Weston Vacation Packages 2026 from $566

Weston flight + hotel vacation packages

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

Latchis Hotel

$566

per person

Feb 12 - Feb 15

found 7 hours ago

Roundtrip flight included

Tampa (TPA) 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.

Mount Snow Grand Summit Resort

$1,500

per person

Feb 12 - Feb 15

found 7 hours ago

Roundtrip flight included

Tampa (TPA) to Springfield (VSF)

Ski-in/ski-out access, a full-service spa, and 2 hot tubs are all featured at this smoke-free resort. Enjoy a meal from the restaurant and freebies like WiFi in public areas and an area shuttle. You'll appreciate the outdoor pool, bar/lounge, and laundry facilities.

Mount Snow Lodging

Save 100% on your flight

$3,796

per person

Feb 12 - Feb 15

found 7 hours ago

Roundtrip flight included

Tampa (TPA) to Springfield (VSF)

Chalet 239

$711

per person

Feb 12 - Feb 15

found 7 hours ago

Roundtrip flight included

Tampa (TPA) to Springfield (VSF)

The motel doesn't skimp on freebies - guests receive free on-the-go breakfast and free self parking. A picnic area and a virtual front desk are also provided.

Comfort Inn & Suites Brattleboro I-91

$657

per person

Feb 12 - Feb 15

found 7 hours ago

Roundtrip flight included

Tampa (TPA) to Springfield (VSF)

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

Top Weston hotels deals

COHO Inn & Motor Lodge

287 Vermont Rte 100 Weston VT

$163 nightly

$178 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

A bar/lounge and a terrace are featured at this motel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A garden, a snack bar/deli, and a lobby fireplace are also on offer.

Breakfast included

Parking included

The Weston

630 Main St Weston VT

$414 nightly

$452 total

Dec 25 - Dec 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.

Spa

Pet friendly

Comfort Inn Rutland - Killington

19 Allen St Rutland VT

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$158 total

Jan 4 - Jan 5, 2026

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

Killington Mountain Lodge, Tapestry Collection by Hilton

2617 Killington Rd Killington VT

Free Cancellation

Reserve now, pay when you stay

$196 nightly

$215 total

Jan 21 - Jan 22, 2026

Total with taxes and fees

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

The Mountain Inn at Killington

47 Old Mill Rd Killington VT

Get rates

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

$139 nightly

$151 total

Jan 4 - Jan 5, 2026

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

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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(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.

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 $566. 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.