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.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $1,072, price is now $873 per person
$873
per person
Nov 30 - Dec 6
found 4 hours ago
Roundtrip non-stop 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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,934, price is now $1,512 per person
$1,512
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
1846 Inn and Tavern

1846 Inn and Tavern

3 out of 5
Price was $1,290, price is now $1,039 per person
$1,039
per person
Nov 30 - Dec 6
found 4 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. A garden is provided and the front desk is staffed around-the-clock.
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $3,419, price is now $2,812 per person
$2,812
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
An outdoor pool is featured at this apartment, along with a virtual front desk. Take advantage of the free self parking.
Summit Lodge

Summit Lodge

3 out of 5
Price was $1,508, price is now $1,271 per person
$1,271
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
This smoke-free hotel features 2 outdoor pools, a hot tub, and a restaurant. Enjoy the seasonal outdoor pool and free perks like full breakfast and free self parking. A bar/lounge, a 24-hour front desk, and a poolside bar are also provided.

Top Windsor County hotels deals

Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
$206 nightly
The price is $226 total per night
$226 total
Oct 18 - Oct 19
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
$689 nightly
The price is $758 total per night
$758 total
Oct 27 - Oct 28
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
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
$243 nightly
The price is $267 total per night
$267 total
Oct 26 - Oct 27
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
Hotel Coolidge

Hotel Coolidge

3 out of 5
39 South Main Street White River Junction VT
$131 nightly
The price is $144 total per night
$144 total
Oct 27 - Oct 28
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
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$155 nightly
The price is $168 total per night
$168 total
Oct 21 - Oct 22
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
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
$296 nightly
The price is $326 total per night
$326 total
Oct 29 - Oct 30
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
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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.
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 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 $873, 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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