Title: Ski Vacations in City Island 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) # City Island 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 City Island 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 $690 per person Feb 13 - Feb 16 found 23 hours ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.2/10 Wonderful! (2,008 reviews) It was an ok 3 stat hostel. Reviewed on Dec 10, 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 $1,086 per person Jan 12 - Jan 19 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (NYC) 9.2/10 Wonderful! (1,002 reviews) Electric charging in back Reviewed on Dec 9, 2025 ![The Fifth Avenue Hotel](https://images.trvl-media.com/lodging/97000000/96480000/96472700/96472655/d0a5c1e1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Fifth Avenue Hotel Manhattan CA $2,266 per person Jan 29 - Feb 3 found 23 hours ago Roundtrip flight included Calgary (YYC) to New York (JFK) 9.6/10 Exceptional! (159 reviews) What an incredibly beautiful place this hotel is! Staff cannot do enough and made ourspecial anniversary stay truly perfect..the hotel is beautifully decorated and immaculate throughout. Cannot recommend this enough Reviewed on Nov 17, 2025 ![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 $1,498 per person Jan 29 - Feb 3 found 23 hours ago Roundtrip flight included Calgary (YYC) to New York (JFK) 9/10 Wonderful! (1,002 reviews) helpful staff, nice rooms, location Reviewed on Nov 24, 2025 ![Sheraton New York Times Square Hotel](https://images.trvl-media.com/lodging/1000000/10000/100/87/576ccb20_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sheraton New York Times Square Hotel Manhattan CA $735 per person Feb 12 - Feb 17 found 2 days ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 7.4/10 Good! (5,413 reviews) Cleaning (clean towels and empty trash) was only done upon request and rooms need updating. Reviewed on Dec 10, 2025 Don't see what you're looking for? See all available trips from Columbus to City Island [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-11/2026-01-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=NYC&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Ski holidays in City Island Price found within the past 48 hours. Click for updated prices. ![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 $1,498 per person Jan 29 - Feb 3 found 23 hours ago Roundtrip flight included Calgary (YYC) to New York (JFK) 9/10 Wonderful! (1,002 reviews) helpful staff, nice rooms, location Reviewed on Nov 24, 2025 ![The Fifth Avenue Hotel](https://images.trvl-media.com/lodging/97000000/96480000/96472700/96472655/d0a5c1e1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Fifth Avenue Hotel Manhattan CA $2,266 per person Jan 29 - Feb 3 found 23 hours ago Roundtrip flight included Calgary (YYC) to New York (JFK) 9.6/10 Exceptional! (159 reviews) What an incredibly beautiful place this hotel is! Staff cannot do enough and made ourspecial anniversary stay truly perfect..the hotel is beautifully decorated and immaculate throughout. Cannot recommend this enough Reviewed on Nov 17, 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 $3,354 per person Jan 12 - Jan 19 found 19 hours ago Roundtrip non-stop flight included Vancouver (YVR) to New York (JFK) 8.8/10 Excellent! (1,000 reviews) The view is soooo good! Reviewed on Dec 2, 2025 Don't see what you're looking for? See all available trips from Columbus to City Island [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-11/2026-01-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=NYC&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Ski holidays in City Island 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 $690 per person Feb 13 - Feb 16 found 23 hours ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.2/10 Wonderful! (2,008 reviews) It was an ok 3 stat hostel. Reviewed on Dec 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 $1,675 per person Feb 13 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YYZ) to New York (NYC) 8.8/10 Excellent! (1,000 reviews) The view is soooo good! Reviewed on Dec 2, 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 $1,014 per person Feb 13 - Feb 16 found 18 hours 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 City Island [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-11/2026-01-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=NYC&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Ski holidays in City Island 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 $825 per person Feb 16 - Feb 20 found 18 hours ago Roundtrip non-stop flight included Vancouver (YVR) to New York (JFK) 9.2/10 Wonderful! (2,008 reviews) It was an ok 3 stat hostel. Reviewed on Dec 10, 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 $1,344 per person Feb 11 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YYZ) to New York (JFK) 9/10 Wonderful! (1,723 reviews) recently stayed at the Lotte Palace Hotel and was disappointed with several aspects of my experience. I had to call guest services five separate times just to have the blinds in our room fixed, and they only came on the last day as we were checking out. On top of that, one of the days no one came to clean the room or take out the trash, which was very surprising for a hotel at this price point. For the amount I paid, I expected a nicer room and better service overall. The only standout positive was the location, which truly is excellent. Would I stay here again? Unfortunately, no. The service issues made the stay far below expectations. Reviewed on Dec 11, 2025 ![Hyatt Union Square New York](https://images.trvl-media.com/lodging/6000000/5490000/5487000/5486911/9a008500_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Union Square New York Manhattan CA $892 per person Jan 26 - Jan 30 found 16 hours ago Roundtrip flight included Toronto (YTO) to New York (JFK) 8.6/10 Excellent! (1,001 reviews) The staff is terrific! The hotel is in a great location, and the rooms are quiet, clean, and comfortable. Reviewed on Nov 30, 2025 Don't see what you're looking for? See all available trips from Columbus to City Island [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-11/2026-01-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=NYC&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the ultimate ski vacation in City Island #### What are some benefits when booking ski vacations in City Island? 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 City Island? 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 City Island, 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 City Island with some as cheap as CA $690\. 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 City Island. 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 City Island. #### Can I book all-inclusive ski vacations in City Island? 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 City Island 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 City Island'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 City Island? 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 City Island. 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 City Island ](https://expedia.ca/Cheap-Flights-To-City-Island.d6247728.Travel-Guide-Flights)[ City Island Hotels ](https://expedia.ca/City-Island-Hotels.d6247728.Travel-Guide-Hotels)[ City Island Vacation Rentals ](https://expedia.ca/City-Island-Vacation-Rentals.d6247728.Travel-Guide-VacationRentals)[ City Island Car Rentals ](https://expedia.ca/Car-Rentals-In-City-Island.d6247728.Car-Rental-Guide)[ City Island Vacations ](https://expedia.ca/City-Island.d6247728.Destination-Travel-Guides)[ Things to do in City Island ](https://expedia.ca/Things-To-Do-In-City-Island.d6247728.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.