Vacations Close To Windham Vineyards and Winery

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Windham Vineyards and Winery Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hotel Vienna

Hotel Vienna

3 out of 5
Price was $644, price is now $539 per person
$539
per person
Sep 7 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Hudson (HCC)
Fresh croissants for breakfast

Reviewed on Aug 6, 2026

Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $1,149, price is now $903 per person
$903
per person
Sep 7 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Hudson (HCC)
It is so clear to me that the staff here has a strong team culture and loves what they do, every single person was kind, helpful, enthusiastic and wanted to ensure we had a wonderful time. The entire vibe of the hotel was perfect in balance; easy activity to entertain younger ones but a very chill vibe for adults. Cannot wait to come back!

Reviewed on Aug 8, 2026

Eastwind Windham

Eastwind Windham

3.5 out of 5
Price was $913, price is now $847 per person
$847
per person
Sep 7 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Hudson (HCC)

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Best Lodging Options Near Windham Vineyards and Winery

Catskills Mountain Home Near Windham w/ Fireplace & Open Living Deer Run Lodge by Avantstay

Catskills Mountain Home Near Windham w/ Fireplace & Open Living Deer Run Lodge by Avantstay

3 out of 5
Prattsville NY
2.92 km from Windham Vineyards and Winery
Stay at this cottage in Prattsville. Enjoy free parking, patios, and in-room washers/dryers. Popular attractions Windham Mountain Resort and Ashland Park are ...
Cave Mountain Motel

Cave Mountain Motel

2.5 out of 5
10978 STATE RTE 23 Windham NY
3.79 km from Windham Vineyards and Winery
Stay at this motel in Windham. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Windham Mountain Resort and Windham Vineyards and Winery ...
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.