
Montgomery Vacations
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Top Hotel Deals

Super 8 by Wyndham Montgomery Maybrook
207 Montgomery Rd, Montgomery, NY
2.92 km from city center
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. ...

Holiday Inn Express & Suites Montgomery by IHG
2105 Route 208, Montgomery, NY
2.63 km from city center
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 ...

The Kartrite Resort & Indoor Waterpark
555 Resorts World Drive, Monticello, NY
37.06 km from city center
Stay at this 4-star family-friendly hotel in Monticello. Enjoy 5 restaurants, 2 bars/lounges, and water park access (surcharge). Our guests praise the helpful ...

Quality Inn Poughkeepsie
536 Haight Ave, Building A, Poughkeepsie, NY
33.78 km from city center
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...

Resorts World Catskills Casino
888 Resorts World Drive, Monticello, NY
37.32 km from city center
Stay at this 4.5-star luxury hotel in Monticello. Enjoy a full-service spa, 6 restaurants, and a casino. Our guests praise the helpful staff and the clean rooms ...

Wildflower Farms, Auberge Collection
2702 Main St, Gardiner, NY
18.69 km from city center
Stay at this 5-star luxury resort in Gardiner. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mohonk Lake and Tuthilltown Spirits are ...

Overlook Lodge at Bear Mountain
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
30.87 km from city center
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 ...

Sleep Inn & Suites Middletown - Goshen
3491 Route 6, Middletown, NY
20.02 km from city center
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 ...

Hampton Inn Harriman Woodbury
60 Centre Dr, Central Valley, NY
25.26 km from city center
Book a stay at this business-friendly hotel in Woodbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...

Hampton Inn & Suites Poughkeepsie
2361 South Rd, Poughkeepsie, NY
29.02 km from city center
Book a stay at this golf hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...

Quality Inn & Suites Fishkill South near I-84
849 Route 52, Fishkill, NY
26.43 km from city center
Book a stay at this business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...

Americas Best Value Inn New Paltz
7 Terwilliger Ln, New Paltz, NY
27.64 km from city center
Book a stay at this business-friendly motel in New Paltz. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
915 Union Ave, New Windsor, NY
14.01 km from city center
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 ...
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, Dec 18 - Sun, Dec 21
MCO
Orlando Intl.
SWF
Stewart Intl.
$280 Roundtrip, found 4 days ago
$280
Roundtrip
found 4 days ago

Thu, Dec 18 - Sun, Dec 21
MCO
Orlando Intl.
SWF
Stewart Intl.
$285 Roundtrip, found 4 days ago
$285
Roundtrip
found 4 days ago

Thu, Dec 18 - Sun, Dec 21
MCO
Orlando Intl.
SWF
Stewart Intl.
$290 Roundtrip, found 4 days ago
$290
Roundtrip
found 4 days ago