Montgomery Vacations from $584
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Your Montgomery Vacation
The vibrant city of Montgomery is calling. Discover its highlights and hidden gems with a Montgomery vacation package that's customized to you. A trip to Montgomery is a terrific opportunity to sightsee. Be sure to visit big-name attractions such as Angry Orchard, Thomas Bull Memorial Park and Orange County Arboretum. Whoever you're going away with and whether your budget is big or small, your dream Montgomery vacation is just a few clicks away with Expedia.
The Latest Montgomery Vacation Packages
- Eurostars The Chemists’ Club Hotel
Jan 15 - Jan 18Eurostars The Chemists’ Club Hotel + Flight
Manhattan3 nights4.0 star property9.4/10 - Exceptional (565 reviews)Roundtrip • Atlanta (ATL) - New York (JFK)ATL - LGA • Nonstop LGA - ATL • Nonstop$982$584found 7 hours agoper traveler - JW Marriott Essex House New York
Jan 20 - Jan 24JW Marriott Essex House New York + Flight
Manhattan4 nights4.5 star property8.8/10 - Excellent (1,000 reviews)Roundtrip • Atlanta (ATL) - New York (JFK)ATL - JFK • Nonstop JFK - ATL • Nonstop - The Langham, New York, Fifth Avenue
Jan 16 - Jan 22The Langham, New York, Fifth Avenue + Flight
Manhattan6 nights5.0 star property9.6/10 - Exceptional (1,000 reviews)Roundtrip • Atlanta (ATL) - New York (JFK)ATL - JFK • Nonstop JFK - ATL • Nonstop - Loews Regency New York Hotel
Jan 16 - Jan 22Loews Regency New York Hotel + Flight
Manhattan6 nights5.0 star property9.2/10 - Wonderful (1,001 reviews)Roundtrip • Atlanta (ATL) - New York (JFK)ATL - JFK • Nonstop JFK - ATL • Nonstop - The St. Regis New York
Jan 16 - Jan 22The St. Regis New York + Flight
Manhattan6 nights5.0 star property9.2/10 - Wonderful (295 reviews)"The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong"Reviewed November 6, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - JFK • Nonstop JFK - ATL • Nonstop$4,089$2,480found 1 day agoper traveler
Where to stay near Montgomery
Middletown
For travelers seeking a vibrant city experience, Middletown is the ideal base for exploring the rich offerings of the region. With attractions like the Orange County Fairgrounds and Highland Lakes State Park, visitors can enjoy a mix of entertainment and outdoor activities. The nearby shopping mall center adds to the appeal for those wanting to indulge in retail therapy. Just about 11 miles by car from Montgomery, Middletown makes for a smart choice for your stay, combining convenience with diverse experiences.
Newburgh
Experience the charm of Newburgh, a great hub for travelers looking for a weekend getaway or family vacation. With popular attractions like the Dia Beacon art museum, the modern Mount Saint Mary's College, and the scenic Algonquin Park, Newburgh offers a delightful mix of culture and outdoor experiences. Located about 12 miles by car from Montgomery, it’s an ideal choice for visitors wanting easy access to a variety of activities. Newburgh is a smart hotel booking option for your stay.
Beacon
If you are a family or adventure seeker, look no further than Beacon, a city known for its vibrant arts scene and outdoor activities. Enjoy exploring the renowned Dia Beacon art museum, take in the stunning views at Fishkill Ridge, or unwind at the nearby parks and lakes. With Beacon located about 16 miles by car from Montgomery, it’s an ideal choice for a weekend getaway filled with cultural and recreational experiences. Beacon makes for a smart hotel booking choice for your visit.
Gardiner
Ideally situated for outdoor enthusiasts and families, Gardiner offers a gateway to breathtaking attractions like the Shawangunk Mountains, Mohonk Lake, and Minnewaska State Park. Travelers can immerse themselves in nature with activities ranging from hiking to skiing, making it a perfect spot for weekend getaways. Just about a 13-mile drive from Montgomery, Gardiner is an excellent choice for those seeking adventure and scenic beauty while enjoying a relaxing stay.
Goshen
Travelers visiting the area often choose Goshen, especially those seeking a weekend getaway or a family-friendly experience. This charming city offers a delightful blend of nature and entertainment, with attractions like the Orange County Fairgrounds, Highland Lakes State Park, and Touro College of Osteopathic Medicine nearby. Located about 10 miles by car from Montgomery, Goshen provides easy access to a variety of activities, making it a smart choice for your next hotel booking.
