Holiday houses in Roscoe

4.98 out of 5 average rating, 105 reviews

Cabin@Crow Hill: unplug and reconnect with nature

Escape it all, listen to the birds and near by Buck Brook. Explore the Catskills with plenty of hiking, lakes, and fly fishing. The stars are incredible, so as you sit on the balcony or at the fire pit look up. Crow Hill is located on a quiet road away from the bustle of town. The wifi is moderate due to the location, so it allows you to unplug. Crow Hill is dog friendly ( no cats) and perfect for a family getaway. The cabin is deep cleaned and sanitized between guests. Come take a break!

4.99 out of 5 average rating, 136 reviews

Wonder's Never Cease: Hot Tub, Sauna & Cold Plunge

Hi, I'm Wonder! Welcome to my magical Catskills cabin escape - quiet & with a private spa. Ideal for romantic getaways, vacations w family & friends, or wellness retreats. Nestled in nature, our clean log cabin offers a natural, chemical-free hot tub, sauna & cold plunge. Enjoy views from the porch, cozy by the wood stove, grill epic meals, indulge in the spa & explore hikes & cute towns. Child, infant, pet friendly. Helpful host! Book to reconnect with nature, one another & yourself.

4.93 out of 5 average rating, 141 reviews

Parkston Schoolhouse

Relax and unwind in this historic converted one-room schoolhouse. Built in 1870, the Parkston Schoolhouse served all grade levels in the Livingston Manor area. The schoolhouse was retired and converted to a cozy cottage style home in the mid 20th century and has recently been renovated into a stylish tiny home getaway. The home is tucked into the hillside along the beautiful, winding Willowemoc Creek and is set amidst a lush Catskill landscape just a five minute drive from Livingston Manor.

4.94 out of 5 average rating, 155 reviews

Cabin in Walton

The Mill House: Creekside Catskills Spring Escape

Nestled in the heart of the Catskills and just a 2.5-hour drive from NYC, escape to a winter retreat where you can reconnect with nature and enjoy the serene beauty of the season. This historic gem underwent a meticulous restoration in 2021, marrying its saw mill heritage with contemporary luxuries, including a Nest thermostat, smart speakers, keyless entry, and fast wifi. Original exposed post and beam construction and Scandinavian-inspired design make for a unique and cozy atmosphere.

4.97 out of 5 average rating, 118 reviews

Chalet in Roscoe

Sunday Mountain House - Cozy Catskills Chalet

Sunday Lodge & Mountain House is a peaceful retreat on 5 acres in the Catskill Mountains. Our home is located about 2-2.5 hours from NYC, and minutes from the charming towns of Roscoe and Livingston Manor. Tucked away on a mountain road, this is the perfect a place to relax and unwind. You can sleep. You can sip. You can cook. You can workout. You can hang. Outside of our doors you can fish. You can hike. You can stargaze. You can play. A place to do everything or nothing at all.

4.96 out of 5 average rating, 154 reviews

Roscoe Cabin Pet Friendly

Roscoecabinpetfriendly: A Tranquil Escape in Roscoe, NY Nestled in the woods known as Trout Town USA, our rustic farmhouse cabin offers the perfect retreat for city dwellers seeking relaxation and adventure. Enjoy the scenic 14-mile drive through the mountains to Bethel Woods Concerts with no traffic. Book your mountain escape with us today and enjoy fresh, clean air, beautiful scenery, and a cozy, well-equipped cabin . We look forward to hosting you and your furry friends soon.

4.87 out of 5 average rating, 123 reviews

Home in Roscoe

Modern Rustic Tiny Home in the Catskills

Enjoy this tiny home nestled among five acres of Catskills Forest on a two home lot, just a short distance from essential Catskills towns like Roscoe and Callicoon. The house is a newly built modern studio with a sleeping loft, kitchen, bathroom, wood stove, and large sundeck. It has a separate driveway from the second house on the lot, to maximize privacy for you and your group. Enjoy the wifi, luxury furnishings, thoughtful amenities, and Smart TV in our retreat from the city!

4.95 out of 5 average rating, 305 reviews

River view:

Rental is located next to a busy road , if you are not comfortable with some traffic at certain times of the day then this may not be for you I would also note that this home is small inside but very comfortable . There is a cozy yard to relax in next to a fire pit and a table and chairs if you would like to eat outside. I will provide firewood for one night, and charcoal for grill for one night as well. Located 1/4 mile from home is a local place to purchase extra wood .

4.91 out of 5 average rating, 173 reviews

Butternut Farm Cottage

Butternut Farm Cottage is an 1880's farmhouse. One and a half story great room with wood burning stove, kitchen, dishwasher; laundry room, two bathrooms and library with TV and Wifi. Lots of natural light. Sound system throughout. Covered porch. Comfortable beds. BBQ grill and fire-pit. Good for couples, solo adventurers, business travelers, families, and medium size groups (up to 6). **While not an issue for most some ambient noise from Rt. 17 is heard when outside.

