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 $262, price is now $219 per person
$219
per person
Feb 7 - Feb 9
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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.
Homewood Suites Stewart Airport
Price was $686, price is now $547 per person
$547
per person
Jan 11 - Jan 16
found 6 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newburgh (SWF)
This hotel features an indoor pool and a 24-hour gym. Enjoy the hot tub and free perks like buffet breakfast and free self parking. Free WiFi in public areas, a lobby fireplace, and express check-out are also on offer.
Wildflower Farms, Auberge Collection
Save 100% on your flight
Price was $2,448, price is now $2,139 per person
$2,139
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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.
Newburgh Inn
Price was $256, price is now $229 per person
$229
per person
Jan 23 - Jan 25
found 5 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newburgh (SWF)
Free WiFi in public areas is available at this hotel. Traveling on business? Take advantage of the conference center and conference space on site. Take advantage of the free self parking.
Howard Johnson by Wyndham Newburgh/West Point
Price was $470, price is now $435 per person
$435
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
San Antonio (SAT) to Newburgh (SWF)
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.
Top Montgomery hotels deals
Holiday Inn Express & Suites Montgomery by IHG
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.
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.
Breakfast included
Parking included
Borland House Inn
130 Clinton Street Montgomery NY
$114 nightly
The price is $129 total per night
$129 total
Dec 14 - Dec 15
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
$216 nightly
The price is $244 total per night
$244 total
Dec 14 - Dec 15
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.
Quality Inn Poughkeepsie
536 Haight Ave, Building A Poughkeepsie NY
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $108 total per night
$108 total
Dec 17 - Dec 18
Total with taxes and fees
This hotel features an indoor pool and a 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.
Pool
Breakfast included
Overlook Lodge at Bear Mountain
55 Hessian Drive Bear Mountain NY
Free Cancellation
Reserve now, pay when you stay
$102 nightly
The price is $116 total per night
$116 total
Dec 22 - Dec 23
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
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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