Search Deals onWindham County Vacation Packages
Windham County Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
North Star Lodge and Resort
Price was $1,094, price is now $1,042 per person
$1,042
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Rutland (RUT)
Book a stay at this family-friendly hotel in Killington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Killington Resort and Killington School for Tennis are located nearby.
The Shire Woodstock
Price was $1,201, price is now $1,082 per person
$1,082
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 $1,620, price is now $1,506 per person
$1,506
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
The Vesper
Price was $1,308, price is now $1,218 per person
$1,218
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Springfield (VSF)
Stay at this 3-star B&B in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Billings Park and Trail and Dana House Museum are located nearby.
Solitude Village at Okemo
Clock Tower Base Area
Price was $1,476, price is now $1,382 per person
$1,382
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Okemo Mountain Lodging
Clock Tower Base Area
Price was $1,421, price is now $1,334 per person
$1,334
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Mountain Lodge at Okemo
Clock Tower Base Area
Price was $1,362, price is now $1,283 per person
$1,283
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Springfield (VSF)
Stay at this 3-star ski hotel in Ludlow. Enjoy free WiFi, free parking, and a free area shuttle. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.
Jackson Gore Village
Jackson Gore Base Area
Price was $1,458, price is now $1,373 per person
$1,373
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
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 ...
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. ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
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 ...
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 19 hours ago
$299
Roundtrip
found 19 hours ago
Sun, Dec 7 - Wed, Dec 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$304 Roundtrip, found 19 hours ago
$304
Roundtrip
found 19 hours ago
Thu, Dec 4 - Mon, Dec 8
LGA
LaGuardia
RUT
Rutland Southern Vermont Regional
$320 Roundtrip, found 19 hours ago
$320
Roundtrip
found 19 hours ago
Sun, Dec 7 - Mon, Dec 8
EWR
Newark Liberty Intl. Airport
RUT
Rutland Southern Vermont Regional
$344 Roundtrip, found 13 hours ago
$344
Roundtrip
found 13 hours ago
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