Windsor Vacations from $570
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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 $771, price is now $570 per person
$570
per person
May 21 - May 25
found 3 hours ago
Roundtrip flight included
New York (NYC) to Springfield (VSF)
8.6/10 Excellent! (860 reviews)
If you love retro/vintage/history/ quiet and pet friendly this place is wonderful for a short stay and lowkey weekend. So many cool local businesses and delicious food. We went for a show at the stone church- walking distance from hotel! And everything we could have needed was easily accessible. They have a bar downstairs and a movie theatre in the hotel! All rooms have record players and vinyls to play with more available. Big rooms. “Dated” but it’s keeping with the retro style- very clean and neat. Only negatives were the parking lot (really small but we got a spot! There’s plenty of on street parking and a nearby parking garage as well). Staff was so friendly and helpful!
This would be a great “staycation” or mom night away as well. Stop at some of the amazing thrift/vintage/2nd hand stores for books, music, clothes and more. If you’re a crafter, Bobbins’and Skeins and Beadnik are great places to take a look at. I’d definitely come back!
Reviewed on Mar 30, 2026
Woodstock Inn & Resort
Price was $1,160, price is now $956 per person
$956
per person
May 15 - May 18
found 1 hour ago
Roundtrip flight included
Detroit (DTW) to Springfield (VSF)
9.2/10 Wonderful! (570 reviews)
Always an Amazing time when we stay here. Property well maintained, staff is super friendly and the food here is above and beyond. Did I mention I got married here 👍👍
Reviewed on Apr 5, 2026
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
Price was $735, price is now $622 per person
$622
per person
May 15 - May 18
found 1 hour ago
Roundtrip flight included
Detroit (DTW) to Springfield (VSF)
8.6/10 Excellent! (851 reviews)
No inflatable mattress offered anymore.
Reviewed on Mar 18, 2026
Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
Price was $788, price is now $673 per person
$673
per person
May 15 - May 18
found 1 hour ago
Roundtrip flight included
Detroit (DTW) to Springfield (VSF)
7.8/10 Good! (28 reviews)
Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June.
Reviewed on Jun 26, 2025
Discover the most popular places to visit in Windsor
Paradise Park
Explore the great outdoors at Paradise Park, a lovely green space in Windsor. Wander the riverfront in this quaint area.
Brownsville Trail
You can take time to visit Brownsville Trail during your travels to Windsor. Discover the mountain views in this family-friendly area, or seek out the ski slopes.
American Precision Museum
You can spend time exploring the galleries in American Precision Museum in Windsor. Wander the riverfront in this quaint area.
Windsor Hotel Deals
Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $143 total per night from Apr 17 to Apr 18
$143 total
Apr 17 - Apr 18
Total with taxes and fees
7.4/10 Good! (1,006 reviews)
it was good
Reviewed on Apr 8, 2026
White River Inn and Suites
91 Ballardvale Drive White River Junction VT
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $149 total per night from May 3 to May 4
$149 total
May 3 - May 4
Total with taxes and fees
7/10 Good! (1,001 reviews)
Great stay.
Reviewed on Apr 11, 2026
Fireside Inn & Suites West Lebanon
25 Airport Road West Lebanon NH
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $149 total per night from May 3 to May 4
$149 total
May 3 - May 4
Total with taxes and fees
8.2/10 Very Good! (1,004 reviews)
I genuinely enjoyed my stay from the beautiful atrium with a koi pond to enjoy a cocktail or your complimentary buffet breakfast. The indoor pool & hot tub was very pleasant. There is also a massage chair free to use. Its very conveniently located just off the highway & surrounded by anything you ...
Reviewed on Apr 8, 2026
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 |
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Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
