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.
The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain

2.5 out of 5
Price was $478, price is now $375 per person
$375
per person
Oct 23 - Oct 27
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
This motel features a restaurant, an outdoor pool, and a bar/lounge. 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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Save 100% on your flight
Price was $2,038, price is now $1,373 per person
$1,373
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Greensboro (GSO) 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
Save 100% on your flight
Price was $927, price is now $673 per person
$673
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Greensboro (GSO) 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.
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was $1,076, price is now $848 per person
$848
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free buffet breakfast each morning. A garden is also provided.
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $1,176, price is now $972 per person
$972
per person
Sep 20 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Lebanon (LEB)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. A grocery/convenience store, a computer station, and laundry facilities are also on offer.

Top Windsor County hotels deals

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 1 - Sep 2
Total includes 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 Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
$198 nightly
The price is $218 total per night
$218 total
Aug 27 - Aug 28
Total includes 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
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd, Quechee, VT
$132 nightly
The price is $145 total per night
$145 total
Aug 24 - Aug 25
Total includes 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
Hotel Coolidge

Hotel Coolidge

3 out of 5
39 South Main Street, White River Junction, VT
Free Cancellation
Reserve now, pay when you stay
$153 nightly
The price is $169 total per night
$169 total
Sep 10 - Sep 11
Total includes 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
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
Reserve now, pay when you stay
$125 nightly
The price is $136 total per night
$136 total
Sep 1 - Sep 2
Total includes 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
Comfort Inn White River Junction

Comfort Inn White River Junction

2.5 out of 5
56 Ralph Lehman Dr, White River Junction, VT
$135 nightly
The price is $149 total per night
$149 total
Aug 31 - Sep 1
Total includes taxes and fees
A gym, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A picnic area is provided and the front desk is staffed around-the-clock.
Breakfast included
Pet friendly
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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.

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Weston which includes interior views
Weston featuring food
Weston featuring a waterfall
Weston featuring signage
Weston showing food

Frequently asked questions

How much are vacation packages to Windsor County?
With vacation packages being sold from as little as $375, 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.