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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, 172 reviews

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

GeorgeRating, 5 stars3 months 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, 194 reviews

Daydream Mountain Art-Chateau | Hot Tub & Pool

KristenRating, 5 stars2 weeks ago
The house is so beautiful and unique, and there is art everywhere you look. It inspires creativity! The hot tub and pool are incredible. The house has everything you need to feel at home. It's quiet and peaceful, and the view is out of this world. This is such a wonderful place for a getaway. Our family had a great time, and we can't wait to visit again soon! Olia made sure we had everything we needed and provided great suggestions for things to do in the area. It was an amazing holiday getaway!
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 stars3 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 Elka Park
4.91 out of 5 average rating, 604 reviews

Secluded home by Hunter Mountain

JessicaRating, 5 stars3 weeks ago
This place was lovely! Super cozy, very well decorated, and hosts a wonderful view! Judi’s was kind, understanding, responsive, and all around a wonderful host. We came here for a friend’s birthday and he was blown away. Thank you for everything, and we plan to come again soon!
Guest favorite
Chalet in Willow
4.89 out of 5 average rating, 156 reviews

Cozy Silo Home w Mountain Views near Woodstock

ChristinaRating, 5 stars1 month 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.
Top guest favorite
Chalet in Hensonville
4.96 out of 5 average rating, 361 reviews

2BDR- Cozy Windham/Hunter Escape

AzulRating, 5 stars4 days ago
We spent a couple days here for my birthday weekend, and it was really chill and quiet! The house itself is very cozy, extremely clean, and comes with all the basics you’d need for a weekend away. The hiking trails and views in the area are gorgeous. I will absolutely be revisiting this little spot!
Guest favorite
Chalet in Bainbridge
4.91 out of 5 average rating, 119 reviews

Western Catskills Paradise Four-Season Retreat

StacieRating, 5 stars1 month ago
This was our second stay at the property. Great place for our family to meet up and have quality time together. Great surroundings and love the pond. Rained most of our trip this time but was able to enjoy the enclosed patio so we could still feel like we were outside but under cover. We will be back again in the future.
Guest favorite
Chalet in East Stroudsburg
4.92 out of 5 average rating, 439 reviews

Cozy House - Lovely Fairytale TreeHouse - Hot Tub

AngeloRating, 5 stars4 days ago
Had a great weekend with the family here! Recommend for anyone with little ones.

Luxury chalet rentals

Superhost
Chalet in Gouldsboro
4.9 out of 5 average rating, 102 reviews

Mountain Cabin: Outdoor Pool & Lake Access, Sauna

MikeRating, 5 stars3 weeks ago
Myself and a few friends stayed at the cabin for a bachelor party, and we couldn’t have asked for a better spot. The cabin was reasonably priced and well located, with plenty of space for 8 guys (and probably 1-2 more). The hosts were detailed and responsive - we found everything we needed in the guidebook they provided. It was complete with detailed descriptions and how-to videos for the sauna and outdoor fire pit.
Guest favorite
Chalet in Pocono Summit
4.98 out of 5 average rating, 141 reviews

Summit | Lake | Chalet

MichaelRating, 5 stars4 months ago
The cabin is warm, cozy and comfortable. It was a perfect location for a couples weekend. The kitchen is loaded with great appliances and tools so we had a great time cooking. The sauna and hot tub are an attractive addition too, we barely left the cabin all weekend. Thanks Jermaine!
Top guest favorite
Chalet in Pocono Lake
4.93 out of 5 average rating, 262 reviews

Heidi's Chalet - Modern, Hot Tub, Lake Access

WilliamRating, 5 stars4 days ago
Absolutely beautiful location and wonderful hosts. By far the most accommodating stay we have ever had. It felt like home the entire time. Super safe, friendly and welcoming community. Jessica and Scott left nothing to chance. Everything needed and more was provided. They've thought of everything, even things we wouldn't have thought of, so it was a true getaway. Any time we're in the Poconos we will be looking to Jessica first.
Top guest favorite
Chalet in Windham
4.99 out of 5 average rating, 135 reviews

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

KennyRating, 5 stars3 weeks ago
This Airbnb in the Catskills was absolutely perfect, especially for such a special weekend—we got engaged in the area and couldn’t have asked for a better place to come back to and celebrate! The house is beautiful, with a stunning backyard, an amazing hot tub, and a basement full of games that kept everyone entertained. There were plenty of beds, so it was super comfortable for our group. Stephanie was incredible—she made everything so easy and was super responsive anytime we needed anything. You can tell she puts so much thought into making sure guests have a great experience. This is honestly the best Airbnb I’ve ever stayed at. It felt like a mix of cozy and fun, with everything we needed to make the weekend unforgettable. Hoping to come back in the future!
Guest favorite
Chalet in Leeds
4.96 out of 5 average rating, 140 reviews

