Title: Ski 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 Ski 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 Ski hotel deals 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 $722 per person Mar 14 - Mar 17 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 9.2/10 Wonderful! (2,008 reviews) Amazing room! We booked the family loft and it was amazing. Super comfy beds and free mini bar! Very clean hotel and amazing staff! Thank you! Reviewed on Jan 11, 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 $1,005 per person Feb 13 - Feb 16 found 1 day ago Roundtrip flight included Montreal (YUL) to New York (JFK) 9.2/10 Wonderful! (136 reviews) Great rooms, staff and food Reviewed on Sep 28, 2025 ![The Inn At Fox Hollow Hotel](https://images.trvl-media.com/lodging/1000000/880000/871900/871849/9f9215cb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Inn At Fox Hollow Hotel CA $1,296 per person Apr 1 - Apr 6 found 1 hour ago Roundtrip non-stop flight included Vancouver (YVR) to New York (JFK) 9.2/10 Wonderful! (1,002 reviews) The only issues was the lack of insulation. You can hear people talking throughout the halls from the room Reviewed on Jan 10, 2026 ![Fouquet's New York](https://images.trvl-media.com/lodging/89000000/88280000/88270900/88270883/aba7521d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fouquet's New York Manhattan CA $1,506 per person Mar 14 - Mar 17 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 9.6/10 Exceptional! (60 reviews) Lovely staff. Incredible property. The hype is real. This is by far and away the nicest property we’ve stayed at in Manhattan in a long time. Reviewed on Oct 10, 2025 ![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 $2,630 per person Mar 3 - Mar 6 found 18 hours ago Roundtrip non-stop 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/2026-02-11/2026-02-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Ski holidays in Thimble Islands Price found within the past 48 hours. Click for updated prices. ![Fouquet's New York](https://images.trvl-media.com/lodging/89000000/88280000/88270900/88270883/aba7521d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fouquet's New York Manhattan CA $1,506 per person Mar 14 - Mar 17 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 9.6/10 Exceptional! (60 reviews) Lovely staff. Incredible property. The hype is real. This is by far and away the nicest property we’ve stayed at in Manhattan in a long time. Reviewed on Oct 10, 2025 ![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 $2,630 per person Mar 3 - Mar 6 found 18 hours ago Roundtrip non-stop 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 ![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 $2,250 per person Apr 2 - Apr 6 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to New York (JFK) 9/10 Wonderful! (1,001 reviews) It was a wonderful stay! Loved this location. The staff were genuinely friendly and helpful. No attitude with fake smiles. I can't wait) it to come back to NYC so I can stay there again! Reviewed on Jan 11, 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/2026-02-11/2026-02-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Ski 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 $722 per person Mar 14 - Mar 17 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 9.2/10 Wonderful! (2,008 reviews) Amazing room! We booked the family loft and it was amazing. Super comfy beds and free mini bar! Very clean hotel and amazing staff! Thank you! Reviewed on Jan 11, 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 $1,005 per person Feb 13 - Feb 16 found 1 day ago Roundtrip flight included Montreal (YUL) to New York (JFK) 9.2/10 Wonderful! (136 reviews) Great rooms, staff and food Reviewed on Sep 28, 2025 ![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 $1,243 per person Mar 29 - Apr 1 found 21 hours 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 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/2026-02-11/2026-02-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Ski holidays in Thimble Islands Price found within the past 48 hours. Click for updated prices. ![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 $1,327 per person Apr 2 - Apr 6 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.2/10 Wonderful! (3,348 reviews) Great location to Broadway, Times Square and subways. Reviewed on Jan 11, 2026 ![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 $1,354 per person Feb 14 - Feb 18 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9/10 Wonderful! (2,346 reviews) Traveled with family for the holidays . Felt safe , staff was friendly and helpful. Reviewed on Jan 9, 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 $1,426 per person Apr 2 - Apr 6 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.2/10 Wonderful! (2,008 reviews) Amazing room! We booked the family loft and it was amazing. Super comfy beds and free mini bar! Very clean hotel and amazing staff! Thank you! Reviewed on Jan 11, 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/2026-02-11/2026-02-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the ultimate ski vacation in Thimble Islands #### What are some benefits when booking ski vacations in Thimble Islands? If you're interested in skiing, there's nothing quite like a ski vacation. These trips are designed to allow you to enjoy being on the slopes and relax in tranquil and convenient accommodations at the end of the day. Amenities on ski trips can be pretty upscale, so it's easy to relax in a hot tub or at a spa in between your skiing excursions. Plus, they can put you right