Find Hotels with Bars in Montgomery, NY

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Our top choices for Montgomery hotels with a bar

Exterior
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3.0 star property
Crown Heights
9.0 out of 10, Wonderful, (1007)
"Lovely property, wonderful staff will definitely return back."
United States
Dennis
$101 nightly
The price is $117
Dec 14 - Dec 15
Total with taxes and fees
Hyatt Place Poughkeepsie / Hudson Valley
Outdoor pool
LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York

3.0 star property
Goshen
8.8 out of 10, Excellent, (33)
"We loved everything from the staff to the stay "
United States
Arnassia
$294 nightly
The price is $346
Dec 22 - Dec 23
Total with taxes and fees
LEGOLAND Hotel NEW York
Restaurant
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1005)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
$104 nightly
The price is $118
Jan 8 - Jan 9, 2026
Total with taxes and fees
Overlook Lodge at Bear Mountain
Exterior
Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3.0 star property
Poughkeepsie
8.8 out of 10, Excellent, (1002)
"Clean room and friendly staff "
United States
Kelly
$84 nightly
The price is $95
Dec 25 - Dec 26
Total with taxes and fees
Courtyard by Marriott Poughkeepsie
Lobby
Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill

3.0 star property
Fishkill
8.6 out of 10, Excellent, (1005)
"Brayden was great"
United States
Will
$92 nightly
The price is $104
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hilton Garden Inn Fishkill
Bar (on property)
DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

4.0 star property
Downtown Poughkeepsie
8.4 out of 10, Very Good, (1000)
"Courteous staff, clean and well outfitted rooms, nice breakfast buffet. "
United States
Kaye
$102 nightly
The price is $119
Dec 14 - Dec 15
Total with taxes and fees
DoubleTree by Hilton Poughkeepsie Convention Center
Property grounds
Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 star property
Monticello
8.6 out of 10, Excellent, (1107)
"It is a great place to stay"
United States
Caonabo
$194 nightly
The price is $216
Dec 11 - Dec 12
Total with taxes and fees
Resorts World Catskills Casino
Fireplace
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

3.0 star property
Middletown
8.6 out of 10, Excellent, (1002)
"The hotel was very clean, enjoyed my stay would recommend "
United States
Jessica
$93 nightly
The price is $109
Dec 28 - Dec 29
Total with taxes and fees
Courtyard by Marriott Middletown Goshen
Property amenity
Residence Inn by Marriott Fishkill

Residence Inn by Marriott Fishkill

3.0 star property
Fishkill
9.4 out of 10, Exceptional, (403)
"Excellent stay!"
United States
Margaret
$127 nightly
The price is $144
Jan 3 - Jan 4, 2026
Total with taxes and fees
Residence Inn by Marriott Fishkill
Premium bedding, down comforters, in-room safe, laptop workspace
The Heartwood

The Heartwood

3.5 star property
Arlington
9.8 out of 10, Exceptional, (228)
"Thanks this place is amazing we loved it. "
United States
Scott
$149 nightly
The price is $173
Dec 14 - Dec 15
Total with taxes and fees
The Heartwood
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.
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Top Montgomery Hotel Reviews

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

10/10 Excellent
"Clean, people very nice, thank you."
Aaron 2-night trip
Posted 3 days ago
Hampton Inn & Suites Poughkeepsie

Frequently asked questions

Searching for hotels with bars in Montgomery?
Montgomery features 23 properties to choose from, and likely many will have a bar where you can unwind with a late-night cocktail. While you're here, consider a visit to City Winery Hudson Valley and Orange County Arboretum.
What are the best hotels with bars in Montgomery?
Below are some of top hotels with bars in and around Montgomery: Super 8 by Wyndham Montgomery Maybrook: Hotel with 5 restaurants. Enjoy the 2 bars, water park, and breakfast. Holiday Inn Express & Suites Montgomery by IHG: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Borland House Inn: Hotel with 6 restaurants. Enjoy the 6 bars, full-service spa, and casino. The Kartrite Resort & Indoor Waterpark: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Quality Inn Poughkeepsie: Resort with restaurant. Enjoy the 3 bars, free WiFi, and free parking.
What is there to do in Montgomery?
In the area, you can visit Angry Orchard, Ice Time Sports Complex, and Brotherhood Winery, then find a cozy spot for a nightcap. Other places to see include City Winery Hudson Valley and Orange County Arboretum. Montgomery is appreciated for its restaurants.
When is the best time to visit Montgomery?
Visiting local bars in Montgomery is more fun when you know what the weather holds. These temperatures and rainfall averages can help you decide the best time for bar hopping. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Montgomery are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.
How can I get to Montgomery and around the area?
You might want to make the most of these transportation choices in and around Montgomery: Fly into Stewart Intl. Airport (SWF), which is located 8 mi (12.9 km) away from the city center. If you'd like to explore around the area, consider renting a car to take in more sights.

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