A forested hiking trail with rocky steps and fallen leaves.

Search Vacation Homes in Bear Mountain

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Bear Mountain vacation homes

1. 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.
3BR West Point Retreat-3min to Back Gate+ King Bed

2. 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 ¥31,706
¥56,659 total
includes taxes & fees
Dec 8 - Dec 9
Lovely 3BR Home with parking-Walk to WP Gate!

3. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
"House was exactly as described. Would stay again."
United States
Beth M.
The price is ¥33,719
¥57,579 total
includes taxes & fees
Dec 8 - Dec 9
Fabulous 3bdrm Home w/parking!

4. Perfect 2BR with Free Parking! Walk to West Point!

Perfect 2BR with Free Parking! Walk to West Point!
Highland Falls
The price is ¥32,031
¥51,489 total
includes taxes & fees
Nov 16 - Nov 17
Perfect 2BR with Free Parking! Walk to West Point!

5. Hudson Valley/West Point Retreat w/ parking!

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
The price is ¥46,525
¥75,972 total
includes taxes & fees
Dec 8 - Dec 9
Hudson Valley/West Point Retreat w/ parking!

6. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (43 reviews)
"We’ve actually stayed here twice so that should tell you we enjoy the space and the host is lovely."
United States
Heather M.
The price is ¥35,948
¥61,765 total
includes taxes & fees
Nov 16 - Nov 17
Contemporary Cozy Cottage

7. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
Cornwall
10.0 out of 10, Exceptional, (16 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is ¥38,984
¥70,019 total
includes taxes & fees
Nov 16 - Nov 17
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

8. Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
8.0 out of 10, Very good, (3 reviews)
"This home was just as advertised and perfect for a girls weekend getaway. It was clean, cozy and a picture-perfect fall view. Would highly recommend."
United States
Karen W.
The price is ¥52,972
¥99,027 total
includes taxes & fees
Nov 19 - Nov 20
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

9. Spacious 4-bedroom house in northern Westchester with sweeping views

Spacious 4-bedroom house in northern Westchester with sweeping views
Montrose
The price is ¥79,086
¥98,313 total
includes taxes & fees
Nov 14 - Nov 15
Spacious 4-bedroom house in northern Westchester with sweeping views

10. Bright Cornwall-On-Hudson Vacation Rental!

Bright Cornwall-On-Hudson Vacation Rental!
Cornwall-On-Hudson
10.0 out of 10, Exceptional, (35 reviews)
"Very comfortable house and great location."
United States
Betty B.
The price is ¥49,049
¥108,519 total
includes taxes & fees
Nov 22 - Nov 23
Bright Cornwall-On-Hudson Vacation Rental!

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

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
8.8 out of 10, Excellent, (23 reviews)
"Great place, but you can hear red everything going on outside your room with the restaurant downstairs and other people in the common area. But I’d definitely come back here"
United States
Joseph
The price is ¥14,236
¥24,600 total
includes taxes & fees
Nov 16 - Nov 17
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

12. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is ¥27,001
¥42,836 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

13. NEW! Cozy 3BR Home Near West Point & Hudson Valley - King Bed

NEW! Cozy 3BR Home Near West Point & Hudson Valley - King Bed
New Windsor
The price is ¥33,072
¥78,701 total
includes taxes & fees
Nov 15 - Nov 16
NEW! Cozy 3BR Home Near West Point & Hudson Valley - King Bed

14. Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair

Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair
Monroe
10.0 out of 10, Exceptional, (5 reviews)
"The combination of an antique, old-style house with a modernized interior featuring all the amenities you could dream of made for an enjoyable and cozy experience. The house is located right at the back of the lake in a quiet neighborhood and comes fully equipped with:- A spacious layout- High-speed Wi-Fi- Useful massage chair - Fun recreational areas- Lovely decorThis house will truly become a staple in the area."
United States
Moshe F.
The price is ¥94,261
¥175,856 total
includes taxes & fees
Nov 15 - Nov 16
Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair

15. Waterfront Home with Hot Tub, Firepit, and Kayaks

Waterfront Home with Hot Tub, Firepit, and Kayaks
Greenwood Lake
10.0 out of 10, Exceptional, (47 reviews)
"We have stayed here a few times and the house is always perfect. Will stay here again in the future! "
United States
Lex S.
The price is ¥31,315
¥77,175 total
includes taxes & fees
Dec 1 - Dec 2
Waterfront Home with Hot Tub, Firepit, and Kayaks

16. Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8

Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8
Chester
8.8 out of 10, Excellent, (3 reviews)
"Thank you for the weekend. We had a great time and Sugarloaf was a great location for us all to catch up."
United States
Jeff S.
The price is ¥44,097
¥114,560 total
includes taxes & fees
Nov 15 - Nov 16
Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8

17. Country House w/Hot Tub, Deck, Grill & Fire Pit

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
9.8 out of 10, Exceptional, (69 reviews)
"We had a nice weekend at the Country House. I would recommend this property to friends and family. "
United States
Mike T.
The price is ¥45,055
¥82,257 total
includes taxes & fees
Nov 18 - Nov 19
Country House w/Hot Tub, Deck, Grill & Fire Pit

18. Panoramic Fall Foliage Escape, Fire Pit, Wood Stove

Panoramic Fall Foliage Escape, Fire Pit, Wood Stove
Greenwood Lake
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home...it is clear that much thought and time went into the decor and functionality....complete with welcomed amenities."
United States
andrea e.
The price is ¥33,104
¥59,861 total
includes taxes & fees
Nov 15 - Nov 16
Panoramic Fall Foliage Escape, Fire Pit, Wood Stove

19. Hudson View Hot Tub · Walk to Waterfront

Hudson View Hot Tub · Walk to Waterfront
Newburgh
10.0 out of 10, Exceptional, (1 review)
"The home has recently been renovated and it is very well presented with luxury furnishings and an excellently stocked kitchen. Views are amazing over the Hudson towards Beacon."
United States
Rachel M.
The price is ¥54,469
¥127,722 total
includes taxes & fees
Nov 15 - Nov 16
Hudson View Hot Tub · Walk to Waterfront

20. Lakefront Paradise Pool + Paddle Boats Sleeps 12

Lakefront Paradise Pool + Paddle Boats Sleeps 12
Monroe
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful week long stay. The house is beautiful and right on the lake, with beautiful views and sunsetsWe were there for a West Point Graduation and was about a 30 minute drive to the school, even on the busy days of the parade and graduation dayThe house had plenty of room for our group and the host was easy to get ahold of. There are 4 official bedroom and 4 bathrooms and a basement and 2 office/den, 2 washer and dryers - one in the top floor and another in the basement which has...
United States
Courtney D.
The price is ¥75,169
¥219,866 total
includes taxes & fees
Dec 8 - Dec 9
Lakefront Paradise Pool + Paddle Boats Sleeps 12
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Bear Mountain Hotel Reviews

Find out more about Bear Mountain

Bear Mountain Vacation Homes information

Number of reviews
242
Accommodation
202 Vacation Homes
Lowest Price
¥24,600
Highest Price
¥219,866

Explore a world of travel with Expedia