
Chalet vacation rentals in Woodstock
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Top-rated chalet rentals in Woodstock
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Popular amenities for Woodstock chalet rentals
Family-friendly chalet rentals

Daydream Mountain Art-Chateau | Hot Tub & Pool
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!

Hunter Chalet 1 ml to Slopes Privately Convenient
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.

Cozy Art Chalet | Hot Tub, Ski & Hike Escape
An awesome place for a ski getaway! The house is beautiful, and just down the road from the mountain. Would highly recommend!

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!

Secluded home by Hunter Mountain
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!

Serene & Bright: Minnewaska Mtn Views ~ Deck ~BBQ
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!

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!

Scandinavian-Style Chalet with Scenic Views
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

Blue Spruce Chalet — Hot Tub, Pet Friendly
Cedric’s home was great! Exactly as described and nicer than the photos. Cedric was responsive and a great host. Would definitely visit again!

Windham West Chalet
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!

Windham Mountain Chalet with hot tub
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.

Clearview Mt House • 2 Mins to Main • Hike & Swim
Cozy little house on side of Hunter Mtn. Very comfortable and had all amenities needed to accommodate two families with small children.

Charming & Private Catskill Chalet
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.

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!

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

Secluded mountain chalet in oddly hip Fleischmanns
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

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

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

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.

Maple Lodge - Luxury Cabin
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!

Mayflower - Lake access/hot tub/game room/pets
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 on the Waterfront with Lovely Interior
Great stay away from busy nyc. Private and warm

Lake &Hunter Ski Resort Luxury Chalet/HotTub/Sauna
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+.

Eagles' retreat
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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- Hunter Mountain
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Howe Caverns
- Windham Mountain
- Thunder Ridge Ski Area
- The Kartrite Resort & Indoor Waterpark
- John Boyd Thacher State Park
- Albany Center Gallery
- Catamount Mountain Ski Resort
- Resorts World Catskills
- Taconic State Park
- Bash Bish Falls State Park
- Hudson Highlands State Park
- Walkway Over the Hudson State Historic Park
- Brotherhood, America's Oldest Winery
- Zoom Flume
- Hunter Mountain Resort
- Kent Falls State Park
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Villa Roma Ski Resort
- Hancock Shaker Village
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