Weston Vacation Packages 2025/2026 from $563

Weston flight + hotel vacation packages

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

Mountaineer Inn

per person

Jul 25 - Jul 28

found 2 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Springfield (VSF)

A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and express check-in are also on offer.

The Shire Woodstock

per person

Jul 26 - Jul 29

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) 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.

Winterplace at Okemo

Clock Tower Base Area

per person

Jul 25 - Jul 28

found 2 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Springfield (VSF)

Ski-in/ski-out access and an indoor pool are featured at this smoke-free aparthotel. Enjoy the hot tub and perks like free self parking and free WiFi. Express check-out, laundry facilities, and barbecue grills are also on offer.

Jackson Gore Village

Jackson Gore Base Area

per person

Jul 25 - Jul 28

found 2 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Springfield (VSF)

This smoke-free hotel features ski-in/ski-out access, a full-service spa, and 2 restaurants. 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.

Solitude Village at Okemo

Clock Tower Base Area

per person

Jul 25 - Jul 28

found 2 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Springfield (VSF)

Ski-in/ski-out access and an outdoor pool are featured at this smoke-free aparthotel. Enjoy the indoor pool and perks like free self parking and free WiFi. A gym, a hot tub, and a sauna are also on offer.

Top Weston hotels deals

The Weston

630 Main St, Weston, VT

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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

NEW Charming ski retreat w/heated plunge pool & endless views in peaceful Weston

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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 hot tub and conveniences like a garden and barbecue grills.

Pool

Hot Tub

The Equinox Golf Resort & Spa

3567 Main Street Route 7A, Manchester, VT

Free Cancellation

Reserve now, pay when you stay

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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

Comfort Inn Rutland - Killington

19 Allen St, Rutland, VT

Free Cancellation

Reserve now, pay when you stay

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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 hot tub and free perks like continental breakfast and free self parking.

Pool

Hot Tub

Killington Mountain Lodge, Tapestry Collection by Hilton

2617 Killington Rd, Killington, VT

Free Cancellation

Reserve now, pay when you stay

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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.

Hot Tub

Pet friendly

Kimpton Taconic Hotel by IHG

3835 Main St., Manchester, VT

Free Cancellation

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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.

Pool

Pet friendly

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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 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.

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.

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 $563. 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.