Search Deals onRoxbury Vacation Packages
Roxbury Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Eastwind Windham
Price was $810, price is now $735 per person
$735
per person
Jan 10 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) 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.
Loved the stay here as well as the friendly staff. Jamie who had helped us check in was very friendly, helpful and made us feel welcome. Location was very dog friendly. Our room was very clean, quiet and had a beautiful scene of nature. Nice place to choose for a quiet get away stay.
Reviewed on Oct 20, 2026

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain
Save 100% on your flight
Price was $3,028, price is now $2,252 per person
$2,252
per person
Jan 10 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) 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 $1,171, price is now $918 per person
$918
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Chicago (MDW) 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.
This was the perfect end to my trip. I was traveling for work and mentioned to the staff that I really needed quiet to rest up to continue on my journey. They gave me the perfect room, quiet, and I slept like a baby! They went above and beyond to help me and I appreciate it so very much. Was bummed I didn’t have time to try out the sauna and heated pool but next time for sure! I did however try the Windham path which was lovely to start the morning. 10/10 will be back!
Reviewed on Nov 5, 2026

Hotel Vienna
Price was $1,024, price is now $817 per person
$817
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Chicago (MDW) 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.
Great staff
Reviewed on Nov 4, 2026

Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort
Price was $1,883, price is now $1,588 per person
$1,588
per person
Jan 10 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) 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.

The Haüs Windham
Price was $2,511, price is now $2,142 per person
$2,142
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Chicago (MDW) 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.
This stay was disappointing. The owners seem to be trying, but so many things were wrong that we wished we had stayed elsewhere.
The good: Great location for exploring the Catskills, especially in Fall, and convenient for skiing. Our Franklin Suite was spacious, beds comfortable, bathrooms remodeled, Wi-Fi good, and gym nice. Staff responded promptly to complaints.
The bad: Check-in required uploading photos and credit card information through a separate link despite booking through Hotels.com. With no front desk, finding our suite was difficult. Two junker cars blocked the signage and belonged to staff, who started them at 6:30 a.m. outside our window. One apparently had no muffler!
The room was more run-down than the photos suggested, with deferred maintenance, a hole in the ceiling from a previous leak, and sliding doors nearly impossible to open.
The “fully stocked kitchen” had one wine glass, two forks, dirty dishes, lipstick-stained glasses, and few supplies. No ice trays; we were told to buy ice. The dining table seated only four, although the suite sleeps six or more. Cleanliness was mediocre, with crumbs, dead bugs, and dirty dishes left behind. Even facial tissues were missing.
Bottom line: Staff were responsive, but cleanliness, maintenance, and attention to detail fell short. This might suit a group of guys on a casual ski weekend, but for a romantic Catskills getaway, we’d look elsewhere. Albergo Alegria or Wylder Windham, both nearby, looked much better.
Reviewed on Oct 24, 2026

Windham NY Escape
Price was $1,284, price is now $1,106 per person
$1,106
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Chicago (MDW) 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.
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 $3,028, price is now $2,252 per person
$2,252
per person
Jan 10 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) 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.
$110 Roundtrip, found 3 days ago
$110
Roundtrip
found 3 days ago

Thu, Jan 21 - Sun, Jan 24
PIE
St. Petersburg-Clearwater Intl.
SWF
Stewart Intl.
$132 Roundtrip, found 6 days ago
$132
Roundtrip
found 6 days ago

Mon, Dec 7 - Fri, Dec 18
PIE
St. Petersburg-Clearwater Intl.
ALB
Albany Intl.
$213 Roundtrip, found 3 days ago
$213
Roundtrip
found 3 days ago

Fri, Jan 15 - Sun, Jan 17
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Discover Other Travel Deals
- Plattekill Mountain Vacations
- Hunter Mountain Vacations
- Belleayre Mountain Ski Center Vacations
- Windham Mountain Resort Vacations
- Catskill State Park Vacations
- Hobart Book Village Vacations
- Windham Country Club Vacations
- Belleayre Beach Vacations
- West Branch Delaware River Vacations
- Esopus Creek Vacations
- Giant Ledge Trailhead 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


