Bear Mountain Holiday Rentals

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Check prices for these dates

Tonight
31 Dec - 1 Jan
Tomorrow
1 Jan - 2 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Bear Mountain holiday 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 HK$735
HK$1,476 total
includes taxes & fees
26 Jan - 27 Jan 2026
Cozy 1-bedroom retreat minutes from West Point!
Outdoor dining
Stylish & Peaceful Getaway on 3 Private Acres

Holiday Home in Goshen

Stylish & Peaceful Getaway on 3 Private Acres
2.0 star property
9.0 out of 10, Wonderful, (12)
"Great location!"
United States
Alozie E.
The price is HK$2,241
HK$3,408 total
includes taxes & fees
2 Jan - 3 Jan 2026
Stylish & Peaceful Getaway on 3 Private Acres
Exterior
House on the Babbling Brook- Quiet 2BR + King Bed!

Holiday Home in Highland Falls

House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (5)
"Good stay, awesome place"
United States
Scott G.
The price is HK$755
HK$2,745 total
includes taxes & fees
1 Jan - 2 Jan 2026
House on the Babbling Brook- Quiet 2BR + King Bed!
Exterior
Rustic Cabin in Fishkill!

Cabin in Fishkill

Rustic Cabin in Fishkill!
10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
The price is HK$2,354
HK$3,500 total
includes taxes & fees
1 Jan - 2 Jan 2026
Rustic Cabin in Fishkill!
Interior
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work

Cottage in Putnam Valley

Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
9.8 out of 10, Exceptional, (23)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is HK$1,424
HK$3,826 total
includes taxes & fees
4 Jan - 5 Jan 2026
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
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 HK$856
HK$1,872 total
includes taxes & fees
4 Jan - 5 Jan 2026
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Interior
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Holiday 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 HK$686
HK$1,199 total
includes taxes & fees
5 Jan - 6 Jan 2026
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
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 HK$874
HK$2,130 total
includes taxes & fees
4 Jan - 5 Jan 2026
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
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 HK$1,226
HK$2,126 total
includes taxes & fees
5 Jan - 6 Jan 2026
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Exterior
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

Holiday Home in Cornwall

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
2.0 star property
10.0 out of 10, Exceptional, (1)
"The house was beautiful, kitchen was new, bathroom is new, bedding and towels were soft and warm. Lots of thoughtful touches like fluffy socks upon arrival, nespresso coffee and lots of instructions and nightlights. Owner was incredibly responsive and we would absolutely stay there again. One of the cleanest places we have ever stayed. "
United States
Claire G.
The price is HK$1,679
HK$3,278 total
includes taxes & fees
2 Jan - 3 Jan 2026
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
1 bedroom
Natural Getaway at Lakeside Orchard Farm Retreat

Apartment in Monroe

Natural Getaway at Lakeside Orchard Farm Retreat
2.0 star property
The price is HK$716
HK$1,751 total
includes taxes & fees
4 Jan - 5 Jan 2026
Natural Getaway at Lakeside Orchard Farm Retreat
Property grounds
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Holiday 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 HK$996
HK$3,411 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Outdoor dining
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Holiday Home in Fishkill

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
9.4 out of 10, Exceptional, (52)
"Quiet, clean and comfortable! Great stay!"
United States
Joseph G.
The price is HK$1,926
HK$2,460 total
includes taxes & fees
4 Jan - 5 Jan 2026
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
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 HK$615
HK$2,877 total
includes taxes & fees
2 Jan - 3 Jan 2026
Cozy Modern Stay - Walk to West Point & Main St!
Dining
Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Holiday Home in Goshen

Renovated House w/Hot Tub, Deck, Grill & Fire Pit
10.0 out of 10, Exceptional, (59)
"Clean and comfortable accommodations, very close to Legoland and Castle Fun Center! The kids loved the room with bunk beds, and it had a big selection of children's books and some toys, which was a nice bonus!"
United States
Jennifer K.
The price is HK$1,926
HK$3,709 total
includes taxes & fees
4 Jan - 5 Jan 2026
Renovated House w/Hot Tub, Deck, Grill & Fire Pit
Fridge, microwave, oven, stovetop
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

Apartment in Croton-on-Hudson

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
10.0 out of 10, Exceptional, (6)
"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 HK$1,034
HK$2,347 total
includes taxes & fees
6 Jan - 7 Jan 2026
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Interior
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

Holiday Home in Warwick

5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
2.0 star property
10.0 out of 10, Exceptional, (5)
"Had a lovely weekend in the little red barn. And the little market next door has the best breakfast egg and bacon sandwich."
United States
michelle d.
The price is HK$1,513
HK$3,445 total
includes taxes & fees
3 Jan - 4 Jan 2026
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
Property grounds
Fun, Friends, and Family Lakefront Home w/Dock and Beach

Holiday Home in Mahopac

Fun, Friends, and Family Lakefront Home w/Dock and Beach
10.0 out of 10, Exceptional, (12)
"Super convenient location :)"
United States
Sean M.
The price is HK$2,626
HK$5,663 total
includes taxes & fees
4 Jan - 5 Jan 2026
Fun, Friends, and Family Lakefront Home w/Dock and Beach
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 HK$700
HK$2,140 total
includes taxes & fees
20 Jan - 21 Jan 2026
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
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 HK$1,154
HK$2,274 total
includes taxes & fees
11 Jan - 12 Jan 2026
Relaxing Farm Cottage Escape, 10 Min from 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.
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Top Bear Mountain Hotel Reviews

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

10/10 Excellent
"Superb place to stay."
Denessy 1-night trip
Posted 2 days ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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 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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of 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 that 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 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.