Search Deals onWindham County Vacation Packages
Windham County Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Vesper
Price was $1,071, price is now $981 per person
$981
per person
Nov 27 - Dec 1
found 5 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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.
The Shire Woodstock
Price was $1,197, price is now $1,011 per person
$1,011
per person
Nov 27 - Dec 1
found 5 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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.
North Star Lodge and Resort
Price was $1,105, price is now $1,010 per person
$1,010
per person
Nov 27 - Dec 1
found 5 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 Killington School for Tennis are located nearby.
Winterplace at Okemo
Clock Tower Base Area
Price was $1,393, price is now $1,277 per person
$1,277
per person
Nov 27 - Dec 1
found 5 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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 $1,256, price is now $1,160 per person
$1,160
per person
Nov 27 - Dec 1
found 5 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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 $1,200, price is now $1,111 per person
$1,111
per person
Nov 27 - Dec 1
found 5 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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 $1,139, price is now $1,059 per person
$1,059
per person
Nov 27 - Dec 1
found 5 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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 $1,237, price is now $1,151 per person
$1,151
per person
Nov 27 - Dec 1
found 5 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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 1 day ago
$299
Roundtrip
found 1 day ago
Sun, Dec 7 - Wed, Dec 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$304 Roundtrip, found 1 day ago
$304
Roundtrip
found 1 day ago
Thu, Dec 4 - Mon, Dec 8
LGA
LaGuardia
RUT
Rutland Southern Vermont Regional
$320 Roundtrip, found 2 hours ago
$320
Roundtrip
found 2 hours ago
Sun, Dec 7 - Mon, Dec 8
EWR
Newark Liberty Intl. Airport
RUT
Rutland Southern Vermont Regional
$344 Roundtrip, found 22 hours ago
$344
Roundtrip
found 22 hours ago
Discover Other Travel Deals
- Brattleboro Vacations
- West Dover Vacations
- Stratton Vacations
- Londonderry Vacations
- Putney Vacations
- Jamaica Vacations
- Grafton Vacations
- Newfane Vacations
- Bellows Falls Vacations
- Wardsboro Vacations
- West Wardsboro Vacations
- Whitingham Vacations
- South Londonderry Vacations
- West Townshend Vacations
- Jacksonville Vacations
- East Dover Vacations
