Chalet holiday rentals in Woodstock

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Popular amenities for Woodstock chalet rentals

Family-friendly chalet rentals

Top Guest favourite
Chalet in Catskill
4.96 out of 5 average rating, 195 reviews

Daydream Mountain Art-Chateau | Hot Tub & Pool

WhitneyRating, 5 stars5 days ago
We had a magical weekend away and our stay was everything we hoped it would be, and more. Olia was incredibly responsive, friendly, and all around wonderful to connect with. The house was a magical time capsule holding the best of energy and a glimpse into the 70s - so fun. The pool and patio were awesome, with open and friendly spaces inside too, all made for the best of entertaining spaces. We could not have asked for a better weekend away, and we cannot wait to plan our next trip! Thank you!
Guest favourite
Chalet in Jewett
4.97 out of 5 average rating, 182 reviews

Private Catskills Home w. Hot Tub, near Ski Mnt

Gina-LouiseRating, 5 stars4 months ago
Great place that was clean, comfortable and cozy. There were excellent instructions for everything and my family loved the hot tub!
Guest favourite
Chalet in Elka Park
4.91 out of 5 average rating, 606 reviews

Secluded home by Hunter Mountain

IvanRating, 5 stars6 days ago
We enjoyed our stay so much that I booked another night for the following weekend. The place is simple and beautiful. Secluded, surrounded by a pine forest, with a cozy meadow. The house has everything you need. While we were having dinner, a deer mama and her little Bambi were grazing right outside the windows. A wonderful experience in every way.
Guest favourite
Chalet in Kerhonkson
4.93 out of 5 average rating, 85 reviews

Serene & Bright: Minnewaska Mtn Views ~ Deck ~BBQ

BrandonRating, 5 stars1 month ago
Justin’s place was great! Beautiful views, comfortable space with everything you need, and pretty centrally situated for exploring the region. Hope to come back again!
Top Guest favourite
Chalet in Hensonville
4.96 out of 5 average rating, 362 reviews

2BDR- Cozy Windham/Hunter Escape

JulianRating, 5 stars5 days ago
We had a relaxing and beautiful time at Simone place. Even though I had no signal at arriving it was very easy to connect to your wifi and then access the premises. I wished we had stayed longer, and used the fireplace outside one night. Thanks for making our stay as smoothly as possible. If you are looking for a quiet weekend away from the city, with having all amenities and be able to cook a proper meal at night, this is the perfect place. The House gave us the perfect private gateway. Not far from the Kaaterskill Falls, there's plenty of other trails/ hikes in the area. Thanks for having us, until next time.
Top Guest favourite
Chalet in Cragsmoor
5 out of 5 average rating, 242 reviews

Scandinavian-Style Chalet with Scenic Views

VikromRating, 5 stars3 weeks ago
Beautiful chalet with even better views - perfect for a calm and peaceful get away from the city, near hiking trails and 7 min from town for restaurants, had a great weekend and hope to be back soon
Guest favourite
Chalet in Woodstock
4.94 out of 5 average rating, 119 reviews

Marigold - Stream side Cabin W/Hot Tub & Fireplace

MelissaRating, 5 stars2 months ago
We had a spectacular long weekend here. We enjoyed the clean and simple spaces and especially enjoyed looking at the stars at night from the hot tub. It was so peaceful to be surrounded by woods and yet a short drive to downtown Woodstock. We’d definitely stay here again!
Top Guest favourite
Chalet in Willow
4.92 out of 5 average rating, 99 reviews

Gorgeous Mountain Views, 4 Acre Retreat, Hot Tub

AlexRating, 5 stars3 weeks ago
Could not be more impressed with both the house and host. They made our trip a wonderful special experience.

Luxury chalet rentals

Top Guest favourite
Chalet in Windham
4.99 out of 5 average rating, 135 reviews

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

KennyRating, 5 stars1 month 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 favourite
Chalet in Maplecrest
4.98 out of 5 average rating, 81 reviews

Secluded Catskills Designer Lodge - Windham/Hunter

PatriciaRating, 5 stars3 months ago
Wonderful! The house is really beautiful, with large windows and stunning views of the birch forest and a meandering stream. It is very clean, nicely decorated, and cozy. We especially enjoyed the hot tub and fireplace. The kitchen has everything you could possibly need. Nik is friendly and responsive. The location is great too, feels like a nature retreat but an easy drive to restaurants and skiing at Hunter Mountain.
Guest favourite
Chalet in Leeds
4.96 out of 5 average rating, 140 reviews

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

ElizabethRating, 5 stars2 weeks 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
Top Guest favourite
Chalet in Elka Park
4.97 out of 5 average rating, 93 reviews

