Chalet vacation rentals in Woodstock

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Popular amenities for Woodstock chalet rentals

Family-friendly chalet rentals

Top guest favorite
A kidney-shaped pool is set against a sunlit patio, showcasing clear water with a mosaic stone border. The house features a sloped roof and large blue-framed doors leading out to the outdoor space, with a dining area and grill visible in the background.
Chalet in Catskill
4.96 out of 5 average rating, 193 reviews

Daydream Mountain Art-Chateau | Hot Tub & Pool

KristenRating, 5 stars1 week 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!
A spacious chalet with a warm wooden exterior is surrounded by trees. A large deck with wooden railings extends from the upper level. Dual green garage doors are visible, and a gravel driveway leads to the front of the home, enhancing the sense of privacy.
Chalet in Hunter
4.92 out of 5 average rating, 154 reviews

Hunter Chalet 1 ml to Slopes Privately Convenient

JeffRating, 5 stars28 months ago
A great place to stay. Truly she thought of everything. The only thing stopping anyone from having a great time in this place is just bad luck. The hot tub is so nice, and a lot nicer than a typical at home tub. The chalet was a great space and decorated incredibly. I would recommend this place to anyone.
Superhost
The exterior of the chalet features large windows that allow natural light to fill the interior. A hot tub is situated on the deck, along with outdoor seating and a grill, surrounded by tranquil wooded views.
Chalet in Hunter
4.7 out of 5 average rating, 156 reviews

Cozy Art Chalet | Hot Tub, Ski & Hike Escape

MathewRating, 5 stars4 months ago
An awesome place for a ski getaway! The house is beautiful, and just down the road from the mountain. Would highly recommend!
Guest favorite
A charming country home is illuminated by soft evening light, surrounded by trees. A fire pit, constructed of stones, sits in the foreground, with a warm fire flickering. The expansive deck offers outdoor seating, providing a serene setting for gatherings.
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
A contemporary home is set amidst vibrant autumn foliage, showcasing a blend of warm wood tones and large windows. The grassy area in front invites relaxation, while the surrounding trees enhance the rustic charm of the property.
Chalet in Elka Park
4.91 out of 5 average rating, 603 reviews

Secluded home by Hunter Mountain

JessicaRating, 5 stars2 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
A cozy living area is highlighted by a deep blue sofa, accented with light-colored pillows. A large ottoman sits in front, while abundant natural light streams through multiple windows, showcasing a scenic view of the outdoor landscape.
Chalet in Kerhonkson
4.93 out of 5 average rating, 84 reviews

Serene & Bright: Minnewaska Mtn Views ~ Deck ~BBQ

BrandonRating, 5 stars4 weeks 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 favorite
Chalet in Hensonville
4.96 out of 5 average rating, 359 reviews

2BDR- Cozy Windham/Hunter Escape

AmyRating, 5 stars2 months 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!
Top guest favorite
A modern living area is showcased, featuring a plush dark sofa and a live-edge coffee table at its center. Large sliding glass doors provide expansive views of the surrounding landscape, while polished concrete floors complement the wood-paneled ceiling. A flat-screen TV is mounted for entertainment.
Chalet in Cragsmoor
5 out of 5 average rating, 242 reviews

Scandinavian-Style Chalet with Scenic Views

VikromRating, 5 stars1 week 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

Luxury chalet rentals

Top guest favorite
An aerial view captures the log chalet surrounded by vibrant autumn foliage. The large deck features warm lighting and a hot tub, while the driveway accommodates parked vehicles. The property is framed by lush greenery, providing a serene natural backdrop.
Chalet in Windham
5 out of 5 average rating, 51 reviews

Blue Spruce Chalet — Hot Tub, Pet Friendly

PabloRating, 5 stars1 week ago
Cedric’s home was great! Exactly as described and nicer than the photos. Cedric was responsive and a great host. Would definitely visit again!
Guest favorite
A scenic view showcases rolling hills and vibrant foliage, indicative of a seasonal transition. In the foreground, a flower box filled with red blooms adds a touch of color against the backdrop of a serene landscape under a moody sky.
Chalet in Windham
5 out of 5 average rating, 11 reviews

Windham West Chalet

ElenaRating, 5 stars3 months ago
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!
Superhost
The spacious living area is highlighted by high vaulted ceilings and large windows that allow natural light to fill the space. A cozy sectional sofa is paired with coffee tables, and a dining area is visible in the background, creating an inviting atmosphere for gatherings.
Chalet in Windham
4.93 out of 5 average rating, 71 reviews

Windham Mountain Chalet with hot tub

KarinRating, 5 stars4 months ago
This mountain retreat was just perfect for our two families to drive up in our all-wheel drive vehicles (we got a lot of snow) and meet up to ski together for the weekend. There was a great basement area for the boys to play video games, pool, foosball and just hang out. The hot tub provided us all a nice way to relax after skiing at Hunter one day and tubing at Windham another day. Such a great view of the beautiful mountains from the deck. The kitchen was well appointed with all that we needed to make some large dinners for the hungry crew. The beautiful fireplace kept us extra warm and cozy while we watched the NFL playoff games and played family games at night. There was plenty of room with lots of bedrooms, beds and bathrooms for all of us. We hope to come back again.
Guest favorite
A spacious gray couch is positioned in front of large windows, revealing views of the surrounding trees and distant mountains. A single brown throw pillow adds a touch of warmth to the seating area, inviting relaxation and connection with the outdoor landscape.
Chalet in Hunter
5 out of 5 average rating, 22 reviews

