Weston Vacation Packages 2026 from $440

Weston flight + hotel vacation packages

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

Okemo Mountain Lodging by Vail Resorts

Clock Tower Base Area

$440

per person

Jun 12 - Jun 15

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Springfield (VSF)

This vacation home features laundry facilities. Take advantage of the free self parking.

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area

$476

per person

Jun 12 - Jun 15

found 1 day ago

Roundtrip flight included

Orlando (MCO) 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.

Hideaway Inn Mt. Snow

$442

per person

Jun 12 - Jun 15

found 1 day ago

Roundtrip flight included

Orlando (MCO) 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.

The Covered Bridge Inn

$459

per person

Jun 10 - Jun 13

found 2 hours ago

Roundtrip flight included

New York (NYC) to Springfield (VSF)

This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning.

Lincoln Inn & Gallery

West Woodstock

$650

per person

Jun 15 - Jun 18

found 7 hours ago

Roundtrip non-stop flight included

New York (NYC) to Springfield (VSF)

This inn doesn't skimp on freebies - guests receive free WiFi and free self parking. A fireplace in the lobby and a picnic area are also provided.

Top Weston hotels deals

Killington Mountain Lodge, Tapestry Collection by Hilton

2617 Killington Rd Killington VT

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$134 total

May 25 - May 26

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 Mountain Inn at Killington

47 Old Mill Rd Killington VT

Free Cancellation

Reserve now, pay when you stay

$156 nightly

$172 total

May 10 - May 11

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

Pointe at Castle Hill Resort

2940 State Route 103 Cavendish VT

$138 nightly

$150 total

May 11 - May 12

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 & Spa

3567 Main Street Route 7A Manchester VT

Free Cancellation

Reserve now, pay when you stay

$154 nightly

$170 total

May 17 - May 18

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

Days Inn by Wyndham Rutland/Killington Area

401 US-7 Rutland VT

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$139 total

May 11 - May 12

Total with taxes and fees

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

Pool

Breakfast included

Comfort Inn Rutland - Killington

19 Allen St Rutland VT

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$157 total

May 17 - May 18

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

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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(13 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 $440. 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.