Title: Thimble Islands Vacation Packages & Trips 2025/2026 from CA $1,144 | 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) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Thimble Islands Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 when you book a flight and hotel together\* ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package ### Rest easy Plan, book, and manage your trip all in one place ## Top Thimble Islands Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Hotel Riu Plaza Manhattan Times Square](https://images.trvl-media.com/lodging/61000000/60680000/60677500/60677495/0bd08347_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Manhattan Times Square Manhattan CA $1,144 per person Jan 11 - Jan 18 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 9.2/10 Wonderful! (3,359 reviews) Great location right in Times Square, a little sketchy in some of the third party operations Reviewed on Oct 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-11/2026-01-18/?FromAirport=YHM&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=60677495&paandie=true&dealMarker=S5sRAu-L2ds_ZXrv2pvXpHkkQBlUh8IXWaRDT8q28GXSehveClUW2U1vluevhn_e) ![Hotel Riu Plaza New York Times Square](https://images.trvl-media.com/lodging/12000000/11680000/11677800/11677770/8c07d74e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza New York Times Square Manhattan CA $1,247 per person Jan 11 - Jan 18 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 9/10 Wonderful! (2,748 reviews) La habitación muy pequeña para lo costosos que es el hotel, el bufet de primera lo recomiendo 100%. Reviewed on Oct 24, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-11/2026-01-18/?FromAirport=YHM&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=11677770&paandie=true&dealMarker=S5sRAu-L2ds_ZXrv2pvXpIdZAY9Ekiw3gLztHF4R9cX3LLJbJbHghlVh1nN8UuLS) ![1 Hotel Brooklyn Bridge](https://images.trvl-media.com/lodging/16000000/15400000/15399700/15399642/7801a5d8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Brooklyn Bridge CA $1,677 per person Jan 2 - Jan 6 found 1 day ago Roundtrip flight included Toronto (YYZ) to New York (JFK) 8.8/10 Excellent! (1,012 reviews) Nice hotel , needs a bit of tender love and care ! Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-02/2026-01-06/?FromAirport=YYZ&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=15399642&paandie=true&dealMarker=q1ZHan5DLLB94fcYxsgQK45tj7iWjn342f4Tuc6DjVODJr0Od5dU1VRxz30lZt9T) ![Courtyard New York Manhattan/ Midtown East](https://images.trvl-media.com/lodging/1000000/160000/151300/151297/9d70bdbc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Courtyard New York Manhattan/ Midtown East Manhattan CA $1,469 per person Dec 12 - Dec 14 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9/10 Wonderful! (2,333 reviews) perfect place to stay, very walkable, clean and safe area Reviewed on Oct 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-14/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=151297&paandie=true&dealMarker=8hXe3TWR6KnKbyZw6VvS4dKErGH_SQXPBDziGElup0j8AnF5VS2V5vUiUusggG_P) ## Ready to book your vacation to Thimble Islands? Choose your dates ## Thimble Islands Hotel Deals ![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/dd69cbb4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### New Haven Hotel 229 George Street, New Haven, CT Fully refundableReserve now, pay when you stay CA $160 CA $183 total Nov 23 - Nov 24 includes taxes & fees 9/10 Wonderful! (1,849 reviews) Very clean and wonderful staff Reviewed on Oct 22, 2025 [](https://expedia.ca/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%2F2025&selected=36721&PinnedHotelID=36721&HadPinnedHotel=true®ionId=6341069) ![Motel 6 New Haven - Branford, CT](https://images.trvl-media.com/lodging/1000000/60000/50400/50320/c15293e5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Motel 6 New Haven - Branford, CT 320 E Main St, Branford, CT Fully refundable CA $93 CA $109 total Oct 29 - Oct 30 includes taxes & fees 7/10 Good! (1,001 reviews) Room was clean and spacious, close to some nice food places Reviewed on Oct 19, 2025 [](https://expedia.ca/Hotel-Search?startDate=29%2F10%2F2025&endDate=30%2F10%2F2025&selected=50320&PinnedHotelID=50320&HadPinnedHotel=true®ionId=6341069) ![Omni New Haven Hotel at Yale](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/7466af25_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Omni New Haven Hotel at Yale 155 Temple St, New Haven, CT Fully refundableReserve now, pay when you stay CA $212 CA $243 total Nov 23 - Nov 24 includes taxes & fees 8.4/10 Very Good! (1,000 reviews) Great location and very accommodating staff Reviewed on Oct 23, 2025 [](https://expedia.ca/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%2F2025&selected=49957&PinnedHotelID=49957&HadPinnedHotel=true®ionId=6341069) [See all 985 properties in Thimble Islands](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F10%2F2025&endDate=27%2F10%2F2025®ionId=6341069) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Frequently asked questions ### Can I cancel my flight booking to Thimble Islands due to COVID-19? > Many airlines now offer more flexibility due to COVID-19. Our [Customer Service Portal](https://www.expedia.ca/service/?langId=1033) will