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Find vacation rentals that suit your style

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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
$264 nightly
The price is $266
$266 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.
$1,169 nightly
The price is $1,323
$1,323 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




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




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




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




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




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




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




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




The Orange Inn Boutique Hotel
The Orange Inn Boutique HotelGoshen
10/10 Excellent
Well maintained and clean property , inside and out. We could have gotten more of an overview of the property when we checked in, but we managed. Ample parking available in their parking lot in the back. One thing I was surprised about -for a luxury inn , they had polyester sheets instead of cotton sheets. Overall great stay.
Well maintained and clean property , inside and out. We could have gotten more of an overview of the property when we checked in, but we managed. Ample parking available in their parking lot in the back. One thing I was surprised about -for a luxury inn , they had polyester sheets instead of cotton sheets. Overall great stay.
Kevin




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




Parkway House Goshen Family-Friendly Bed & Breakfast
Parkway House Goshen Family-Friendly Bed & BreakfastGoshen
10/10 Excellent
What a amazing property the stuff are amazin
What a amazing property the stuff are amazin
Crystal




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




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




Stagecoach Inn
Stagecoach InnGoshen
10/10 Excellent
This Inn is a relaxation paradise.Warm & welcoming staff, beautiful & extremely comfortable room ,with a choice of elegantly designed rooms throughout the Inn to enjoy a drink or dinner .The food is delicious!Everything we order from apps to entrees ,desserts & drinks right down to the bkfst was wonderful!I highly recommend booking a night or 2 here.We will definitely be back!
This Inn is a relaxation paradise.Warm & welcoming staff, beautiful & extremely comfortable room ,with a choice of elegantly designed rooms throughout the Inn to enjoy a drink or dinner .The food is delicious!Everything we order from apps to entrees ,desserts & drinks right down to the bkfst was wonderful!I highly recommend booking a night or 2 here.We will definitely be back!
Alissa




The Heartwood
The HeartwoodArlington
10/10 Excellent
All great cheating system was a little noisy but still an excellent experience. Would definitely stay here again.
All great cheating system was a little noisy but still an excellent experience. Would definitely stay here again.
Paulette




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




Home2 Suites By Hilton Poughkeepsie
Home2 Suites By Hilton PoughkeepsiePoughkeepsie
10/10 Excellent
Comfy. Homey. Clean. Brightly lit and cheery lobby area. Great breakfast setup. Nice bedding. Spacious suite style. Easy and quick drive to Marist. Very small downers: Parking lot a tad cramped and narrow. Muddy construction lot in front. Desk staff tends to stray away from the desk and there was no telling when they would be back. Could use a desk sign or something saying "Back in 15 minutes."
Comfy. Homey. Clean. Brightly lit and cheery lobby area. Great breakfast setup. Nice bedding. Spacious suite style. Easy and quick drive to Marist. Very small downers: Parking lot a tad cramped and narrow. Muddy construction lot in front. Desk staff tends to stray away from the desk and there was no telling when they would be back. Could use a desk sign or something saying "Back in 15 minutes."
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
