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Find vacation rentals that suit your style

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Apartments

Aparthotels

Cottages

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Chalets
Our top choices for Montgomery chalets




1. Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside saunaGardiner
9.8 out of 10, Exceptional, (30 reviews)
9.8/10
Exceptional
(30 reviews)
"Wonderful stay!"
"Wonderful stay!"Bernice
$318 nightly
The price is $321
$321 total
Nov 19 - Nov 20
Total with taxes and fees




2. Mountain View Retreat w/ Hot Tub, Theater, and Gym
Mountain View Retreat w/ Hot Tub, Theater, and GymWarwick
10.0 out of 10, Exceptional, (6 reviews)
10/10
Exceptional
(6 reviews)
"Amazing stay on a beautiful place!"
"Amazing stay on a beautiful place!"Dorian G.
$1,166 nightly
The price is $1,319
$1,319 total
Nov 8 - Nov 9
Total with taxes and fees
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.
Learn more about Montgomery
Stroll through charming streets lined with historic buildings, soaking in the small-town atmosphere of this Hudson Valley gem. Explore nearby wineries and parks, or catch a show at the City Winery for a perfect blend of culture and nature.

Top reviews in Montgomery




Holiday Inn Express & Suites Montgomery by IHG
Holiday Inn Express & Suites Montgomery by IHGMontgomery
10/10 Excellent
Great stay
Great stay
Marissa




Borland House Inn
Borland House InnMontgomery
10/10 Excellent
Lovely place. Very special, can’t wait to return.
Lovely place. Very special, can’t wait to return.
Kate




La Quinta Inn & Suites by Wyndham Middletown-Goshen
La Quinta Inn & Suites by Wyndham Middletown-GoshenMiddletown
10/10 Excellent
I loved how clean my room was. It was simple but had everything you needed. It was very quiet and I didn’t not hear anything from outside my room while I was in there.
I loved how clean my room was. It was simple but had everything you needed. It was very quiet and I didn’t not hear anything from outside my room while I was in there.
Jordan




Harvest Inn
Harvest InnPine Bush
10/10 Excellent
I've stayed at Harvest Inn for more than 15 years. It keeps getting better.
I've stayed at Harvest Inn for more than 15 years. It keeps getting better.
Elizabeth




Tin Brook Bed & Breakfast
Tin Brook Bed & BreakfastWalden
10/10 Excellent
Adorable gift shop in the breakfast area. Friendly host (Carrie?). Could have used some bottled water
Adorable gift shop in the breakfast area. Friendly host (Carrie?). Could have used some bottled water
Anonymous traveler




Candlewood Suites Middletown Goshen by IHG
Candlewood Suites Middletown Goshen by IHGMiddletown
10/10 Excellent
Very Good
Very Good
Moraivic




Tru by Hilton Middletown
Tru by Hilton MiddletownMiddletown
10/10 Excellent
Love coming to this hotel, it has a wonderful atmosphere, caring staff and the environment is throughly clean and friendly. Saxida is very lovley and accommodating she definitely cares about the guests that come in and any problems that may occur she is urgent to fix it I appreciate how she remembered who I was and her energy is full of light. I appreciate everything this hotel has to offer and will be returning to make more fun memories in the future!
Love coming to this hotel, it has a wonderful atmosphere, caring staff and the environment is throughly clean and friendly. Saxida is very lovley and accommodating she definitely cares about the guests that come in and any problems that may occur she is urgent to fix it I appreciate how she remembered who I was and her energy is full of light. I appreciate everything this hotel has to offer and will be returning to make more fun memories in the future!
Daniela




The Dominion House Bed & Breakfast
The Dominion House Bed & BreakfastChester
10/10 Excellent
Lovely period home. Owners were friendly, courteous and informative. Breakfast was delicious. Overall stay was very enjoyable and would stay again.
Lovely period home. Owners were friendly, courteous and informative. Breakfast was delicious. Overall stay was very enjoyable and would stay again.
Cindy




Homewood Suites Stewart Airport
Homewood Suites Stewart AirportNew Windsor
10/10 Excellent
Needed a place to stay when moving to the area. This hotel was conveniently located and very affordable - especially considering what you get! The suites were fantastic - spacious, everything we needed, kitchenettes. On top of that they serve a good hot breakfast every morning and a manager's reception (which is essentially a meal) four nights a week. What a deal! Friendly, helpful staff too. I truly don't have anything negative to say about this hotel.
Needed a place to stay when moving to the area. This hotel was conveniently located and very affordable - especially considering what you get! The suites were fantastic - spacious, everything we needed, kitchenettes. On top of that they serve a good hot breakfast every morning and a manager's reception (which is essentially a meal) four nights a week. What a deal! Friendly, helpful staff too. I truly don't have anything negative to say about this hotel.
Anonymous traveler