help you answer most questions about flight changes or cancellations. It's also good to check the terms and conditions of your fare — preferably before booking! ### What's the best way to find cheap flights to Thimble Islands that have flexible change policies? > At Expedia, we've been channeling our inner yogi to bring you the most flexible airfares in town. Simply tick the "No change fee" box under the filter subheading "Flexible change policies" to find the best flights to Thimble Islands. ### What are some of the general tips for travelers to Thimble Islands during the COVID-19 outbreak? > In the face of the COVID-19 outbreak, traveling today comes with more challenges than in the past. Take note of these valuable tips before jumping on your flight to Thimble Islands: > > - Before you book a flight, check if any travel bans or restrictions apply — in both your origin and destination. Stay informed with the latest updates by reviewing government and airport websites. > - Wear a face mask during airport screening. A TSA officer will ask you to adjust your mask to verify your identity. > - To reduce the likelihood of cross-contamination, place your boarding pass on the reader yourself and then hold it up for inspection. Do not hand your boarding pass directly to a TSA officer. > - One container of liquid hand sanitizer is now permitted in your carry-on luggage. It must be no larger than 12 oz (350 ml), and you'll need to take it out of your bag for X-ray scanning. > - Empty everything from your pockets, like your keys, phone and wallet, and place them in your carry-on instead of into bins. This will minimize handling during screening. > - If you're bringing food on the plane with you, place it in a clear plastic bag and then into a scanning bin. This reduces the likelihood that a TSA agent will need to touch your carry-on bag or food container for inspection. ### How can I find cheap tickets to Thimble Islands? > One of the best ways to get a hold of cheap tickets to Thimble Islands is to be flexible with your dates. Search for your flights, then click "flexible dates" at the top of your results. It'll bring up the cheapest prices for nearby days. The best price for a flight to Thimble Islands in the last seven days was . Booking in advance will usually help you walk away with an even better deal. ### When is the cheapest time to fly to Thimble Islands? > If you can be flexible with what date you travel to Thimble Islands, leave early in the week. The most economical day to take off is generally Tuesday, followed closely by Monday. Saturday is typically the priciest day, with many people preferring to fly on weekends. ### How much is a plane ticket to Thimble Islands? > In the last seven days, plane tickets to Thimble Islands varied from to . ### Which airlines with flights to Thimble Islands employ COVID-19 cleanliness policies? > From the moment you check in until you leave your arrivals gate, American Airlines has implemented a raft of enhanced measures to help prevent the spread of COVID-19. 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[National Helicopter Museum](https://www.expedia.ca/National-Helicopter-Museum-Stratford.d553248621561886330.Vacation-Attraction) - [New Britain Vacations](https://www.expedia.ca/New-Britain.d8920.Destination-Travel-Guides) - [New Haven Vacations](https://www.expedia.ca/New-Haven.d180036.Destination-Travel-Guides) - [Oak Street Beach](https://www.expedia.ca/Oak-Street-Beach-West-Haven.d6247013.Vacation-Attraction) - [Palace Theatre](https://www.expedia.ca/Palace-Theatre-Waterbury.d6247005.Vacation-Attraction) - [Pilgrim Mall Shopping Center](https://www.expedia.ca/Pilgrim-Mall-Shopping-Center-Woodbury.d553248621563220790.Vacation-Attraction) - [Sterling Memorial Library at Yale University](https://www.expedia.ca/Sterling-Memorial-Library-At-Yale-University-Downtown-New-Haven.d6071481.Vacation-Attraction) - [Westfield Connecticut Post Mall](https://www.expedia.ca/Westfield-Connecticut-Post-Mall-Milford.d6163930.Vacation-Attraction) - [Yale University Art Gallery](https://www.expedia.ca/Yale-University-Art-Gallery-Downtown-New-Haven.d6071487.Vacation-Attraction) - [Yale University](https://www.expedia.ca/Yale-University-Downtown-New-Haven.d502016.Vacation-Attraction) ### Cars - [Car rental Branford](https://www.expedia.ca/Car-Rentals-In-Branford.d6243.Car-Rental-Guide) - [Car rental East Haven](https://www.expedia.ca/Car-Rentals-In-East-Haven.d7792.Car-Rental-Guide) - [Car rental Guilford](https://www.expedia.ca/Car-Rentals-In-Guilford.d183062.Car-Rental-Guide) - [Enterprise Rental Cars in Branford](https://www.expedia.ca/Enterprise-Car-Rentals-In-Branford.d6243-c15.Car-Rental-Guide-Suppliers) - [Sixt Rental Cars in Branford](https://www.expedia.ca/Sixt-Car-Rentals-In-Branford.d6243-c35.Car-Rental-Guide-Suppliers) ### Vacation Rental - [Guilford Vacation Rentals](https://www.expedia.ca/Guilford-Vacation-Rentals.d183062.Travel-Guide-VacationRentals) ### Other - [Things to do in Branford](https://www.expedia.ca/Things-To-Do-In-Branford.d6243.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. 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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)