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 $786, price is now $619 per person
$619
per person
Feb 16 - Feb 20
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
Stay at this 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.
Mountain Green Resort
Save 100% on your flight
Price was $2,741, price is now $1,962 per person
$1,962
per person
Feb 11 - Feb 15
found 16 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Rutland (RUT)
Book a stay at this business-friendly apartment in Killington. Enjoy free WiFi, free parking, and in-room washers/dryers. Popular attractions Killington Resort and Pico Mountain at Killington Ski Resort are located nearby.
Jackson Gore Village
Jackson Gore Base Area
Save 100% on your flight
Price was $2,628, price is now $2,038 per person
$2,038
per person
Feb 16 - Feb 20
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
Book a stay at this 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.
The Suites at Killington Center
Price was $1,920, price is now $1,559 per person
$1,559
per person
Feb 11 - Feb 15
found 16 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Rutland (RUT)
Stay at this condo in Killington. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Killington Resort and Pico Mountain at Killington Ski Resort are located nearby.
The Vermont Inn
Price was $1,095, price is now $913 per person
$913
per person
Feb 11 - Feb 15
found 16 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Rutland (RUT)
Book a stay at this family-friendly B&B in Rutland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Pico Mountain at Killington Ski Resort and Killington Resort are located nearby.
Killington Mountain Lodge, Tapestry Collection by Hilton
Price was $1,506, price is now $1,258 per person
$1,258
per person
Feb 11 - Feb 15
found 16 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Rutland (RUT)
Book a stay at this 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 Pico Mountain at Killington Ski Resort are located nearby.
Mt Green 1-d09 in Killington
Price was $2,704, price is now $2,269 per person
$2,269
per person
Feb 11 - Feb 15
found 16 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Rutland (RUT)
Stay at this apartment in Killington. Enjoy free parking, a full-service spa, and a fitness center. Popular attractions Killington Resort and Pico Mountain at Killington Ski Resort are located nearby.
North Star Lodge and Resort
Price was $1,294, price is now $1,087 per person
$1,087
per person
Feb 11 - Feb 15
found 16 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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 Pico Mountain at Killington Ski Resort are located nearby.
3-4 Night Vacations in Windham County
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Windham County
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Windham County
Mount Snow Grand Summit Resort
89 Grand Summit Way West Dover VT
Book a stay at this 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 ...
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 ...
The Black Bear Lodge at Stratton Mountain Resort
5 Village Lodge Road Stratton VT
Book a stay at this ski resort in Stratton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
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. ...
The Putney Inn
57 Putney Landing Rd Putney VT
Book a stay at this business-friendly motel in Putney. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
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. ...
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
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 ...
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.
Sat, Feb 7 - Sun, Feb 15
JFK
John F. Kennedy Intl.
LEB
Lebanon Municipal
$269 Roundtrip, found 5 days ago
$269
Roundtrip
found 5 days ago
Sun, Feb 1 - Tue, Feb 3
JFK
John F. Kennedy Intl.
LEB
Lebanon Municipal
$275 Roundtrip, found 1 day ago
$275
Roundtrip
found 1 day ago
Mon, Feb 9 - Mon, Feb 9
LGA
LaGuardia
LEB
Lebanon Municipal
$291 Roundtrip, found 4 hours ago
$291
Roundtrip
found 4 hours ago
Mon, Feb 9 - Tue, Feb 10
EWR
Newark Liberty Intl. Airport
LEB
Lebanon Municipal
$307 Roundtrip, found 2 days ago
$307
Roundtrip
found 2 days ago
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