Hotels in Montgomery

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Check prices for these dates

Tonight
Oct 27 - Oct 28
Tomorrow
Oct 28 - Oct 29
This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Where to stay in Montgomery?

A Holiday Inn Express & Suites building with a covered entrance, stone facade, and a parking area with a bench.

1. Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG
2.5 star property
Montgomery
8.8 out of 10, Excellent, (939 reviews)
Near the train station, this Montgomery hotel offers convenience with a 24-hour health club and café. Free breakfast, WiFi and parking make stays stress-free. Close to City Winery Hudson Valley and only 16 minutes from Stewart Airport.
The price is $120
$142 total
includes taxes & fees
Nov 22 - Nov 23
Holiday Inn Express & Suites Montgomery by IHG
A neatly made bed with white linens, flanked by two bedside tables with lamps, and two framed paintings on the wall above.

2. Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook
2.5 star property
Montgomery
6.4 out of 10, Good, (1,010 reviews)
At Super 8 Montgomery Maybrook, wake up to complimentary breakfast before exploring nearby City Winery Hudson Valley. Free WiFi and parking enhance your stay while the attentive staff, praised by fellow travelers, ensures a pleasant experience.
The price is $74
$87 total
includes taxes & fees
Nov 16 - Nov 17
Super 8 by Wyndham Montgomery Maybrook
A two-story house with a porch, a front door, and a small garden area with potted plants.

3. Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (197 reviews)
Escape to this charming Victorian B&B in Montgomery, featuring a restaurant, snack bar, and serene garden terrace. Enjoy facials and complimentary breakfast before exploring nearby City Winery Hudson Valley and Orange County Farmers Museum.
The price is $144
$175 total
includes taxes & fees
Oct 29 - Oct 30
Borland House Inn
Exterior

4. Tin Brook Bed & Breakfast

Tin Brook Bed & Breakfast
3.0 star property
Walden
9.4 out of 10, Exceptional, (140 reviews)
Warm, inviting atmosphere awaits at this Walden B&B where complimentary breakfast energizes your day. Explore nearby attractions with ease, knowing your car is safely parked in the free lot when you return to this cozy Hudson Valley haven.
The price is $138
$156 total
includes taxes & fees
Oct 28 - Oct 29
Tin Brook Bed & Breakfast
A spacious hotel lobby with a high ceiling, wooden beams, a large mural, and a seating area with a sofa and chairs.

5. Harvest Inn

Harvest Inn
2.5 star property
Pine Bush
9.4 out of 10, Exceptional, (565 reviews)
Experience countryside charm at this Pine Bush hotel, where a seasonal outdoor pool awaits summer guests. Enjoy complimentary breakfast, WiFi, and parking while exploring nearby Brimstone Hill Winery and Angry Orchard. Clean rooms and attentive staff ensure a comfortable retreat.
The price is $197
$223 total
includes taxes & fees
Oct 28 - Oct 29
Harvest Inn
A hotel entrance with a covered walkway, a prominent sun logo, and a modern facade.

6. La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (1,002 reviews)
Discover serene comfort near LEGOLAND® New York at this Middletown gem. The indoor pool invites morning swims, while free breakfast, parking, and WiFi enhance your stay. Explore nearby restaurants or visit Galleria at Crystal Run after a peaceful night's rest.
The price is $105
$125 total
includes taxes & fees
Nov 18 - Nov 19
La Quinta Inn & Suites by Wyndham Middletown-Goshen
A breakfast area with a counter displaying hard-boiled eggs, a bowl of green apples, and various pastries.

7. Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,007 reviews)
Modern accommodations just minutes from LEGOLAND® New York. This hotel offers complimentary English breakfast, WiFi, and parking. Energize at the 24-hour fitness center or relax on the terrace after exploring nearby Orange County Fairgrounds.
The price is $80
$95 total
includes taxes & fees
Nov 9 - Nov 10
Tru by Hilton Middletown
A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.

8. Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.4 out of 10, Very good, (1,004 reviews)
This quiet Middletown hotel offers a seasonal outdoor pool and free breakfast just minutes from LEGOLAND® New York. Clean rooms provide comfort after visiting the Galleria at Crystal Run mall. With free WiFi and parking, plus fitness center access, guests praise the helpful staff.
The price is $80
$94 total
includes taxes & fees
Nov 18 - Nov 19
Hampton Inn by Hilton Middletown
An outdoor patio area with seating, a fire feature, and a view of the surrounding buildings.

9. Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
3.0 star property
Middletown
9.0 out of 10, Wonderful, (796 reviews)
Immersive indoor pool and 24-hour fitness center complement spacious suites at this Middletown hotel. Located near Galleria at Crystal Run and LEGOLAND® New York, enjoy free breakfast, WiFi, and parking with friendly staff ready to assist.
The price is $112
$136 total
includes taxes & fees
Nov 4 - Nov 5
Home2 Suites by Hilton Middletown
A landscaped outdoor area with a fire feature, seating, and a pathway.

10. Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very good, (1,003 reviews)
Enjoy American cuisine at The Bistro or unwind at the bar after exploring nearby LEGOLAND® and Galleria at Crystal Run. This Middletown hotel offers free WiFi, free parking, and is praised for its exceptionally helpful staff.
The price is $101
$119 total
includes taxes & fees
Nov 8 - Nov 9
Courtyard by Marriott Middletown Goshen
A hotel lobby with a bar area, a television screen displaying news, and decorative metal sculptures.

11. Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport
2.5 star property
Newburgh
9.2 out of 10, Wonderful, (1,002 reviews)
The price is $135
$160 total
includes taxes & fees
Nov 22 - Nov 23
Hampton Inn & Suites Newburgh Stewart Airport
A Courtyard Marriott hotel with a covered entrance, outdoor seating area, and multiple balconies.

12. Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport
3.0 star property
Newburgh
8.2 out of 10, Very good, (811 reviews)
This quiet Newburgh hotel offers an indoor pool and American cuisine at The Bistro. Located 2.1 mi from Stewart Airport with free WiFi and parking. Ice Time Sports Complex and Resorts World Hudson Valley are nearby, plus a 24-hour fitness center.
The price is $173
$205 total
includes taxes & fees
Nov 8 - Nov 9
Courtyard by Marriott Newburgh Stewart Airport
A Red Roof Inn & Suites building with a two-story structure, a balcony, and an American flag.

13. Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2.0 star property
New Windsor
8.4 out of 10, Very good, (1,016 reviews)
This business-friendly hotel offers a complimentary airport shuttle and is only 1.6 mi from Stewart Airport. Enjoy the indoor pool after a workout in the fitness center. With free WiFi and parking, plus proximity to Resorts World, convenience meets comfort.
The price is $99
$117 total
includes taxes & fees
Nov 1 - Nov 2
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
A large, two-story white house with a wrap-around porch and a small front garden.

14. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (238 reviews)
Unwind at this charming B&B with a refreshing outdoor pool, lush garden, and peaceful terrace. After complimentary breakfast, explore nearby hiking trails or head to LEGOLAND and Woodbury Common Premium Outlets, both within 15 minutes.
The price is $108
$122 total
includes taxes & fees
Nov 9 - Nov 10
The Dominion House Bed & Breakfast
A hotel indoor pool with lounge chairs, a hot tub, and a warning sign.

15. Homewood Suites Stewart Airport

Homewood Suites Stewart Airport
3.0 star property
New Windsor
9.2 out of 10, Wonderful, (1,000 reviews)
Positioned 3.2 mi from Stewart Airport with complimentary shuttle service, this New Windsor hotel offers free breakfast, WiFi, and parking. Enjoy the indoor pool and 24-hour fitness center while staying near Hamilton Fish Bridge and Purple Heart Hall of Honor.
The price is $165
$195 total
includes taxes & fees
Nov 1 - Nov 2
Homewood Suites Stewart Airport
A hotel with a modern facade, multiple floors, and a covered entrance area.

16. Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG
2.5 star property
Middletown
8.8 out of 10, Excellent, (788 reviews)
Situated just minutes from LEGOLAND® New York and Galleria at Crystal Run, this hotel offers a refreshing indoor pool and fitness center. Enjoy complimentary breakfast, WiFi, and parking while the helpful staff ensures a pleasant stay in clean, business-friendly accommodations.
The price is $122
$144 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Express & Suites Middletown - Goshen by IHG
A reception area with a curved wooden reception desk, a glass table, and a chandelier.

17. Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point
2.0 star property
Newburgh
6.2 out of 10, Good, (1,003 reviews)
This tranquil hotel offers a remarkably quiet atmosphere despite its convenient location. Just 4 minutes from Stewart Airport and near Hamilton Fish Bridge, enjoy complimentary WiFi, parking, and on-the-go breakfast daily.
The price is $87
$103 total
includes taxes & fees
Nov 1 - Nov 2
Howard Johnson by Wyndham Newburgh/West Point
A hotel room with a bed, two bedside tables with lamps, a wall-mounted telephone, and a large black and white windmill painting.

18. Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown
2.5 star property
Middletown
6.0 out of 10, Good, (1,002 reviews)
Experience peaceful relaxation at this Middletown motel, just 15 minutes from LEGOLAND. Surrounded by restaurants and shopping, guests enjoy complimentary WiFi, free parking, and attentive 24-hour service near Galleria at Crystal Run.
The price is $71
$83 total
includes taxes & fees
Nov 1 - Nov 2
Super 8 by Wyndham Middletown
A compact hotel room with a sofa, a small dining table, a kitchenette with a microwave, and a window with curtains.

