Weston Vacation Packages 2026 from $531

Weston flight + hotel vacation packages

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

Hideaway Inn Mt. Snow

$531

per person

Oct 1 - Oct 4

found 1 day ago

Roundtrip flight included

Tampa (TPA) to Springfield (VSF)

This hotel features a seasonal outdoor pool and a hot tub. Enjoy the free ski shuttle and onsite ski storage. Enjoy the sauna and perks like free self parking and free WiFi.

Vikings Villages Resort

Save 100% on your flight

$1,004

per person

Nov 1 - Nov 7

found 4 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to Springfield (VSF)

A rooftop terrace is featured at this hotel, along with free self parking. WiFi in public areas is free. A garden, a lobby fireplace, and a picnic area are also on offer.

The Shire Woodstock

$1,234

per person

Nov 6 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Tampa (TPA) to Springfield (VSF)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area

$933

per person

Nov 6 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Tampa (TPA) 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.

1846 Inn and Tavern

$608

per person

Oct 1 - Oct 4

found 1 day ago

Roundtrip flight included

Tampa (TPA) to Springfield (VSF)

A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. A garden is provided and the front desk is staffed around-the-clock.

Top Weston hotels deals

The Weston

630 Main St Weston VT

$275 nightly

$300 total

Aug 25 - Aug 26

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.

The Mountain Inn at Killington

47 Old Mill Rd Killington VT

Free Cancellation

Reserve now, pay when you stay

$146 nightly

$161 total

Aug 25 - Aug 26

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.

Comfort Inn Rutland - Killington

19 Allen St Rutland VT

Free Cancellation

$133 nightly

$147 total

Aug 30 - Aug 31

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.

Kimpton Taconic Hotel by IHG

3835 Main St. Manchester VT

Free Cancellation

$257 nightly

$283 total

Sep 9 - Sep 10

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a seasonal outdoor pool on site, and a 24-hour front desk and a terrace are also provided.

Killington Mountain Lodge, Tapestry Collection by Hilton

2617 Killington Rd Killington VT

Free Cancellation

Reserve now, pay when you stay

$155 nightly

$171 total

Aug 30 - Aug 31

Total with taxes and fees

This hotel features a 24-hour gym and a hot tub. Traveling on business? Take advantage of the 2 conference rooms, along with free WiFi in public areas. Self parking, a terrace, and a lobby fireplace are also offered.

The Equinox Golf Resort & Spa

3567 Main Street Route 7A Manchester VT

Free Cancellation

Reserve now, pay when you stay

$223 nightly

$245 total

Sep 7 - Sep 8

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.

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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.

Stay near popular Weston attractions

Weston Playhouse

7.8/10 (14 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.

See properties

Frequently asked questions

How much are vacation packages to Weston?

You'll be surprised — you can find yourself in Weston for only $531. 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.