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Hotels in Montgomery
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Where to stay in Montgomery?
Borland House Inn
Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (144)
9.2/10
Wonderful
(144)
- Elegant Victorian escape with garden terrace near Hudson Valley attractions.
The price is $114
$114
$129 total
includes taxes & fees
Dec 28 - Dec 29
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, (801)
8.8/10
Excellent
(801)
- Enjoy a quick commute at this Montgomery haven with modern fitness and dining.
The price is $90
$90
$102 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Super 8 by Wyndham Montgomery Maybrook
Super 8 by Wyndham Montgomery Maybrook
2.5 star property
Montgomery
6.4 out of 10, (1002)
6.4/10
(1002)
- Enjoy a comfortable stay near City Winery with helpful staff and daily buffet breakfast.
The price is $74
$74
$84 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Courtyard by Marriott Newburgh Stewart Airport
Courtyard by Marriott Newburgh Stewart Airport
3.0 star property
Newburgh
8.2 out of 10, Very Good, (697)
8.2/10
Very Good
(697)
- A peaceful stay just minutes from the airport with complimentary shuttle service.
The price is $97
$97
$115 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The Crossroads Hotel, Newburgh
The Crossroads Hotel, Newburgh
3.0 star property
Newburgh
7.2 out of 10, Good, (702)
7.2/10
Good
(702)
- Peaceful retreat near Stewart Airport with convenient amenities and free parking.
The price is $98
$98
$116 total
includes taxes & fees
Dec 24 - Dec 25
Harvest Inn
Harvest Inn
2.5 star property
Pine Bush
9.4 out of 10, Exceptional, (560)
9.4/10
Exceptional
(560)
- Enjoy a serene countryside stay in Pine Bush with access to seasonal pool and cafe.
The price is $219
$219
$248 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Hampton Inn by Hilton Middletown
Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1007)
8.6/10
Excellent
(1007)
- Stay by the LEGOLAND® New York theme park and enjoy a refreshing outdoor pool.
The price is $75
$75
$89 total
includes taxes & fees
Dec 29 - Dec 30
Homewood Suites Stewart Airport
Homewood Suites Stewart Airport
3.0 star property
New Windsor
9.2 out of 10, Wonderful, (1002)
9.2/10
Wonderful
(1002)
- Restful suites near Stewart Airport with pool and fitness for transit-friendly comfort.
The price is $134
$134
$152 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Hampton Inn & Suites Newburgh Stewart Airport
Hampton Inn & Suites Newburgh Stewart Airport
2.5 star property
Newburgh
9.2 out of 10, Wonderful, (979)
9.2/10
Wonderful
(979)
The price is $106
$106
$125 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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, (940)
9.4/10
Exceptional
(940)
- Unwind in this tranquil hotel near Legoland, with pool and fitness amenities.
The price is $118
$118
$140 total
includes taxes & fees
Dec 28 - Dec 29
Courtyard by Marriott Middletown Goshen
Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.6 out of 10, Excellent, (1003)
8.6/10
Excellent
(1003)
- Warm indoor pool and 24-hour fitness center just minutes from LEGOLAND® New York.
The price is $93
$93
$109 total
includes taxes & fees
Dec 28 - Dec 29
Residence Inn by Marriott Middletown Goshen
Residence Inn by Marriott Middletown Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (317)
9.4/10
Exceptional
(317)
- Experience vibrant Middletown with easy access to LEGOLAND® New York and local attractions.
The price is $170
$170
$201 total
includes taxes & fees
Jan 11 - Jan 12, 2026
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, (1005)
8.4/10
Very Good
(1005)
- Unwind by the indoor pool near Stewart Airport, just minutes from downtown.
The price is $101
$101
$114 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Home2 Suites by Hilton Middletown
Home2 Suites by Hilton Middletown
3.0 star property
Middletown
9.0 out of 10, Wonderful, (746)
9.0/10
Wonderful
(746)
- Stylish extended-stay accommodation with a convenient fitness center and pool.
The price is $165
$165
$198 total
includes taxes & fees
Dec 25 - Dec 26
Tru by Hilton Middletown
Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (959)
8.6/10
Excellent
(959)
- Convenient stay near LEGOLAND® with free amenities for families and business trips.
The price is $95
$95
$112 total
includes taxes & fees
Jan 16 - Jan 17, 2026
Super 8 by Wyndham Middletown
Super 8 by Wyndham Middletown
2.5 star property
Middletown
6.0 out of 10, (1000)
6.0/10
(1000)
- Quiet retreat with nearby dining options and easy access to LEGOLAND New York.
