Montgomery Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Top Hotel Deals
Holiday Inn Express & Suites Montgomery by IHG
2105 Route 208 Montgomery NY
Book a stay at this business-friendly hotel in Montgomery. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Super 8 by Wyndham Montgomery Maybrook
207 Montgomery Rd Montgomery NY
Book a stay at this business-friendly motel in Montgomery. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
The Kartrite Resort & Indoor Waterpark
555 Resorts World Drive Monticello NY
Book a stay at this family-friendly hotel in Monticello. Enjoy 5 restaurants, 2 bars/lounges, and water park access (surcharge). Our guests praise the helpful ...
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Resorts World Catskills Casino
888 Resorts World Drive Monticello NY
Book a stay at this luxury hotel in Monticello. Enjoy a full-service spa, 6 restaurants, and a casino. Our guests praise the helpful staff and the clean rooms ...
Overlook Lodge at Bear Mountain
55 Hessian Drive Bear Mountain NY
Book a stay at this spa hotel in Bear Mountain. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Holiday Inn Express Poughkeepsie by IHG
2750 South Road Poughkeepsie NY
Stay at this hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
915 Union Ave New Windsor NY
Book a stay at this business-friendly hotel in New Windsor. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the ...
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Book a stay at this business-friendly hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
La Quinta Inn & Suites by Wyndham Middletown-Goshen
551 Route 211 E Middletown NY
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
SureStay Plus Hotel by Best Western Highland Poughkeepsie
3423 US Highway 9W Highland NY
Book a stay at this business-friendly hotel in Highland. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
Hampton Inn by Hilton New Paltz
4 South Putt Corners Road New Paltz NY
Book a stay at this business-friendly hotel in New Paltz. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
DoubleTree by Hilton Poughkeepsie Convention Center
40 Civic Center Plz Poughkeepsie NY
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
LEGOLAND Hotel NEW York
1 LEGOLAND BLVD Goshen NY
Book a stay at this family-friendly hotel in Goshen. Enjoy free breakfast, free WiFi, and an outdoor pool. Popular attractions LEGOLAND® New York and Triangle ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Thu, Sep 17 - Mon, Sep 21
MCO
Orlando Intl.
SWF
Stewart Intl.
$211
Roundtrip
found 1 day ago
Thu, Sep 17 - Mon, Sep 21
MCO
Orlando Intl.
SWF
Stewart Intl.
$216
Roundtrip
found 1 day ago
Thu, Sep 17 - Mon, Sep 21
MCO
Orlando Intl.
SWF
Stewart Intl.
$221
Roundtrip
found 1 day ago
Thu, Sep 17 - Mon, Sep 21
MCO
Orlando Intl.
SWF
Stewart Intl.
$228
Roundtrip
found 4 days ago
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