Title: Cayman Islands Ski Vacations 2026 | Expedia.com ![](https://images.trvl-media.com/place/33/815d3643-df65-4394-9dea-463c72e1fd4e.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Cayman Islands Ski Vacations ## Book a Ski Hotel + Flight or Car together to unlock savings Photo by Cayman Islands Department of Tourism - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 ## Top Ski vacation packages in Cayman Islands Price found within the past 48 hours. Click for updated prices. ![Shangri-La Boutique Bed & Breakfast](https://images.trvl-media.com/lodging/10000000/9810000/9800600/9800559/ffc02cbf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Shangri-La Boutique Bed & Breakfast $933 per person Mar 28 - Apr 1 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to George Town (GCM) 9.8/10 Exceptional! (198 reviews) The room was spotless, Rosa was an absolute pleasure to work with all my needs wet met. I keeper booked taxi to and from location, provided transport to dinner one day. I will return yearly. If you are looking for a nice place to getaway and relax this is the best place for exactly that, in my opinion. Everything was provided from toiletries to sunscreen and bug spray. Beach chairs, snorkel equipment, bikes, any so much more! Reviewed on Feb 19, 2026 ![VIDA Cayman](https://images.trvl-media.com/lodging/101000000/100320000/100315100/100315092/8f768f3f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### VIDA Cayman $1,054 per person Mar 28 - Apr 1 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to George Town (GCM) 9.8/10 Exceptional! (8 reviews) Staff was great, the rooms were new and spotless, located on the north end. Shower/sink heat was hit or miss, beach is not what I expected. Reviewed on Jan 31, 2026 ![The Westin Grand Cayman Seven Mile Beach Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/14900/14859/e7a9c815_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Grand Cayman Seven Mile Beach Resort & Spa $2,353 per person Mar 28 - Apr 1 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to George Town (GCM) 9/10 Wonderful! (1,004 reviews) It was sooooo busy! Could hardly get a beach chair. Didn’t honor my Marriott Ambassador status because I booked on Expedia (missed out on points and breakfast). Room and bed was comfy. Won’t be returning. Reviewed on Feb 17, 2026 ![Hotel Indigo Grand Cayman by IHG](https://images.trvl-media.com/lodging/97000000/96930000/96922200/96922163/6e584603_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Indigo Grand Cayman by IHG $1,736 per person Mar 28 - Apr 1 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to George Town (GCM) 9.8/10 Exceptional! (432 reviews) Beautiful property. Reviewed on Feb 17, 2026 ![Ocean Paradise](https://images.trvl-media.com/lodging/5000000/4520000/4513300/4513286/15df0357_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ocean Paradise $1,718 per person Mar 28 - Apr 1 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to George Town (GCM) 9.6/10 Exceptional! (38 reviews) Wonderful property! We enjoyed our stay very much! Reviewed on Sep 30, 2024 Don't see what you're looking for? See all available trips from Columbus to Cayman Islands [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-21/2026-03-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CYM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Ski vacations in Cayman Islands Price found within the past 48 hours. Click for updated prices. ![The Grove](https://images.trvl-media.com/lodging/110000000/109760000/109750700/109750667/1d6bc223_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Grove $1,479 per person Apr 28 - May 3 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to George Town (GCM) 10/10 Exceptional! (42 reviews) Clean modern and close to beach shops and restaurants. Reviewed on Feb 20, 2026 ![Kimpton Seafire Resort + Spa by IHG](https://images.trvl-media.com/lodging/15000000/14770000/14761400/14761342/4afac615_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Seafire Resort + Spa by IHG Save 100% on your flight $5,851 per person May 15 - May 22 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to George Town (GCM) 9.8/10 Exceptional! (953 reviews) The room was great! I loved the view and the pillows were great. The night lights in the room are unique. I loved the frozen grapes and popsicles they hand out on the beach. I fell pampered. Great and such kind people. Loved my stay! Reviewed on Feb 4, 2026 ![Caribbean Club Luxury Condo Hotel](https://images.trvl-media.com/lodging/6000000/5180000/5173500/5173420/d465f5bd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Caribbean Club Luxury Condo Hotel Save 100% on your flight $4,639 per person Apr 28 - May 3 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to George Town (GCM) 9.8/10 Exceptional! (45 reviews) Don't see what you're looking for? See all available trips from Columbus to Cayman Islands [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-21/2026-03-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CYM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Ski vacations in Cayman Islands Price found within the past 48 hours. Click for updated prices. ![Shangri-La Boutique Bed & Breakfast](https://images.trvl-media.com/lodging/10000000/9810000/9800600/9800559/ffc02cbf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Shangri-La Boutique Bed & Breakfast $779 per person Apr 9 - Apr 12 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to George Town (GCM) 9.8/10 Exceptional! (198 reviews) The room was spotless, Rosa was an absolute pleasure to work with all my needs wet met. I keeper booked taxi to and from location, provided transport to dinner one day. I will return yearly. If you are looking for a nice place to getaway and relax this is the best place for exactly that, in my opinion. Everything was provided from toiletries to sunscreen and bug spray. Beach chairs, snorkel equipment, bikes, any so much