Title: Romantic Vacations in Thimble Islands 2026 | Expedia.ca ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Thimble Islands Romantic Vacations ## 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 ## Flight and Romantic hotel deals in Thimble Islands Price found within the past 48 hours. Click for updated prices. ![Park Central Hotel New York](https://images.trvl-media.com/lodging/1000000/10000/4200/4164/cb48c512_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Central Hotel New York Manhattan CA $1,313 per person May 21 - May 28 found 8 hours ago Roundtrip flight included Hamilton (YHM) to Newark Liberty Intl. Airport (EWR) 7.6/10 Good! (3,962 reviews) Overall, this was a really disappointing experience. The lobby itself is beautiful and has a great ambience, and the staff were polite. The rooms were clean and the basic amenities were fine. However, the biggest issue was that the hotel did not deliver what was advertised on Expedia. The room we received looked much older and more worn than the photos online and was definitely not in the same condition that was promised. We also specifically booked a suite with queen beds, but when we arrived we were given two double beds instead. When we brought this up, the hotel did not accommodate us and still charged the same price we originally paid, saying it wasn’t their problem since the booking was through Expedia. Another major downside was the parking. Because the garage is connected to the hotel, it costs $52 per day. If you take your car out during the day and need to re-enter, you are charged another $52\. That’s in U.S. dollars, which makes it even more expensive for international travelers once conversion rates are considered. Overall, while the lobby and staff were nice, the room quality and the lack of flexibility with the booking made the stay not worth the price. I would not recommend staying here if you’re expecting the rooms to match the photos online. Reviewed on Mar 12, 2026 ![WestHouse New York](https://images.trvl-media.com/lodging/7000000/6470000/6468000/6467973/a11ba963_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### WestHouse New York Manhattan CA $1,333 per person Apr 20 - Apr 27 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Newark Liberty Intl. Airport (EWR) 8.4/10 Very Good! (1,003 reviews) All staff we came into contact with from front desk to housekeeping to breakfast/happy hour to doormen were super attentive, very friendly and seemed to sincerely see us. The happy hour/dinner and breakfast provided surprisingly good food, lots of variety and very generous pours! Sonia was a standout and we looked forward to seeing her each evening. Beds and bedding very comfortable. Room nicely appointed and clean. Reviewed on Mar 1, 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 CA $3,373 per person May 7 - May 12 found 4 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (1,003 reviews) Excellent staff, clean room, fantastic onsite restaurants. Reviewed on Mar 10, 2026 ![Loews Regency New York Hotel](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Loews Regency New York Hotel Manhattan CA $2,661 per person Apr 20 - Apr 27 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Newark Liberty Intl. Airport (EWR) 9/10 Wonderful! (1,002 reviews) Excellent stay, very clean spacious rooms. Location is great - close to everything. Only downfall was the bathroom, very tiny with a pedestal sink right next to the toilet, not great for women who need to get ready. Reviewed on Feb 24, 2026 ![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 $2,096 per person May 21 - May 28 found 8 hours ago Roundtrip flight included Hamilton (YHM) to Newark Liberty Intl. Airport (EWR) 9.2/10 Wonderful! (3,419 reviews) Great place to stay near Times Square. Reviewed on Mar 12, 2026 Don't see what you're looking for? See all available trips from Columbus to Thimble Islands [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-13/2026-04-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Romantic holidays in Thimble Islands Price found within the past 48 hours. Click for updated prices. ![WestHouse New York](https://images.trvl-media.com/lodging/7000000/6470000/6468000/6467973/a11ba963_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### WestHouse New York Manhattan CA $1,333 per person Apr 20 - Apr 27 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Newark Liberty Intl. Airport (EWR) 8.4/10 Very Good! (1,003 reviews) All staff we came into contact with from front desk to housekeeping to breakfast/happy hour to doormen were super attentive, very friendly and seemed to sincerely see us. The happy hour/dinner and breakfast provided surprisingly good food, lots of variety and very generous pours! Sonia was a standout and we looked forward to seeing her each evening. Beds and bedding very comfortable. Room nicely appointed and clean. Reviewed on Mar 1, 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 CA $3,373 per person May 7 - May 12 found 4 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (1,003 reviews) Excellent staff, clean room, fantastic onsite restaurants. Reviewed on Mar 10, 2026 ![Loews Regency New York Hotel](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Loews Regency New York Hotel