Book Exclusive Windsor County Vacation Packages

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Search vacation packages deals in Windsor County's top destinations

Woodstock

Vacations
Woodstock
aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

Chester

Vacations
Chester

Top Windsor County hotels deals

Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
The price is CA $160 per night
CA $160
CA $176 total
May 31 - Jun 1
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 $566 per night
CA $566
CA $684 total
May 31 - Jun 1
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
Hotel Coolidge

Hotel Coolidge

3 out of 5
39 South Main Street White River Junction VT
Free cancellation
The price is CA $146 per night
CA $146
CA $161 total
May 31 - Jun 1
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 Briggs Opera House and Barrette Center for the Arts are located nearby.
Pet-friendly
Parking included
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Free cancellation
Reserve now, pay when you stay
The price is CA $213 per night
CA $213
CA $254 total
Jun 21 - Jun 22
includes taxes & fees
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.
Pet-friendly
Parking included
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
The price is CA $245 per night
CA $245
CA $321 total
Jun 17 - Jun 18
includes taxes & fees
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and a fitness center. 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
The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

3 out of 5
1119 Quechee Main Street Quechee VT
The price is CA $235 per night
CA $235
CA $258 total
Jun 3 - Jun 4
includes taxes & fees
Book a stay at this golf hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Wilderness Trails and Vermont Institiute of Natural Science are located nearby.
Breakfast included
Parking included
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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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Frequently asked questions

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