Hampton Inn by Hilton Middletown
Hampton Inn by Hilton MiddletownMiddletown
10/10 Excellent
10/10! Super close to whatever you need, comfy beds and beautiful atmosphere. Perfect place to bring the kids after Legoland 😁
10/10! Super close to whatever you need, comfy beds and beautiful atmosphere. Perfect place to bring the kids after Legoland 😁
Destiny




Courtyard by Marriott Newburgh Stewart Airport
Courtyard by Marriott Newburgh Stewart AirportNewburgh
10/10 Excellent
Clean room, clean premises. lobby area was clean, smelled great and they had fresh water with lemon for the guests. Pool area was clean and was fully stocked with towels. Staff was friendly, Nicole checked me in, she was friendly, made me feel welcome and asked if everything in the room was okay after check in. Close to the highway, airport and shopping. Will stay again if in the area.
Clean room, clean premises. lobby area was clean, smelled great and they had fresh water with lemon for the guests. Pool area was clean and was fully stocked with towels. Staff was friendly, Nicole checked me in, she was friendly, made me feel welcome and asked if everything in the room was okay after check in. Close to the highway, airport and shopping. Will stay again if in the area.
Michelle




Courtyard by Marriott Middletown Goshen
Courtyard by Marriott Middletown GoshenMiddletown
10/10 Excellent
We only stayed one night, but we will be back. It seemed like a really nice place with more to offer than surrounding hotels.
We only stayed one night, but we will be back. It seemed like a really nice place with more to offer than surrounding hotels.
Kathleen




Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Red Roof Inn & Suites Newburgh – Stewart Airport/ West PointNew Windsor
10/10 Excellent
Red Roof was very nice first time staying at Red Roof and it was one of the cleanest hotel I stayed in. I can't believe I've been missing out.
Red Roof was very nice first time staying at Red Roof and it was one of the cleanest hotel I stayed in. I can't believe I've been missing out.
Belinda




Residence Inn by Marriott Middletown Goshen
Residence Inn by Marriott Middletown GoshenMiddletown
10/10 Excellent
Everything was beautiful, it looks like a new property. My only complaint was after shutting off the air conditioner/heater it still remained on and was very noisy keeping my wife and I up most of the night. Even switching the circuit breaker off didn’t solve the problem.
I’m not one to complain though and didn’t bother the staff at the late hour. I still wouldn’t hesitate to stay at a residence inn property in the future.
Everything was beautiful, it looks like a new property. My only complaint was after shutting off the air conditioner/heater it still remained on and was very noisy keeping my wife and I up most of the night. Even switching the circuit breaker off didn’t solve the problem.
I’m not one to complain though and didn’t bother the staff at the late hour. I still wouldn’t hesitate to stay at a residence inn property in the future.
Joseph




Super 8 by Wyndham Montgomery Maybrook
Super 8 by Wyndham Montgomery MaybrookMontgomery
10/10 Excellent
Clean, basic lodging, with comfortable mattress, nice hot shower, no-nonsense toilet, no loud A/C that keeps very basic yet spacious room comfortable. Scrambled egg n sausage, toasted waffles breakfast, fresh coffee.
Clean, basic lodging, with comfortable mattress, nice hot shower, no-nonsense toilet, no loud A/C that keeps very basic yet spacious room comfortable. Scrambled egg n sausage, toasted waffles breakfast, fresh coffee.
david




Holiday Inn Express & Suites Middletown - Goshen by IHG
Holiday Inn Express & Suites Middletown - Goshen by IHGMiddletown
10/10 Excellent
We liked everything about the hotel!
The room was clean, breakfast was delicious, the staff was so friendly!
We can't say enough nice things about the hotel!
We liked everything about the hotel!
The room was clean, breakfast was delicious, the staff was so friendly!
We can't say enough nice things about the hotel!
Kathleen




Home2 Suites by Hilton Middletown
Home2 Suites by Hilton MiddletownMiddletown
10/10 Excellent
Loved the large spacious and well laid out room. Breakfast was great but the space was a bit crowded.
Loved the large spacious and well laid out room. Breakfast was great but the space was a bit crowded.
Anonymous traveler
