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Aug 15 - Aug 17
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Browse Select Montgomery Vacation Homes

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Relax on the serene deck, surrounded by bare trees and a frozen lake.

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (301)
"The lake views at this house are absolutely worth the trip and the money. It's a beautiful spot. And the host, Don, is super responsive, thoughtful and accommodating. Highly recommend!"
The price is CA $618
CA $818 total
includes taxes & fees
Aug 24 - Aug 25
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Relax in this serene outdoor seating area with a covered patio overlooking a lush garden.

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.8 out of 10, Exceptional, (27)
"Perfect for small family stay over for a wedding ! "
The price is CA $356
CA $461 total
includes taxes & fees
Aug 31 - Sep 1
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Relax in a hot tub with a serene lake and forest view.

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

9.8 out of 10, Exceptional, (17)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is CA $427
CA $907 total
includes taxes & fees
Aug 13 - Aug 14
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Enjoy cooking in this well-equipped kitchen with a large island, oven, and stainless steel range hood.

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
9.8 out of 10, Exceptional, (12)
"A group of girlfriends stayed for a 2 night visit. Everything was just as listed, the home was in the perfect location, well stocked, and beautiful inside. We would definitely return again. "
The price is CA $550
CA $814 total
includes taxes & fees
Aug 13 - Aug 14
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Experience the classic elegance of this beautifully appointed room, featuring a stunning chandelier, comfortable sofa, and elegant artwork.

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

6.0 out of 10, (1)
"Although the original check-in process was fine, the host became unresponsive to our questions during the stay. We were able to figure out the answers to our questions, but it would have been nice to hear anything at all. We went so far as to text the host because we became concerned after radio silence for 3 days. Once she did respond she didn't apologize for not getting back to us and ghosting us for days. "
The price is CA $166
CA $262 total
includes taxes & fees
Aug 13 - Aug 14
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Red Barn Retreat - Shawangunk Mountains Getaway
Enjoy al fresco dining on this outdoor deck with a barbecue grill and seating for four.

Red Barn Retreat - Shawangunk Mountains Getaway

10.0 out of 10, Exceptional, (50)
"The property is close to Minawaska State Park where we went hiking. We enjoyed the hot tub and had a nice stay. There are a number of nice restaurants nearby too."
Red Barn Retreat - Shawangunk Mountains Getaway
Play, Swim & Unwind: Family Home in Glen Wild!
Fridge, microwave, stovetop, dishwasher

Play, Swim & Unwind: Family Home in Glen Wild!

8.0 out of 10, Very good, (1)
"Had an issue with the Internet when we arrived. The maintenance people cut the cable coming into the house when they were cutting the grass. It was hard to work while I was there as I expected to have Internet access. Eventually it was fixed but it took a few days. Aside from this the house was pleasant and the kids loved the pool and basketball court. "
Play, Swim & Unwind: Family Home in Glen Wild!
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Terrace/patio

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

9.6 out of 10, Exceptional, (8)
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Enjoy a serene view of lush greenery from the bay window, accompanied by a stylish seating area with a vase of flowers.

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

10.0 out of 10, Exceptional, (1)
"My girlfriend and I loved our stay here! We stayed for one night and it was perfect for what we needed. Very clean with easy self-check-in. The host was very responsive with all inquiries. Short walk to nice downtown area as well!"
The price is CA $129
CA $221 total
includes taxes & fees
Sep 2 - Sep 3
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
The Warwick Inn Boutique Amity Room 3 an Hour from NYC
Interior

The Warwick Inn Boutique Amity Room 3 an Hour from NYC

8.6 out of 10, Excellent, (4)
"Was happy with the room, nice property easy to walk to main street. Would stay there again."
The price is CA $152
CA $247 total
includes taxes & fees
Aug 11 - Aug 12
The Warwick Inn Boutique Amity Room 3 an Hour from NYC
Dog friendly private 3-bedroom house bordering the Mohonk Preserve
Escape to a secluded cabin nestled among the trees, with a charming front porch and staircase leading to the upper level.

