Title: Thimble Islands Vacation Packages & Trips 2025/2026 from CA $1,275 | 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. ![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 $1,275 per person Jan 4 - Jan 7 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 8.8/10 Excellent! (1,006 reviews) Nice hotel , needs a bit of tender love and care ! Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-04/2026-01-07/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=15399642&paandie=true&dealMarker=pR9UFpWCspfo1o7DesoYmQwHMMpamQcRu8HG7o7Z67CG8z2PO-uqC1Pdyc7_rd7E) ![Beechmont - Perfect for Family Retreat!](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/78c118d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Beechmont - Perfect for Family Retreat! CA $3,149 per person Dec 29 - Jan 5 found 1 day ago Roundtrip flight included Toronto (YYZ) to New Haven (HVN) No reviews [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-05/?FromAirport=YYZ&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&hotelId=119248411&paandie=true&dealMarker=cnEzPXNCoF5zc6B5aXxn3ZthNKYeQU8nuaUPABdMOrfu4oMnq2CGDSG04Ayj5-Fb) ![NobleDEN Hotel](https://images.trvl-media.com/lodging/9000000/8690000/8682300/8682234/cb1dc844_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### NobleDEN Hotel Manhattan CA $1,603 per person Nov 27 - Dec 2 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to New York (JFK) 9.8/10 Exceptional! (1,344 reviews) This is my go to hotel! Do yourself a favor and get the balcony room! Reviewed on Oct 13, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-27/2025-12-02/?FromAirport=YEG&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=8682234&paandie=true&dealMarker=cnEzPXNCoF5zc6B5aXxn3V2fHRI03NY70jd0JsPd-kNvGZUKC5kdLU0kH8Bw1Hha) ![Omni Berkshire Place](https://images.trvl-media.com/lodging/1000000/30000/23600/23597/7e55a973_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Omni Berkshire Place Manhattan CA $1,965 per person Dec 18 - Dec 22 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to New York (JFK) 9.2/10 Wonderful! (1,985 reviews) Dated since my last visit here 5 years ago, but still enjoyed the comfy beds and great location! Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-18/2025-12-22/?FromAirport=YEG&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23597&paandie=true&dealMarker=JpHxkfHsMAhgTw5YWfMpzZM5YAs42vA5D3uXhR6OFtcMfzzMWQ-SEgiffPrep5y4) ![Hotel Seville Nomad, in the Unbound Collection by Hyatt](https://images.trvl-media.com/lodging/18000000/17940000/17939200/17939186/186b385b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Seville Nomad, in the Unbound Collection by Hyatt Manhattan CA $1,961 per person Dec 28 - Jan 2 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to New York (JFK) 8.6/10 Excellent! (1,115 reviews) Small room but I was by myself. The staff was very knowledgeable and helpful! Definitely recommend! Reviewed on Oct 13, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-28/2026-01-02/?FromAirport=YEG&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=17939186&paandie=true&dealMarker=fCuY3h5fOlWSf-3DOYMaxxe6QCtO55hoON0GTZob0Paz74nxQ5Qr48HYxVTk5hRo) ## Ready to book your vacation to Thimble Islands? Choose your dates ## Thimble Islands Hotel Deals ![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 $235 CA $270 total Oct 29 - Oct 30 includes taxes & fees 8.4/10 Very Good! (1,013 reviews) "Clean, comfortable, elegant. Beautiful view from the top floor." Reviewed on Oct 12, 2025 [](https://expedia.ca/Hotel-Search?startDate=29%2F10%2F2025&endDate=30%2F10%2F2025&selected=49957&PinnedHotelID=49957&HadPinnedHotel=true®ionId=6341069) ![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 $184 total Oct 26 - Oct 27 includes taxes & fees 9/10 Wonderful! (1,833 reviews) "We stayed one night. The staff was welcoming, the room clean and quiet, the bed very comfortable." Reviewed on Oct 12, 2025 [](https://expedia.ca/Hotel-Search?startDate=26%2F10%2F2025&endDate=27%2F10%2F2025&selected=36721&PinnedHotelID=36721&HadPinnedHotel=true®ionId=6341069) ![Hyatt Place Milford / New Haven](https://images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/0336d577_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Place Milford / New Haven 190 Old Gate Lane, Milford, CT CA $154 CA $178 total Nov 2 - Nov 3 includes taxes & fees 8.6/10 Excellent! (1,160 reviews) "Yes" Reviewed on Oct 11, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=1562702&PinnedHotelID=1562702&HadPinnedHotel=true®ionId=6341069) [See all 986 properties in Thimble Islands](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=16%2F10%2F2025&endDate=17%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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