Title: Luxury 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 Luxury 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 Luxury hotel deals in Thimble Islands Price found within the past 48 hours. Click for updated prices. ![Hotel Alameda Highline](https://images.trvl-media.com/lodging/5000000/4340000/4339600/4339531/165c4fb8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Alameda Highline Manhattan CA $706 per person Mar 6 - Mar 9 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 7.6/10 Good! (793 reviews) No frills but good location and meets all the needs. Reviewed on Jan 4, 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 CA $839 per person Mar 12 - Mar 15 found 20 hours ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.2/10 Wonderful! (136 reviews) Great rooms, staff and food Reviewed on Sep 28, 2025 ![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 $1,000 per person Apr 10 - Apr 13 found 16 hours ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 9/10 Wonderful! (2,790 reviews) Room bathroom the door Reviewed on Jan 14, 2026 ![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 $1,538 per person Mar 6 - Mar 11 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to New York (JFK) 9/10 Wonderful! (1,723 reviews) Room is outdated in appliance. No refill of the minibar. Bad quality of breakfast. Only one bar open for eating. Reviewed on Jan 13, 2026 ![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 $929 per person Mar 6 - Mar 9 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 9.2/10 Wonderful! (2,008 reviews) excellent location and large room and bathroom Reviewed on Jan 14, 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/2026-02-14/2026-02-21/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Luxury 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 $1,187 per person Mar 6 - Mar 8 found 13 hours ago Roundtrip flight included Toronto (YTO) to New York (JFK) 8.8/10 Excellent! (1,000 reviews) This hotel was FABULOUS! The view you see if the view you get! STUNNING magazine worthy view of the Brooklyn bridge. Almost kid free. The rooftop bar and lounge had stunning views of the Brooklyn bridge and Hudson river. Just minutes away from Manhattan and close enough to walk to the Bridge. Room service was excellent. Very clean room. Reviewed on Jan 3, 2026 ![The Langham, New York, Fifth Avenue](https://images.trvl-media.com/lodging/4000000/3630000/3630000/3629903/f11b4f1b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, New York, Fifth Avenue Manhattan CA $1,301 per person Mar 16 - Mar 19 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.4/10 Exceptional! (1,001 reviews) The Langham properties have become a go to for us and it’s because of the service delivery standards experienced at the London, Pasadena and NYC properties. Our 4 night stay was a busy one as our December 31st arrival meant we had to be quick at checking in time to head out for our dinner plans. Staff has always been exceptionally professional and went so far as to be recognized by two staff members from our previous stay. There are many great hotels in NYC, but the Langham’s 5th Avenue location is absolutely, positively perfect. Thank you for the warm welcome and excellent customer service. Reviewed on Jan 5, 2026 ![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 $1,706 per person Mar 26 - Mar 29 found 1 day ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 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/2026-02-14/2026-02-21/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Luxury holidays in Thimble Islands Price found within the past 48 hours. Click for updated prices. ![Hotel Alameda Highline](https://images.trvl-media.com/lodging/5000000/4340000/4339600/4339531/165c4fb8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Alameda Highline Manhattan CA $706 per person Mar 6 - Mar 9 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 7.6/10 Good! (793 reviews) No frills but good location and meets all the needs. Reviewed on Jan 4, 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 CA $839 per person Mar 12 - Mar 15 found 20 hours ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.2/10 Wonderful! (136 reviews) Great rooms, staff and food Reviewed on Sep 28, 2025 ![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 $1,000 per person Apr 10 - Apr 13 found 16 hours ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 9/10 Wonderful! (2,790 reviews) Room bathroom the door Reviewed on Jan 14, 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/2026-02-14/2026-02-21/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Luxury holidays in Thimble Islands Price found within the past 48 hours. Click for updated prices. ![Hotel Alameda Highline](https://images.trvl-media.com/lodging/5000000/4340000/4339600/4339531/165c4fb8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Alameda Highline Manhattan CA $884 per person Mar 19 - Mar 23 found 19 hours ago Roundtrip flight included Toronto (YTO) to New York (JFK) 7.6/10 Good! (793 reviews) No frills but good location and meets all the needs. Reviewed on Jan 4, 2026 ![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 $1,227 per person Apr 6 - Apr 10 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9/10 Wonderful! (2,790 reviews) Room bathroom the door Reviewed on Jan 14, 2026 ![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 $1,913 per person Feb 20 - Feb 24 found 1 day ago Roundtrip flight included Montreal (YUL) to New York (JFK) 8.8/10 Excellent! (1,000 reviews) This hotel was FABULOUS! The view you see if the view you get! STUNNING magazine worthy view of the Brooklyn bridge. Almost kid free. The rooftop bar and lounge had stunning views of the Brooklyn bridge and Hudson river. Just minutes away from Manhattan and close enough to walk to the Bridge. Room service was excellent. Very clean room. Reviewed on Jan 3, 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/2026-02-14/2026-02-21/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the perfect luxury Thimble Islands vacation with Expedia #### What are some benefits when booking luxury Thimble Islands vacations? When you book a luxury Thimble Islands vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax. #### How can I find all-inclusive luxury vacations in Thimble Islands? If you're looking for something luxurious in Thimble Islands, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together. #### Can I book a cheap luxury vacation? While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $706, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 75\. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first. #### Are there luxury spa vacations? Yes, luxury spa vacations are available and quite popular in Thimble Islands. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search. #### What should I look for in a luxury family vacation in Thimble Islands? When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Thimble Islands. #### Can I book last-minute luxury vacations? Yes, last-minute bookings are often available in Thimble Islands. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces. #### What can help me find the best luxury vacation deals in Thimble Islands? You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Thimble Islands or travelling to more obscure destinations altogether can often lead to lower prices. #### Can I book a luxury vacation that is fully refundable? Yes, fully refundable reservations are sometimes available on luxury vacation packages in Thimble Islands. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking. #### Why should I book my luxury vacation with Expedia? When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings. ## 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 Luxury Vacation Destinations > - [Luxury vacations in India ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/80/India) > - [Luxury vacations in France ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/59/France) > - [Luxury vacations in Switzerland ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/174/Switzerland) > - [Luxury vacations in Canada ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/31/Canada) > - [Luxury vacations in Jamaica ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/88/Jamaica) > - [Luxury vacations in Italy ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/86/Italy) > - [Luxury vacations in New Zealand ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/133/New-Zealand) > - [Luxury vacations in the Maldives ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/109/Maldives) > - [Luxury vacations in Costa Rica ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/42/Costa-Rica) > - [Luxury vacations in Florida Keys ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6023765/Florida-Keys) > - [Luxury vacations in Mexico ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/117/Mexico) > - [Luxury vacations in the Caribbean ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6022969/Caribbean) > - [Luxury vacations in Zanzibar ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/4186/Zanzibar) > - [Luxury vacations in Cancun ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/179995/Cancun) > - [Luxury vacations in Kerala ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/602187/Kerala) > - [Luxury vacations in Australia ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/10/Australia) > - [Luxury vacations in Puglia ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6048562/Puglia) > - [Luxury vacations in Cuba ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/44/Cuba) > - [Luxury vacations in Cyprus ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/45/Cyprus) ## 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