Weston Vacation Packages 2026 from $1,103

Weston flight + hotel vacation packages

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

The Vesper

$1,103

per person

Dec 2 - Dec 6

found 4 hours ago

Roundtrip flight included

Oklahoma City (OKC) to Springfield (VSF)

This bed & breakfast doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A virtual front desk are provided for your convenience.

Sinclair Inn Bed and Breakfast

$1,114

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Jacksonville (JAX) 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.

Lincoln Inn & Gallery

$1,380

per person

Dec 2 - Dec 6

found 4 hours ago

Roundtrip flight included

Oklahoma City (OKC) to Springfield (VSF)

This guesthouse 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.

Deer Brook Inn

$1,213

per person

Dec 2 - Dec 6

found 4 hours ago

Roundtrip flight included

Oklahoma City (OKC) to Springfield (VSF)

Woodstock Inn & Resort

$1,952

per person

Dec 2 - Dec 6

found 4 hours ago

Roundtrip flight included

Oklahoma City (OKC) 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.

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 $1,103. 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.