19. Microtel Inn & Suites by Wyndham Middletown

Microtel Inn & Suites by Wyndham Middletown
2.0 star property
Middletown
6.8 out of 10, Good, (1,002 reviews)
Wake up refreshed at this welcoming Middletown hotel where complimentary continental breakfast jumpstarts your day. Just a short drive from LEGOLAND® New York and Galleria at Crystal Run, enjoy free WiFi and parking while helpful staff ensure a pleasant stay.
The price is $94
$110 total
includes taxes & fees
Nov 1 - Nov 2
Microtel Inn & Suites by Wyndham Middletown
A hotel sign for Candlewood Suites, an IHG hotel, with a parking lot and cars in front.

20. Candlewood Suites Middletown Goshen by IHG

Candlewood Suites Middletown Goshen by IHG
2.5 star property
Middletown
9.4 out of 10, Exceptional, (92 reviews)
Set in Middletown, this hotel offers convenient access to LEGOLAND® New York and Galleria at Crystal Run. Just 28 minutes from Stewart Intl. Airport and 22 minutes from Harriman Station, it's perfectly positioned for regional exploration.
The price is $118
$139 total
includes taxes & fees
Nov 9 - Nov 10
Candlewood Suites Middletown Goshen by IHG
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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Go beyond your typical stay in Montgomery

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When is the best time to visit Montgomery?

Our prices for hotels in Montgomery are cheapest in February

Price trends for hotels in Montgomery

Pricing is based on two traveler single night rates
View properties in October
Currently viewing crowd sizes and weather for October.

October

High 17°C / low 7°C. Sunny most days.
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October, no crowd data, average high temperature 17 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
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November, no crowd data, average high temperature 10 degrees Celsius, average low temperature 1 degrees Celsius. Partly sunny.
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December, no crowd data, average high temperature 4 degrees Celsius, average low temperature -3 degrees Celsius. Snow likely.
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January, no crowd data, average high temperature 1 degrees Celsius, average low temperature -7 degrees Celsius. Snow likely.
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February, no crowd data, average high temperature 3 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
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March, no crowd data, average high temperature 8 degrees Celsius, average low temperature -2 degrees Celsius. Snow likely.
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April, no crowd data, average high temperature 14 degrees Celsius, average low temperature 4 degrees Celsius. Partly sunny.
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May, no crowd data, average high temperature 21 degrees Celsius, average low temperature 9 degrees Celsius. Sunny most days.
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June, no crowd data, average high temperature 25 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
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July, no crowd data, average high temperature 29 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
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August, no crowd data, average high temperature 28 degrees Celsius, average low temperature 16 degrees Celsius. Sunny most days.
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September, no crowd data, average high temperature 24 degrees Celsius, average low temperature 13 degrees Celsius. Sunny most days.
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Monthly weather averages (˚C)

Top landmarks in Montgomery

Orange County Arboretum

8.0/10 (6 reviews)
Why not give yourself a treat with a trip to Orange County Arboretum, one of the family attractions located 3.8 mi (6.2 km) from central Montgomery. If you'd also like to explore some of the parks in Montgomery, Thomas Bull Memorial Park is a short walk away.
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Learn more about Montgomery

Wander through a Hudson Valley time capsule where Clinton Street's historic buildings house shops that seem to have escaped the modern rush. The Orange County Arboretum offers botanical respite in Thomas Bull Memorial Park, with gardens that change their personality each season. City Winery Hudson Valley provides tastings with a side of culture in an atmospheric setting. Highland Lakes State Park rewards hikers with views that explain why painters have been drawn to this region for centuries. Nearby LEGOLAND New York amplifies childhood imagination. Lake Minnewaska Beach provides summer swimming with mountain backdrops. This former Revolutionary War outpost now serves as a charming refuge for New Yorkers seeking weekend sanctuary from city life.

See all hotels in Montgomery
A suspension bridge over a calm river with reflections, surrounded by hills and a clear sky.

Check out reviews of Montgomery hotels guests love

A Holiday Inn Express & Suites building with a covered entrance, stone facade, and a parking area with a bench.
Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG
Montgomery

10/10 Exceptional

Great stay
United States
Marissa
Reviewed April 12, 2025
Holiday Inn Express & Suites Montgomery by IHG

Frequently Asked Questions

What accommodations do travelers like in Montgomery?

Guests like Holiday Inn Express & Suites Montgomery by IHG, Super 8 by Wyndham Montgomery Maybrook and La Quinta Inn & Suites by Wyndham Middletown-Goshen.

Where can I find free parking with my stay in Montgomery?

Park your car for free at Borland House Inn.

Can I book a refundable hotel in Montgomery?

If you're looking for the flexibility to change your plans to Montgomery, most accommodations offer refundable* rates you can book. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.

Where can I stay in Montgomery if I want a vacation home instead of a traditional hotel?

If you're looking for a good alternative to a hotel, look over our selection of 14 vacation homes.

What will the weather in Montgomery be like during my trip?

July and August are typically the warmest months in Montgomery when the average temp is 69°F. January and February are the coldest months when the average temperature is 31°F. October and August are the months with the most rain.

Why should I book my Montgomery hotel through Hotels.com?

There are lots of reasons to book your Montgomery trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.