A forested hiking trail with rocky steps and fallen leaves.

Bear Mountain Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Bear Mountain vacation rentals

A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
$302 nightly
The price is $311
Oct 18 - Oct 19
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A house with a view of a bridge and mountains.

2. 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, (148 reviews)
"We had a great stay!!"
United States
Jasmine
$279 nightly
The price is $330
Oct 20 - Oct 21
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A living room with a sofa, two armchairs, a TV, and a coffee table.

3. Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
8.4 out of 10, Very good, (5 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$197 nightly
The price is $218
Oct 19 - Oct 20
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

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

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
9.8 out of 10, Exceptional, (13 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
$379 nightly
The price is $405
Oct 20 - Oct 21
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

5. Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (20 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
$439 nightly
The price is $451
Nov 2 - Nov 3
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

6. 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.
$278 nightly
The price is $309
Oct 18 - Oct 19
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

7. Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.4 out of 10, Exceptional, (8 reviews)
"Great location and super host. "
United States
James U.
$457 nightly
The price is $469
Nov 2 - Nov 3
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A wooden coffee table with two decorative planters in a living room.

8. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (26 reviews)
"Clean and modern with good amenities. Would stay here again. "
United States
Daniel C.
$255 nightly
The price is $285
Oct 18 - Oct 19
Total with taxes and fees
Walk to WP Gate + Free Parking!
A room with a wooden floor, a white door with a number, and a window with blinds.

9. 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.
$295 nightly
The price is $337
Oct 19 - Oct 20
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
A modern kitchen with stainless steel appliances, a marble countertop, and a dining area with white chairs.

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

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
$322 nightly
The price is $369
Oct 19 - Oct 20
Total with taxes and fees
Hudson Valley/West Point Retreat w/ parking!
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

11. 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.
$312 nightly
The price is $350
Nov 16 - Nov 17
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A hallway with a wooden door, a black table with a sign, and large green plants.

12. 3BR Near West Point | Coffee Bar | Sleeps 6

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay at Joseph’s home. The property was very clean, spacious, and well prepared for guests. My work team and I felt comfortable right away, and the house had everything we needed for both a productive and relaxing stay.Joseph was always kind, professional, and quick to respond, which made a big difference. I would recommend this property without hesitation."
United States
ROHID S.
$436 nightly
The price is $448
Nov 3 - Nov 4
Total with taxes and fees
3BR Near West Point | Coffee Bar | Sleeps 6
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

13. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (41 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
$357 nightly
The price is $408
Oct 18 - Oct 19
Total with taxes and fees
Contemporary Cozy Cottage
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

14. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (19 reviews)
"Great rooms and service,"
United States
Anonymous traveler
$79 nightly
The price is $89
Nov 12 - Nov 13
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
A brick building with a sign reading 'Lobby' in front.

15. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.2 out of 10, Wonderful, (20 reviews)
"Great place to stay,"
United States
Anonymous traveler
$79 nightly
The price is $91
Nov 12 - Nov 13
Total with taxes and fees
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A living room with a fireplace, a painting, shelves with decorative items, and a television.

16. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (50 reviews)
"We enjoyed our stay, property was as described. It's convenient to many of the Hudson Valley small towns, including West Point."
United States
Mike W.
$262 nightly
The price is $296
Oct 19 - Oct 20
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
A deck with Adirondack chairs, a fire pit, and a grill.

17. 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, (15 reviews)
"Everything you could ask for!!"
United States
Elisabeth
$372 nightly
The price is $439
Oct 21 - Oct 22
Total with taxes and fees
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
Step up to a warm welcome - our charming entryway, complete with a hanging birdhouse, sets the tone for a peaceful stay.

18. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Putnam Valley
9.8 out of 10, Exceptional, (25 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
$457 nightly
The price is $504
Oct 20 - Oct 21
Total with taxes and fees
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Interior

19. Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Warwick
10.0 out of 10, Exceptional, (53 reviews)
"Great location in the heart of Warwick, NY. Easy to walk around town and visit the local restaurants!"
United States
Francis
$210 nightly
The price is $238
Nov 1 - Nov 2
Total with taxes and fees
Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
A neatly made bed with a black and white duvet, a wooden headboard, and a bedside table with a lamp. There are three framed artworks on the wall above the bed.

20. 'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (3 reviews)
"Great stay!"
United States
Ann S.
$270 nightly
The price is $309
Nov 1 - Nov 2
Total with taxes and fees
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
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

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

10/10 Excellent
"The place is like new, I highly recommend"
KURT 1-night trip
Posted 3 hours ago
Sleep Inn & Suites Monroe - Woodbury

Find out more about Bear Mountain

Everything you need to know about Bear Mountain vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Bear Mountain vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Bear Mountain vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Bear Mountain vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bear Mountain. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Bear Mountain in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $89 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Bear Mountain rentals

At Expedia, we put the best Bear Mountain vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Bear Mountain rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Bear Mountain vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Bear Mountain. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This vacation home rental near Bear Mountain is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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

Explore the area and family-friendly sights such as Rockland Bakery, or get out into nature at a spot like Lake Tiorati Beach. 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.