New England Ski Vacations

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

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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

New England Ski Vacation Packages

Rugged peaks packed with snow make this northeastern region a must-ski destination for alpine adventurers. Book a New England ski vacation package and get your downhill thrills at popular snowy escapes like Bretton Woods Ski Area and Jiminy Peak Mountain Resort.

Get ready for epic days on the slopes at Stowe Mountain Resort in Vermont, a snow-covered playground with 468 skiable acres that include 116 trails. Skiers of all stripes also head to Sunday River in Maine, which has 870 skiable acres spread across eight interconnected peaks. Satisfy your ski cravings on its 135 glades and trails. Other winter activities here include snowboarding, snowshoeing and ski biking. Jiminy Peak Mountain Resort in Hancock is another cool New England ski vacation package destination. Choose from various ski pass types, including three-day tickets and season passes. Prices start from $34 for a four-hour lift ticket. After an intense day of skiing at Bretton Woods Ski Area, pamper yourself at the 25,000-square-foot spa at Omni Mount Washington Resort while enjoying views of Mount Washington. New Hampshire's largest ski area also features an impressive après-ski. Continue your post-slope relaxation at Fabyan's Restaurant, which is housed in a historic railroad station.

Top Ski vacation packages in New England

Price found within the past 48 hours. Click for updated prices.
Establishment Hotel

Establishment Hotel

Sydney Central Business District
$1,575
per person
Nov 5 - Nov 8
found 5 hours ago
Roundtrip flight included
New York (JFK) to Sydney (SYD)
9/10 Wonderful! (694 reviews)
Rydges Darling Square Apartment Hotel

Rydges Darling Square Apartment Hotel

Sydney Central Business District
$1,668
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
8.8/10 Excellent! (1,568 reviews)
Room good, friendly staff. Very noisy during weekends from street

Reviewed on Aug 29, 2026

Pullman Sydney Hyde Park

Pullman Sydney Hyde Park

Darlinghurst
$1,811
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sydney (SYD)
8.6/10 Excellent! (1,004 reviews)
Great location and beautiful accommodations! Would stay here again!

Reviewed on Aug 30, 2026

Furama Darling Harbour

Furama Darling Harbour

Haymarket
$1,630
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sydney (SYD)
8.4/10 Very Good! (1,004 reviews)
Great place to stay handy to lots of amenities.lovely new foyer to sit and relax with a coffee

Reviewed on Sep 2, 2026

Amora Hotel Jamison Sydney

Amora Hotel Jamison Sydney

Sydney Central Business District
$1,809
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sydney (SYD)
9/10 Wonderful! (1,524 reviews)
Don't see what you're looking for?
See all available trips from Chicago to New England
View all trips

5* Ski vacations in New England

Price found within the past 48 hours. Click for updated prices.
Establishment Hotel

Establishment Hotel

Sydney Central Business District
$1,575
per person
Nov 5 - Nov 8
found 5 hours ago
Roundtrip flight included
New York (JFK) to Sydney (SYD)
9/10 Wonderful! (694 reviews)
Pullman Sydney Hyde Park

Pullman Sydney Hyde Park

Darlinghurst
$1,811
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sydney (SYD)
8.6/10 Excellent! (1,004 reviews)
Great location and beautiful accommodations! Would stay here again!

Reviewed on Aug 30, 2026

Amora Hotel Jamison Sydney

Amora Hotel Jamison Sydney

Sydney Central Business District
$1,809
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sydney (SYD)
9/10 Wonderful! (1,524 reviews)
Don't see what you're looking for?
See all available trips from Chicago to New England
View all trips

3 Night Ski vacations in New England

Price found within the past 48 hours. Click for updated prices.
Rydges Camperdown

Rydges Camperdown

Camperdown
$1,191
per person
Oct 24 - Oct 25
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to Sydney (SYD)
8.2/10 Very Good! (1,005 reviews)
Disappointing stay. Reception was not very welcoming, which was disappointing from the moment we arrived. I also couldn’t believe we were charged $36 to park at the hotel. How can you charge your own paying guests that much just to park on the premises? It felt excessive and really took away from the overall experience.

Reviewed on Sep 1, 2026

YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

Sydney Central Business District
$1,643
per person
Nov 30 - Dec 1
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Sydney (SYD)
8.2/10 Very Good! (2,897 reviews)
This place has one of the only 2 elevators broken for the entire week and the only one working broken down last 2 days. We all had to walk up and down the stairs. My floor was 8th but it had 20 floors. Not acceptable.

Reviewed on Sep 2, 2026

Four Seasons Hotel Sydney

Four Seasons Hotel Sydney

The Rocks
$1,291
per person
Oct 24 - Oct 25
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to Sydney (SYD)
9.6/10 Exceptional! (2,263 reviews)
Great location and great view.

Reviewed on Sep 2, 2026

Don't see what you're looking for?
See all available trips from Chicago to New England
View all trips

4 Night Ski vacations in New England

Price found within the past 48 hours. Click for updated prices.
Chic Apartment With Sun Lounge Near Manly Beach

Chic Apartment With Sun Lounge Near Manly Beach

Manly
$1,532
per person
Oct 9 - Oct 12
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
No reviews
North-east Facing Modern 2-bed Apartment

North-east Facing Modern 2-bed Apartment

Freshwater
$1,707
per person
Oct 9 - Oct 12
found 7 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
No reviews
Lovely Harbourside 1-bed Close To Sydney Landmarks

Lovely Harbourside 1-bed Close To Sydney Landmarks

Kurraba Point
$1,576
per person
Oct 9 - Oct 12
found 10 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
No reviews
Don't see what you're looking for?
See all available trips from Chicago to New England
View all trips

Planning your New England ski vacation

What are some things I should consider when booking a New England 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 New England ski packages?

Right now, ski trips start at just $1,191. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in New England?

Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in New England. 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 New England cost?

Sensational ski trips to New England start from $1,191. 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 New England?

The best time to hit the slopes in New England 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 New England 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 New England 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 New England with Expedia?

Simple search and fantastic filters make it easy to find, build, and book your dream New England ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.