Windsor County Vacation Packages 2026 from $624

Search vacation packages deals in Windsor County's top destinations

A red convertible car parked in front of a brick house with black shutters and a white picket fence.

Woodstock

Vacations

Windsor County flight + hotel vacation packages

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

Bentley House Bed and Breakfast

$624

per person

Aug 25 - Aug 28

found 1 day ago

Roundtrip non-stop flight included

Kansas City (MCI) to Rutland (RUT)

This bed & breakfast doesn't skimp on freebies - guests receive free breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A lobby fireplace, a communal living room, and luggage storage are also on offer.

Top Windsor County hotels deals

Align Inn Vermont

5817 Woodstock Rd Quechee VT

$122 nightly

$135 total

Jul 3 - Jul 4

Total with taxes and fees

This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Woodstock Inn & Resort

Fourteen The Green Woodstock VT

$499 nightly

$549 total

Jul 12 - Jul 13

Total with taxes and fees

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.

On The River Inn

1653 West Woodstock Road Woodstock VT

$228 nightly

$251 total

Jul 6 - Jul 7

Total with taxes and fees

This hotel features an indoor pool, a hot tub, and a restaurant. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

Pool

Hot Tub

The Shire Woodstock

46 Pleasant St. Woodstock VT

Free Cancellation

Reserve now, pay when you stay

$183 nightly

$202 total

Jul 26 - Jul 27

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.

Pet friendly

Parking included

Hotel Coolidge

39 South Main Street White River Junction VT

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$134 total

Jul 14 - Jul 15

Total with taxes and fees

A restaurant, free self parking, and a 24-hour front desk are among this hotel's amenities. WiFi in public areas is free. A coffee shop, a terrace, and a lobby fireplace are also on offer.

Pet friendly

Parking included

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

485 Hotel Road Brownsville VT

Free Cancellation

$154 nightly

$168 total

Jul 28 - Jul 29

Total with taxes and fees

This resort features a restaurant, an outdoor tennis court, and a bar/lounge. A business center, a lobby fireplace, and a picnic area are also on offer.

Restaurant

Air conditioning

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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.

Stay near popular Windsor County attractions

A snow-covered ski resort with ski lifts, buildings, and a mountain backdrop.

Okemo Mountain Resort

9.2/10 (510 reviews)

Hit the slopes in Ludlow with a visit to Okemo Mountain Resort. Discover the mountain views in this quaint area.

See properties

Photos of local treasures

Browse Windsor County vacation photos for more inspiration

A river flowing through a forest with autumn foliage.

A river winding through a forest with autumn foliage.

A river flowing through a forested valley with a bridge in the distance.

A calm lake surrounded by dense green forest and a clear sky.

Frequently asked questions

How much are vacation packages to Windsor County?

With vacation packages being sold from as little as $624, there's no need to wipe out your bank balance for your trip to Windsor County. Travelocity is here to help. Bundle flights, hotels and experiences into a package and receive some impressive discounts. The more you book, the bigger the savings.

Where can I get the best vacation package deals for Windsor County?

No matter your adventure, Travelocity can help you lock in an unbeatable Windsor County package deal. The only thing you need to do is pick and choose between our 400 air carriers and 1,000,000 properties worldwide.

Why should I purchase my Windsor County vacation bundle via Travelocity?

Because you'll never roam alone if you book with us, and we offer round-the-clock support and excellent service to boot. Add to that our Price Match Guarantee and countless destinations and experiences to select from. We're here to help you have the trip of a lifetime.

Can I save on my Windsor County car rental if I combine it with my hotel or flight?

You sure can with our Windsor County vacation packages. With one of these, there are lots of ways to make your hard-earned cash go further. Bundle any two or more car, hotel, flight and tour bookings and watch your savings start to grow. With your own set of wheels, all the attractions around Windsor County are a fun road trip away.

Which airport is best for Windsor County?

Lebanon Municipal Airport (LEB) and Rutland Southern Vermont Regional Airport (RUT) are your best options for jetting to Windsor County.

What is there to do in Windsor County?

You'll be happy to know Windsor County is teeming with wonderful photo-ops, however Montshire Museum of Science and Weston Playhouse are among the best of them.