The price is $77
$77
$90 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Howard Johnson by Wyndham Newburgh/West Point
Howard Johnson by Wyndham Newburgh/West Point
2.0 star property
Newburgh
6.0 out of 10, (1006)
6.0/10
(1006)
- Peaceful lodging near Stewart Airport with easy train access and free amenities.
The price is $78
$78
$92 total
includes taxes & fees
Dec 29 - Dec 30
Microtel Inn & Suites by Wyndham Middletown
Microtel Inn & Suites by Wyndham Middletown
2.0 star property
Middletown
7.0 out of 10, Good, (1000)
7.0/10
Good
(1000)
- Convenient lodging near LEGOLAND® New York with free breakfast to fuel family fun.
The price is $101
$101
$120 total
includes taxes & fees
Dec 25 - Dec 26
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, (697)
8.8/10
Excellent
(697)
- Experience a comfortable stay near LEGOLAND® New York with an indoor pool.
The price is $123
$123
$145 total
includes taxes & fees
Dec 28 - Dec 29
Newburgh Inn
Newburgh Inn
2.0 star property
Newburgh
5.4 out of 10, (115)
5.4/10
(115)
- Experience comfort minutes from Stewart Airport with free parking and WiFi.
The price is $81
$81
$102 total
includes taxes & fees
Dec 29 - Dec 30
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.
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.
Budget hotels in Montgomery and vicinity
8.6 out of 10, Excellent, (1007)
8.6/10
Excellent
(1007)
The price is $75
$75
$89 total
includes taxes & fees
Dec 29 - Dec 30
SureStay Plus Hotel by Best Western Highland Poughkeepsie
SureStay Plus Hotel by Best Western Highland Poughkeepsie2.5 star property
Highland
7.8 out of 10, Good, (949)
7.8/10
Good
(949)
The price is $80
$80
$90 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Americas Best Value Inn at Central Valley-Woodbury
Americas Best Value Inn at Central Valley-Woodbury2.0 star property
Central Valley
7.2 out of 10, Good, (1000)
7.2/10
Good
(1000)
The price is $82
$82
$100 total
includes taxes & fees
Dec 31 - Jan 1, 2026
9.0 out of 10, Wonderful, (1002)
9.0/10
Wonderful
(1002)
The price is $86
$86
$97 total
includes taxes & fees
Jan 4 - Jan 5, 2026
9.4 out of 10, Exceptional, (1006)
9.4/10
Exceptional
(1006)
The price is $87
$87
$99 total
includes taxes & fees
Jan 1 - Jan 2, 2026
8.6 out of 10, Excellent, (1005)
8.6/10
Excellent
(1005)
The price is $84
$84
$95 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Quality Inn & Suites Fishkill South near I-84
Quality Inn & Suites Fishkill South near I-842.5 star property
Fishkill
8.8 out of 10, Excellent, (1006)
8.8/10
Excellent
(1006)
The price is $89
$89
$101 total
includes taxes & fees
Dec 29 - Dec 30
Holiday Inn Express & Suites Montgomery by IHG
Holiday Inn Express & Suites Montgomery by IHG2.5 star property
Montgomery
8.8 out of 10, Excellent, (801)
8.8/10
Excellent
(801)
The price is $90
$90
$102 total
includes taxes & fees
Jan 4 - Jan 5, 2026
8.8 out of 10, Excellent, (1004)
8.8/10
Excellent
(1004)
The price is $91
$91
$103 total
includes taxes & fees
Dec 25 - Dec 26
8.6 out of 10, Excellent, (1002)
8.6/10
Excellent
(1002)
The price is $92
$92
$104 total
includes taxes & fees
Dec 29 - Dec 30
Courtyard by Marriott Middletown Goshen
Courtyard by Marriott Middletown Goshen3.0 star property
Middletown
8.6 out of 10, Excellent, (1003)
8.6/10
Excellent
(1003)
The price is $93
$93
$109 total
includes taxes & fees
Dec 28 - Dec 29
8.6 out of 10, Excellent, (959)
8.6/10
Excellent
(959)
The price is $95
$95
$112 total
includes taxes & fees
Jan 16 - Jan 17, 2026
7.8 out of 10, Good, (501)
7.8/10
Good
(501)
The price is $93
$93
$108 total
includes taxes & fees
Dec 29 - Dec 30
Comfort Suites Fishkill near Interstate 84
Comfort Suites Fishkill near Interstate 842.5 star property
Fishkill
9.2 out of 10, Wonderful, (1000)
9.2/10
Wonderful
(1000)
The price is $94
$94
$106 total
includes taxes & fees
Dec 29 - Dec 30
Holiday Inn Express Hotel & Suites Chester by IHG
Holiday Inn Express Hotel & Suites Chester by IHG2.5 star property
Chester
8.6 out of 10, Excellent, (1009)
8.6/10
Excellent
(1009)
The price is $95
$95
$112 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG2.5 star property
Fishkill
8.4 out of 10, Very Good, (1002)
8.4/10
Very Good
(1002)
The price is $95
$95
$107 total
includes taxes & fees
Jan 9 - Jan 10, 2026
7.6 out of 10, Good, (596)
7.6/10
Good
(596)
The price is $95
$95
$107 total
includes taxes & fees
Dec 28 - Dec 29
7.4 out of 10, Good, (150)
7.4/10
Good
(150)
The price is $95
$95
$107 total
includes taxes & fees
Dec 24 - Dec 25
7.2 out of 10, Good, (264)
7.2/10
Good
(264)
The price is $95
$95
$103 total
includes taxes & fees
Dec 26 - Dec 27
Sleep Inn & Suites Middletown - Goshen
Sleep Inn & Suites Middletown - Goshen2.5 star property
Middletown
8.6 out of 10, Excellent, (1006)
8.6/10
Excellent
(1006)
The price is $100
$100
$118 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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.
