Weston Vacation Packages 2026/2026 from $722

Weston flight + hotel vacation packages

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

Chalet 239

$722

per person

Jan 29 - Feb 2

found 17 hours ago

Roundtrip non-stop flight included

Wilmington (ILM) to Springfield (VSF)

The motel doesn't skimp on freebies - guests receive free on-the-go breakfast and free self parking. A picnic area and a virtual front desk are also provided.

Jackson Gore Village

Jackson Gore Base Area

Save 100% on your flight

$1,444

per person

Jan 29 - Feb 3

found 1 day ago

Roundtrip flight included

Wilmington (ILM) to Springfield (VSF)

Ski-in/ski-out access, 2 restaurants, and 3 hot tubs are all featured at this smoke-free hotel. There's a free ski shuttle, and ski lessons, ski passes and ski storage are available on site. Bring the family and enjoy the mini golf, playground, and arcade/game room.

Mount Snow Grand Summit Resort

Save 100% on your flight

$1,454

per person

Jan 29 - Feb 2

found 17 hours ago

Roundtrip non-stop flight included

Wilmington (ILM) to Springfield (VSF)

Ski-in/ski-out access, a full-service spa, and 2 hot tubs are all featured at this smoke-free resort. Enjoy a meal from the restaurant and freebies like WiFi in public areas and an area shuttle. You'll appreciate the outdoor pool, bar/lounge, and laundry facilities.

Woodstock Inn & Resort

$1,458

per person

Jan 29 - Feb 3

found 1 day ago

Roundtrip flight included

Wilmington (ILM) to Springfield (VSF)

This luxury resort features a golf course, a full-service spa, and 4 restaurants. Enjoy the 2 indoor tennis courts and perks like free valet parking and free WiFi. Relax with a drink at one of the 2 bars/lounges and enjoy the 2 hot tubs and indoor pool.

Mountain Lodge at Okemo

Clock Tower Base Area

$1,265

per person

Jan 29 - Feb 3

found 1 day ago

Roundtrip flight included

Wilmington (ILM) to Springfield (VSF)

A restaurant and a gym are featured at this hotel. Take advantage of ski passes and ski storage on site, and enjoy downhill skiing and sledding. Families will appreciate the onsite laundry facilities and babysitting.

Top Weston hotels deals

Charming mountain retreat with pool, fire pit, glamping loft, and endless views

Weston VT

Get rates

This vacation home features an outdoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the sauna and conveniences like a garden and barbecue grills.

The Weston

630 Main St Weston VT

$405 nightly

$441 total

Dec 11 - Dec 12

Total with taxes and fees

This luxury guesthouse features a full-service spa and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A garden, luggage storage, and concierge services are also on offer.

Spa

Pet friendly

The Mountain Inn at Killington

47 Old Mill Rd Killington VT

Free Cancellation

Reserve now, pay when you stay

$167 nightly

$184 total

Dec 9 - Dec 10

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the free ski shuttle and onsite ski storage. Enjoy the gym and free perks like continental breakfast and free self parking.

Killington Mountain Lodge, Tapestry Collection by Hilton

2617 Killington Rd Killington VT

Free Cancellation

Reserve now, pay when you stay

$167 nightly

$184 total

Dec 14 - Dec 15

Total with taxes and fees

This hotel features a 24-hour gym and a hot tub. There's a free ski shuttle, and ski passes and ski storage are available on site. WiFi in public areas is free.

Comfort Inn Rutland - Killington

19 Allen St Rutland VT

Free Cancellation

Reserve now, pay when you stay

$116 nightly

$128 total

Dec 10 - Dec 11

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and free perks like continental breakfast and free self parking.

Pool

Hot Tub

The Equinox Golf Resort & Spa

3567 Main Street Route 7A Manchester VT

Free Cancellation

Reserve now, pay when you stay

$218 nightly

$240 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.

Pool

Hot Tub

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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.

Popular places to visit

Weston Playhouse

3.5/5(12 reviews)

You can make plans for a show at Weston Playhouse during your stay in Weston. Discover the mountain views in this romantic area, or enjoy its ski slopes.

Weston Priory

4.5/5(2 reviews)

You can find out about the history of Weston when you stop by Weston Priory. Discover the mountain views in this romantic area, or enjoy its ski slopes.

Mill Museum

You can spend time exploring the galleries in Mill Museum during your travels in Weston. Discover the mountain views in this romantic area, or enjoy its ski slopes.

Frequently asked questions

How much are vacation packages to Weston?

You'll be surprised — you can find yourself in Weston for only $722. Here at Travelocity, we save you time and money with our awesome vacation package deals. With flights, hotels and experiences all ready to be snapped up, why wait any longer?

Where can I get the best vacation package deals for Weston?

Your dream vacation can be booked through Travelocity. With access to 400 air carriers and an incredible 1,000,000 properties around the world, finding the perfect Weston package deal couldn't be simpler.

Why should I purchase my Weston vacation package via Travelocity?

We have experiences and destinations to suit every type of traveler, excellent service and 24/7 customer support. To top that off, we'll match any lower price you find with our Price Match Guarantee.

Can I save on my Weston car rental if I bundle it with my hotel or flight?

You certainly can — bundle your hotel, flight and car into a Weston vacation package and you'll save loads. With so much to uncover in the Weston area, that set of wheels will come in handy. Once you've slid into the driver's seat, hit the wide open road and cruise toward Fenway Park, a well-known attraction around 110 mi from Weston.

Which airport is best for Weston?

Lebanon Municipal Airport (LEB) is one place you can kick off your Weston adventure. Sitting 35 mi northeast of Weston, it welcomes travelers from all over every day. Another fantastic option is Rutland Southern Vermont Regional Airport (RUT), 18 mi away from central Weston.

What is there to do in Weston?

Weston Playhouse is just one of the memorable sights that make Weston such a great place to visit. But allow yourself enough time to roam its lesser-known attractions too. This is often where the best memories are created.

Where should I stay when visiting Weston?

If you're looking for a place to lay your head, have a look at the Mountain cabin by skiing with fireplaces & well-equipped kitchen - dog-friendly. It's the top pick for many visitors.