A wooden bridge over a river, surrounded by autumn-colored trees and a hill in the background.

Bear Mountain Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Bear Mountain vacation rentals

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, (140 reviews)
"We had a great stay!!"
United States
Jasmine
The price is ￥32,419
￥54,154 total
includes taxes & fees
Aug 3 - Aug 4
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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, (3 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 ￥23,518
￥41,700 total
includes taxes & fees
Jul 29 - Jul 30
Cozy 1-bedroom retreat minutes from West Point!
Terrace/patio

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (10 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is ￥20,466
￥65,500 total
includes taxes & fees
Aug 1 - Aug 2
House on the Babbling Brook- Quiet 2BR + King Bed!
Interior

Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is ￥33,576
￥61,965 total
includes taxes & fees
Jul 29 - Jul 30
Lovely 3BR Home with parking-Walk to WP Gate!
Coffee/tea maker, fridge, microwave, oven

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
The price is ￥29,416
￥51,138 total
includes taxes & fees
Jul 29 - Jul 30
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Exterior detail

West Point at Your Doorstep! Walk to Academy • Mountain Views • Easy Parking

West Point at Your Doorstep! Walk to Academy • Mountain Views • Easy Parking
Highland Falls
9.4 out of 10, Exceptional, (29 reviews)
"Our stay was excellent! Extremely clean, everything we needed. Walkable to everything in town. Great communication work h Host. We will definitely be staying again. "
United States
Joelle M.
The price is ￥53,212
￥87,238 total
includes taxes & fees
Jul 31 - Aug 1
West Point at Your Doorstep! Walk to Academy • Mountain Views • Easy Parking
3 bedrooms, desk, iron/ironing board, travel crib

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (18 reviews)
"Sweet abode. Cozy, clean and amazing location. The cute coffee bar was a nice bonus. Would definitely stay there again. "
United States
Danica J.
The price is ￥24,396
￥74,774 total
includes taxes & fees
Jul 29 - Jul 30
Local Artist Inspired | Walk to WestPoint + King Bed
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.2 out of 10, Wonderful, (10 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is ￥56,217
￥90,143 total
includes taxes & fees
Aug 26 - Aug 27
Fabulous 3bdrm Home w/parking!
TV

Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (24 reviews)
"Would definitely stay here again! It was a great experience!"
United States
Jodi P.
The price is ￥53,982
￥83,566 total
includes taxes & fees
Aug 26 - Aug 27
Walk to WP Gate + Free Parking!
Coffee/tea maker, fridge, microwave, oven

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (35 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
The price is ￥36,839
￥69,289 total
includes taxes & fees
Aug 3 - Aug 4
Contemporary Cozy Cottage
Property grounds

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.4 out of 10, Very Good, (7 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
The price is ￥23,741
￥80,388 total
includes taxes & fees
Jul 29 - Jul 30
3BR West Point Retreat-3min to Back Gate+ King Bed
Coffee/tea maker, fridge, oven, stovetop

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.6 out of 10, Exceptional, (23 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is ￥21,285
￥53,103 total
includes taxes & fees
Aug 18 - Aug 19
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Outdoor spa tub

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Cornwall
10.0 out of 10, Exceptional, (10 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is ￥31,927
￥65,565 total
includes taxes & fees
Jul 29 - Jul 30
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Smart TV, video games, DVD player, books

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (7 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is ￥35,169
￥67,188 total
includes taxes & fees
Aug 2 - Aug 3
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Dining

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (93 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
The price is ￥44,993
￥79,175 total
includes taxes & fees
Aug 8 - Aug 9
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
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 ￥34,234
￥88,540 total
includes taxes & fees
Aug 2 - Aug 3
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Cottage (2 Bedrooms) | Interior

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
The price is ￥34,711
￥84,583 total
includes taxes & fees
Aug 11 - Aug 12
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Interior

Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is ￥37,003
￥43,020 total
includes taxes & fees
Aug 5 - Aug 6
Harriman Outdoor Center - Mountain Laurel Cabin
Private kitchen

Perfect and Spacious Hudson Valley Escape!

Perfect and Spacious Hudson Valley Escape!
Cornwall
8.0 out of 10, Very Good, (2 reviews)
"Great host, very responsive and accommodating. The house was very clean and comfortable."
United States
Joseph S.
The price is ￥57,322
￥134,825 total
includes taxes & fees
Jul 29 - Jul 30
Perfect and Spacious Hudson Valley Escape!
Coffee/tea maker, fridge, microwave, oven

Amazing Home Near West Point, Shopping, Skiing and Legoland

Amazing Home Near West Point, Shopping, Skiing and Legoland
Monroe
10.0 out of 10, Exceptional, (15 reviews)
The price is ￥57,306
￥121,654 total
includes taxes & fees
Jul 29 - Jul 30
Amazing Home Near West Point, Shopping, Skiing and Legoland
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Bear Mountain Hotel Reviews

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

10/10 Excellent
"Great!"
Beth 2-night trip
Posted 3 hours ago
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

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
  • Use the map to find apartments and other holiday homes in the Bear Mountain neighbourhood you prefer
  • 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 vacation rentals in Bear Mountain?

Yes, we give you a choice of vacation rentals close to the most popular local attractions in Bear Mountain, or you can go with a more remote option if you're looking for relaxation. Nature enthusiasts will enjoy the mountain landscape and lakeside in Bear Mountain. Make sure you allow time to enjoy the forests during your vacation.

What's the top vacation rental that Bear Mountain has to offer?

Cozy Cabin with Sauna & Firepit!: This vacation home rental near Bear Mountain offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave.

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

Explore the area and family-friendly sights such as LEGOLAND® New York, or get out into nature at a spot like Manitoga The Russel Wright Design Center. While here, Bear Mountain State Park and Harriman State Park are other places worth a visit.

What’s a vacation rental in Bear Mountain like?

A vacation rental is a private property you can stay in for short or long periods in Bear Mountain. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a small group gathering.