4.93 out of 5 average rating, 227 reviews

Roscoe Retreat

Located in Trout Town USA ! Secluded, 1600 sq ft log home, 3 bedrooms, 2.5 baths on 5 private acres. Magnificent year round Catskill Mountain views. Beaver kill River is 5 minutes away! Stunning indoor fireplace, relaxing front porch and large back deck with gas BBQ. Internet and satellite T.V. in bedrooms, with Netflix and HBO. Spacious outdoor, w/ gazebo, hammock , picnic table & hot tub! Less than 2hrs from 2hrs from the GWB this is a great year round getaway!

4.98 out of 5 average rating, 142 reviews

Tent in Livingston Manor

Milkweed Camp - Glamping in a Blueberry Field

Our off-grid canvas tent is situated at the edge of a meadow, surrounded by blueberry bushes. It's just 4.5 miles to Main St in Livingston Manor, and 35 minutes to Bethel Woods. We provide a full-size bed (w/ heated mattress pad), fire pit, firewood, propane heater, and solar power. You have access to a private outhouse with composting toilet & outdoor shower on-site, and a conventional shared bathroom if you preferred. We are an LGBTQ+ inclusive space.

Place to stay in Downsville

4.87 out of 5 average rating, 180 reviews

Half Moon: Fairytale Catskills Retreat

Enjoy nature in style at this fairytale in the forest. This idyllic escape combines whimsical structures, curated gathering spaces and a private wooded hillside surrounded by hiking trails and quaint towns. Disclaimer: This is a rustic cabin. Heating is from a wood-burning stove, there is no AC. The bath house is a separate structure from the cabin, up a hillside with stone steps. Cooking is via charcoal grills, small outdoor kitchenette or fire.

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Other great holiday rentals in Roscoe

4.91 out of 5 average rating, 99 reviews

Apartment in Roscoe

1br 1ba apt w living room, kitchenette &free wifi

GaryRating, 5 stars2 weeks ago

Private, clean and comfortable, walk to everything in town. Restaurants, Fly shops, antiques and more. Our host was responsive and helpful. "Trout town" lives up to it's name and this place is a great base to run your Catskills fishing adventure out of.

Tiny home in Livingston Manor

4.86 out of 5 average rating, 66 reviews

Riverside Tiny Home!

AshleyRating, 5 stars3 days ago

The cabin was super cute and cozy, it made camping feel right at home. Listening to the stream outside was the best part! And our German Shepherd loved it just as much as us! Highly recommend!

5 out of 5 average rating, 27 reviews

Home in Roscoe

Spacious 4 Bedroom in the Heart of Roscoe NY

ChristineRating, 5 stars5 months ago

We had a great stay at Reynan's house with my husband and 2.5 year old son. The house was in a super convenient location—close to Roscoe and near other charming towns like Livingston Manor (10 mins) and Callicoon (20 mins).The home itself was well-equipped with all the cooking supplies we needed, which made cooking easy and enjoyable after we stopped at the cute wine shops and markets in town. The working fireplace added a cozy touch and was great for relaxing in the evenings.Our host went above and beyond to make our stay enjoyable. They were very communicative and accommodating, offering a flexible check-in time and responding quickly to any questions. When we had an issue with our car, they were incredibly responsive and helpful, which we truly appreciated. The local recommendations they provided were spot-on and added so much to our experience. This home offered everything we needed for a comfortable and memorable getaway.

4.99 out of 5 average rating, 77 reviews

Home in Roscoe

The Muskoday Lake House - Modern Lakefront Oasis

MichelleRating, 5 stars3 weeks ago

Stayed for a long weekend with our pup. The house was perfect, they thought of everything! Amazing lake view. 14 minute drive to town and just under 20 to the next town. Plenty of good food, drinks and shopping! Thank you Marzena for being an exceptional host!

5 out of 5 average rating, 38 reviews

Cabin in Saugerties

Luxury A-Frame Cabin w/ Hot Tub

BingRating, 5 stars1 week ago

We absolutely loved our stay at Fil & Ellie’s place, it made it the highlight of our trip. From the minute we walked in, it felt so calm. The place is beautiful with all the amenities. We enjoyed the hot tub, grill, fireplace. We’ve been to the Catskills countless times and this is the best experience due to the wonderful stay. Thank you!

5 out of 5 average rating, 16 reviews

Tiny home in Roscoe

Hope | A Peaceful Tiny Home

AndreaRating, 5 stars8 months ago

Our stay at Hope was superb! The house is nestled at the end of a small country road, and it is ideally situated so that the house looks out onto a babbling brook and mountain forest that was beginning to show fall colors while we were there. The house itself has everything you need for a weekend away, and it is both an excellent home base for anyone looking to hike the abundant nearby trails, or an ideal place for reading and quiet reflection (we spent much of our time watching the leaves through the picture window). Seth and Morena were the consummate hosts – check-in was a breeze, and we could tell that every aspect of the stay had been thoughtfully considered. I would highly recommend staying at Hope!

4.92 out of 5 average rating, 13 reviews

Villa in Roscoe

Lakefront, newly renovated home in the Catskills

MeganRating, 5 stars9 months ago

Our family weekend at Casa Julia was awesome. All 3 generations loved the layout of the house and the beautiful lake across the street. The house was nicely decorated, matched the pictures, and had everything we needed. It was a great home base for relaxation and exploring the Catskills!