Plan your trip
Check prices for these dates, December 15 – 16, 2026
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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.
Stroll through charming streets lined with historic buildings, soaking in the small-town atmosphere of this Hudson Valley gem. Explore nearby wineries and parks, or catch a show at the City Winery for a perfect blend of culture and nature.
You may be able to find reasonable rates at these Montgomery accommodations, which get positive reviews from our guests: Holiday Inn Express & Suites Montgomery by IHG - Guests can enjoy free breakfast, free WiFi, and free parking at this hotel. Super 8 by Wyndham Montgomery Maybrook - Property features at this motel include free breakfast, free WiFi, and free parking.
The weather is important when you want to venture out and explore, so here's a little information that may be helpful: The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Montgomery are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.
Generally, Montgomery is known for its gardens, restaurants, and coffee shops. Major attractions include Woodbury Common Premium Outlets. Get out into nature with places like Thomas Bull Memorial Park, Orange County Arboretum, and Algonquin Park. Cultural attractions include Paramount Theatre, Dia Beacon, and Harness Racing Museum and Hall of Fame.
Keep this information about transit options in and around Montgomery in your back pocket to make the most of your stay: You can fly into the closest airport, which is Stewart Intl. Airport (SWF), 8 mi (12.9 km) away from the city center.