Bear Mountain Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Tonight
Dec 27 - Dec 28
Tomorrow
Dec 28 - Dec 29
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Bear Mountain vacation rentals

Fridge, oven, stovetop, cookware/dishes/utensils
Cozy 1-bedroom retreat minutes from West Point!

Apartment in Highland Falls

Cozy 1-bedroom retreat minutes from West Point!
10.0 out of 10, Exceptional, (1)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is ￥14,796
￥29,695 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Cozy 1-bedroom retreat minutes from West Point!
Exterior
House on the Babbling Brook- Quiet 2BR + King Bed!

Vacation Home in Highland Falls

House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (5)
"A clean and convenient place to stay for visiting our cadet at West Point. Our hosts were very communicative and helpful. The home and parking situation was just as described. Nice quiet neighborhood, well maintained home. Hearing the babbling broom outside the living room window was very relaxing. Plan on staying here again!"
United States
Maria L.
The price is ￥17,019
￥57,547 total
includes taxes & fees
Jan 12 - Jan 13, 2026
House on the Babbling Brook- Quiet 2BR + King Bed!
Exterior detail
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Apartment in Highland Falls

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
9.8 out of 10, Exceptional, (14)
"Great Unit."
United States
Rudy R.
The price is ￥14,091
￥41,650 total
includes taxes & fees
Jan 21 - Jan 22, 2026
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Interior
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Vacation Home in Warwick

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
9.4 out of 10, Exceptional, (8)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
The price is ￥13,809
￥24,125 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Children's area
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Cottage in Goshen

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
9.8 out of 10, Exceptional, (12)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
The price is ￥23,187
￥45,682 total
includes taxes & fees
Dec 29 - Dec 30
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
1 bedroom, WiFi, bed sheets
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Apartment in Beacon

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
10.0 out of 10, Exceptional, (32)
"Great time and great place to stay "
United States
S S.
The price is ￥17,175
￥37,568 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
2 bedrooms, in-room safe, desk, iron/ironing board
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

Apartment in CROTON HDSN

Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
9.8 out of 10, Exceptional, (90)
"I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon."
United States
Jill D.
The price is ￥17,547
￥43,109 total
includes taxes & fees
Dec 28 - Dec 29
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
Interior
Villa Verde B&B, bsm, Greenwood Lake NY

Aparthotel in Greenwood Lake

Villa Verde B&B, bsm, Greenwood Lake NY
10.0 out of 10, Exceptional, (12)
"The breakfast was lovely!"
United States
Tara
The price is ￥24,514
￥45,218 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Villa Verde B&B, bsm, Greenwood Lake NY
Exterior
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

Apartment in Croton-on-Hudson

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
10.0 out of 10, Exceptional, (2)
"Great stay!"
United States
Ann S.
The price is ￥16,231
￥37,852 total
includes taxes & fees
Jan 5 - Jan 6, 2026
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Property grounds
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Vacation Home in Highland Falls

Sleek Escape: Modern 3 BR- 4 Min from West Point !
10.0 out of 10, Exceptional, (3)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is ￥20,298
￥68,769 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Exterior
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Vacation Home in Hopewell Junction

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
9.0 out of 10, Wonderful, (10)
"We had a great last minute visit to Hopewell Junction and enjoyed a lovely stay at the chapel! It’s a very unique experience and quiet and peaceful. We enjoyed the bbq and an evening fire with smores! "
United States
Esther P.
The price is ￥23,749
￥40,292 total
includes taxes & fees
Dec 28 - Dec 29
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Smart TV
Grant - A Tranquil One Bedroom Steps from River

Apartment in Newburgh

Grant - A Tranquil One Bedroom Steps from River
9.6 out of 10, Exceptional, (41)
"Wonderful place! Beautifully decorated, high ceilings, yard, and easy access to the river and cafes. Perfect getaway from the city. Will stay again!"
United States
Emily G.
The price is ￥16,863
￥40,450 total
includes taxes & fees
Dec 30 - Dec 31
Grant - A Tranquil One Bedroom Steps from River
Fridge, microwave, oven, stovetop
Local Artist Inspired | Walk to WestPoint + King Bed

Apartment in Highland Falls

Local Artist Inspired | Walk to WestPoint + King Bed
9.2 out of 10, Wonderful, (9)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
The price is ￥17,175
￥62,570 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Local Artist Inspired | Walk to WestPoint + King Bed
Fridge, microwave, oven, stovetop
Cozy Modern Stay - Walk to West Point & Main St!

Apartment in Highland Falls

Cozy Modern Stay - Walk to West Point & Main St!
2.0 star property
The price is ￥13,116
￥58,687 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Cozy Modern Stay - Walk to West Point & Main St!
Fridge, microwave, oven, stovetop
Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in Newburgh

Cabin in the heart of the Hudson Valley, Cabin 3
9.8 out of 10, Exceptional, (14)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is ￥26,388
￥43,527 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Cabin in the heart of the Hudson Valley, Cabin 3
Dining
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

Apartment in Warwick

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
10.0 out of 10, Exceptional, (33)
"Great location within walking distance of boutiques and restaurants. Enjoyed our stay. "
United States
Cynthia W.
The price is ￥18,737
￥40,628 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
1 bedroom, WiFi, bed sheets
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Apartment in Beacon

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
9.8 out of 10, Exceptional, (42)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is ￥17,175
￥35,952 total
includes taxes & fees
Jan 27 - Jan 28, 2026
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Fridge, microwave, oven, stovetop
Lux APT Your home away from home.

Apartment in Beacon

Lux APT Your home away from home.
10.0 out of 10, Exceptional, (2)
"Very clean and great place to stay. "
United States
Charlene D.
The price is ￥22,172
￥42,216 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Lux APT Your home away from home.
Fridge, microwave, oven, stovetop
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Apartment in Highland Falls

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
10.0 out of 10, Exceptional, (5)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
The price is ￥25,576
￥43,799 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
1 bedroom, WiFi, bed sheets
Charming 1-bedroom apartment in Carmel with WiFi, AC

Apartment in Carmel Hamlet

Charming 1-bedroom apartment in Carmel with WiFi, AC
9.0 out of 10, Wonderful, (2)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is ￥21,079
￥43,488 total
includes taxes & fees
Dec 28 - Dec 29
Charming 1-bedroom apartment in Carmel with WiFi, AC
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

Sleepy Hollow Hotel

Sleepy Hollow Hotel

10/10 Excellent
"Clean comfortable room. Courteous staff. Excellent food."
Sara 1-night trip
Posted 4 days ago
Sleepy Hollow Hotel

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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental near Bear Mountain offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and kitchenware, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 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.