Deals on vacations and trips to Montgomery
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Montgomery flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Sleep Inn & Suites Middletown - Goshen
Price was $312, price is now $241 per person
$241
per person
Jan 29 - Feb 1
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
The Kartrite Resort & Indoor Waterpark
Save 100% on your flight
Price was $791, price is now $616 per person
$616
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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.
The Crossroads Hotel, Newburgh
Price was $658, price is now $517 per person
$517
per person
Jan 18 - Jan 25
found 24 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Newburgh (SWF)
A gym is featured at this hotel, along with free self parking. WiFi in public areas is free. A fireplace in the lobby is provided and the front desk is staffed around-the-clock.
Courtyard by Marriott Newburgh Stewart Airport
Save 100% on your flight
Price was $363, price is now $298 per person
$298
per person
Jan 30 - Feb 2
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) 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
2105 Route 208 Montgomery NY
Free Cancellation
$86 nightly
The price is $97 total per night
$97 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
207 Montgomery Rd Montgomery NY
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $90 total per night
$90 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.
Borland House Inn
130 Clinton Street Montgomery NY
$114 nightly
The price is $129 total per night
$129 total
Dec 16 - Dec 17
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
555 Resorts World Drive Monticello NY
Free Cancellation
Reserve now, pay when you stay
$209 nightly
The price is $236 total per night
$236 total
Dec 18 - Dec 19
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
55 Hessian Drive Bear Mountain NY
Free Cancellation
Reserve now, pay when you stay
$96 nightly
The price is $109 total per night
$109 total
Dec 20 - Dec 21
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
60 Centre Dr Central Valley NY
Free Cancellation
Reserve now, pay when you stay
$95 nightly
The price is $117 total per night
$117 total
Dec 21 - Dec 22
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
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.
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.
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.
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