Search Deals onGilboa Vacation Packages
Gilboa Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Windham NY Escape
Price was $890, price is now $797 per person
$797
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
Stay at this cabin in Hensonville. Enjoy free WiFi, free parking, and an in-room coffeemaker. Popular attractions Windham Country Club and Windham Mountain Resort are located nearby.
The best
Reviewed on Oct 6, 2025
Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain
Save 100% on your flight
Price was $6,130, price is now $4,762 per person
$4,762
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
Stay at this cottage in Hensonville. Enjoy free parking and air conditioning. Popular attractions Hunter Mountain and Windham Mountain Resort 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 $6,142, price is now $4,775 per person
$4,775
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
Stay at this cottage in Hensonville. Enjoy free parking, volleyball on site, and a pool table. Popular attractions Hunter Mountain and Windham Mountain Resort are located nearby.
Wylder Hotel Windham
Price was $1,378, price is now $1,214 per person
$1,214
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Hudson (HCC)
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Country Club and Windham Mountain Resort are located nearby.
Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort
Price was $3,365, price is now $3,061 per person
$3,061
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Hudson (HCC)
Stay at this chalet in Windham. Enjoy free WiFi, free parking, and a sauna. Popular attractions Windham Country Club and Windham Mountain Resort are located nearby.
The Haüs Windham
Price was $1,075, price is now $983 per person
$983
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Windham Country Club and Windham Mountain Resort are located nearby.
Firstly I would like to say communication with the staff is extremely difficult. Constantly having to call multiple times to get to someone. For example, the code given for room wasn’t correct and communication took forever. There was no toiletries whatsoever and since communication was so hard it forced us to buy our own paper towels, towels, rags, etc. The property was nice but it was clear no housekeeping had been in there before we came. The nature was probably the only thing that made up for all the inconveniences.
Reviewed on Aug 13, 2026
Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House
Price was $2,381, price is now $2,338 per person
$2,338
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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 Country Club and Windham Vineyards and Winery are located nearby.
Gilboa Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain
Save 100% on your flight
Price was $6,142, price is now $4,775 per person
$4,775
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
Discover Other Travel Deals
- Hubbard Hill Vacations
- Hunter Mountain Vacations
- Kaaterskill Falls Vacations
- Windham Mountain Resort Vacations
- Howe Caverns Vacations
- Catskill State Park Vacations
- Belleayre Mountain Ski Center Vacations
- North-South Lake Campground & Day Use Area Vacations
- SUNY Cobleskill Vacations
- Esopus Creek Vacations
- Hobart Book 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
