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Montgomery flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
Price was $287, price is now $287 per person
$287
per person
Mar 10 - Mar 13
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Free self parking, a computer station, and luggage storage are also offered.
YO1 Longevity & Health Resorts, Catskills

YO1 Longevity & Health Resorts, Catskills

4 out of 5
Save 100% on your flight
Price was $1,068, price is now $765 per person
$765
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the indoor pool and perks like free self parking.
The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
Save 100% on your flight
Price was $766, price is now $586 per person
$586
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
A water park, 5 restaurants, and an outdoor pool are all featured at this smoke-free hotel. There's fun for all ages with a lazy river and a bowling alley, and families will appreciate the onsite laundry facilities. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

5 out of 5
Save 100% on your flight
Price was $2,786, price is now $2,603 per person
$2,603
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free resort. Relax with a drink at one of the 3 bars/lounges and enjoy free perks like valet parking and WiFi in public areas. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and concierge services.
Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Price was $339, price is now $339 per person
$339
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like free self parking.

Top Montgomery hotels deals

Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG

2.5 out of 5
2105 Route 208 Montgomery NY
Free Cancellation
$90 nightly
The price is $102 total per night
$102 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-in, and conference space. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Parking included
Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook

2.5 out of 5
207 Montgomery Rd Montgomery NY
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $89 total per night
$89 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This motel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free buffet breakfast each morning. A safe deposit box is provided and the front desk is staffed around-the-clock.
Breakfast included
Parking included
Borland House Inn

Borland House Inn

3 out of 5
130 Clinton Street Montgomery NY
$114 nightly
The price is $129 total per night
$129 total
Dec 28 - Dec 29
Total with taxes and fees
This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the express check-in, express check-out, and airport shuttle. A restaurant, concierge services, and a virtual front desk are also provided.
Breakfast included
Spa
The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
555 Resorts World Drive Monticello NY
Free Cancellation
Reserve now, pay when you stay
$216 nightly
The price is $244 total per night
$244 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
A water park, 5 restaurants, and an outdoor pool are all featured at this smoke-free hotel. There's fun for all ages with a lazy river and a bowling alley, and families will appreciate the onsite laundry facilities. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.
Pool
Restaurant
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $113 total per night
$113 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
A full-service spa and a restaurant are featured at this smoke-free hotel. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. There's a bar/lounge on site, and concierge services and barbecue grills are also provided.
Pool
Spa
Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

2.5 out of 5
60 Centre Dr Central Valley NY
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $120 total per night
$120 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and free train station pick-up. Free perks include on-the-go breakfast, free self parking, and a shopping center shuttle.
Pool
Breakfast included
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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.

Popular places to visit

Orange County Arboretum

Take the family on an outing to Orange County Arboretum during your trip to Montgomery. Take in the festivals while you're in the area.

Orange County Arboretum

City Winery Hudson Valley

You can enjoy a tasting or tour at City Winery Hudson Valley during your travels to Montgomery. While in this family-friendly area, you can enjoy the restaurants.

City Winery Hudson Valley

Thomas Bull Memorial Park

1/5(1 review)

Explore the great outdoors at Thomas Bull Memorial Park, a lovely green space in Montgomery. Take in the festivals in this family-friendly area.

Thomas Bull Memorial Park

Frequently asked questions

How much are vacation packages to Montgomery?
$287 is all you'll need for an exciting break in Montgomery. Bundle your hotel and flights into a Travelocity package and see the savings start to add up. With prices this good, traveling has never been so accessible.
How long should my Montgomery vacation be?
About 2 nights is what many visitors book for their Montgomery vacation. That's a good starting point, but there's loads more to explore if you allow yourself a little longer.
Where can I get the best vacation package deals for Montgomery?
You'll come across an excellent range of Montgomery package deals on Travelocity. With no less than 400 airlines and 1,000,000 properties around the globe, crafting a dream getaway will be easy.
Why should I book my Montgomery vacation package with Travelocity?
You'll not only save lots, but you can also access our round-the-clock support, top-notch service and a Price Match Guarantee. Explore every nook-and-cranny across the globe, uncover hidden gems and forge unforgettable memories — we'll take care of the little details.
Can I save on my Montgomery car rental if I bundle it with hotels and flights?
Combining your car, hotel and flight into a Montgomery vacation package is an easy way to score an incredible deal. Plus, having your own set of wheels gives you freedom to make your way to all those big sights you want to check out. Sitting 55 mi away from Montgomery, Times Square is one place that should be on your agenda. Load up the car and make a day trip of it.
Which airport is best for Montgomery?
Liberty Intl. Airport (EWR) is 60 mi from the downtown area and is the starting point for many adventures. Alternatively, LaGuardia Airport (LGA) is 55 mi away from central Montgomery and Stewart Intl. Airport (SWF) is 8 mi away from central Montgomery.
What is there to do in Montgomery?
Orange County Arboretum deserves to be on your to-do list. After you've crossed off this top attraction, simply wander the streets of Montgomery and find out what makes this wonderful place tick.
Where should I stay when visiting Montgomery?
If you're searching for a place to base yourself, check out the Super 8 by Wyndham Montgomery Maybrook. It's the top choice for many visitors.

Photos of local treasures

Browse Montgomery vacation photos for more inspiration

Photo by ViajandoconAna Rustrian
Photo by ViajandoconAna Rustrian
Photo by ViajandoconAna Rustrian
Photo by ViajandoconAna Rustrian