Windsor Vacations from $739
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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.
The Vesper
Price was $859, price is now $739 per person
$739
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
9.2/10 Wonderful! (44 reviews)
The Vesper was a great find in Woodstock VT. Close to downtown to walk to everything. Rooms are spotless and charming. We would definitely stay at the Vesper BnB again.
Reviewed on Nov 9, 2025
The Shire Woodstock
Save 100% on your flight
Price was $2,137, price is now $1,558 per person
$1,558
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
8.8/10 Excellent! (881 reviews)
After reading reviews I was pleasantly surprised of the high quality of our room. We had a premium king room in the river house. Was large and bathroom was also large with a jacuzzi tub, shared balcony overlooking the river. Walking distance to town, shops and restaurants. Only stayed one night for a wedding in town but overall had a very good experience!
Reviewed on Dec 7, 2025
Jackson Gore Village
Jackson Gore Base Area
Save 100% on your flight
Price was $2,091, price is now $1,684 per person
$1,684
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
8.6/10 Excellent! (834 reviews)
Very clean, everyone was so nice. Food at restaurant is a little pricey but was very good.
Reviewed on Nov 30, 2025
Okemo Mountain Lodging
Clock Tower Base Area
Save 100% on your flight
Price was $3,678, price is now $3,018 per person
$3,018
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) 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
Mountain Lodge at Okemo
Clock Tower Base Area
Price was $1,857, price is now $1,555 per person
$1,555
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
8/10 Very Good! (219 reviews)
We really enjoyed our stay at the Mountain Lodge at Okemo, it was clean and our room was newly renovated and very cute. Would definitely recommend!!
Reviewed on Oct 6, 2025
Discover the most popular places to visit in Windsor
American Precision Museum
You can spend time exploring the galleries in American Precision Museum 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.
Paradise Park
4/5(4 reviews)
Explore the great outdoors at Paradise Park, a lovely green space in Windsor. Wander the riverfront in this quaint area.
Windsor Hotel Deals
White River Inn and Suites
91 Ballardvale Drive White River Junction VT
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $133 total per night from Jan 4 to Jan 5
$133 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
6.8/10 (1,002 reviews)
It was good.
Reviewed on Dec 6, 2025
Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd Killington VT
$188 nightly
The price is $206 total per night from Dec 14 to Dec 15
$206 total
Dec 14 - Dec 15
Total with taxes and fees
7.2/10 Good! (1,002 reviews)
Clean room and bathroom. Alex at the desk was very helpful and nice.
Reviewed on Dec 5, 2025
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$379 nightly
The price is $417 total per night from Dec 16 to Dec 17
$417 total
Dec 16 - Dec 17
Total with taxes and fees
9.2/10 Wonderful! (552 reviews)
Top notch service. Great property and beautiful room. Went for anniversary and it did not disappoint. Romantic hotel and town
Reviewed on Nov 26, 2025
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.