Manhattan CA $2,661 per person Apr 20 - Apr 27 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Newark Liberty Intl. Airport (EWR) 9/10 Wonderful! (1,002 reviews) Excellent stay, very clean spacious rooms. Location is great - close to everything. Only downfall was the bathroom, very tiny with a pedestal sink right next to the toilet, not great for women who need to get ready. Reviewed on Feb 24, 2026 Don't see what you're looking for? See all available trips from Columbus to Thimble Islands [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-13/2026-04-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Romantic holidays in Thimble Islands Price found within the past 48 hours. Click for updated prices. ![WestHouse New York](https://images.trvl-media.com/lodging/7000000/6470000/6468000/6467973/a11ba963_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### WestHouse New York Manhattan CA $954 per person May 14 - May 17 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 8.4/10 Very Good! (1,003 reviews) All staff we came into contact with from front desk to housekeeping to breakfast/happy hour to doormen were super attentive, very friendly and seemed to sincerely see us. The happy hour/dinner and breakfast provided surprisingly good food, lots of variety and very generous pours! Sonia was a standout and we looked forward to seeing her each evening. Beds and bedding very comfortable. Room nicely appointed and clean. Reviewed on Mar 1, 2026 ![The Fifth Avenue Hotel](https://images.trvl-media.com/lodging/97000000/96480000/96472700/96472655/183802ec_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Fifth Avenue Hotel Manhattan CA $2,014 per person May 25 - May 28 found 14 hours ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 9.6/10 Exceptional! (196 reviews) Absolutely everything. Amazingly appointed room, very friendly stafff. Reviewed on Mar 1, 2026 ![The Mark](https://images.trvl-media.com/lodging/1000000/20000/19800/19712/9915b062_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Mark Manhattan CA $2,352 per person Apr 24 - Apr 27 found 1 day ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 9.6/10 Exceptional! (703 reviews) Liked it a lot! As usual Reviewed on Mar 6, 2026 Don't see what you're looking for? See all available trips from Columbus to Thimble Islands [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-13/2026-04-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Romantic holidays in Thimble Islands Price found within the past 48 hours. Click for updated prices. ![New York Marriott Marquis](https://images.trvl-media.com/lodging/1000000/20000/15900/15838/0e1f57c3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### New York Marriott Marquis Manhattan CA $1,350 per person May 17 - May 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 9.2/10 Wonderful! (4,331 reviews) We went to attend the Grand Marshal Saint Patrick’s Day Gala. Safer to stay then drive upstate NY. Reviewed on Mar 12, 2026 ![The Pierre, A Taj Hotel, New York](https://images.trvl-media.com/lodging/1000000/30000/20300/20213/2d8a9a16_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Pierre, A Taj Hotel, New York Manhattan CA $2,731 per person May 1 - May 5 found 1 day ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 9.2/10 Wonderful! (1,007 reviews) Excellent service, rooms, and food Reviewed on Mar 4, 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 CA $3,009 per person Apr 30 - May 4 found 1 day ago Roundtrip flight included Calgary (YYC) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (1,003 reviews) Excellent staff, clean room, fantastic onsite restaurants. Reviewed on Mar 10, 2026 Don't see what you're looking for? See all available trips from Columbus to Thimble Islands [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-13/2026-04-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan unforgettable romantic Thimble Islands vacations #### What are some of the benefits of booking a romantic Thimble Islands vacation? When booking a romantic Thimble Islands vacation, you'll find quite a few options to make the experience with your partner absolutely unforgettable. Luxury amenities like hot tubs and spa facilities are prominent, but a lot of romantic vacation getaways also make it easy to explore some of the best spots in Connecticut. #### How can I find the best vacation packages for couples? If you're looking for a romantic vacation getaway, all you have to do is implement the romantic search filter. That will automatically remove any property that isn't suitable for couples. Just put in your travel dates and the Thimble Islands destination, and you'll be met with an array of options for you and your partner to enjoy. #### Can I find cheap romantic vacations for 2 in Thimble Islands? Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $954 and can enjoy savings of up to 41 when you book your hotel and flight together. Budget and luxury options are both available along with everything in between. Sorting your results by price will allow you to view the cheapest options first. #### What do I need to consider when booking a romantic getaway in Thimble Islands? Romantic vacation getaways succeed based on catering to what you and your partner specifically want to do. Think about what your partner enjoys and what you want to do as a couple, then opt for something that is especially geared toward fulfilling your ideal romantic vacation getaway experience. Search filters for amenities and proximity to certain attractions throughout Thimble Islands certainly come in handy here. #### What amenities should I look for in a luxury romantic vacation? If you and your partner are interested in luxury, you won't have to look far for a romantic vacation getaway that fits. In luxury accommodations, you can enjoy amenities like room service and a hot tub. Some accommodations may even have their own spa facilities complete with massage services that will add an extra touch of romance to your excursion to Thimble Islands. #### Can I book a romantic Thimble Islands vacation with a hot tub? Yes, and it's easy when you take advantage of available search filters. All you have to do is implement the hot tub filter from the amenities section into your search. This will automatically remove any stays from your search results that do not have hot tubs in them. #### How can I find romantic vacation getaways that are all-inclusive? An all-inclusive trip allows you to plan out your romantic vacation getaway in advance, letting you get a solid number on cost and a full itinerary before you set out. To start this kind of planning, simply apply the filter for all-inclusive trips in your Thimble Islands search. #### Can I book a romantic trip to Thimble Islands that is fully refundable? Several romantic Thimble Islands vacations come with fully refundable reservations. You can filter for this specifically, but every accommodation will list its policy for cancellation in their policy section, which is visible after clicking on a search result. Always make sure to check their policy to determine the requirements. #### Why should I book a romantic vacation with Expedia? Booking your trip with Expedia makes the entire planning process that much easier, as we're your convenient, all-in-one stop for all your travel needs. You can book your stay and your flight, with special discounts potentially available for booking together. Additionally, you can enjoy more discounts by becoming an Expedia Rewards member and getting points to put toward your next booking. Becoming a member is free, so don't hesitate to take advantage. ## 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.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) ### Top Romantic Vacation Destinations > - [Romantic vacations in Toronto ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178314/Toronto) > - [Romantic vacations in Nova Scotia ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/11173/Nova-Scotia) > - [Romantic vacations in Montreal ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178288/Montreal) > - [Romantic vacations in Vancouver ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178315/Vancouver) > - [Romantic vacations in Quebec ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/180017/Quebec) > - [Romantic vacations in the Niagara Falls ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/602721/Niagara-Falls) > - [Romantic vacations in Alberta ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/11111/Alberta) > - [Romantic vacations in Victoria ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/1418/Victoria) > - [Romantic vacations in Jasper ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/8028/Jasper) > - [Romantic vacations in Banff ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/4332/Banff) > - [Romantic vacations in Ottawa ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178296/Ottawa) > - [Romantic vacations in Mont Tremblant ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/55374/Mont-Tremblant) > - [Romantic vacations in Kingston ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/180034/Kingston) > - [Romantic vacations in Whistler ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/4115/Whistler) > - [Romantic vacations in Winnipeg ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/6141041/Winnipeg) > - [Romantic vacations in Muskoka ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/6343146/Muskoka-District) > - [Romantic vacations in Collingwood ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/11938/Collingwood) > - [Romantic vacations in Calgary ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178245/Calgary) > - [Romantic vacations in Canada ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/31/Canada) ## More Vacations Ideas [Flights to Thimble Islands ](https://expedia.ca/Cheap-Flights-To-Thimble-Islands.d6341069.Travel-Guide-Flights)[ Thimble Islands Hotels ](https://expedia.ca/Thimble-Islands-Hotels.d6341069.Travel-Guide-Hotels)[ Thimble Islands Vacation Rentals ](https://expedia.ca/Thimble-Islands-Vacation-Rentals.d6341069.Travel-Guide-VacationRentals)[ Thimble Islands Car Rentals ](https://expedia.ca/Car-Rentals-In-Thimble-Islands.d6341069.Car-Rental-Guide)[ Thimble Islands Vacations ](https://expedia.ca/Thimble-Islands.d6341069.Destination-Travel-Guides) \* Savings based on package bookings compared to the price of the same components booked separately. 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