Book Exclusive Windsor County Vacation Packages

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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
Woodstock
A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

Chester

Vacations
Chester

Windsor County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was CA $1,255, price is now CA $1,106 per person
CA $1,106
per person
Oct 2 - Oct 4
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
Book a stay at this business-friendly hotel in Randolph Center. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Whale Dance Sculpture and Montague Golf Club are located nearby.
Deerfield Valley Inn

Deerfield Valley Inn

2 out of 5
Price was CA $1,346, price is now CA $1,209 per person
CA $1,209
per person
Oct 9 - Oct 12
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
Stay at this B&B in West Dover. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was CA $1,598, price is now CA $1,452 per person
CA $1,452
per person
Oct 9 - Oct 12
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was CA $1,355, price is now CA $1,260 per person
CA $1,260
per person
Oct 9 - Oct 12
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Timber Ripper Mountain Coaster are located nearby.
Mount Snow Lodging by Vail Resorts

Mount Snow Lodging by Vail Resorts

3 out of 5
Price was CA $1,427, price is now CA $1,335 per person
CA $1,335
per person
Oct 9 - Oct 12
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
Book a stay at this ski hotel in West Dover. Enjoy free WiFi, free parking, and ski-in/ski-out access. Popular attractions Mount Snow and Ego Alley Ski Lift are located nearby.

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
The price is CA $137 per night
CA $137
CA $151 total
Aug 24 - Aug 25
includes taxes & fees
Book a stay at this business-friendly hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Quechee Gorge Bridge and Quechee Gorge Village are located nearby.
Pool
Breakfast included
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is CA $563 per night
CA $563
CA $680 total
Sep 7 - Sep 8
includes taxes & fees
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Middle Covered Bridge and Woodstock Town Hall Theatre are located nearby.
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
The price is CA $191 per night
CA $191
CA $231 total
Aug 24 - Aug 25
includes taxes & fees
Stay at this resort in Brownsville. Enjoy a business center, a fireplace in the lobby, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions Mount Ascutney and Mt Ascutney State Park are located nearby.
Restaurant
Air conditioning
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
The price is CA $350 per night
CA $350
CA $416 total
Sep 8 - Sep 9
includes taxes & fees
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Union Arena Community Center and Five Elm Arches are located nearby.
Pool
Hot tub
Hotel Coolidge

Hotel Coolidge

3 out of 5
39 South Main Street White River Junction VT
Free cancellation
Reserve now, pay when you stay
The price is CA $174 per night
CA $174
CA $191 total
Sep 6 - Sep 7
includes taxes & fees
Book a stay at this business-friendly hotel in White River Junction. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Quechee Gorge Bridge and Briggs Opera House are located nearby.
Pet-friendly
Parking included
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
The price is CA $246 per night
CA $246
CA $271 total
Aug 25 - Aug 26
includes taxes & fees
Stay at this B&B in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast in our reviews. Popular attractions Union Arena Community Center and Five Elm Arches are located nearby.
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 CA $1,106, 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.