Search Deals onRound Top Vacation Packages
Round Top Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Eastwind Windham
Price was $613, price is now $516 per person
$516
per person
Nov 11 - Nov 13
found 1 day ago
Roundtrip flight included
Chicago (CHI) 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
Hotel Vienna
Save 100% on your flight
Price was $1,467, price is now $995 per person
$995
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Miami (MIA) 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.
Hotel was clean, had pretty Catskills Mountains views, and fire pits, pool and sauna. Staff was helpful.
Reviewed on Oct 11, 2026
Wylder Hotel Windham
Save 100% on your flight
Price was $1,868, price is now $1,330 per person
$1,330
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Miami (MIA) 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.
The Haüs Windham
Save 100% on your flight
Price was $2,911, price is now $2,349 per person
$2,349
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Miami (MIA) 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.
Clean beautiful staff is fabulous kitchen is very well stocked for cooking. Good luck with your establishment thank you for the wonderful stay
Reviewed on Oct 7, 2026
Windham NY Escape
Price was $757, price is now $660 per person
$660
per person
Nov 11 - Nov 13
found 1 day ago
Roundtrip flight included
Chicago (CHI) 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 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Discover Other Travel Deals
- Blackhead Mountain Country Club Vacations
- Hunter Mountain Vacations
- Kaaterskill Falls Vacations
- Windham Mountain Resort Vacations
- Bard College Vacations
- Catskill State Park Vacations
- Hudson River Vacations
- Olana State Historic Site Vacations
- Ashokan Rail Trail- Woodstock Dike Trailhead Vacations
- HITS-on-the-Hudson Vacations
- North-South Lake Campground & Day Use Area Vacations
- Lake Taghkanic State Park Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
