Chalk Sound Drive Ski Holidays

Book a Ski Hotel + Flight or Car together to unlock savings

Photo by Curt Aftanas

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 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

    Packages with flights are ATOL protected

Top flight + Ski hotel deals in Chalk Sound Drive

Price found within the past 48 hours. Click for updated prices.
West Bay Club

West Bay Club

Grace Bay
Save 100% on your flight
£1,604
per person
3 Dec - 7 Dec
found 1 day ago
Return flight included
Toronto (YYZ) to Providenciales (PLS)
9.4/10 Exceptional! (1,003 reviews)
Le Vele Resort

Le Vele Resort

Grace Bay
Save 100% on your flight
£2,145
per person
5 Nov - 12 Nov
found 21 hours ago
Return direct flight included
London (LON) to Providenciales (PLS)
9.2/10 Wonderful! (67 reviews)
Beautiful beach, perfect! Staff friendly and helpful. Easy walk to grocery and restaurants on beach or sidewalk. Comfortable bed. Only complaint is blackout curtains did not function.

Reviewed on 2 Aug 2026

Windsong on the Reef

Windsong on the Reef

Grace Bay
Save 100% on your flight
£2,189
per person
5 Nov - 12 Nov
found 21 hours ago
Return direct flight included
London (LON) to Providenciales (PLS)
9.2/10 Wonderful! (1,290 reviews)
Point Grace

Point Grace

Grace Bay
Save 100% on your flight
£1,773
per person
3 Dec - 7 Dec
found 1 day ago
Return flight included
Toronto (YYZ) to Providenciales (PLS)
9.6/10 Exceptional! (343 reviews)
The minute we arrived, we were greeted. All the staff were super friendly. Everything was super clean and really close to everything downtown!

Reviewed on 24 Sept 2026

Beachfront at Windsong on the Reef

Beachfront at Windsong on the Reef

Grace Bay
Save 100% on your flight
£2,851
per person
1 Nov - 8 Nov
found 2 hours ago
Return direct flight included
London (LON) to Providenciales (PLS)
9.2/10 Wonderful! (194 reviews)
Don't see what you're looking for?
See all available trips from Toronto to Chalk Sound Drive
View all trips

5* Ski holidays in Chalk Sound Drive

Price found within the past 48 hours. Click for updated prices.
The Palms Turks and Caicos

The Palms Turks and Caicos

Grace Bay
Save 100% on your flight
£2,538
per person
3 Dec - 7 Dec
found 1 day ago
Return flight included
Toronto (YYZ) to Providenciales (PLS)
9.2/10 Wonderful! (1,000 reviews)
Beachfront at Windsong on the Reef

Beachfront at Windsong on the Reef

Grace Bay
Save 100% on your flight
£2,851
per person
1 Nov - 8 Nov
found 2 hours ago
Return direct flight included
London (LON) to Providenciales (PLS)
9.2/10 Wonderful! (194 reviews)
Ambergris Cay Private Island - All-Inclusive

Ambergris Cay Private Island - All-Inclusive

Save 100% on your flight
£10,498
per person
1 Nov - 8 Nov
found 2 hours ago
Return direct flight included
London (LON) to Providenciales (PLS)
9.8/10 Exceptional! (29 reviews)
Excellent place, excellent staff and beautiful private island. I cannot say a single bad thing about this place. We are planning to go back here every year. Thank you Ambergris Cay!

Reviewed on 28 Sept 2026

Don't see what you're looking for?
See all available trips from Toronto to Chalk Sound Drive
View all trips

4 Night Ski holidays in Chalk Sound Drive

Price found within the past 48 hours. Click for updated prices.
Le Vele Resort

Le Vele Resort

Grace Bay
Save 100% on your flight
£1,183
per person
3 Dec - 7 Dec
found 1 day ago
Return flight included
Toronto (YYZ) to Providenciales (PLS)
9.2/10 Wonderful! (67 reviews)
Beautiful beach, perfect! Staff friendly and helpful. Easy walk to grocery and restaurants on beach or sidewalk. Comfortable bed. Only complaint is blackout curtains did not function.

