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 $655, price is now $569 per person
$569
per person
Dec 16 - Dec 19
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $717, price is now $601 per person
$601
per person
Dec 16 - Dec 19
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
A private beach and a restaurant are featured at this smoke-free lodge. Enjoy the seasonal outdoor pool and perks like free self parking. There's a bar/lounge on site, and a terrace and barbecue grills are also provided.
The Mountain Top Inn & Resort

The Mountain Top Inn & Resort

3.5 out of 5
Price was $822, price is now $693 per person
$693
per person
Nov 3 - Nov 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
This resort features a private beach, ski-in/ski-out access, and a restaurant. Enjoy a day at the beach kayaking, or relax with sun loungers. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.
Green Trails Inn

Green Trails Inn

3 out of 5
Price was $673, price is now $585 per person
$585
per person
Dec 16 - Dec 19
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Lebanon (LEB)
A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A coffee shop and a garden are also provided.
1846 Inn and Tavern

1846 Inn and Tavern

3 out of 5
Price was $860, price is now $754 per person
$754
per person
Dec 16 - Dec 19
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.

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 21 - Oct 22
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
$479 nightly
The price is $527 total per night
$527 total
Nov 2 - Nov 3
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
$150 nightly
The price is $165 total per night
$165 total
Nov 3 - Nov 4
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
Free Cancellation
$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
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$183 nightly
The price is $202 total per night
$202 total
Nov 1 - Nov 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
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
$174 nightly
The price is $190 total per night
$190 total
Oct 26 - Oct 27
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 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 $569, 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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