Windsor Vacations from $574
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Windsor Vacation
Food, history, entertainment and more … There's so much to experience with a Windsor vacation package. And with the ability to customize your city break, you know it'll be one that's hard to forget. If sightseeing is on the agenda during your trip to Windsor, stop by leading attractions like Mount Ascutney, Blow-Me-Down Bridge and Mt Ascutney State Park. Whoever you're escaping with and whether your budget is big or small, your ultimate Windsor vacation is only clicks away with Expedia.
The Latest Windsor vacation packages
Price found within the past 48 hours. Click for updated prices.
Latchis Hotel
Price was $1,036, price is now $843 per person
$843
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Springfield (VSF)
8.6/10 Excellent! (941 reviews)
Main Street Brattleboro so great, near Restaurants and entertainment. We saw a film downstairs, LPs and are Record player in Rooms!
Reviewed on Aug 3, 2026
Grand Summit Resort, A Vail Resorts Property
Price was $949, price is now $801 per person
$801
per person
Oct 15 - Oct 20
found 2 days ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
8.6/10 Excellent! (297 reviews)
Host in restaurant let us stand at the host stand while he finished up his conversation with friends or regulars at bar until he realized to seat us. Took over 45 minutes to get a hamburger and pork slider sliders. Served to us at 9:00 pm sat at 8:10pm. Needed to hurry because they played the “Closing Time “ song 3 times in a row as they served us. Oh and we were the only couple in the dinning area. So no other orders were in the kitchen since we arrived. Felt pushed out after or order took over 45 minutes to arrive.
Reviewed on Aug 3, 2026
Stay near popular Windsor attractions
Windsor Hotel Deals
Fireside Inn & Suites West Lebanon
25 Airport Road West Lebanon NH
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $169 total per night from Sep 6 to Sep 7
$169 total
Sep 6 - Sep 7
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
"The room was roomy and clean. The hotel was super clean. The front desk staff was very helpful. The pool was excellent and the breakfast was delightful."
Reviewed on Aug 5, 2026
Align Inn Vermont
5817 Woodstock Rd Quechee VT
$138 nightly
The price is $152 total per night from Aug 10 to Aug 11
$152 total
Aug 10 - Aug 11
Total with taxes and fees
9.4/10 Exceptional! (1,277 reviews)
"Everything was clean and comfortable. Staff was enjoyable. Restaurant next door was so good and we could walk to it"
Reviewed on Aug 5, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$479 nightly
The price is $527 total per night from Aug 16 to Aug 17
$527 total
Aug 16 - Aug 17
Total with taxes and fees
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.
Find the Best Windsor Vacation Packages
Windsor Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Lebanon Municipal Airport (LEB) |
Population | 2,100 |
Max Temp Winter | 25ºF |
Max Temp Summer | 75ºF |
Top Sights | Mt Ascutney State Park, Harpoon Brewery and Quechee State Park |
More vacations you might like
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
