Search Deals on
Windham County Vacation Packages

Windham County Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $1,470, price is now $1,235 per person
$1,235
per person
Feb 12 - Feb 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 helpful staff and the clean rooms in our reviews. Popular attractions Green Mountain Shopping Plaza and Spartan Arena are located nearby.
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $3,491, price is now $2,732 per person
$2,732
per person
Feb 12 - Feb 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $3,106, price is now $2,464 per person
$2,464
per person
Feb 12 - Feb 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
Price was $1,456, price is now $1,253 per person
$1,253
per person
Feb 12 - Feb 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Price was $4,701, price is now $4,061 per person
$4,061
per person
Feb 12 - Feb 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 Pico Mountain at Killington Ski Resort are located nearby.
Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Clock Tower Base Area
Price was $16,831, price is now $15,001 per person
$15,001
per person
Feb 12 - Feb 17
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Springfield (VSF)
Book a stay at this 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

Okemo Mountain Lodging

3.5 out of 5
Clock Tower Base Area
Price was $6,124, price is now $5,491 per person
$5,491
per person
Feb 12 - Feb 17
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Springfield (VSF)
Stay at this vacation home in Ludlow. Enjoy free parking, daily housekeeping, and laundry facilities. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Jackson Gore Village

Jackson Gore Village

3 out of 5
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 2 hours 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.

3-4 Night Vacations in Windham County

Price found within the past 48 hours. Click for updated prices.
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $1,208, price is now $942 per person
$942
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,219, price is now $1,002 per person
$1,002
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Okemo Mountain Lodging

Okemo Mountain Lodging

3.5 out of 5
Clock Tower Base Area
Save 100% on your flight
Price was $1,963, price is now $1,624 per person
$1,624
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Save 100% on your flight
Price was $1,822, price is now $1,511 per person
$1,511
per person
Feb 13 - Feb 16
found 1 hour ago
Roundtrip flight included
New York (NYC) to Springfield (VSF)

5-7 Night Vacations in Windham County

Price found within the past 48 hours. Click for updated prices.
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was $1,255, price is now $1,021 per person
$1,021
per person
Feb 12 - Feb 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Rutland (RUT)
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $4,604, price is now $3,532 per person
$3,532
per person
Feb 12 - Feb 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Springfield (VSF)
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $3,491, price is now $2,732 per person
$2,732
per person
Feb 12 - Feb 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Rutland (RUT)
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $3,106, price is now $2,464 per person
$2,464
per person
Feb 12 - Feb 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Rutland (RUT)

Cheap Hotel Deals in Windham County

The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
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 ...
Opens in a new windowThe Covered Bridge Inn
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
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 ...
Opens in a new windowMount Snow Grand Summit Resort
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

3 out of 5
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 ...
Opens in a new windowThe Black Bear Lodge at Stratton Mountain Resort
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
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. ...
Opens in a new windowComfort Inn & Suites Brattleboro I-91
The Putney Inn

The Putney Inn

2.5 out of 5
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 ...
Opens in a new windowThe Putney Inn
Latchis Hotel

Latchis Hotel

2.5 out of 5
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. ...
Opens in a new windowLatchis Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
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 ...
Opens in a new windowHampton Inn Brattleboro
Econo Lodge Brattleboro

Econo Lodge Brattleboro

2 out of 5
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 ...
Opens in a new windowEcono Lodge Brattleboro
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.

JetBlue Airways
Sat, Feb 7 - Sun, Feb 15
JFK
John F. Kennedy Intl.
LEB
Lebanon Municipal
$269 Roundtrip, found 4 days ago
$269
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Sat, Feb 7 from John F. Kennedy Intl. to Lebanon Municipal, returning Sun, Feb 15, priced at $269 found 4 days ago
JetBlue Airways
Sun, Feb 1 - Tue, Feb 3
JFK
John F. Kennedy Intl.
LEB
Lebanon Municipal
$275 Roundtrip, found 13 hours ago
$275
Roundtrip
found 13 hours ago
Select JetBlue Airways flight, departing Sun, Feb 1 from John F. Kennedy Intl. to Lebanon Municipal, returning Tue, Feb 3, priced at $275 found 13 hours ago
American Airlines
Mon, Feb 9 - Mon, Feb 9
LGA
LaGuardia
LEB
Lebanon Municipal
$291 Roundtrip, found 23 hours ago
$291
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Mon, Feb 9 from LaGuardia to Lebanon Municipal, returning Mon, Feb 9, priced at $291 found 23 hours ago
Delta
Mon, Feb 9 - Tue, Feb 10
EWR
Newark Liberty Intl. Airport
LEB
Lebanon Municipal
$307 Roundtrip, found 1 day ago
$307
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Feb 9 from Newark Liberty Intl. Airport to Lebanon Municipal, returning Tue, Feb 10, priced at $307 found 1 day ago