Deals on vacations and trips to Windsor County

Save when you book Windsor County, VT package deals

Choose two or more items and save on your trip:

Search vacation packages deals in Windsor County's top destinations

Ludlow showing street scenes

Ludlow

Vacations
Ludlow

Windsor County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $666, price is now $551 per person
$551
per person
Feb 2 - Feb 8
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Springfield (VSF)
Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $820, price is now $623 per person
$623
per person
Feb 2 - Feb 8
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
Price was $1,019, price is now $777 per person
$777
per person
Feb 2 - Feb 8
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Springfield (VSF)
This bed & breakfast features free WiFi in public areas, barbecue grills, and free self parking. A free bus station shuttle is offered as well. A garden, a lobby fireplace, and express check-in are also on offer.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Save 100% on your flight
Price was $2,684, price is now $2,210 per person
$2,210
per person
Feb 2 - Feb 8
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Rutland (RUT)
This cabin doesn't skimp on freebies - guests receive free WiFi and free self parking. Enjoy ski-in/ski-out access and onsite ski storage. Enjoy the sauna and conveniences like express check-out and laundry facilities.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $1,048, price is now $873 per person
$873
per person
Feb 5 - Feb 11
found 1 day ago
Roundtrip non-stop 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.

Top Windsor County hotels deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$359 nightly
The price is $395 total per night
$395 total
Jan 19 - Jan 20, 2026
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
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
Free Cancellation
Reserve now, pay when you stay
$120 nightly
The price is $132 total per night
$132 total
Jan 4 - Jan 5, 2026
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
$143 nightly
The price is $156 total per night
$156 total
Jan 8 - Jan 9, 2026
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
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Free Cancellation
Reserve now, pay when you stay
$163 nightly
The price is $179 total per night
$179 total
Jan 11 - Jan 12, 2026
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
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
$144 nightly
The price is $157 total per night
$157 total
Jan 5 - Jan 6, 2026
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
Jackson Gore Village

Jackson Gore Village

3 out of 5
111 Jackson Gore Road Ludlow VT
$378 nightly
The price is $415 total per night
$415 total
Jan 22 - Jan 23, 2026
Total with taxes and fees
Ski-in/ski-out access, 2 restaurants, and 3 hot tubs are all featured at this smoke-free hotel. There's a free ski shuttle, and ski lessons, ski passes and ski storage are available on site. Bring the family and enjoy the mini golf, playground, and arcade/game room.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Windsor County
View all properties
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

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 $551, 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.

Explore More Ways to Travel with Travelocity