Deals on vacations and trips to Windsor County

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

Woodstock

Vacations
Woodstock

Windsor County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $1,217, price is now $1,017 per person
$1,017
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Save 100% on your flight
Price was $2,510, price is now $1,830 per person
$1,830
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $1,303, price is now $1,057 per person
$1,057
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Lebanon (LEB)
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.
Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Clock Tower Base Area
Price was $1,371, price is now $1,122 per person
$1,122
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
Ski-in/ski-out access and an indoor pool are featured at this smoke-free aparthotel. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the hot tub and conveniences like express check-out and laundry facilities.
Mountain Green Resort

Mountain Green Resort

4 out of 5
Save 100% on your flight
Price was $3,725, price is now $3,057 per person
$3,057
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
An outdoor pool is featured at this apartment, along with a virtual front desk. Take advantage of the free self parking.

Top Windsor County hotels deals

Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $140 total per night
$140 total
Aug 24 - Aug 25
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

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$449 nightly
The price is $494 total per night
$494 total
Sep 7 - Sep 8
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.
Pool
Hot Tub
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
485 Hotel Road Brownsville VT
Free Cancellation
$154 nightly
The price is $168 total per night
$168 total
Aug 17 - Aug 18
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
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$270 nightly
The price is $296 total per night
$296 total
Sep 8 - Sep 9
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
Hotel Coolidge

Hotel Coolidge

3 out of 5
39 South Main Street White River Junction VT
Free Cancellation
$132 nightly
The price is $145 total per night
$145 total
Sep 6 - Sep 7
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
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
$179 nightly
The price is $197 total per night
$197 total
Aug 25 - Aug 26
Total with taxes and fees
A restaurant and a bar/lounge are featured at this bed & breakfast. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, and a lobby fireplace are also on offer.
Parking included
Free WiFi
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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 romantic area.
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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 forest with autumn foliage.
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 $1,017, 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.

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