next to the slopes. You'll even find a variety of different vacation types available whether you're looking for family friendly, cheap, or even last minute ski vacations. #### How can I book the best ski vacation in Thimble Islands? It is most important to implement the ski filter in your search when trying to find a ski vacation that will make you happy. Using the filter will automatically remove any entries that don't offer the skiing opportunities you want. After that, you'll need to think about what specifically you want from Thimble Islands, and think about the time of year that's best to visit. #### How can I find cheap ski vacations? Cheap ski vacations are readily available in Thimble Islands with some as cheap as CA $722\. You can see the cheapest options by sorting your accommodation choices by price, which automatically puts the least-expensive results at the top of the list. You may also want to consider an accommodation with a kitchen, so you can cook instead of eating out. #### Can I book ski packages? Yes, ski packages are readily available throughout Thimble Islands. All you have to do is put in your travel dates and see what's available. When you book a ski package, you may be able to enjoy discounts with savings of up to 46 when you book your accommodation and your flight together. #### What should I consider when booking family ski vacations? The key to a successful family ski vacation is ensuring that your family is kept happy and entertained. Consider what your family members are interested in and the kind of vacation they want. If they have little skiing experience, for example, you may want to opt for an accommodation that offers ski lessons or a kid's club. Various slope difficulties may be essential in providing opportunities for everyone at Thimble Islands. #### Can I book all-inclusive ski vacations in Thimble Islands? Yes, all-inclusive ski trips are available and may be precisely what you're looking for. All you have to do is include the filter for all-inclusive stays, and your search results will only show the accommodations that provide this handy feature that allows you to plan your entire trip to Thimble Islands in advance. #### What's the best time of year to plan a ski trip? The apparent answer to when you should plan a ski trip is in winter, but other details are important too. If you book for Thimble Islands's high season around January and February, you'll likely find increased prices. It's generally best to opt for the early or late season in December and April, as prices tend not to be quite as high. #### How can I find the best deals on ski packages in Thimble Islands? When you're looking for cheap ski vacations, there are a few factors you can take advantage of to help get the best deals. Travelling during the off-season can be cheaper since there's more availability. However, the beginning and end of the season tend to be the most affordable for skiing. #### Can I book a ski vacation that's fully refundable? Being fully refundable is a feature you'll find on several accommodation packages in Thimble Islands. You can even search for it explicitly using a filter for full refundability. #### Why should I book a ski vacation package with Expedia? When you book with Expedia, you'll find everything you need for cheap ski vacations, luxury ski vacations and everything in between in one central location. You may even be able to enjoy discounts for booking your accommodation and your flight together with savings of up to 46\. With Expedia Rewards, you can earn points towards your next booking. ## 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 Ski Vacation Destinations > - [Ski vacations in Whistler ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/4115/Whistler) > - [Ski vacations in Banff ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/4332/Banff) > - [Ski vacations in Mont Tremblant ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/55374/Mont-Tremblant) > - [Ski vacations in Jasper ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/8028/Jasper) > - [Ski vacations in Jackson ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/180006/Jackson) > - [Ski vacations in France ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/59/France) > - [Ski vacations in Quebec ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/180017/Quebec) > - [Ski vacations in Queenstown ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/3611/Queenstown) > - [Ski vacations in Lake Louise ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/10115/Lake-Louise) > - [Ski vacations in Nelson ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/6194600/Nelson) > - [Ski vacations in Kitzbuhel ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/6346453/Kitzbuehel) > - [Ski vacations in Switzerland ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/174/Switzerland) > - [Ski vacations in La Plagne ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/6034464/La-Plagne) > - [Ski vacations in St Gervais ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/3000402612/St-Gervais-Sur-Mare) > - [Ski vacations in Austria ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/11/Austria) > - [Ski vacations in Germany ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/64/Germany) > - [Ski vacations in Wengen ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/6186871/Wengen) > - [Ski vacations in Ontario ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/2680/Ontario) > - [Ski vacations in Colorado ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/207/Colorado) ## 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