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Check prices for these dates

Next weekend
Aug 22 - Aug 24
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Aug 29 - Aug 31
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Sep 12 - Sep 14
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Oct 10 - Oct 12

Browse Select Bear Mountain 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, (302)
"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 $454 total
includes taxes & fees
Aug 31 - Sep 1
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel stove, and ample counter space.

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (86)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
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 $402
CA $872 total
includes taxes & fees
Aug 13 - Aug 14
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
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
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, (9)
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 $151
CA $246 total
includes taxes & fees
Aug 19 - Aug 20
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 12 - Aug 13
The Warwick Inn Boutique Amity Room 3 an Hour from NYC
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Cozy living room with a fireplace, flat-screen TV, and comfortable seating area.

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

9.0 out of 10, Wonderful, (37)
"Perfect spot for a get together with friends... kitchen, dining room and living room all connected so you're always together and not missing out on the fun. Comfy couches and plenty of space for large board games."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.
Microwave, oven, stovetop, dishwasher

Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.

Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.
Modern NY Home w/ Views By Hudson Valley Hiking!
Relax in this stylish living space with a large sofa, matching ottoman, and modern light fixture.

Modern NY Home w/ Views By Hudson Valley Hiking!

9.8 out of 10, Exceptional, (25)
"Lovely home and great proximity to Taconic Parkway for all points north and south. Owner very accomodating"
Modern NY Home w/ Views By Hudson Valley Hiking!
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!
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Prepare meals in the spacious kitchen with a large island and appliances.

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

10.0 out of 10, Exceptional, (36)
"Perfect for our family’s visit to West Point. Great location "
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
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
Stylish & Peaceful Getaway on 3 Private Acres
Relax on the covered deck with a view of lush greenery and trees, featuring a round table, cushioned seating, and a flat-screen TV.

Stylish & Peaceful Getaway on 3 Private Acres

2.0 star property
8.6 out of 10, Excellent, (7)
"The location is close to legoland which is nice. They had connect 4 and some playing cards otherwise the property isnt great for little ones due to some odd decor choices. There were ants and a spider and unsure about the cleaning. Thermostat didnt adjust and dishwasher didnt work. Tvs were hard to use. Wish there had been printed instructions for where to find things in the house, as well as recommendations in the town. Didnt use outdoor deck because too cold but also couldnt open the door and...
The price is CA $396
CA $579 total
includes taxes & fees
Aug 12 - Aug 13
Stylish & Peaceful Getaway on 3 Private Acres
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Kitchen features stainless steel appliances, a large window, and wooden shelves.

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

10.0 out of 10, Exceptional, (54)
"Awesome property. Will visit again. "
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Bright Cornwall-On-Hudson Vacation Rental!
Enjoy cooking in this well-lit kitchen with a stainless steel range, oven, and cabinetry.

Bright Cornwall-On-Hudson Vacation Rental!

10.0 out of 10, Exceptional, (22)
"Property was perfect for our needs."
Bright Cornwall-On-Hudson Vacation Rental!
Home: 2 Mi to Thayer Gate at U.S. Military Academy
Kitchen features microwave, toaster, and oven, along with a large sink and staircase to the upper level.

Home: 2 Mi to Thayer Gate at U.S. Military Academy

10.0 out of 10, Exceptional, (2)
"Your home was amazing! My family and I enjoyed every minute! "
Home: 2 Mi to Thayer Gate at U.S. Military Academy
Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town
Enjoy cooking in this kitchen with sleek appliances, light grey cabinetry, and a wooden floor.

Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town

10.0 out of 10, Exceptional, (3)
"The house was big enough for 2 families. It was very clean and comfortable. The property is beautiful and Cold Springs was the perfect spot for everything we wanted to do while in NY. The caretakers were very responsive and accommodating. We would definitely stay here again. "
Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town
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 Bear Mountain Hotel Reviews

Wingate by Wyndham Fishkill

Wingate by Wyndham Fishkill

10/10 Excellent
"Beautiful renovated hotel. We loved our stay here"
Eliza 1-night trip
Posted 1 day ago
Wingate by Wyndham Fishkill