Clearview Mt House • 2 Mins to Main • Hike & Swim

MichaelRating, 5 stars3 months ago
Cozy little house on side of Hunter Mtn. Very comfortable and had all amenities needed to accommodate two families with small children.
Top guest favorite
Chalet in West Kill
4.95 out of 5 average rating, 96 reviews

Charming & Private Catskill Chalet

CarolynRating, 5 stars1 month ago
We found the accomodations to be perfect - spacious, clean, well supplied, and so comfortable for our group. What a peaceful and relaxing setting! Thank you, Donald, for staying in touch and making us feel at home. I highly recommend this property for anyone planning a group gathering, celebration, or simply a restful getaway.
Guest favorite
A spacious four-bedroom house is presented against a snowy landscape, showcasing a combination of wooden shingles and stone. Large windows provide ample natural light, while multiple balconies offer outdoor seating. The property is surrounded by protective stone walls and wooded views.
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!
Top guest favorite
The spacious living room features vaulted ceilings and a large stone fireplace. Comfortable leather couches, plush recliner chairs, and stylish swivel chairs are arranged around a central coffee table. Large windows offer natural light and views of the surrounding landscape.
Chalet in Windham
4.98 out of 5 average rating, 125 reviews

Luxe Lodge w/ Mt View | Hot Tub, Fire Pit, Game Rm

MartaRating, 5 stars2 weeks ago
This was a great place for our family getaway. The house is truly made with a womens touch. From water bottles on each nightstand, the little cute pieces of decor to an awesome welcome basket with wine and other yummy things. There is a toddler staircase gate and small baby portable crib, high chair and even toddler utensils. We loved the game room downstairs and especially the top tier karaoke machine. Chess table was a nice addition too. Kitchen is full of machines like kitchen aid mixer if you are planing to cook. With so many people it was wonderful to have this many bathrooms in the house and everyone got their own bedroom. We didn’t have the nicest weather but there are indoor places around to go and honestly plenty to do inside here in this house. One downside was the, not so clean, hot tub. Milky water and gunky sponges that filter the water. Hopefully it was a one off time thing because we are definitely planning on going back.
Guest favorite
The exterior of a chalet home is illuminated at dusk, showcasing a combination of rustic architecture and modern touches. Tall trees frame the property, with solar panels visible on the roof. Warm lights from windows create a welcoming glow against the darkening sky.
Chalet in Fleischmanns
4.95 out of 5 average rating, 19 reviews

Secluded mountain chalet in oddly hip Fleischmanns

ChiokeRating, 5 stars6 months ago
The cabin was much better than me had intended it to be. We definitely enjoyed spending the Thanksgiving weekend there although it was also for my best friend’s bachelorette weekend Such a nice uncomfortable space Matthew was very accommodating and friendly in the way that he helped us with directions and ways to maintain the space Definitely thinking to make it a yearly thing that we do

Lakefront chalet rentals

Guest favorite
An outdoor deck is shown with a relaxing lounge area, featuring wooden chairs and a grill. A hot tub is positioned to one side, while a fire pit sits in the center. The serene lake view is framed by trees, creating a peaceful setting.
Chalet in Hunter
4.98 out of 5 average rating, 154 reviews

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

MariaRating, 5 stars2 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.
Superhost
Chalet in Athens
4.86 out of 5 average rating, 49 reviews

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

KatieRating, 5 stars1 month 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 favorite
Chalet in Athens
4.89 out of 5 average rating, 103 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
The living room features a spacious arrangement of light-colored sofas, accompanied by a wooden coffee table with board games. A wood beam complements the space, leading to a modern kitchen equipped with sleek appliances and a counter with bar stools.
Chalet in Lanesville
5 out of 5 average rating, 6 reviews

Maple Lodge - Luxury Cabin

RashmiRating, 5 stars1 week ago
I had an amazing stay at this cozy retreat in the Catskills! The house was exactly as described and more—clean, well-equipped, and tucked away in a peaceful, scenic location. Waking up to the sounds of nature and sipping coffee on the porch was the perfect way to start each day. The host was incredibly responsive and thoughtful, providing quick responses and making check-in a breeze. Whether you're looking to hike, unwind by the fire pit, or just enjoy the quiet beauty of the mountains, this place is ideal. Highly recommend for anyone looking to escape the city and recharge in nature. I’ll definitely be coming back!
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 stars1 week 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!
A chalet is depicted, surrounded by bare trees under a clear blue sky. The wooden structure features a dark shingle roof and multiple windows. A deck extends from the house, providing views of a serene body of water visible in the background.
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
Guest favorite
Chalet in Hunter
4.97 out of 5 average rating, 33 reviews

Lake &Hunter Ski Resort Luxury Chalet/HotTub/Sauna

JungRating, 5 stars2 weeks 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 favorite
A bald eagle is perched on a bare tree branch, set against a clear blue sky. The eagle's distinctive white head and dark brown body are highlighted, with delicate twigs surrounding it. Soft, wispy clouds are visible in the background.
Chalet in Rosendale
5 out of 5 average rating, 9 reviews

Eagles' retreat

KarolinaRating, 5 stars1 week ago
Had a wonderful stay at this charming little house by the river. The place was spotless, fully equipped with everything we needed, and surrounded by beautiful, peaceful scenery. Perfect for a relaxing getaway - highly recommended!

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