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Chalet vacation rentals in Bear Mountain

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Popular amenities for Bear Mountain chalet rentals

Family-friendly chalet rentals

Guest favorite
Chalet in Pocono Summit
4.93 out of 5 average rating, 171 reviews

15% Off Weekly & 40% Off Monthly Rates! Wowza!

GeorgeRating, 5 stars1 month ago
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.
Top guest favorite
Chalet in Catskill
4.96 out of 5 average rating, 191 reviews

Daydream Mountain Art-Chateau | Hot Tub & Pool

MonikaRating, 5 stars2 weeks ago
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.
Guest favorite
Chalet in Jewett
4.97 out of 5 average rating, 182 reviews

Private Catskills Home w. Hot Tub, near Ski Mnt

Gina-LouiseRating, 5 stars2 months ago
Great place that was clean, comfortable and cozy. There were excellent instructions for everything and my family loved the hot tub!
Guest favorite
Chalet in Pocono Pines
4.84 out of 5 average rating, 287 reviews

PoconoARTE CABIN/Pocono Pines/Lake Naomi /PA

RachelRating, 5 stars2 months ago
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.
Guest favorite
Chalet in Elka Park
4.9 out of 5 average rating, 598 reviews

Secluded home by Hunter Mountain

ClaireRating, 5 stars1 day ago
very cosy for friends of 4. There are so many details of arts and family history in the house, respect that!
Top guest favorite
Chalet in Hensonville
4.96 out of 5 average rating, 359 reviews

2BDR- Cozy Windham/Hunter Escape

AmyRating, 5 stars1 month ago
Such a great and cozy stay! Minutes from town center and Windham, so easy to check in / check out. Very happy we stayed here!
Guest favorite
Chalet in Willow
4.89 out of 5 average rating, 155 reviews

Cozy Silo Home w Mountain Views near Woodstock

ChristinaRating, 5 stars1 week ago
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.
Guest favorite
Chalet in Bainbridge
4.91 out of 5 average rating, 117 reviews

Western Catskills Paradise Four-Season Retreat

LynnRating, 5 stars1 week ago
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

Top guest favorite
Chalet in Windham
4.98 out of 5 average rating, 131 reviews

Gorgeous Modern Lodge w/ Mt View - 5 Min to Skiing

RachelRating, 5 stars1 week ago
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!
Guest favorite
Chalet in Mount Tremper
4.98 out of 5 average rating, 107 reviews

Modern Mountain Chalet on 15 Acre Catskills Estate

JonathanRating, 5 stars2 months ago
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.
Guest favorite
Chalet in Leeds
4.96 out of 5 average rating, 136 reviews

Catskill Chalet: Hot Tub, Fire Pit, Cozy, Private

RayaRating, 5 stars1 week ago
Genesis is a wonderful host - very responsive and accommodating. The house was absolutely beautiful and we’d love to come back again sometime!
Superhost
Chalet in Ruby
4.9 out of 5 average rating, 115 reviews

Enchanting Upstate Cabin w Pool, Firepit

ErinRating, 5 stars2 months ago
Beautiful home, even better in person! Clean and cozy. Each room was stylishly and uniquely decorated. Great for large groups.
Top guest favorite
Chalet in Olivebridge
4.99 out of 5 average rating, 152 reviews

Spruced Moose Lodge & Treehouse w. Hot Tub & Pool!

SeanRating, 5 stars2 weeks ago
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!
Guest favorite
Chalet in East Stroudsburg
4.97 out of 5 average rating, 158 reviews

A-Frame | Lake | Kayaks | Firepit | Hot Tub

HollyRating, 5 stars1 week ago
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.
Guest favorite
Chalet in Mount Tremper
4.98 out of 5 average rating, 145 reviews

Secluded Woodstock Retreat with Pool and Sauna

BarryRating, 5 stars2 months ago
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.
Guest favorite
Chalet in Windham
4.88 out of 5 average rating, 189 reviews

Beautiful Windham Ski/Summer House

AmyRating, 5 stars3 months ago
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

Guest favorite
Chalet in Hunter
4.98 out of 5 average rating, 153 reviews

THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE

CarmenRating, 5 stars2 weeks ago
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.
Superhost
Chalet in Albrightsville
4.89 out of 5 average rating, 53 reviews

Fabulous Lakefront chalet with boats & ski access

JohnRating, 5 stars3 months ago
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!
Guest favorite
Chalet in Athens
4.89 out of 5 average rating, 103 reviews

Waterfront Lake Home, close to Hunter & Windham

HilaryRating, 5 stars1 day ago
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.
Top guest favorite
Chalet in Pocono Pines
4.96 out of 5 average rating, 135 reviews

Pocono Win✴Game Room+Hot Tub✴Lake Naomi GOLDEN OWL

TimikaRating, 5 stars3 weeks ago
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.
Guest favorite
Chalet in Glen Spey
4.9 out of 5 average rating, 132 reviews

Mayflower - Lake access/hot tub/game room/pets

FrançoisRating, 5 stars4 weeks ago
Great place for families, there is a lot of room and toys for kids, and the lake is just a short walk away!
Superhost
Chalet in Tobyhanna
4.81 out of 5 average rating, 244 reviews

Lakefront Chalet in Poconos

ThersaRating, 5 stars7 months ago
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.
Superhost
Chalet in Monticello
4.86 out of 5 average rating, 129 reviews

Catskills Lakefront Escape with Hot Tub

KimberlyRating, 5 stars1 month ago
Really good home. Great location for relaxing and being on the water. The lake was slightly frozen but, it was still amazing.
Superhost
Chalet in Pocono Township
4.9 out of 5 average rating, 63 reviews

Lakeside Access + Nature Cabin #4/Camelback Resort

KwabenaRating, 5 stars2 weeks ago
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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