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.
Go beyond your typical stay in Montgomery
Family friendly
Pet friendly
Apartment
Cottage
When is the best time to visit Montgomery?
When is the best time to visit Montgomery?Our prices for hotels in Montgomery are cheapest in March
When is the best time to visit Montgomery?
When is the best time to visit Montgomery?
Our prices for hotels in Montgomery are cheapest in March
Price trends for hotels in Montgomery
Pricing is based on two traveler single night rates
Currently viewing crowd sizes and weather for December.
Typical weather for Montgomery
December
Moderate crowds
High 4°C / low -3°C. Snow likely.
View properties in December 4°
December, Moderate crowds, average high temperature 4 degrees Celsius, average low temperature -3 degrees Celsius. Snow likely.
-3°
1°
January, Low crowds, average high temperature 1 degrees Celsius, average low temperature -7 degrees Celsius. Snow likely.
-7°
3°
February, Low crowds, average high temperature 3 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
8°
March, Low crowds, average high temperature 8 degrees Celsius, average low temperature -2 degrees Celsius. Snow likely.
-2°
14°
April, Low crowds, average high temperature 14 degrees Celsius, average low temperature 4 degrees Celsius. Partly sunny.
4°
21°
May, Moderate crowds, average high temperature 21 degrees Celsius, average low temperature 9 degrees Celsius. Sunny most days.
9°
25°
June, Moderate crowds, average high temperature 25 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
29°
July, High crowds, average high temperature 29 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
17°
28°
August, High crowds, average high temperature 28 degrees Celsius, average low temperature 16 degrees Celsius. Sunny most days.
16°
24°
September, High crowds, average high temperature 24 degrees Celsius, average low temperature 13 degrees Celsius. Sunny most days.
13°
17°
October, High crowds, average high temperature 17 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
7°
10°
November, Moderate crowds, average high temperature 10 degrees Celsius, average low temperature 1 degrees Celsius. Partly sunny.
1°
Monthly weather averages (˚C)
Top landmarks in Montgomery
Learn more about Montgomery
Montgomery is well-known for its attractions such as City Winery Hudson Valley and Orange County Arboretum. Visitors to this family-friendly city speak highly of the restaurants whereas sights include Highland Lakes State Park and Orange County Tennis Center.
Check out reviews of Montgomery hotels guests love
Courtyard by Marriott Poughkeepsie
10/10 Excellent
"A nice, clean hotel perfect for a quick business/recreational trip"
Resorts World Catskills Casino
10/10 Excellent
"Excellent "
Hampton Inn Harriman Woodbury
10/10 Excellent
"Verry clean"
The Kartrite Resort & Indoor Waterpark
10/10 Excellent
"Amazing experience… must do it"
Hyatt Place Poughkeepsie / Hudson Valley
10/10 Excellent
"Staff very helpful."
Sleep Inn & Suites Monroe - Woodbury
10/10 Excellent
"Clean. Easy exit off highway. Great hotel for the price just needed a safe clean overnight bed."
Hampton Inn & Suites Poughkeepsie
10/10 Excellent
"Very clean. Friendly staff. Breakfast was excellent. Room was great. What a surprise that Santa was there for breakfast. Would definitely go back."
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
10/10 Excellent
"Great staff, comfy room "
Sleep Inn & Suites Middletown - Goshen
10/10 Excellent
"Very nice and cleab"
Frequently asked questions
What accommodations do travelers like in Montgomery?
Holiday Inn Express & Suites Montgomery by IHG and Super 8 by Wyndham Montgomery Maybrook are a couple of accommodations that are popular with guests.
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 11 vacation homes. In addition, you can choose from 5 apartments.
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.