Search for Cheap Deals on
Hotels in Montgomery

Check Last Minute Montgomery Hotel Deals

Tonight Feb 21 - Feb 22Next weekend Feb 27 - Mar 1

Choose from 1226 Montgomery Hotel Deals

Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG

2.5 out of 5
2105 Route 208 Montgomery NY
  • 27 min walk from City Winery Hudson Valley
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 ...
8.8/10 Excellent! (825 reviews)
Clean spacious room my TV did not work only complaint I have I didn’t make a big stink about it because I just use the room to sleep and I came in from partying

Reviewed on Feb 15, 2026

Holiday Inn Express & Suites Montgomery by IHG
Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook

2.5 out of 5
207 Montgomery Rd Montgomery NY
  • 4 min drive from City Winery Hudson Valley
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. ...
6.4/10 (1,003 reviews)
My husband and I stayed the weekend and were very pleased with the woman at the front counter!! I didn’t get her name, but we checked in around 8pm on a Friday night. She was super friendly and helped us with our WiFi login problems. The room itself was clean. The only complaints we have is that ...

Reviewed on Feb 19, 2026

Super 8 by Wyndham Montgomery Maybrook
The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
555 Resorts World Drive Monticello NY
  • 55 min drive from City Winery Hudson Valley
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 ...
8.2/10 Very Good! (1,975 reviews)
First of First the Main revolving door wasnt working, the Heat on our room kept going off,

Reviewed on Feb 21, 2026

The Kartrite Resort & Indoor Waterpark
Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 out of 5
888 Resorts World Drive Monticello NY
  • 56 min drive from City Winery Hudson Valley
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 ...
8.8/10 Excellent! (1,095 reviews)
Friendly staff

Reviewed on Feb 19, 2026

Resorts World Catskills Casino
Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3 out of 5
2641 South Road/Route 9 Poughkeepsie NY
  • 43 min drive from City Winery Hudson Valley
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,014 reviews)
Good

Reviewed on Feb 21, 2026

Courtyard by Marriott Poughkeepsie
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
551 Route 211 E Middletown NY
  • 23 min drive from City Winery Hudson Valley
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 ...
9.4/10 Exceptional! (975 reviews)
All great. Only problem was no dog walk due to snow

Reviewed on Feb 16, 2026

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
  • 33 min drive from City Winery Hudson Valley
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 ...
8.6/10 Excellent! (1,006 reviews)
Had a great stay! The staff were awesome! The rooms were clean and beds very comfortable! Location is very convenient. The breakfast buffet was plentiful and great!

Reviewed on Feb 20, 2026

Sleep Inn & Suites Middletown - Goshen
Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2.5 out of 5
2361 South Rd Poughkeepsie NY
  • 41 min drive from City Winery Hudson Valley
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 ...
9/10 Wonderful! (1,002 reviews)
Super clean, good breakfast, friendly staff- highly recommend!

Reviewed on Feb 21, 2026

Hampton Inn & Suites Poughkeepsie
Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

2.5 out of 5
60 Centre Dr Central Valley NY
  • 38 min drive from City Winery Hudson Valley
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 ...
9.2/10 Wonderful! (1,061 reviews)
Nice and comfortable clean room my favorite was the pool definitely will come back and stay again with my family 😀

Reviewed on Feb 21, 2026

Hampton Inn Harriman Woodbury
DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

4 out of 5
40 Civic Center Plz Poughkeepsie NY
  • 46 min drive from City Winery Hudson Valley
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 ...
8.4/10 Very Good! (1,005 reviews)
Almost everything was great. BUT I can't understand why a hotel that is so good in every other aspect won't put in a wake up in call system.

Reviewed on Feb 21, 2026

DoubleTree by Hilton Poughkeepsie Convention Center
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
  • 42 min drive from City Winery Hudson Valley
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 ...
9/10 Wonderful! (1,015 reviews)
Everything was excellent was the 2nd time there

Reviewed on Feb 20, 2026

Hyatt Place Poughkeepsie / Hudson Valley
Courtyard by Marriott Fishkill

Courtyard by Marriott Fishkill

3 out of 5
17 Westage Drive Fishkill NY
  • 43 min drive from City Winery Hudson Valley
Book a stay at this business-friendly hotel in Fishkill. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
8.8/10 Excellent! (747 reviews)
Exceptional

Reviewed on Feb 20, 2026

Courtyard by Marriott Fishkill
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.

Find cheap hotels in Montgomery

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Montgomery hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Montgomery.

Choosing the right hotel in New York has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Montgomery’s 1,226 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $87. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Montgomery hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Montgomery. No matter your reason for visiting Montgomery, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Montgomery hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Montgomery for as low as $87.

How many hotels are there in Montgomery?

With over 1,226 hotels in Montgomery, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $87.

How to find cheap car rentals in Montgomery?

Finding a cheap car rental deal in Montgomery is as easy as scoring cheap hotels in Montgomery. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.