Windsor County Vacations & Trips from $348
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Your Windsor County Vacation
With a Windsor County vacation package, you can forget about planning hassles and instead focus on experiencing everything this exciting destination has on offer. Begin your trip to Windsor County with some time exploring Ludlow visiting popular sights like Weston Playhouse and Lake Rescue. Norwich is another top city that lures crowds from near and far. Quechee Gorge Bridge and Quechee Gorge Village are two of the leading places to see in this destination. From the instant you book your Windsor County vacation to the second you come back home, Expedia will take care of you each step of the way.
Top destinations in Windsor County
Ludlow
The Latest Windsor County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Price was $428, price is now $348 per person
$348
per person
Jan 9 - Jan 11
found 24 hours ago
Roundtrip flight included
Washington (DCA) to Rutland (RUT)
9/10 Wonderful! (774 reviews)
Very welcoming, spacious, clean.
Perfect for a family of 4.
Reviewed on Nov 18, 2025
Jackson Gore Village
Jackson Gore Base Area
Save 100% on your flight
Price was $1,856, price is now $1,444 per person
$1,444
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip flight included
Wilmington (ILM) 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
The Quechee Inn at Marshland Farm
Save 100% on your flight
Price was $850, price is now $671 per person
$671
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
9/10 Wonderful! (1,000 reviews)
Beautiful Inn. Pretty, clean and well maintained. Close to Woodstock. Vt and shops. Highly recommend
Reviewed on Sep 30, 2025
Solitude Village at Okemo
Clock Tower Base Area
Save 100% on your flight
Price was $13,037, price is now $10,404 per person
$10,404
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip flight included
Wilmington (ILM) to Springfield (VSF)
8/10 Very Good! (31 reviews)
Our room was really nice! It was the bathrooms the reason why we didn't rate this place better. We did let the front desk know
Both bathrooms had mold in the showers. One person in our party is extremely allergic to mold. I myself could clean the mold off, which I did partially. The dishwasher had dirty dishes in also.
Reviewed on Oct 8, 2025
Econo Lodge Brattleboro
Price was $543, price is now $440 per person
$440
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Springfield (VSF)
5.4/10 (591 reviews)
Lobby small but nice, staff good. First room was not made up. 2nd room smelled bad, musty. 3rd room tolerable. REALLY needs an upgrade to the walls, doors, etc. drywall chipped, door not fitting well (cracks), curtain barely covers window.
Sinks, toilet and shower were newer, nice. Bed was fine, comfy, looked clean. Nice to have Burger King and Circle K across street. All in all, what do you expect for $60. I would probably not stay here again, but it was OK for 1 night.
Reviewed on Nov 22, 2025
Find the Best Windsor County Vacation Packages
Windsor County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Rutland Southern Vermont Regional Airport (RUT) |
Top Sights | Buttermilk Falls, Echo Lake and Lake Rescue |
Windsor County Hotel Deals
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
Align Inn Vermont
5817 Woodstock Rd Quechee VT
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $138 total per night from Jan 7 to Jan 8
$138 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
9.2/10 Wonderful! (1,039 reviews)
The most beautiful scenic views!
Reviewed on Nov 30, 2025
The Shire Woodstock
46 Pleasant St. Woodstock VT
Fully refundableReserve now, pay when you stay
$171 nightly
The price is $188 total per night from Dec 17 to Dec 18
$188 total
Dec 17 - Dec 18
Total with taxes and fees
8.6/10 Excellent! (885 reviews)
Wonderful place to stay!
Reviewed on Dec 3, 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.
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