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

ElizabethRating, 5 stars1 week ago
This was a beautiful home, perfect for our family’s weekend needs. The instructions for arrival, the stay, and departure were all very clear and communication was proactive. Thank you
Superhost
Chalet in Ruby
4.91 out of 5 average rating, 117 reviews

Enchanting Upstate Cabin w Pool, Firepit

KimberlyRating, 5 stars1 week ago
I spent a week at Fouz and Chris's place with my family (8 adults, a toddler and two dogs) and we had very relaxing, enjoyable, comfortable stay. The house is in a quiet, private area and a short distance from places of interest for hikes, restaurants, museums, historical sites, etc. We received great recommendations from the hosts.
Guest favorite
Chalet in Tobyhanna
4.98 out of 5 average rating, 163 reviews

Chalet, Outdoor Kitchen Lounge TV Hot Tub & Sauna!

JamieRating, 5 stars1 month ago
We had a fantastic stay at this Airbnb! I visited with my two daughters and two of their friends, it was the perfect spot for a relaxing family getaway. The home was clean, cozy, and well-stocked with everything we needed. We especially loved the hot tub, sauna, and fire pit—such fun and relaxing amenities that made our stay feel extra special. The neighborhood was quiet and safe, and the host was incredibly thoughtful and responsive, which made the whole experience smooth and enjoyable. Highly recommend for families or anyone looking to unwind in comfort—we’d absolutely stay again!
Guest favorite
Chalet in Pocono Lake
4.97 out of 5 average rating, 134 reviews

Chalet Escape w/sauna, hot tub Bliss Pet friendly

AntonioRating, 5 stars1 month ago
We have been renting in the area for several years now, and I have to say this trip was one of our most pleasant stays. Kellie was always responsive and available when we needed to ask a question. The house was exactly like the listing. It was clean, and all amenities listed were available. The lights and ceiling fans were meticulously labeled making it easy to navigate through the floors. The yard was amazing and securely fenced, and our pups could enjoy the space as much as we did. The water in the hot tub was clean and clear and the sauna worked exactly as described. It was so easy to begin relaxing as soon as we got there, and everyone had a blast. We will definitely come back here in the future.

Lakefront chalet rentals

Guest favorite
Chalet in Hunter
4.98 out of 5 average rating, 154 reviews

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

MariaRating, 5 stars3 weeks ago
Our group at a great time at Nataliya’s in Hunter! The lake was absolutely the highlight, we made full use of the kayaks. Hunter itself is a little sleepy even when we went in May but we enjoyed exploring it and nearby Leeds and Tannersville.
Guest favorite
Chalet in Athens
4.89 out of 5 average rating, 104 reviews

Waterfront Lake Home, close to Hunter & Windham

HilaryRating, 5 stars1 month 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, 136 reviews

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

RichaRating, 5 stars2 weeks ago
We enjoyed our stay! The game room was really a the highlight for us. Whitney’s very responsive and made sure we had a great time during our stay! Definitely recommended !
Guest favorite
Chalet in Glen Spey
4.9 out of 5 average rating, 133 reviews

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

BillRating, 5 stars2 weeks ago
3rd times the charm!!! This was 3rd straight year myself & my crew(family), plus Charlie(Golden Retriever) have been to Alyson & Rob's house! Even though Mother Nature wasn't on our side all weekend, we still had an awesome weekend! Daytime down by the lake, then spending nights around the fire with a few cocktails is a great weekend! Rob & Alyson are quick with a reply to any questions! Looking forward to next year for Round 4! Highly recommend!
Superhost
Chalet in Tobyhanna
4.81 out of 5 average rating, 245 reviews

Lakefront Chalet in Poconos

DanaRating, 5 stars8 months ago
We had a wonderful time staying here! The fall foliage was beautiful, and it was still warm enough to take the boat out on the lake. Arek’s place had everything we needed. Great place for a Pocono getaway.
Superhost
Chalet in Monticello
4.86 out of 5 average rating, 132 reviews

Catskills Lakefront Escape with Hot Tub

JaredRating, 5 stars2 weeks ago
Fantastic house that was exactly as advertised! Very clean and everything was in working order. We had no issues to speak of and would rent this house again in a heartbeat.
Guest favorite
Chalet in Albrightsville
4.97 out of 5 average rating, 106 reviews

Pocono Lakefront Home (Placid Lake)

KatherineRating, 5 stars5 months ago
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!
Superhost
Chalet in Forestburgh
4.87 out of 5 average rating, 15 reviews

Serenity at Lake Joseph | Lakefront•Hot Tub•Ski

MelissaRating, 5 stars1 week ago
Margies place was exactly what our family needed! The games downstairs kept the kids busy during the rain we had. The view is absolutely breathtaking and the hot tub, so relaxing! Definitely highly recommend coming here!

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