Thorne Hollow - Mountain Ski Getaway with HotTub

JaclynRating, 5 stars3 weeks ago
This home was absolutely perfect! The host was incredibly responsive and the house was spotless. She truly thought of everything—even welcoming us with a bottle of wine, which was such a thoughtful touch. Thank you for a wonderful stay!
Top Guest favourite
Chalet in Windham
5 out of 5 average rating, 38 reviews

Mountain Views-Game Room-Hot Tub-5 minutes to town

NikkiRating, 5 stars2 weeks ago
Melanie was a fantastic host. She was responsive and helpful. The house is beautiful, nestled in the trees on your own little piece of the mountain. There are many great hikes and restaurants close by. There is a great little coffee shop and breakfast spot within five minutes. The property even has some little waterfalls and areas to explore. Our daughters had fun playing games in the game room and have developed a love of shuffleboard. We were able to cook dinners and have a nice fire outside under the stars with everything we needed. This is a great house for a mountain getaway.
Superhost
Chalet in Fleischmanns
4.75 out of 5 average rating, 36 reviews

Belleayre View: Paramount Views, Hot Tub + Firepit

TheresaRating, 5 stars3 months ago
This was the perfect place to stay for our weekend girls trip to Belleayre mountain. Everything was exactly as expected. We hope to stay again next year!
Superhost
Chalet in Windham
4.88 out of 5 average rating, 189 reviews

Beautiful Windham Ski/Summer House

AmyRating, 5 stars4 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!
Guest favourite
Chalet in Prattsville
4.93 out of 5 average rating, 88 reviews

White Holiday Cozy Chalet Pool/Hot Tub/bubble room

Franchesk JRating, 5 stars6 days ago
My group and I had the best stay! Super friendly and communicative hosts. Very comfortable and cozy house. Great place to stay for different types of guests!

Lakefront chalet rentals

Guest favourite
Chalet in Hunter
4.98 out of 5 average rating, 155 reviews

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

AndrewRating, 5 stars2 weeks ago
Beautiful house in a beautiful location! We loved all the space and amenities, especially the hot tub and sauna. The host was very helpful and responsive as we were planning our trip. Half of our party had stayed there before and wanted to go back. Thanks for a great stay!
Superhost
Chalet in Athens
4.86 out of 5 average rating, 49 reviews

Large & Sunny Lakefront Home-kayaks/fire pit/games

KatieRating, 5 stars2 months ago
This was such a relaxing home to spend a celebratory weekend in! We had a great time at Adnan's home over the weekend. The setting is so peaceful, right on the water and we enjoyed the fire pit one evening. The space is large, with plenty of room for all. The house is a little bit dated, but with that said, it had everything we needed for a lake-weekend! On top of that, Adnan could not have been more accommodating and responsive.
Guest favourite
Chalet in Athens
4.9 out of 5 average rating, 105 reviews

Waterfront Lake Home, close to Hunter & Windham

RickyRating, 5 stars6 days ago
We had a great stay. Very convenient check-in and check-put process. Enjoyed having a lot of things to do at the house and in the community. Thanks!
Guest favourite
Chalet in Glen Spey
4.9 out of 5 average rating, 133 reviews

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

BillRating, 5 stars3 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!
Chalet in Liberty
4.69 out of 5 average rating, 51 reviews

Chalet on the Waterfront with Lovely Interior

MjRating, 5 stars5 months ago
Great stay away from busy nyc. Private and warm
Superhost
Chalet in Monticello
4.86 out of 5 average rating, 133 reviews

Catskills Lakefront Escape with Hot Tub

MichelleRating, 5 stars6 days ago
Great location so peaceful and serene!
Guest favourite
Chalet in Hunter
4.97 out of 5 average rating, 33 reviews

Lake &Hunter Ski Resort Luxury Chalet/HotTub/Sauna

JungRating, 5 stars1 month ago
This was a very nice home with plenty of space for our whole group and easy access to the lake. Valentyna was highly responsive to our questions/messages during the stay and provided helpful house rules/instructions. Note that the study area is not a separate room but a corner/nook in one of the bedrooms, so plan accordingly. Overall, would definitely recommend for large groups of 16+.
Top Guest favourite
Chalet in Rosendale
5 out of 5 average rating, 13 reviews

Eagles' retreat

M&MRating, 5 stars6 days ago
Henri’s house was perfect for our weekend getaway. We arrived at night and the driveway has lovely lights all the way down. It is very peaceful, beautiful and cozy. Loved that there are so many windows and the deck is great. All the instructions were very clear. He also had some fun historical facts about the area and great food recommendations.

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