Deals on vacations and trips to Windsor County

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A wooden covered bridge with a sign reading 'Slippery When Wet' and a sign above the entrance that says 'Michael's Bridge.'

Woodstock

Vacations
Woodstock

Windsor County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $1,046, price is now $967 per person
$967
per person
Feb 4 - Feb 7
found 12 hours ago
Roundtrip flight included
Wilmington (ILM) to Rutland (RUT)
This hotel features an indoor pool and a sauna. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
Price was $1,535, price is now $1,202 per person
$1,202
per person
Dec 24 - Dec 27
found 23 hours ago
Roundtrip non-stop flight included
Houston (IAH) 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.
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $2,371, price is now $1,947 per person
$1,947
per person
Feb 4 - Feb 7
found 12 hours ago
Roundtrip flight included
Wilmington (ILM) to Rutland (RUT)
An outdoor pool is featured at this apartment, along with a virtual front desk. Take advantage of the free self parking.
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,992, price is now $1,642 per person
$1,642
per person
Feb 4 - Feb 7
found 12 hours ago
Roundtrip flight included
Wilmington (ILM) to Rutland (RUT)
An outdoor pool, free self parking, and laundry facilities are featured at this condo. WiFi in public areas is free. Concierge services, barbecue grills, and a virtual front desk are also on offer.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,754, price is now $1,528 per person
$1,528
per person
Dec 24 - Dec 27
found 23 hours ago
Roundtrip non-stop flight included
Houston (IAH) 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.

Top Windsor County hotels deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$369 nightly
The price is $406 total per night
$406 total
Nov 30 - Dec 1
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
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
111 Jackson Gore Road Ludlow VT
$210 nightly
The price is $231 total per night
$231 total
Nov 19 - Nov 20
Total with taxes and fees
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.
Pool
Hot Tub
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$149 nightly
The price is $163 total per night
$163 total
Dec 6 - Dec 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
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$167 nightly
The price is $181 total per night
$181 total
Dec 15 - Dec 16
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
Free Cancellation
Reserve now, pay when you stay
$153 nightly
The price is $168 total per night
$168 total
Dec 14 - Dec 15
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
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
$144 nightly
The price is $157 total per night
$157 total
Nov 17 - Nov 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
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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 historic courthouse with a prominent clock tower and a brick facade.
A red covered bridge with a stop sign and a sign reading "TAFTSVILLE CLEARANCE TO FEET."
A river flowing through a forest with autumn foliage.
A river winding through a forest with autumn foliage.
A forest with autumn foliage.

Frequently asked questions

How much are vacation packages to Windsor County?
With vacation packages being sold from as little as $967, 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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