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Round Top Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Wylder Hotel Windham
Price was $776, price is now $657 per person
$657
per person
Nov 14 - Nov 17
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Hudson (HCC)
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Eastwind Windham
Price was $746, price is now $685 per person
$685
per person
Nov 14 - Nov 17
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Hudson (HCC)
Book a stay at this golf hotel in Windham. Enjoy free WiFi, free parking, and 2 bars/lounges. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
The restaurant was out of most dishes, not many other options. It’s ran by a small group of individuals so it’s hard to get a hold of people. Overall, the day was okay.
Reviewed on Oct 6, 2026
The Haüs Windham
Price was $739, price is now $695 per person
$695
per person
Nov 14 - Nov 17
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Hudson (HCC)
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Just go to this location
Reviewed on Oct 14, 2026
Windham NY Escape
Price was $920, price is now $868 per person
$868
per person
Nov 14 - Nov 17
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Hudson (HCC)
Stay at this cabin in Hensonville. Enjoy free WiFi, free parking, and an in-room coffeemaker. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
The best
Reviewed on Oct 6, 2025
Round Top Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
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