
Chalet vacation rentals in Bear Mountain
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Top-rated chalet rentals in Bear Mountain
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Popular amenities for Bear Mountain chalet rentals
Family-friendly chalet rentals

15% Off Weekly & 40% Off Monthly Rates! Wowza!
My wife and I enjoyed our winter anniversary stay at the cabin. It was clean and cozy. We enjoyed time by the fire place, free streaming services, and the Keurig(bring bottled water for coffee). The area around the cabin was very walkable in a development with two lakes. It was close to amenities like Walmart (we had to purchase wash clothes and firewood), the interstate and food. We recommend to bring your own pillow if you like them soft. The water pressure was fine in the kitchen but low in the bathroom. Jessica was easily reached to work out any questions. If you are looking for a cozy, comfortable cabin close to everything, stay with Jessica. We would stay again.

Daydream Mountain Art-Chateau | Hot Tub & Pool
Incredibly beautiful area and truly unique home. Vintage vibes and lots of personal touches and creative art; my brother who is a musician loved all the instruments. I was there just with my family but this seems like an incredible place to party with a big group or family - lots of beds, baby cribs, high chairs, toys and games, art easels and more. This is a memorable Airbnb for anyone to stay in!

Private Catskills Home w. Hot Tub, near Ski Mnt
Great place that was clean, comfortable and cozy. There were excellent instructions for everything and my family loved the hot tub!

PoconoARTE CABIN/Pocono Pines/Lake Naomi/PA
My husband and I adored this place! It was in a beautiful location that was very peaceful, which was just what we were looking for. It was a nice escape from the city where we are from. It was a very friendly community and the lake was a walk away. We were fortunate enough to be during a snowstorm and it made everything mystical and cozy. We got to stay in, cook a nice meal, watch movies and see the snow fall! The place was absolutely beautiful and everything you could imagine/hope for as a cabin in the poconos. It had absolutely everything we needed and more! The pictures don’t even do the beauty and warmth of this home justice! Magda was very welcoming, attentive to our needs, and quick with her responses. We felt at home and would love to come back and enjoy another getaway in this dreamy woodsy wonder.

Secluded home by Hunter Mountain
very cosy for friends of 4. There are so many details of arts and family history in the house, respect that!

2BDR- Cozy Windham/Hunter Escape
Such a great and cozy stay! Minutes from town center and Windham, so easy to check in / check out. Very happy we stayed here!

Cozy Silo Home w Mountain Views near Woodstock
Cozy Silo Home is a perfect description of Olga's home! The silo is really unusual, with lots of windows/lighting and is comfortable and nicely decorated. It's a short drive from Woodstock, which is a fantastic area with lots of shopping, restaurants, etc. It's also very close to great hiking and other outdoor activities. At the house, we spent most of our time outside on the large balcony/patio and cooking meals on the outdoor grill. We booked last-minute and Olga was very responsive, answered all our questions and made things very easy for us. We live in NYC and a weekend in/around Woodstock is a great way to recharge and reconnect with nature. We definitely recommend Olga's silo home for a weekend or longer!! Note: stairs are required to enter into the home and to get to the bedrooms/bathrooms, so don't bring anything too bulky or heavy.

Western Catskills Paradise Four-Season Retreat
We had an amazing time with our family at this peaceful home. It was easy to find, offered plenty of space, and made for a truly relaxing getaway.
Luxury chalet rentals

Windham West Chalet
Huge, retro house just 5 mins away from the mountain. Stayed over Presidents’ weekend with 6 adults and 4 kids. Beautiful family/great room with a massive dining table. Very warm and cozy. Bring sleeping masks tho - some bedrooms had upper windows that didn’t have shades (lower had shades for privacy). Would definitely come back!

Modern Mountain Chalet on 15 Acre Catskills Estate
Lovely stay with family and friends. The host went out of his way to ensure our arrival was smooth, even with a very icy driveway and up to two inches of snow falling. The space is beautiful, secluded and serene. But also close to restaurants in Mt. Tremper and good hikes.

Catskill Chalet: Hot Tub, Fire Pit, Cozy, Private
Genesis is a wonderful host - very responsive and accommodating. The house was absolutely beautiful and we’d love to come back again sometime!