Dog friendly private 3-bedroom house bordering the Mohonk Preserve

10.0 out of 10, Exceptional, (7)
Dog friendly private 3-bedroom house bordering the Mohonk Preserve
Trails Head Tiny House
Steps lead up to a cozy porch with a door in the center.

Trails Head Tiny House

9.2 out of 10, Wonderful, (17)
"A lovely tiny house, great hosts "
The price is CA $110
CA $185 total
includes taxes & fees
Aug 17 - Aug 18
Trails Head Tiny House
The Studio at the Inn at High Falls
Situated in a lush forest, this cabin offers a serene retreat with a symmetrical facade and a well-manicured lawn.

The Studio at the Inn at High Falls

8.0 out of 10, Very good, (26)
"I had a great stay here, it’s just as listed; simple but has everything that I needed, check in was easy, communication was good, and bed was comfortable!"
The price is CA $155
CA $372 total
includes taxes & fees
Aug 11 - Aug 12
The Studio at the Inn at High Falls
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
Private kitchen

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

The price is CA $276
CA $702 total
includes taxes & fees
Aug 11 - Aug 12
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
The Loft At The Inn At High Falls
Cozy attic bedroom with a large bed, bedside table, and window.

The Loft At The Inn At High Falls

9.2 out of 10, Wonderful, (16)
"this was just a lovely stay all around!! Will absolutely stay there again!"
The price is CA $248
CA $492 total
includes taxes & fees
Aug 11 - Aug 12
The Loft At The Inn At High Falls
The Woodbury Cottage
Relax in a serene outdoor space surrounded by lush greenery and trees, perfect for unwinding with a hammock and golf course nearby.

The Woodbury Cottage

8.8 out of 10, Excellent, (23)
"Really enjoyed our stay at this comfy cottage. Easily slept a family of 3 with plenty of room to lounge around. It's an older cottage, but the owner has added a lot of neat touches that make this a nice place to stay in this area."
The Woodbury Cottage
Charming Highland Falls Home < 2 Mi to West Point!
Cozy cottage with a covered porch, gabled roof, and a charming garden.

Charming Highland Falls Home < 2 Mi to West Point!

10.0 out of 10, Exceptional, (9)
"Wonderful front porch "
Charming Highland Falls Home < 2 Mi to West Point!
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons
Cozy living space with a fireplace, comfortable seating, and a dining area.

Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

2.0 star property
9.4 out of 10, Exceptional, (8)
"This property is great, our stay here was just amazing from start to finish. Communication with the host was great, we left some items there and the host was super accommodating. Would recommend this property very highly."
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
Enjoy a spacious room with a high ceiling, large window, and cozy dining area.

Pet-Friendly ‘Pond View Loft' w/ Private Pool!

9.6 out of 10, Exceptional, (11)
"We loved the new furniture and sheets and blankets. Everything was spotless and felt super comfortable and homey. Big space as well! "
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
The House In Highland- Secluded Retreat
Enjoy outdoor dining and relaxation on the spacious deck with comfortable seating and a barbecue grill.

The House In Highland- Secluded Retreat

10.0 out of 10, Exceptional, (9)
"We had an absolutely wonderful stay at Highland House! This beautiful property is nestled in the woods, providing a serene and peaceful environment, yet it is conveniently close to town, making it easy to access local amenities and attractions. The kitchen was a standout feature, stocked with everything you could possibly need. From a Keurig and coffee pot to a tea kettle and KitchenAid mixer, it had all the appliances and utensils necessary for cooking up a storm. The variety of pots and pans...
The House In Highland- Secluded Retreat
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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Top Montgomery Hotel Reviews

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent
"Bed comfort"
Juan 1-night trip
Posted 11 hours ago
La Quinta Inn & Suites by Wyndham Middletown-Goshen