A mountainous landscape with rocky outcrops and autumn-colored trees.
Photo by Marina Timo
Open Photo by Marina Timo

Coastal Connecticut Ski Vacations

Book a 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

Top Ski vacation packages in Coastal Connecticut

Price found within the past 48 hours. Click for updated prices.
  • A Holiday Inn hotel with a covered entrance, multiple floors, and a well-lit facade.
    Dec 11 - Dec 13

    Holiday Inn Cheshire - Southington by IHG + Flight

    Southington
    2 nights
    3.0 star property
    8.2/10 - Very good (1,002 reviews)
    Roundtrip • San Juan (SJU) - Hartford (BDL)
    SJU - BDL • Nonstop BDL - SJU • Nonstop
    $307
    $285
    per traveler
    found 1 day ago
    Holiday Inn Cheshire - Southington by IHG
  • A cozy dining area with a brick fireplace, wooden chairs, and tables set for a meal.
    Jan 15 - Jan 18

    Inn at Middletown + Flight

    Washington Street Historic District
    3 nights
    3.5 star property
    8.8/10 - Excellent (680 reviews)
    Roundtrip • Atlanta (ATL) - Hartford (BDL)
    ATL - BDL • Nonstop BDL - ATL • 1 stop
    $905
    $732
    per traveler
    found 6 hours ago
    Inn at Middletown
  • A spacious hotel lobby with wooden beams, a central seating area, and large windows offering a view.
    Dec 30 - Jan 2

    Heritage Hotel, Golf & Conference Center + Flight

    Southbury
    3 nights
    3.5 star property
    8.4/10 - Very good (1,002 reviews)
    Roundtrip • Miami (MIA) - New Haven (HVN)
    FLL - HVN • Nonstop HVN - FLL • Nonstop
    $742
    $635
    per traveler
    found 1 day ago
    Heritage Hotel, Golf & Conference Center
  • Room
    Dec 11 - Dec 13

    Extended Stay America Suites Hartford Meriden + Flight

    Meriden
    2 nights
    2.5 star property
    7.0/10 - Good (980 reviews)
    Roundtrip • San Juan (SJU) - Hartford (BDL)
    SJU - BDL • Nonstop BDL - SJU • Nonstop
    $323
    $307
    per traveler
    found 1 day ago
    Extended Stay America Suites Hartford Meriden
  • A hotel lobby with a wooden staircase, a reception desk, and a view through large windows.
    Dec 17 - Dec 20

    Econo Lodge Milldale - Southington + Flight

    Milldale
    3 nights
    2.0 star property
    6.6/10 - (610 reviews)
    Roundtrip • Los Angeles (LAX) - Hartford (BDL)
    LAX - BDL • 1 stop BDL - LAX • 1 stop
    $525
    $500
    per traveler
    found 1 day ago
    Econo Lodge Milldale - Southington

Discover the most popular places to visit in Coastal Connecticut

A sunset over a river with buildings in the distance.

Foxwoods Resort Casino

9.0/10 (2,885 reviews)
One of North America's largest resort casinos, Foxwoods offers over 4,800 slot machines and extensive table games. Enjoy live entertainment, fine dining, and shopping at the on-site Tanger Outlets.
See properties

Top Ski Coastal Connecticut Hotels

A hotel lobby with a modern design, featuring a seating area with sofas, a fireplace, and a television mounted on the wall.

Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown
3.0 star property
21.1 mi from Coastal Connecticut
8.6 out of 10, Excellent, (1,293 reviews)
"Excellent Staff"
$89 nightly
The price is $102
Nov 8 - Nov 9
Total with taxes and fees
Courtyard by Marriott Waterbury Downtown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
See all properties in Coastal Connecticut

Planning your Coastal Connecticut ski vacation

What are some things I should consider when booking a Coastal Connecticut 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 Coastal Connecticut ski packages?

Right now, ski trips start at just $285. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Coastal Connecticut?

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

Sensational ski trips to Coastal Connecticut start from $285. 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 Coastal Connecticut?

The best time to hit the slopes in Coastal Connecticut 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 Coastal Connecticut 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 Coastal Connecticut 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 Coastal Connecticut with Expedia?

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