Weston Vacation Packages 2026 from $476

Weston flight + hotel vacation packages

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

Latchis Hotel

$476

per person

Dec 10 - Dec 15

found 18 hours ago

Roundtrip flight included

Chicago (ORD) to Springfield (VSF)

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking and luggage storage are also offered on site.

Vikings Villages Resort

Save 100% on your flight

$781

per person

Dec 10 - Dec 15

found 18 hours ago

Roundtrip flight included

Chicago (ORD) 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.

Woodstock Inn & Resort

Save 100% on your flight

$1,994

per person

Dec 10 - Dec 15

found 18 hours ago

Roundtrip flight included

Chicago (ORD) 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.

Sinclair Inn Bed and Breakfast

$916

per person

Dec 9 - Dec 15

found 6 hours ago

Roundtrip non-stop flight included

Austin (AUS) to Springfield (VSF)

This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast and free WiFi. A garden and a picnic area are also provided.

Holiday Inn Express Hotel & Suites Brattleboro by IHG

$609

per person

Dec 10 - Dec 15

found 18 hours ago

Roundtrip flight included

Chicago (ORD) to Springfield (VSF)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.

Top Weston hotels deals

The Weston

630 Main St Weston VT

$383 nightly

$418 total

Oct 20 - Oct 21

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

$156 nightly

$172 total

Oct 18 - Oct 19

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.

Pool

Breakfast included

Killington Mountain Lodge, Tapestry Collection by Hilton

2617 Killington Rd Killington VT

Free Cancellation

Reserve now, pay when you stay

$204 nightly

$224 total

Oct 18 - Oct 19

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.

Hot Tub

Pet friendly

The Manchester View

77 High Meadow Way & VT-7A Manchester Center VT

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$135 total

Sep 21 - Sep 22

Total with taxes and fees

A seasonal outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.

Pool

Breakfast included

Pointe at Castle Hill Resort

2940 State Route 103 Cavendish VT

$121 nightly

$131 total

Oct 20 - Oct 21

Total with taxes and fees

A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Hot Tub

The Equinox Golf Resort And Spa

3567 Main Street Manchester VT

Free Cancellation

Reserve now, pay when you stay

$272 nightly

$299 total

Oct 19 - Oct 20

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.

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 $476. 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.