Search Deals onHousatonic Vacation Packages
Housatonic Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Vienna
Price was $859, price is now $809 per person
$809
per person
Oct 21 - Oct 24
found 7 hours ago
Roundtrip flight included
Orlando (MCO) 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.
Fresh croissants for breakfast
Reviewed on Aug 6, 2026
Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain
Save 100% on your flight
Price was $5,706, price is now $4,179 per person
$4,179
per person
Oct 21 - Oct 24
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
Stay at this cottage in Hensonville. Enjoy free parking and air conditioning. Popular attractions Windham Mountain Resort and Hunter Mountain are located nearby.
Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain
Save 100% on your flight
Price was $5,555, price is now $4,155 per person
$4,155
per person
Oct 21 - Oct 24
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
Stay at this cottage in Hensonville. Enjoy free parking, volleyball on site, and a pool table. Popular attractions Windham Mountain Resort and Hunter Mountain are located nearby.
The Haüs Windham
Price was $1,229, price is now $1,051 per person
$1,051
per person
Oct 21 - Oct 24
found 7 hours ago
Roundtrip flight included
Orlando (MCO) 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.
Abia mucho ruido en la noche I abian muchas moscas y solo abia 1 cobija y eramos tres
Reviewed on Jul 25, 2026
Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort
Price was $2,573, price is now $2,260 per person
$2,260
per person
Oct 21 - Oct 24
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
Stay at this chalet in Windham. Enjoy free WiFi, free parking, and a sauna. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Red Feather Lodge
Price was $2,595, price is now $2,324 per person
$2,324
per person
Oct 21 - Oct 24
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
Stay at this vacation home in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Windham NY Escape
Price was $1,178, price is now $1,083 per person
$1,083
per person
Oct 21 - Oct 24
found 7 hours ago
Roundtrip flight included
Orlando (MCO) 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
Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House
Price was $2,295, price is now $2,148 per person
$2,148
per person
Oct 21 - Oct 24
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
Book a stay at this business-friendly cottage in Windham. Enjoy free parking, balconies, and in-room washers/dryers. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Housatonic Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Discover Other Travel Deals
- Tanglewood Music Center Vacations
- Jiminy Peak Mountain Resort Vacations
- National Shrine of the Divine Mercy Vacations
- Norman Rockwell Museum Vacations
- Lee Premium Outlets Vacations
- Jacob's Pillow Vacations
- Taconic State Park Vacations
- Ski Butternut Vacations
- Lake Taghkanic State Park Vacations
- The Mount Vacations
- Catamount Ski Area Vacations
- Hancock Shaker Village 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
