
Windsor Vacations from $517
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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 $623, price is now $517 per person
$517
per person
Sep 25 - Sep 27
found 13 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
8.6/10 Excellent! (915 reviews)
Great hotel at the best location for seeing this great town without having to drive or park. Easy walk from train station
Reviewed on Jul 17, 2026

The Shire Woodstock
Price was $2,161, price is now $1,645 per person
$1,645
per person
Sep 21 - Sep 25
found 8 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
8.8/10 Excellent! (954 reviews)
Very nice property. Would be great to have coffee in the rooms. Also very limited hot water. Ran out a few times even after a quick shower.
Reviewed on Jul 12, 2026

Vikings Villages Resort
Price was $705, price is now $540 per person
$540
per person
Sep 25 - Sep 27
found 13 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
10/10 Exceptional! (200 reviews)
Beautiful place, extraordinary, Christina was so kind and accommodating.
Reviewed on Jul 15, 2026

Deer Brook Inn
Price was $841, price is now $735 per person
$735
per person
Sep 25 - Sep 27
found 13 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
10/10 Exceptional! (2 reviews)
Our stay at the Deer Brook Inn was wonderful!
From the moment we arrived and met Carmen and her family, we felt welcomed and very much at home. Our upstairs room was cozy and comfortable. The decor of the entire home is inviting and relaxed.
Carmen's breakfasts are delicious and presented with great care.
In addition to being a gifted cook, she is a natural as Innkeeper. Warm, gracious, attentive and interesting - an absolute delight! Meeting and spending time her was without a doubt one of the best parts of our trip. We would positively stay at Deer Brook Inn again and again.
Reviewed on Jul 13, 2026

Sinclair Inn Bed and Breakfast
Price was $891, price is now $780 per person
$780
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Springfield (VSF)
10/10 Exceptional! (114 reviews)
Holy and Kyle were awesome! Such wonderful breakfasts each day we were there, delicious! So close to everything we wanted to see. We look forward to coming back for our next Vermont getaway!
Reviewed on Jun 19, 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
$141 nightly
The price is $153 total per night from Jul 19 to Jul 20
$153 total
Jul 19 - Jul 20
Total with taxes and fees
8.4/10 Very Good! (1,003 reviews)
"This is a hotel we frequent often. Comfortable rooms, breakfast is ample, great staff. We’ll be back soon."
Reviewed on Jul 17, 2026

Align Inn Vermont
5817 Woodstock Rd Quechee VT
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $154 total per night from Jul 21 to Jul 22
$154 total
Jul 21 - Jul 22
Total with taxes and fees

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
9.4/10 Exceptional! (591 reviews)
"I am terribly sorry to give such a bad review. They put us in the basement they call ground level, the room smelled dank and like mold. Everything stayed wet..towels bathing suits. The people were nice. The elevator smelled like urin and puke..they charge a incidentale fee of 250 dollars a day that ..."
Reviewed on Jul 16, 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
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