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. ![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 $871 per person Feb 6 - Feb 12 found 23 hours ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 8.8/10 Excellent! (1,184 reviews) The staff was over the top helpful and nice. Location is good. Decor is cool too. Little issue with light going on at 2am and windows thin… think street noise. Bring white noise machine. Beds and pillows comfy. Room clean. Nice touch with robe in room. Reviewed on Dec 15, 2025 ![INNSiDE by Meliá New York Nomad](https://images.trvl-media.com/lodging/13000000/12630000/12628000/12627948/24f1e817_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### INNSiDE by Meliá New York Nomad Manhattan CA $876 per person Feb 6 - Feb 12 found 23 hours ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 9.2/10 Wonderful! (2,008 reviews) Staff was great, room was great, hotel was clean. Reviewed on Dec 17, 2025 ![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 $1,173 per person Feb 6 - Feb 12 found 23 hours ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 9.2/10 Wonderful! (3,348 reviews) Nice enjoyable stay! Reviewed on Dec 16, 2025 ![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 $1,101 per person Feb 6 - Feb 12 found 23 hours ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 9.8/10 Exceptional! (1,411 reviews) Very cute and well appointed room! Lovely staff. Free coffee and tea. Reviewed on Dec 15, 2025 ![1 Hotel Central Park](https://images.trvl-media.com/lodging/10000000/9220000/9215600/9215515/524d3c3f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Central Park Manhattan CA $2,018 per person Jan 29 - Feb 3 found 9 hours ago Roundtrip non-stop flight included Vancouver (YVR) to New York (JFK) 9/10 Wonderful! (1,001 reviews) Small hotel with small rooms, but the decor was very nice. Reviewed on Nov 28, 2025 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/2026-01-17/2026-01-24/?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. ![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 $1,251 per person Mar 6 - Mar 8 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 8.8/10 Excellent! (1,000 reviews) i spent lots of money for one night, but there was no breakfast included. I was with my wife as a new married couple to make memories on our 1st night, but the room was terribly heated, and the room service was poor. I called twice for a champagne glass. dinner was amazing with beautiful views. Reviewed on Dec 15, 2025 ![1 Hotel Central Park](https://images.trvl-media.com/lodging/10000000/9220000/9215600/9215515/524d3c3f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Central Park Manhattan CA $2,018 per person Jan 29 - Feb 3 found 9 hours ago Roundtrip non-stop flight included Vancouver (YVR) to New York (JFK) 9/10 Wonderful! (1,001 reviews) Small hotel with small rooms, but the decor was very nice. Reviewed on Nov 28, 2025 ![Pendry Natirar](https://images.trvl-media.com/lodging/103000000/102110000/102101800/102101788/ea5e4ca8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Natirar CA $2,892 per person Feb 6 - Feb 12 found 23 hours ago Roundtrip non-stop flight included Hamilton (YHM) to New York (NYC) 9.8/10 Exceptional! (7 reviews) The staff is lovely and the property gorgeous. The room could have been more complete (no slippers to be found and no in-room mini bar amenities, which was surprising). The grounds are pristine and peaceful. Reviewed on Jun 13, 2025 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/2026-01-17/2026-01-24/?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. ![INNSiDE by Meliá New York Nomad](https://images.trvl-media.com/lodging/13000000/12630000/12628000/12627948/24f1e817_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### INNSiDE by Meliá New York Nomad Manhattan CA $716 per person Feb 16 - Feb 19 found 20 hours ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 9.2/10 Wonderful! (2,008 reviews) Staff was great, room was great, hotel was clean. Reviewed on Dec 17, 2025 ![Lotte New York Palace](https://images.trvl-media.com/lodging/1000000/10000/4900/4818/w1695h1110x0y0-027534be_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lotte New York Palace Manhattan CA $1,040 per person Mar 14 - Mar 17 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9/10 Wonderful! (1,723 reviews) The property was exquisite, very well presented and the Christmas décor was fantastic. Rooms were very nice, and the staff was extremely pleasant with our needs. Reviewed on Dec 17, 2025 ![JW Marriott Essex House New York](https://images.trvl-media.com/lodging/1000000/540000/534200/534143/04695212_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### JW Marriott Essex House New York Manhattan CA $852 per person Mar 14 - Mar 17 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 8.8/10 Excellent! (1,001 reviews) The price was most we ever paid for a room($907 night) We were there for the NYC Marathon and wanted to be in that area. We had a $25 day credit towards food and drinks, one morning we ate in restaurant and breakfast for 2 people was $104 before tip. They charge me $10 cup for coffee when it was complimentary in the lobby. We returned after long day and they did not leave washcloths, I went to front desk, she called housekeeping and said they would have them right up, 30 minutes later I called and they said they were on there way, after waiting I finally returned to front desk and told lady to tell me where to go and I would go get me some washcloths, she went herself and got some, when I returned to room my wife said housekeeping came but said they could only find one washcloth and brought it. $907 night, do your homework before you go. Reviewed on Nov 10, 2025 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/2026-01-17/2026-01-24/?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. ![Margaritaville Resort Times Square](https://images.trvl-media.com/lodging/67000000/66530000/66525900/66525849/a08f45bd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Margaritaville Resort Times Square Manhattan CA $747 per person Jan 20 - Jan 24 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.2/10 Wonderful! (3,941 reviews) Amazing room and view Reviewed on Dec 17, 2025 ![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 $1,226 per person Mar 7 - Mar 11 found 11 hours ago Roundtrip flight included Toronto (YYZ) to New York (JFK) 9/10 Wonderful! (2,346 reviews) Not enough amenities Reviewed on Dec 14, 2025 ![The Lexington Hotel, Autograph Collection](https://images.trvl-media.com/lodging/1000000/30000/20300/20288/bbebe1e0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Lexington Hotel, Autograph Collection Manhattan CA $963 per person Mar 1 - Mar 5 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to New York (JFK) 8.2/10 Very Good! (1,603 reviews) The staff was amazing, the room was very clean and spacious, would definitely recommend anybody to go to this hotel. We loved our stay!! Reviewed on Dec 15, 2025 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/2026-01-17/2026-01-24/?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 $716 and can enjoy savings of up to 39 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. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app