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Windham Vacation Packages

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Windham Flight + Hotel Packages

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The Colonial Motel

The Colonial Motel

2.5 out of 5
Price was $235, price is now $215 per person
$215
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Hudson (HCC)
Stay at this motel in Grand Gorge. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Gilboa Museum and Pratt Museum are located nearby.
Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
Price was $548, price is now $487 per person
$487
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Hudson (HCC)
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions SweetHeart Gallery and Woodstock Artists Association and Museum are located nearby.
The Hidden Inn

The Hidden Inn

4 out of 5
Price was $335, price is now $301 per person
$301
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Hudson (HCC)
Stay at this inn in South Kortright. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Hobart Book Village and Plattekill Mountain are located nearby.
Shadowcrest

Shadowcrest

3.5 out of 5
Price was $291, price is now $263 per person
$263
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Hudson (HCC)
Stay at this guesthouse in Fleischmanns. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Belleayre Mountain Ski Center and Pine Hill Community Center are located nearby.
Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
Price was $384, price is now $346 per person
$346
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Hudson (HCC)
Stay at this hotel in Hunter. Enjoy free WiFi, a sauna, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Hunter Mountain and D Ski Lift are located nearby.
Hotel Vienna

Hotel Vienna

2.5 out of 5
Price was $329, price is now $298 per person
$298
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Hudson (HCC)
Book a stay at this golf hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Overlook Hotel

Overlook Hotel

2 out of 5
Price was $390, price is now $353 per person
$353
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Hudson (HCC)
Stay at this hotel in Saugerties. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Vinnie's Farm Market and HITS-on-the-Hudson are located nearby.
SunView Motel

SunView Motel

2.5 out of 5
Price was $265, price is now $250 per person
$250
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Hudson (HCC)
Book a stay at this golf motel in Tannersville. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hunter Mountain and Mountain Trails Cross Country Ski and Snowshoe Center are located nearby.