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Windham Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Wylder Hotel Windham
Price was $699, price is now $594 per person
$594
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
Room super clean and beautiful property!
Reviewed on Nov 2, 2026

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain
Price was $6,077, price is now $4,711 per person
$4,711
per person
Dec 19 - Dec 24
found 17 hours 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.

Hotel Vienna
Price was $835, price is now $649 per person
$649
per person
Jan 7 - Jan 11
found 18 hours ago
Roundtrip flight included
Nassau (NAS) 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.
Second time staying, it's a great place. Would have given it 5 stars across the board, but the sauna was being worked on and it's one of the reasons why I book the place. That was disappointing, but the rest was all good.
Reviewed on Nov 3, 2026

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain
Price was $3,203, price is now $2,554 per person
$2,554
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.

Eastwind Windham
Price was $1,078, price is now $883 per person
$883
per person
Jan 7 - Jan 11
found 18 hours ago
Roundtrip flight included
Nassau (NAS) 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

Windham NY Escape
Price was $892, price is now $814 per person
$814
per person
Dec 11 - Dec 14
found 1 day 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 Haüs Windham
Price was $1,658, price is now $1,558 per person
$1,558
per person
Dec 19 - Dec 24
found 17 hours 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 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 Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Windham Vacation Packages 5-7 Night Stays
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