Bear Mountain Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Bear Mountain holiday rentals

Interior

Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
3.0 star property
Highland Falls
The price is HK$1,920
HK$4,872 total
includes taxes & fees
2 Jun - 3 Jun
Updated Home w/ Patio Half Mile to West Point
Fridge, microwave, oven, stovetop

Luxury 3BR with King Beds in Montgomery Village

Luxury 3BR with King Beds in Montgomery Village
Montgomery
10.0 out of 10, Exceptional, (2 reviews)
"Excellent location! Very clean and the hosts were quick to respond to communication. We would definitely stay here again. "
United States
Barbara M.
The price is HK$2,118
HK$3,755 total
includes taxes & fees
26 May - 27 May
Luxury 3BR with King Beds in Montgomery Village
Exterior

Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.6 out of 10, Exceptional, (4 reviews)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
The price is HK$3,879
HK$5,577 total
includes taxes & fees
26 May - 27 May
Chestnut on Willow Lake
Terrace/patio

Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
9.8 out of 10, Exceptional, (14 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is HK$1,324
HK$2,212 total
includes taxes & fees
31 May - 1 Jun
Cabin in the heart of the Hudson Valley, Cabin 3
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (138 reviews)
"The space was comfortable and clean with a great view of the Hudson River valley. Perfect for 2 people on a weekend getaway. "
United States
Meredith C.
The price is HK$1,551
HK$2,481 total
includes taxes & fees
27 May - 28 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (32 reviews)
"Cute, clean and perfect for our needs"
United States
Richard H.
The price is HK$1,324
HK$2,184 total
includes taxes & fees
1 Jun - 2 Jun
Cabin in the Heart of the Hudson Valley, Cabin 1
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (34 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is HK$1,763
HK$3,289 total
includes taxes & fees
31 May - 1 Jun
Contemporary Cozy Cottage
Private kitchen

2-bedroom apartment in excellent Newburgh with AC and charm

2-bedroom apartment in excellent Newburgh with AC and charm
Newburgh
10.0 out of 10, Exceptional, (1 review)
"We have stayed here once before overnight while in the area for an event. It is close to where we needed to be and a great value for the price"
United States
Nick L.
The price is HK$1,481
HK$1,906 total
includes taxes & fees
1 Jun - 2 Jun
2-bedroom apartment in excellent Newburgh with AC and charm
Interior

Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.
Newburgh
9.0 out of 10, Wonderful, (15 reviews)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is HK$3,244
HK$4,350 total
includes taxes & fees
6 Jun - 7 Jun
Large,Cozy,Bright Apartment, Business Themed.
Outdoor dining

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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (65 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is HK$1,939
HK$2,523 total
includes taxes & fees
31 May - 1 Jun
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Interior

Entire Lakeview House ~ 1 hour to MetLife ~ Hot Tub~Firepit~Stunning View~Decks

Entire Lakeview House ~ 1 hour to MetLife ~ Hot Tub~Firepit~Stunning View~Decks
Greenwood Lake
10.0 out of 10, Exceptional, (8 reviews)
"We had lovely and relaxing stay at this property! The surrounding area is beautiful and the crowd are amazing!"
United States
Susan R.
The price is HK$2,856
HK$6,121 total
includes taxes & fees
26 May - 27 May
Entire Lakeview House ~ 1 hour to MetLife ~ Hot Tub~Firepit~Stunning View~Decks
Exterior

Modern penthouse suite in a restored grain tower with private roof deck.

Modern penthouse suite in a restored grain tower with private roof deck.
Warwick
10.0 out of 10, Exceptional, (27 reviews)
"Wonderful stay!"
United States
Lisi M.
The price is HK$2,644
HK$4,171 total
includes taxes & fees
29 May - 30 May
Modern penthouse suite in a restored grain tower with private roof deck.
Interior

Harriman Outdoor Center - White Oak Cabin

Harriman Outdoor Center - White Oak Cabin
Haverstraw
The price is HK$1,747
HK$2,009 total
includes taxes & fees
26 May - 27 May
Harriman Outdoor Center - White Oak Cabin
Exterior detail

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is HK$1,775
HK$4,208 total
includes taxes & fees
27 May - 28 May
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
TV

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (2 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is HK$806
HK$1,561 total
includes taxes & fees
26 May - 27 May
Cozy 1-bedroom retreat minutes from West Point!
Exterior

Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (3 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
The price is HK$2,370
HK$3,551 total
includes taxes & fees
26 May - 27 May
Rustic Cabin in Fishkill!
Interior

Family Home Close to Warwick, 5 Mi to Lake!

Family Home Close to Warwick, 5 Mi to Lake!
3.0 star property
Monroe
The price is HK$2,155
HK$5,663 total
includes taxes & fees
10 Jun - 11 Jun
Family Home Close to Warwick, 5 Mi to Lake!
Outdoor spa tub

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Greenwood Lake
9.8 out of 10, Exceptional, (37 reviews)
"Great communication with the host and its a beautiful home. Very clean and a great location with wonderful views."
United States
Frank M.
The price is HK$1,959
HK$4,521 total
includes taxes & fees
9 Jun - 10 Jun
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
TV

Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
Highland Falls
10.0 out of 10, Exceptional, (33 reviews)
"Great location, good communication, and wonderfully appointed."
United States
george l.
The price is HK$1,716
HK$4,495 total
includes taxes & fees
2 Jun - 3 Jun
Updated Home w/ Patio Half Mile to West Point
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

Windrose On Hudson

Windrose On Hudson

8/10 Good
"Beautiful property and lobby. Almost no wifi connection and couldn’t lock the bathroom door"
Jennifer 3-night trip
Posted less than an hour ago
Windrose On Hudson

Find out more about Bear Mountain

Search for holiday rentals in Bear Mountain on Expedia! You can easily find your home rentals, villas, holiday apartments in Bear Mountain using one of the methods below:

  • View our selection of featured holiday rentals in Bear Mountain
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  • Enter your travel dates to view the best deals on holiday rentals in Bear Mountain while they last

Look no further and take a look at our great range of rental properties in Bear Mountain!

Frequently asked questions

Can I find holiday rentals in Bear Mountain?

Yes, there are holiday rentals close to the most popular sights in Bear Mountain, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the mountain landscape and lakeside in Bear Mountain. Make sure you allow time to enjoy the forests during your holiday.

What are some of the best holiday rentals that Bear Mountain has to offer?

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. : This holiday home rental outside of Bear Mountain is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

What’s there to see and do in Bear Mountain?

Explore the area and family-friendly sights such as Ice Time Sports Complex, or get out into nature at a spot like Blue Mountain Reservation. While here, Bear Mountain State Park and Harriman State Park are other places worth a visit.

What’s a holiday rental in Bear Mountain like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Bear Mountain. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for small groups.