media.com/lodging/126000000/125160000/125152000/125151932/c3bd411f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, individually decorated, individually furnished](https://images.trvl-media.com/lodging/126000000/125160000/125152000/125151932/e49e9e7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/126000000/125160000/125152000/125151932/bddafb8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Landing Furnished Apartment Near Yale University [](https://www.expedia.com/New-Haven-Hotels-Landing-Chic-1bd.h125151932.Hotel-Information) Downtown New Haven [](https://www.expedia.com/New-Haven-Hotels-Landing-Chic-1bd.h125151932.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.com/Hotel-Search?startDate=2026-02-23&endDate=2026-02-24®ionId=6341069&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America®ionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=CABIN) Cottages [](https://www.expedia.com/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America®ionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=COTTAGE) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America®ionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=APART_HOTEL) Condos [](https://www.expedia.com/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America®ionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=CONDO) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America®ionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=VACATION_HOME) Apartments [](https://www.expedia.com/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America®ionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=APARTMENT) Houseboats [](https://www.expedia.com/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America®ionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=HOUSE_BOAT) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FThimble-Islands-Vacation-Rentals.d6341069.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.com/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 "The room was beautiful and staff was great!" [](https://expedia.com/New-Haven-Hotels-Hotel-Marcel-New-Haven.h71427300.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 "What a great find and value for the money! Our room was so spacious with a sitting area and small kitchenette included, and the bountiful breakfast sealed the deal. We will definitely be back when we’re in the area." [](https://expedia.com/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![Hilton Garden Inn Shelton](https://images.trvl-media.com/lodging/1000000/290000/287700/287687/18ff21f4_y.jpg) ### Hilton Garden Inn Shelton 10/10 Excellent "nice" [](https://expedia.com/New-Haven-Hotels-Hilton-Garden-Inn-Shelton.h287687.Hotel-Information) ![Springhill Suites Milford](https://images.trvl-media.com/lodging/1000000/490000/487700/487605/88ae4c80_y.jpg) ### Springhill Suites Milford 10/10 Excellent "Third time there like this place. Sorry to see the indoor pool go away" [](https://expedia.com/New-Haven-Hotels-Springhill-Suites-Milford.h487605.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 "Lovely " [](https://expedia.com/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 "Clean" [](https://expedia.com/East-Haven-Hotels-Home2-Suites-By-Hilton-East-Haven-New-Haven.h1461.Hotel-Information) ![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg) ### New Haven Hotel 10/10 Excellent "Clean, well designed rooms." [](https://expedia.com/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 "Staff very friendly, room very accomadating, clean and good breakfast" [](https://expedia.com/New-Haven-Hotels-Holiday-Inn-Express-Branford-New-Haven.h124313.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 "Omg. Where do I start? What impressed me the most was the welcoming staff. Upon arriving in my room, the televisions displayed a personalized welcome message with my name, which was cool. My room was magnificent! Beautiful. Modern. Very clean. Smelled wonderful!" [](https://expedia.com/New-Haven-Hotels-Homewood-Suites-By-Hilton-Orange-New-Haven.h38979983.Hotel-Information) ## Find out more about Thimble Islands **Everything you need to know about Thimble Islands vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Thimble Islands vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on. There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Thimble Islands vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **Thimble Islands vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Thimble Islands. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Thimble Islands in high season. Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $248 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals! **How to find incredible deals on Thimble Islands rentals** At Expedia, we put the best Thimble Islands vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. To find some top Thimble Islands rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Thimble Islands vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Thimble Islands. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. ## Explore a world of travel with Expedia - Trending destinations on Expedia.com - All accommodation types in Thimble Islands ### Trending destinations on Expedia.com - [Destin Vacation Rentals ](https://www.expedia.com/Destin-Vacation-Rentals.d6906.Travel-Guide-VacationRentals) - [Panama City Vacation Rentals ](https://www.expedia.com/Panama-City-Beach-Vacation-Rentals.d8021.Travel-Guide-VacationRentals) - [Hilton Head Vacation Rentals ](https://www.expedia.com/Hilton-Head-Island-Vacation-Rentals.d601684.Travel-Guide-VacationRentals) - [Gulf Shores Vacation Rentals ](https://www.expedia.com/Gulf-Shores-Vacation-Rentals.d603078.Travel-Guide-VacationRentals) - [Key West Vacation Rentals ](https://www.expedia.com/Key-West-Vacation-Rentals.d1187.Travel-Guide-VacationRentals) - [Gatlinburg Vacation Rentals ](https://www.expedia.com/Gatlinburg-Vacation-Rentals.d7474.Travel-Guide-VacationRentals) - 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