
Holiday rentals in Handsome Hollow
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Top-rated holiday rentals in Handsome Hollow
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Handsome Hollow
Top guest favourite

Chalet in Callicoon Center
4.98 out of 5 average rating, 51 reviewsArchitecturally Designed Catskill Chalet
SarahRating, 5 stars1 week ago
This is the second time in three months that we've stayed at Megan's place! We've never stayed in the same AirBnB twice, and that just shows how much we loved it. It's private and secluded, but you're still only 10-15 minutes from town, restaurants, hiking, and breweries. Lots to do in the area, and would love to come back again.
Guest favourite

Home in Hankins
4.88 out of 5 average rating, 50 reviewsPeace AND Style: Hot Tub/Fire Pit/Fully Renovated
DestinyRating, 5 stars2 weeks ago
Our stay was absolutely beautiful and very relaxing . The host was very proactive with answering any questions and making sure we were all set to have a good trip! The house it’s self was stunning as with the area around it.
Guest favourite

Home in Roscoe
4.99 out of 5 average rating, 78 reviewsThe Muskoday Lake House - Modern Lakefront Oasis
DavidRating, 5 stars1 week ago
I rented to celebrate my sister’s birthday with our families. The house it was perfect for our three couples and one teen teenager. It had everything you could think of for an amazing stay. We barbecued dinner, made s’mores around the fire pit and spend time on the lake. It was a great time and can’t wait to go back. Marzena was a great host!
Guest favourite

Home in Roscoe
4.9 out of 5 average rating, 60 reviewsThe Green House. Family Friendly cabin Upstate NY
ForrestRating, 5 stars5 days ago
We had such an incredible stay at The Greenhouse. Meredith is an incredible host with great communication. The house was easy to find and access with Meredith’s detailed instructions. It is very cute and clean. The yard is an awesome added bonus as it provides plenty of space for little kids to run around and play as well as plenty of space for Dogs. It was quite hot out when we visited and the AC unit in the house keep it a very comfortable temperature without any issues. You have the convenience of being close to downtown Roscoe, the Beaverkill River, and other fun activities like Buck Brook Alpaca Farm. While also having privacy and seclusion. We had such a great time and will absolutely be staying with at The Greenhouse on any and all future Roscoe trips!
Superhost

Home in Roscoe
4.69 out of 5 average rating, 16 reviewsModern House Deep in the Woods of Roscoe
MateoRating, 5 stars4 days ago
If you're looking for something incredibly peaceful, artfully (and masterfully) constructed, as well as within a short drive of restaurants, stop reading and book this place right now. I've traveled the world and stayed in many Airbnbs and hotels, yet this home is truly one-of-one. The photos don't do it justice. It's large, full of light, every piece of furniture is intentionally curated, and perhaps best of all, you're really deep, deep in the woods. Forget an alarm, sunlight and birdsong will wake you up (though not in a bad way). Try the Conover Club, down the road, for a 10/10 (I mean it!) dinner. With all of that said, as others mentioned, I likely wouldn't book in winter, because it's a hilly drive to the house. And the doors leading to the patio don't lock, which I didn't mind, but it was slightly off-putting to my friend. Still, safety was never a question in my mind. You're truly off the beaten path. The hosts are also so helpful and ensure you have the best time. Enjoy!
Guest favourite

Cottage in Hancock
4.94 out of 5 average rating, 18 reviewsFrench Woods Farmhouse: TimeOut NY's favorite
TylerRating, 5 stars2 months ago
Absolutely loved our stay! We were looking for quiet, peaceful, and lots of R&R. Bruce was easy to get a hold of and very helpful. Highly recommended!!!
Guest favourite

Cottage in Roscoe
4.98 out of 5 average rating, 45 reviewsCheerful Cottage on the Beaverkill River
NancyRating, 5 stars3 weeks ago
I loved this place. Can’t wait to go back.
Top guest favourite

Cabin in Downsville
5 out of 5 average rating, 27 reviewsModern, Clean, Serene Streamside Catskills Chalet
BristonRating, 5 stars4 days ago
We had a wonderful stay at this cozy cabin! The setting was perfect — total privacy with a peaceful brook right beside the cabin. It felt like our own little retreat. My wife and I loved the quiet and the chance to unwind, and the nearby hiking trails were a great bonus for some outdoor adventure. The cabin was comfortable and exactly as described. Evan was a great host, very responsive and helpful. My only small wish was for blackout blinds or some option to cover the windows—not for sleeping, since it naturally gets dark, but just for extra privacy. Overall, a fantastic getaway spot and we’d happily stay again. Highly recommend for anyone looking to escape and recharge!
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- Hunter Mountain
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- The Kartrite Resort & Indoor Waterpark
- Montage Mountain Resorts
- The Country Club of Scranton
- Resorts World Catskills
- Promised Land State Park
- Elk Mountain Ski Resort
- Salt Springs State Park
- Lackawanna State Park
- Villa Roma Ski Resort
- Chenango Valley State Park
- Claws 'N' Paws
- Hunter Mountain Resort
- Plattekill Mountain