Discover the most popular places to visit in Montgomery
Montgomery Hotel Deals
Holiday Inn Express & Suites Montgomery by IHG
Holiday Inn Express & Suites Montgomery by IHG
Super 8 by Wyndham Montgomery Maybrook
Super 8 by Wyndham Montgomery Maybrook
"Pilar"
La Quinta Inn & Suites by Wyndham Middletown-Goshen
La Quinta Inn & Suites by Wyndham Middletown-Goshen
"Enjoyed our stay there Only down thing was breakfast was from 6 to 9 Breakfast should be extended longer"
"I think i got bed bites from that hotel i can show the pics of the bites. The next day after i spent the night there i started itching i didnt go anywhere else after in that hotel."
Find out more about Montgomery
Things to do in and around Montgomery
Montgomery, New York, is perfect for family-friendly vacations, offering a variety of outdoor adventures and entertainment options. Visitors can enjoy exciting activities like walking trails, relaxing beach vacations, and shopping at local centers. With its blend of fun and education, Montgomery ensures an enjoyable experience for everyone, making it an ideal destination for those seeking adventure and leisure alike.
Shopping
For a delightful shopping experience in Montgomery, visit the Galleria at Crystal Run, just 9 miles away, where you can find a variety of stores and family-friendly activities. If you're up for a drive, check out the Woodbury Common Premium Outlets, located 16 miles away, offering extensive shopping options.
Recreation
Experience the excitement at Ice Time Sports Complex, where you can skate or play hockey in a lively atmosphere. For a cultural escape, head to Paramount Theatre for captivating performances. Enjoy a round of golf surrounded by nature's beauty at West Point Golf Course, perfect for outdoor enthusiasts.
Adventure
Experience the thrill of motor racing at Orange County Fair Speedway, located 10 miles from Montgomery. For family fun, visit Castle Fun Center, an exciting arcade adventure zone 12 miles away. Stay local and enjoy the adventure vibes at the Orange County Tennis Center right in Montgomery.
Nightlife
Experience the vibrant nightlife in Montgomery with a visit to the cozy Montgomery Café for a laid-back vibe. For a livelier scene, check out The Carriage House, where you can enjoy live music and great cocktails. End your night at the local brewery for a taste of craft beer.
Find the best attractions near Montgomery
Montgomery, New York, is a charming destination perfect for families and outdoor enthusiasts. With its urban parks, national and state parks, and nature preserves, visitors can enjoy a variety of outdoor activities and cultural experiences. Don't miss the Montgomery Museum for a glimpse into local history. Whether you're seeking adventure or entertainment, Montgomery offers something for everyone to enjoy during their vacation.
- Dia Beacon: Located 13 miles from Montgomery, Dia Beacon is an impressive contemporary art museum set in a former Nabisco box factory. Its expansive galleries showcase thought-provoking installations and works from renowned artists, all within a unique industrial space that enhances the cultural vibe of the experience.
- Algonquin Park: Just 9 miles away, Algonquin Park is a beautiful urban park perfect for families. With its lush greenery, playgrounds, and walking trails, it offers a relaxing escape in the city, making it ideal for outdoor activities and quality family time.
- Orange County Fairgrounds: Located 10 miles from Montgomery, the Orange County Fairgrounds hosts various events throughout the year. With its lively atmosphere, outdoor activities, and family-friendly attractions, it promises fun and excitement for visitors of all ages.
Best time to go to Montgomery
The best time to visit Montgomery is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.
Tips to save on your trip to Montgomery
- Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
- Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Montgomery.
- Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
- Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.
Frequently Asked Questions
How much does a Montgomery vacation package cost?
You can grab a vacation package to this popular destination from $584 on Expedia. But how much your vacation to Montgomery costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Montgomery?
If you're hoping to score a cheap Montgomery vacation package, consider planning a trip in January, August and December. You're likely to find lower rates on accommodations and flights during these quieter months — ideal for travelers wishing to save money.
How many days is enough for Montgomery?
The ideal length for your Montgomery vacation depends on what you'd like to see. Typically, a handful of days to a week will give you plenty of time to visit all the top sights and explore some hidden gems along the way.
How to find the best Montgomery package deals?
Begin your search for a Montgomery package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Montgomery package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Montgomery escape off to a flying start.
Is it cheaper to book a Montgomery vacation as a package?
You can enjoy significant savings on your Montgomery retreat by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to browse the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Montgomery?
If you're considering a spontaneous Montgomery adventure, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find terrific deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Montgomery vacation packages?
Your Montgomery trip should be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you a little more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.