more! Reviewed on Feb 19, 2026 ![Hotel Indigo Grand Cayman by IHG](https://images.trvl-media.com/lodging/97000000/96930000/96922200/96922163/6e584603_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Indigo Grand Cayman by IHG $1,187 per person Apr 9 - Apr 12 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to George Town (GCM) 9.8/10 Exceptional! (432 reviews) Beautiful property. Reviewed on Feb 17, 2026 ![Kimpton Seafire Resort + Spa by IHG](https://images.trvl-media.com/lodging/15000000/14770000/14761400/14761342/4afac615_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Seafire Resort + Spa by IHG $2,529 per person May 7 - May 10 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to George Town (GCM) 9.8/10 Exceptional! (953 reviews) The room was great! I loved the view and the pillows were great. The night lights in the room are unique. I loved the frozen grapes and popsicles they hand out on the beach. I fell pampered. Great and such kind people. Loved my stay! Reviewed on Feb 4, 2026 Don't see what you're looking for? See all available trips from Columbus to Cayman Islands [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-21/2026-03-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CYM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Ski vacations in Cayman Islands Price found within the past 48 hours. Click for updated prices. ![VIDA Cayman](https://images.trvl-media.com/lodging/101000000/100320000/100315100/100315092/8f768f3f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### VIDA Cayman $1,054 per person Mar 28 - Apr 1 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to George Town (GCM) 9.8/10 Exceptional! (8 reviews) Staff was great, the rooms were new and spotless, located on the north end. Shower/sink heat was hit or miss, beach is not what I expected. Reviewed on Jan 31, 2026 ![Kimpton Seafire Resort + Spa by IHG](https://images.trvl-media.com/lodging/15000000/14770000/14761400/14761342/4afac615_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Seafire Resort + Spa by IHG Save 100% on your flight $2,524 per person May 7 - May 11 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to George Town (GCM) 9.8/10 Exceptional! (953 reviews) The room was great! I loved the view and the pillows were great. The night lights in the room are unique. I loved the frozen grapes and popsicles they hand out on the beach. I fell pampered. Great and such kind people. Loved my stay! Reviewed on Feb 4, 2026 ![The Westin Grand Cayman Seven Mile Beach Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/14900/14859/e7a9c815_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Grand Cayman Seven Mile Beach Resort & Spa $2,353 per person Mar 28 - Apr 1 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to George Town (GCM) 9/10 Wonderful! (1,004 reviews) It was sooooo busy! Could hardly get a beach chair. Didn’t honor my Marriott Ambassador status because I booked on Expedia (missed out on points and breakfast). Room and bed was comfy. Won’t be returning. Reviewed on Feb 17, 2026 Don't see what you're looking for? See all available trips from Columbus to Cayman Islands [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-21/2026-03-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CYM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=THVAD_SPRING_PROMO_33) ## Planning your Cayman Islands ski vacation #### What are some things I should consider when booking a Cayman Islands ski trip package? Yes, you want pristine powder and perfect runs, but take a moment to consider how close you want to be to the slopes, what extras you want from your resort, and—of course—how much après ski you intend to indulge in. #### How can I find cheap Cayman Islands ski packages? Right now, ski trips start at just $779\. Prices and availability are subject to change. Additional terms may apply. #### Can I book a beginner ski package in Cayman Islands? Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Cayman Islands. Book lessons so you can gear up to take on the rest of the mountain with confidence. Après awaits for all after an eventful day in the snow. #### How much does a ski trip to Cayman Islands cost? Sensational ski trips to Cayman Islands start from $779\. Use the budget filter to find powder at your perfect price. As always, prices and availability are subject to change. Additional terms may apply. #### When’s the best time of year to plan a ski trip to Cayman Islands? The best time to hit the slopes in Cayman Islands depends on what you’re looking for. If you’re all about powder-packed pistes and brilliant blue-sky skiing conditions, aim for the middle of the season. Alternatively, if you’re willing to take a chance on start or end of season snow, you’ll bag much cheaper prices —just make sure there’s a spa or après bar to shelter in on white-out days. #### Can I book Cayman Islands ski packages with airfare? Save money on your snow time by booking your accommodation, airfare, and car rental in a brilliant bundle. It’s both convenient and cash-flow friendly. #### Can I book a Cayman Islands ski trip with free cancellation and/or flexible dates? Flexibility is always a bonus when you’re flying down the slopes—and it makes for an easier booking process, too. Check the payment option filter to find trips with free cancellation as well as buy now, pay later options. #### Why should I book a ski package in Cayman Islands with Expedia? Simple search and fantastic filters make it easy to find, build, and book your dream Cayman Islands ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy. ## 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.com/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.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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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 even more - get up to 20% on select hotels 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