Search Deals onRoxbury Vacation Packages
Roxbury Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Vienna
Price was $1,013, price is now $784 per person
$784
per person
Dec 24 - Dec 29
found 2 hours ago
Roundtrip flight included
Chicago (CHI) 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.
Clean room and helpful staff, good location.
Reviewed on Oct 15, 2026
Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain
Save 100% on your flight
Price was $11,554, price is now $7,857 per person
$7,857
per person
Dec 24 - Dec 29
found 2 hours ago
Roundtrip flight included
Chicago (CHI) 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 $11,567, price is now $7,869 per person
$7,869
per person
Dec 24 - Dec 29
found 2 hours ago
Roundtrip flight included
Chicago (CHI) 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.
Wylder Hotel Windham
Save 100% on your flight
Price was $1,308, price is now $984 per person
$984
per person
Dec 24 - Dec 29
found 2 hours ago
Roundtrip flight included
Chicago (CHI) 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 $2,994, price is now $2,405 per person
$2,405
per person
Dec 24 - Dec 29
found 2 hours ago
Roundtrip flight included
Chicago (CHI) 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 $1,369, price is now $1,284 per person
$1,284
per person
Nov 16 - Nov 20
found 9 hours ago
Roundtrip non-stop flight included
Houston (IAH) 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
Eastwind Windham
Price was $1,035, price is now $977 per person
$977
per person
Nov 16 - Nov 20
found 9 hours ago
Roundtrip non-stop flight included
Houston (IAH) 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
Roxbury 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 $4,015, price is now $3,351 per person
$3,351
per person
Nov 16 - Nov 20
found 9 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Hudson (HCC)
Roxbury Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Thu, Dec 3 - Sun, Dec 6
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$100 Roundtrip, found 3 days ago
$100
Roundtrip
found 3 days ago
Thu, Jan 21 - Sun, Jan 24
PIE
St. Petersburg-Clearwater Intl.
SWF
Stewart Intl.
$132 Roundtrip, found 2 days ago
$132
Roundtrip
found 2 days ago
Sun, Oct 25 - Sun, Nov 1
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$182 Roundtrip, found 2 hours ago
$182
Roundtrip
found 2 hours ago
Sat, Oct 31 - Fri, Nov 13
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$289 Roundtrip, found 21 hours ago
$289
Roundtrip
found 21 hours ago
Discover Other Travel Deals
- Plattekill Mountain Vacations
- Hunter Mountain Vacations
- Windham Mountain Resort Vacations
- Belleayre Mountain Ski Center Vacations
- Catskill State Park Vacations
- Hobart Book Village Vacations
- Windham Country Club Vacations
- Belleayre Beach Vacations
- Esopus Creek Vacations
- West Branch Delaware River Vacations
- Vroman's Nose Trailhead 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
