
Chalet vacation rentals in Bear Mountain
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Top-rated chalet rentals in Bear Mountain
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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
This was our second year staying here with friends, and we had such a lovely time. There's plenty to do inside the house itself even on a dreary day, with curiosities and art abound, instruments, games, fireplace, etc, a great kitchen for group meals, and spacious and comfortable rooms otherwise. Olia is very kind and responsive, with plenty tips for the local area. We'd recommend for groups or families in an instant. Nothing like relaxing in the hot tub while looking out at the mountain vista with rain pattering on the porch roof above - pure bliss.

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

Gorgeous Modern Lodge w/ Mt View - 5 Min to Skiing
This is a truly beautiful home and property and we had a wonderful few days enjoying everything it had to offer! The kids between our two families had endless fun with the arcade, hot tub, exploring the property and creek, and the slumber party they got to have in the upper bedroom. As for the adults, we got to unwind and enjoy, as Stefanie has thought of everything as a host and made it a breeze to check in and relax. The couple hiccups or questions we had at the start were quickly answered and resolved through messages and all instructions for check out were easy and straightforward. Would love to book this home during ski season in the future as the views of and proximity to the mountain are amazing!

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!

Enchanting Upstate Cabin w Pool, Firepit
Beautiful home, even better in person! Clean and cozy. Each room was stylishly and uniquely decorated. Great for large groups.

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.

Secluded Woodstock Retreat with Pool and Sauna
My wife and I stayed at Ron’s place for five nights for a winter getaway. We had a great stay, highlights include a comfortable king bed, a quiet setting, a cozy fireplace, and the large ground floor bathroom that feels like your own spa- we thoroughly enjoyed the sauna, huge bathtub, and rain shower. Ron was a great host and was very responsive with any questions we had. We spent many hours watching TV on the screen and projector set up, we grabbed more pillows from upstairs to add some more cushion to the leather couch downstairs.

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!
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.

Fabulous Lakefront chalet with boats & ski access
The house was nice we stayed over new years and It was a nice place together as a group. Each room has its own A/C system and controls, slightly outdated in that regard but allows more customization in that regard. House had no problems staying heated. A large communal space makes it great for larger groups. An older house but that somewhat adds to the retreat experience at the lake and surrounding attractions. I would stay here again. HOA had a lot of rules regarding use of the lake, but as it was winter that didn't affect our stay. Great communication from the host. They have a nicely prepared book of local attractions and places to eat. Thanks for the great stay!

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.

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
- Comedy Cellar
- Mountain Creek Resort
- Apollo Theater
- St. Nicholas Park
- Citi Field
- Yankee Stadium
- MetLife Stadium
- Inwood Hill Park
- United Nations Headquarters
- Bronx Zoo
- Statue of Liberty
- Rockefeller Center
- The Metropolitan Museum of Art
- Central Park Zoo