Search Deals onWindham County Vacation Packages
Windham County Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Shire Woodstock
Price was $1,062, price is now $913 per person
$913
per person
Nov 22 - Nov 26
found 22 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.
Winterplace at Okemo
Clock Tower Base Area
Price was $1,472, price is now $1,290 per person
$1,290
per person
Nov 22 - Nov 26
found 22 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Stay at this 4-star ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.
Solitude Village at Okemo
Clock Tower Base Area
Price was $1,330, price is now $1,179 per person
$1,179
per person
Nov 22 - Nov 26
found 22 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Stay at this 4-star ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.
Woodstock Inn & Resort
Price was $1,548, price is now $1,374 per person
$1,374
per person
Nov 22 - Nov 26
found 22 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Middle Covered Bridge and Woodstock Town Hall Theatre are located nearby.
Jackson Gore Village
Jackson Gore Base Area
Price was $1,313, price is now $1,167 per person
$1,167
per person
Nov 22 - Nov 26
found 22 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Stay at this 3-star spa hotel in Ludlow. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Jackson Gore Parking are located nearby.
Killington Mountain Lodge, Tapestry Collection by Hilton
Price was $1,045, price is now $929 per person
$929
per person
Nov 22 - Nov 26
found 22 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
Stay at this 3.5-star ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
Okemo Mountain Lodging
Clock Tower Base Area
Price was $1,276, price is now $1,137 per person
$1,137
per person
Nov 22 - Nov 26
found 22 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Stay at this 3.5-star vacation home in Ludlow. Enjoy free parking, daily housekeeping, and laundry facilities. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
3-4 Night Vacations in Windham County
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Windham County
Mountaineer Inn
270 Handle Rd, West Dover, VT
Stay at this motel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
The Covered Bridge Inn
1043 Putney Road, Brattleboro, VT
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Econo Lodge Brattleboro
515 Canal St, Brattleboro, VT
Stay at this motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Vermont Marketplace and Estey Organ Museum are located ...
Save an average of 15% on thousands of hotels when you're signed in
Latchis Hotel
50 Main Street, Brattleboro, VT
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Colonial Motel And Spa
889 Putney Rd, Brattleboro, VT
Stay at this 3-star spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ...
Comfort Inn & Suites Brattleboro I-91
1186 Putney Road, Brattleboro, VT
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Mount Snow Grand Summit Resort
89 Grand Summit Way, West Dover, VT
Stay at this 3-star spa resort in West Dover. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Mount Snow and Ego Alley Ski Lift are ...
Travelodge by Wyndham Brattleboro VT
1254 Putney Rd, Brattleboro, VT
Stay at this motel in Brattleboro. Enjoy free WiFi, free parking, and room service. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl ...
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.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sun, Dec 7 - Wed, Dec 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$299 Roundtrip, found 5 hours ago
$299
Roundtrip
found 5 hours ago
Sun, Dec 7 - Wed, Dec 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$304 Roundtrip, found 5 hours ago
$304
Roundtrip
found 5 hours ago
Thu, Dec 4 - Mon, Dec 8
LGA
LaGuardia
RUT
Rutland Southern Vermont Regional
$320 Roundtrip, found 5 hours ago
$320
Roundtrip
found 5 hours ago
Sun, Dec 7 - Mon, Dec 8
EWR
Newark Liberty Intl. Airport
RUT
Rutland Southern Vermont Regional
$344 Roundtrip, found 5 hours ago
$344
Roundtrip
found 5 hours ago
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