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Windham County Vacation Packages

Windham County Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $619, price is now $561 per person
$561
per person
Nov 25 - Nov 29
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Springfield (VSF)
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Timber Ripper Mountain Coaster are located nearby.
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $903, price is now $806 per person
$806
per person
Nov 23 - Nov 27
found 19 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was $829, price is now $753 per person
$753
per person
Nov 25 - Nov 29
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
Book a stay at this luxury hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
The Inn at Weathersfield

The Inn at Weathersfield

4 out of 5
Price was $727, price is now $668 per person
$668
per person
Nov 25 - Nov 29
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
Stay at this inn in Perkinsville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions North Springfield Lake Recreation Area and Stoughton Pond Recreation Area are located nearby.
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $1,114, price is now $867 per person
$867
per person
Dec 10 - Dec 14
found 7 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Sweet Pond State Park and Shattuck Brook Wildlife Management Area are located nearby.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $921, price is now $781 per person
$781
per person
Nov 23 - Nov 28
found 20 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
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. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
The Landgrove

The Landgrove

3.5 out of 5
Price was $1,012, price is now $859 per person
$859
per person
Nov 23 - Nov 28
found 20 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
Book a stay at this family-friendly inn in Londonderry. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Bromley Mountain Ski Resort and Hapgood Pond are located nearby.
Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

2 out of 5
Price was $901, price is now $794 per person
$794
per person
Nov 23 - Nov 28
found 20 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
Book a stay at this golf B&B in Poultney. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Poultney Public Library and Slate Quarry Park are located nearby.

3-4 Night Vacations in Windham County

Price found within the past 48 hours. Click for updated prices.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $650, price is now $568 per person
$568
per person
Dec 10 - Dec 14
found 7 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $903, price is now $806 per person
$806
per person
Nov 23 - Nov 27
found 19 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $1,114, price is now $867 per person
$867
per person
Dec 10 - Dec 14
found 7 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
1846 Inn and Tavern

1846 Inn and Tavern

3 out of 5
Price was $953, price is now $825 per person
$825
per person
Dec 10 - Dec 14
found 7 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)

5-7 Night Vacations in Windham County

Price found within the past 48 hours. Click for updated prices.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $921, price is now $781 per person
$781
per person
Nov 23 - Nov 28
found 20 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,710, price is now $1,478 per person
$1,478
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
The Vesper

The Vesper

3 out of 5
Price was $1,336, price is now $1,230 per person
$1,230
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
The Landgrove

The Landgrove

3.5 out of 5
Price was $1,012, price is now $859 per person
$859
per person
Nov 23 - Nov 28
found 20 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)

Cheap Hotel Deals in Windham County

Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
89 Grand Summit Way West Dover VT
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and a free area shuttle. Popular attractions Mount Snow and Tumbleweed Ski ...
Opens in a new windowGrand Summit Resort, A Vail Resorts Property
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Book a stay at this business-friendly motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Opens in a new windowColonial Motel
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

3 out of 5
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 ...
Opens in a new windowHideaway Inn Mt. Snow
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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
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
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
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
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
Tue, Nov 17 - Wed, Dec 2
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$399 Roundtrip, found 15 hours ago
$399
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Tue, Nov 17 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $399 found 15 hours ago
JetBlue Airways
Tue, Nov 17 - Wed, Dec 2
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$409 Roundtrip, found 15 hours ago
$409
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Tue, Nov 17 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $409 found 15 hours ago
JetBlue Airways
Tue, Nov 17 - Wed, Dec 2
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$419 Roundtrip, found 15 hours ago
$419
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Tue, Nov 17 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $419 found 15 hours ago
JetBlue Airways
Mon, Nov 16 - Wed, Dec 2
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$440 Roundtrip, found 4 days ago
$440
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Mon, Nov 16 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $440 found 4 days ago