Deals on vacations and trips to Windsor County

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Windsor County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $958, price is now $784 per person
$784
per person
Mar 17 - Mar 22
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Lebanon (LEB)
This resort features a restaurant, an indoor pool, and a bar/lounge. There's an outdoor tennis court on site, and a fireplace in the lobby and a picnic area are also provided.
Mountain Green Resort

Mountain Green Resort

4 out of 5
Save 100% on your flight
Price was $2,077, price is now $1,565 per person
$1,565
per person
Mar 17 - Mar 22
found 1 day ago
Roundtrip 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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,039, price is now $851 per person
$851
per person
Mar 17 - Mar 22
found 1 day ago
Roundtrip flight included
Tampa (TPA) 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.
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,576, price is now $1,306 per person
$1,306
per person
Mar 17 - Mar 22
found 1 day ago
Roundtrip flight included
Tampa (TPA) 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.
Beechwood Home in Mendon

Beechwood Home in Mendon

2 out of 5
Save 100% on your flight
Price was $3,312, price is now $2,751 per person
$2,751
per person
Mar 17 - Mar 22
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Rutland (RUT)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. Laundry facilities and barbecue grills are also provided.

Top Windsor County hotels deals

Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
$120 nightly
The price is $132 total per night
$132 total
Feb 11 - Feb 12
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
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$142 nightly
The price is $154 total per night
$154 total
Mar 2 - Mar 3
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
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$349 nightly
The price is $384 total per night
$384 total
Feb 22 - Feb 23
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
$154 nightly
The price is $168 total per night
$168 total
Mar 1 - Mar 2
Total with taxes and fees
This resort features a restaurant, an indoor pool, and a bar/lounge. There's an outdoor tennis court on site, and a fireplace in the lobby and a picnic area are also provided.
Pool
Restaurant
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
$150 nightly
The price is $165 total per night
$165 total
Mar 2 - Mar 3
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
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$197 nightly
The price is $217 total per night
$217 total
Mar 1 - Mar 2
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
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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.

Photos of local treasures

Browse Windsor County vacation photos for more inspiration

Quechee Gorge- Vermont #autumn #colorful #roadtrip #weekendgetaway #travel #adventure #nature #vacation
Quechee Gorge- Vermont #autumn #colorful #roadtrip #weekendgetaway #travel #adventure #nature #vacation
Must stop while in Vermont #autumn #fall #roadtrip #travel #adventure #colorful #vermont
Park at the Queeche gift shop and hike the 0.4 mile trail down to this stunning view of the gorge! Very easy hike and such a gorgeous view.
I found Autumn in Vermont #autumn #pnw #fall #roadtrip #travel #adventure #colorful #nationalparks #vermont

Frequently asked questions

How much are vacation packages to Windsor County?
With vacation packages being sold from as little as $784, 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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