Title: Thimble Islands Vacation Packages 2026 from $343 | 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)[Vacation Rentals in Thimble Islands](https://expedia.com/Thimble-Islands-Vacation-Rentals.d6341069.Travel-Guide-VacationRentals)[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) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Thimble Islands Vacations from $343 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 ## The Latest Thimble Islands vacation packages Price found within the past 48 hours. Click for updated prices. ![Sheraton New York Times Square Hotel](https://images.trvl-media.com/lodging/1000000/10000/100/87/2bf1f7f9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sheraton New York Times Square Hotel Manhattan Save 100% on your flight $343 per person May 6 - May 9 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 7.4/10 Good! (7,139 reviews) Toilet was blocked …very noisy on weekends…had to wait 15 minutes to get an elevator as the hotel was very crowded…. Reviewed on Mar 25, 2026 ![Hotel St. James](https://images.trvl-media.com/lodging/2000000/1150000/1144500/1144474/ecd19bcc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel St. James Manhattan Save 100% on your flight $563 per person May 9 - May 13 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (7,026 reviews) Location was great, staff was helpful and nice, I would recommend Reviewed on Mar 25, 2026 ![Topping Rose House](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/8b4b1f10_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Topping Rose House Save 100% on your flight $1,648 per person Jun 7 - Jun 12 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to New York (JFK) 9.2/10 Wonderful! (143 reviews) Overall it was a great stay! Best part of the cottage was the bathroom with its deep big tub and walk in shower. But the room itself lacked visual appeal & some conveniences usually associated with booking a cottage which is more private and removed from the house. Could use more and better art in the room. I would also trade all the storage space for a mini fridge, tea kettle or coffee maker. Also the only full-size mirror is hidden far back in the bathroom which isn’t terrible but very inconvenient to check the outfit before heading out the door. It’s little odd things that just made it not feel like a luxury stay. And no one mentioned to us beforehand that the sauna, gym, pool area (even though in off season) was under renovation and not available to use. The restaurant was amazing though, room service was wonderful. And staff were adorable. But I don’t know if we would book again tbh. Reviewed on Mar 24, 2026 ![1 Hotel Brooklyn Bridge](https://images.trvl-media.com/lodging/16000000/15400000/15399700/15399642/b1e6b86c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Brooklyn Bridge Save 100% on your flight $1,654 per person May 14 - May 17 found 1 day ago Roundtrip flight included Dallas (DFW) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (1,000 reviews) Excellent staff, clean room, fantastic onsite restaurants. Reviewed on Mar 10, 2026 ![The Ned NoMad](https://images.trvl-media.com/lodging/5000000/4760000/4758700/4758665/73a941da_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ned NoMad Manhattan Save 100% on your flight $1,524 per person Jun 6 - Jun 11 found 1 hour ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 9/10 Wonderful! (119 reviews) Room was great staff not so good Reviewed on Feb 15, 2026 Don't see what you're looking for? See all available trips from Columbus to Thimble Islands [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-26/2026-05-03/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Thimble Islands Hotel Deals ![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### New Haven Hotel 229 George Street New Haven CT Fully refundableReserve now, pay when you stay $105 nightly $121 total Apr 5 - Apr 6 Total with taxes and fees 9/10 Wonderful! (2,052 reviews) Clean room, good bathroom, parking is available, NOT free—- when I used the filter for free parking, the hotel popped up, so a little misleading. But all in all, it was a comfortable stay. Reviewed on Mar 25, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=36721&PinnedHotelID=36721&HadPinnedHotel=true®ionId=6341069) ![Hyatt Place Milford / New Haven](https://images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/80833193_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Place Milford / New Haven 190 Old Gate Lane Milford CT Fully refundableReserve now, pay when you stay $101 nightly $116 total Apr 5 - Apr 6 Total with taxes and fees 8.6/10 Excellent! (1,280 reviews) The best part of the stay was the breakfast. They use real eggs, not that powdered stuff. My only complaint with this property was the bed. It was terrible. The mattress was lumpy and the frame was very noisy. We stayed three nights. By the last morning, my back was so sore. Two nights would be my ... Reviewed on Mar 24, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=1562702&PinnedHotelID=1562702&HadPinnedHotel=true®ionId=6341069) ![Omni New Haven Hotel at Yale](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/b7b5473a_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 $152 nightly $175 total Apr 2 - Apr 3 Total with taxes and fees 8.6/10 Excellent! (1,003 reviews) My wife had a procedure at Yale New Haven and I only one night. It was very convenient and pleasant. I only used the room. Not the bar or restaurant. Reviewed on Mar 18, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F2%2F2026&endDate=4%2F3%2F2026&selected=49957&PinnedHotelID=49957&HadPinnedHotel=true®ionId=6341069) [See all 1,059 properties in Thimble Islands](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F27%2F2026&endDate=3%2F28%2F2026®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. ## Find the Best Thimble Islands Vacation Packages ## Thimble Islands Essential Information | Language | English | | --------------- | ---------------------------------------- | | Currency | U.S dollars | | Closest Airport | Tweed - New Haven Regional Airport (HVN) | ## More vacations you might like ![](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.com/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.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) 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