Spruced Moose Lodge & Treehouse w. Hot Tub & Pool!
Had a small weekend trip away in the mountains. The group had a blast. The landscape was beautiful. It rained one night and snowed the next, so we spent a lot of time indoor; but the place is beautiful, and we definitely plan to come back in warmer weather for a longer time!

A-Frame | Lake | Kayaks | Firepit | Hot Tub
This was our second stay at the cabin. Just as lovely as the first time. It's a clean and cozy cabin. We took our 7 year old son this time and he had a blast. He loved the big round tub in the bathroom. We just adore this house. We will likely come back again in the fall or winter. Thanks to Vera for such a great place to stay.

Tranquil• Nature• Golf• Pool• HotTub• Family Fun
We had a wonderful weekend for my husband’s birthday with our two small children. Edo and Nata helped create a wonderfully intimate birthday celebration with snacks and balloons waiting for us upon entry. They anticipated our needs and had the playpen and highchair set up, making check in with a baby, very easy! As parents, we appreciated all of the kid’s toys, silverware and puzzles left around the space. Don’t hesitate to book!

Beautiful Windham Ski/Summer House
The house was spacious, clean, beautiful and private. We loved the view of Windham Mt from the second floor! The fireplace, expansive but cozy couch and downstairs game room were a hit! Half of my family skied and half stayed at the house to relax. Being 5 minutes from the mountain was fantastic and the house was perfect. Great restaurants nearby, where we had lunch, but the rest of the time we cooked in. Well equipped open kitchen! Hope to be back many times!

Chalet Hot tub AC, WI-FI, Firepit, Deck BBQ
Highly recommend, I rented this space to celebrate my husband’s birthday with friends, and we had everything we needed. Plenty of space, the primary bedroom is huge, and we were able to set up an air mattress. We made dinner and cupcakes and had all the cooking supplies we needed. Rita was thorough in communication, and Arrowhead Lake community is a great place to visit if you are trying to get away in the Pocono area.
Lakefront chalet rentals

THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
The house was well stocked, neat and clean. The property has lots of great outdoor space to relax in. Nataliya was very responsive. Thank you.

Waterfront Lake Home, close to Hunter & Windham
A beautiful, well-appointed, family-friendly place to stay. Teddy's place had everything we needed and more. The beds were comfortable, everything was clean and well maintained, and exactly as described and like the photos show.

Pocono Win✴Game Room+Hot Tub✴Lake Naomi GOLDEN OWL
We enjoyed our stay. Whitney was very helpful from the time I booked until check out. She was always very responsive. The place was beautiful and looked just like the pictures. We truly felt at home, and the kids enjoyed having their own space. I felt a sense of peace while staying at golden owl! I absolutely can not wait to stay again.

Mayflower - Lake access/hot tub/game room/pets
Great place for families, there is a lot of room and toys for kids, and the lake is just a short walk away!

Lakefront Chalet in Poconos
Our family has stayed at Arek's house three times before this trip. The location is great. The house is at the deeper end of the lake, so you can easily swim from the shore. There are three kayaks and a rowboat to use on the lake. The deck is a great place to drink coffee in the morning and eat dinner at night. For creature comforts the beds are super comfortable and the wifi is speedy fast. We will definitely stay there again.

Catskills Lakefront Escape with Hot Tub
Really good home. Great location for relaxing and being on the water. The lake was slightly frozen but, it was still amazing.

Pocono Lakefront Home (Placid Lake)
We really enjoyed our stay here! Paul and Lorraine were great hosts and went above and beyond to make sure we had everything we needed to enjoy our stay. The house itself and the location are beautiful!

Lakeside Access + Nature Cabin #4/Camelback Resort
Great location for a private, cozy getaway with friends or a spouse. Definitely recommend axe throwing, horseback riding, and checking out the outlet mall. Only thing is the food in the area—not the best but does the job! I would recommend bringing some ingredients and snacks to eat. Overall, great experience!
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- Radio City Music Hall
- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Tenement Museum
- Riverside Park
- Mountain Creek Resort
- Comedy Cellar
- Apollo Theater
- St. Nicholas Park
- Citi Field
- Yankee Stadium
- MetLife Stadium
- Inwood Hill Park
- United Nations Headquarters
- Bronx Zoo
- Astoria Park
- Statue of Liberty
- Rockefeller Center
- Minnewaska State Park Preserve