Weston Vacations 2026 from CA $1,129

Weston flight + hotel packages

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

The Shire Woodstock

CA $1,129

per person

Feb 27 - Mar 2

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Springfield (VSF)

Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.

Woodstock Inn & Resort

CA $1,660

per person

Feb 27 - Mar 2

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Springfield (VSF)

Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Middle Covered Bridge and Woodstock Town Hall Theatre are located nearby.

Lincoln Inn & Gallery

West Woodstock

CA $1,192

per person

Feb 27 - Mar 2

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Springfield (VSF)

Stay at this inn in Woodstock. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Union Arena Community Center and Ottaquechee River are located nearby.

Top Weston hotels deals

COHO Inn & Motor Lodge

287 Vermont Rte 100 Weston VT

CA $212

CA $232 total

Jan 27 - Jan 28

includes taxes & fees

Stay at this motel in Weston. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Weston Playhouse and Mill Museum are located nearby.

Breakfast included

Parking included

Pointe at Castle Hill Resort

2940 State Route 103 Cavendish VT

CA $213

CA $243 total

Feb 8 - Feb 9

includes taxes & fees

Book a stay at this spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.

Pool

Hot tub

Killington Mountain Lodge, Tapestry Collection by Hilton

2617 Killington Rd Killington VT

Free cancellation

Reserve now, pay when you stay

CA $238

CA $262 total

Jan 28 - Jan 29

includes taxes & fees

Book a stay at this ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Killington Resort and Pico Mountain at Killington Ski Resort are located nearby.

Hot tub

Pet-friendly

The Mountain Inn at Killington

47 Old Mill Rd Killington VT

CA $277

CA $320 total

Jan 22 - Jan 23

includes taxes & fees

Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Killington Resort and Pico Mountain at Killington Ski Resort are located nearby.

Pool

Breakfast included

Comfort Inn Rutland - Killington

19 Allen St Rutland VT

Free cancellation

Reserve now, pay when you stay

CA $195

CA $215 total

Feb 1 - Feb 2

includes taxes & fees

Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Vermont State Fairgrounds and Green Mountain Shopping Plaza are located nearby.

Pool

Hot tub

Kimpton Taconic Hotel by IHG

3835 Main St. Manchester VT

Free cancellation

CA $259

CA $338 total

Jan 21 - Jan 22

includes taxes & fees

Book a stay at this golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.

Pool

Pet-friendly

Don't see what you're looking for?

See all available properties in Weston

View all properties

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

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

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.

Weston Vacations

Have more fun, worry less and wander wisely in Weston! Make sure your journey gets off to a sensational start by getting to know this appealing destination.

This town can be found 25 miles (40 kilometers) west of Claremont. It's also 25 miles (40 kilometers) southeast of Rutland.

Places to visit in Weston

If you've ever wanted the 'Eat, Pray, Love' experience, why not look into the 'pray' part at Weston Priory? Work on your own spiritual growth and perhaps even find yourself! Want more ideas? The intimacy and mastery of theater is difficult to deny. Buy your tickets for a show at Weston Playhouse and feel the magic for yourself! And that's not all. If you've got an inquisitive mind, it's worth a trip to Mill Museum. You never know what you'll discover here!

Where do you fly into for Weston?

There's nothing more exciting than finally touching down in a brand new place. If you're hopping on a plane to Weston, there's a good chance you'll be stepping out into Rutland Southern Vermont Regional Airport (RUT). It's around 18 miles (29 kilometers) to the northwest of the downtown area. Grab your luggage and get set to start exploring!

Frequently asked questions

How much are vacation packages to Weston?

You'll be surprised — you can find yourself in Weston for only CA $1,129. 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 177 kilometers from Weston.

Which airport is best for Weston?

Lebanon Municipal Airport (LEB) is one place you can kick off your Weston adventure. Sitting 56 kilometers northeast of Weston, it welcomes travelers from all over every day. Another fantastic option is Rutland Southern Vermont Regional Airport (RUT), 29 kilometers 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.