Reviewed on 2 Aug 2026

Dream Villas Provo

Dream Villas Provo

Blue Hills
Save 100% on your flight
£1,477
per person
3 Dec - 7 Dec
found 1 day ago
Return flight included
Toronto (YYZ) to Providenciales (PLS)
9.2/10 Wonderful! (79 reviews)
We had an incredible experience from booking to checkout! The Villas are located in an area that allows you privacy, but the convenience of still being close to dining, and other necessities. The check in and check out process were super simple, and they even made slight accommodations to help us when we had a flight delay. The villa has everything you might need in the kitchen if you choose to prepare meals there. We especially enjoyed the ability to walk steps off our sidewalk onto a beautiful beach, with included loungers, and water activity toys. Host response was always prompt, and again, accommodating to our changing needs. We wouldn’t hesitate to book this location again if we return to T&C.

Reviewed on 24 Sept 2026

Point Grace

Point Grace

Grace Bay
Save 100% on your flight
£1,773
per person
3 Dec - 7 Dec
found 1 day ago
Return flight included
Toronto (YYZ) to Providenciales (PLS)
9.6/10 Exceptional! (343 reviews)
The minute we arrived, we were greeted. All the staff were super friendly. Everything was super clean and really close to everything downtown!

Reviewed on 24 Sept 2026

Don't see what you're looking for?
See all available trips from Toronto to Chalk Sound Drive
View all trips

Planning your Chalk Sound Drive ski holiday

How can I book the best ski holiday to Chalk Sound Drive in 2026/2027?

Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in Chalk Sound Drive. Just choose your dates and see what’s available. You might prefer a hotel with a heated outdoor pool, or a private chalet for après ski parties; either way, use the property filters to your ideal match. If ski-in-ski-out is important, use the map view to find those idyllic slopeside properties.

How can I find cheap Chalk Sound Drive ski holidays?

Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book Chalk Sound Drive accommodation a little further from the lifts and go self-catering to cut back on eating out. Sort your search results by price to find options from £1,183. Prices and availability are subject to change. Additional terms may apply.

Can I book last-minute ski holidays to Chalk Sound Drive?

Use our handy last-minute deals page to look for ski holidays to Chalk Sound Drive at a steal. If your dates are fixed, simply input the details and see what specials are available.

What should I consider when booking family ski holidays in Chalk Sound Drive?

Chalk Sound Drive is well set up for kids. For the teeniest ski-woks, day care in the snow is a blast. As they get older, they love whizzing around on the hill in ski school. Choose a hotel near the lifts and nursery slopes to save a whole lot of ski-carrying hassle in the mornings. With all that extra time and energy, you can take your sweet time to find a family-favourite bolthole on the mountain for hot chocolate with marshmallows ski breaks.

Can I book all-inclusive ski holidays to Chalk Sound Drive?

All-inclusive ski holidays are fairly rare, but you can use our filter to see if there are any available in Chalk Sound Drive. If not, consider booking your flights and accommodation together to save money that way instead.

When's the best time of year to plan a ski trip to Chalk Sound Drive?

Ski season in Chalk Sound Drive generally starts around December and slopes off around April. Keep an eye on the snow forecasts though, as you can often find some brilliant deals at the start or end of the season, when it’s also much quieter.

How can I find the best deals on Chalk Sound Drive ski holiday packages?

If you can be flexible with your ski holiday dates, avoid school holidays and instead buckle up your boots at the start or end of season. Sort your search results by price and look out for self-catered accommodation to save on notoriously expensive ski-resort drinking and dining.

Can I book a Chalk Sound Drive ski trip with free cancellation and/or flexible dates?

If you’re not 100% sure on plans or just want peace of mind, choose a ski holiday with free cancellation. You can use our free cancellation filter to find properties in Chalk Sound Drive that offer it.

Why should I book a ski holiday package in Chalk Sound Drive with Expedia?

Schuss your way to the slopes with Expedia’s smooth booking process. From flights to hotels and even car hire, you’ll find everything you need to plan the ultimate winter wonderland ski holiday.

More holidays you might like

All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays
Golf Holidays
Golf Holidays
Luxury Holidays
Luxury Holidays
gay friendly holiday packages
LGBTQ+ Holidays
LGBTQ+ Holidays
Romantic Holidays
Romantic Holidays
Ski Holidays
Ski Holidays
Pet Friendly Holidays
Pet Friendly Holidays
Where to go when
Where to go when

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.