Search Deals onWindham County Vacation Packages
Windham County Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Cortina Inn
Price was $704, price is now $675 per person
$675
per person
May 21 - May 25
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Book a stay at this business-friendly hotel in Rutland. Enjoy free WiFi, free parking, and a free airport shuttle. Popular attractions Green Mountain Shopping Plaza and Spartan Arena are located nearby.
Comfort Inn Rutland - Killington
Price was $855, price is now $770 per person
$770
per person
May 21 - May 25
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Vermont State Fairgrounds and Green Mountain Shopping Plaza are located nearby.
The Vermont Inn
Price was $846, price is now $800 per person
$800
per person
May 21 - May 25
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Book a stay at this family-friendly B&B in Rutland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Killington Resort and Golden Express Quad are located nearby.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Price was $957, price is now $910 per person
$910
per person
May 21 - May 25
found 22 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Book a stay at this ski cabin in Killington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Killington Resort and Skyeship Express Gondola Stage I are located nearby.
Best Western Inn & Suites Rutland-Killington
Price was $925, price is now $921 per person
$921
per person
May 21 - May 25
found 22 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Stay at this hotel in Rutland. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Green Mountain Rock Climbing Center and Hathaway Farm are located nearby.
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
Save 100% on your flight
Price was $3,942, price is now $3,416 per person
$3,416
per person
Jun 5 - Jun 10
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Book a stay at this golf castle in Bolton Landing. Enjoy free WiFi, free parking, and furnished balconies or patios. Popular attractions Veterans Memorial Park Beach and Adirondack Extreme Adventure Course 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
Colonial Motel And Spa
889 Putney Rd Brattleboro VT
Book a stay at this 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 ...
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 ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
Hideaway Inn Mt. Snow
270 Handle Rd West Dover VT
Book a stay at this ski hotel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and Heavy Metal Ski Lift are ...
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. ...
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. ...
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 South
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, Apr 25 - Sun, May 3
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$156 Roundtrip, found 7 hours ago
$156
Roundtrip
found 7 hours ago
Sat, May 30 - Tue, Jun 2
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$163 Roundtrip, found 22 hours ago
$163
Roundtrip
found 22 hours ago
Tue, Apr 21 - Tue, Apr 28
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$167 Roundtrip, found 7 hours ago
$167
Roundtrip
found 7 hours ago
Sat, May 23 - Wed, Jun 17
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 8 hours ago
$180
Roundtrip
found 8 hours ago
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