Holiday rentals in Round Top

4.91 out of 5 average rating, 159 reviews

Tiny home in Palenville

Unique Tiny House Glamping in the Catskills

Looking for the perfectly romantic glamping getaway? This stunning handcrafted hut was designed by my Buddhist mother for a meditation retreat, and to commune with nature. With unique timbered walls and ceilings, a wood-burning stove (the only heat source), rustic stone detailing on the walls and large glass windows, you'll feel like you're living in the woods, but with the comfort of the indoors. Please note that this is an off-grid camping cabin without water, and only limited electricity.

Guest suite in Palenville

4.94 out of 5 average rating, 196 reviews

Rocky Ledges

Our house was a historic cottage, built in the 1880s. We built a new house around the cottage. We are Artists and our guest bedrooms are in a sense galleries. Guests have the entire second floor, 2 bedrooms, perfect for couples who are traveling together & families with teenagers. The back is the private entrance to the stairs. We live on a quiet and pleasant dead end street. The views of the Catskills & gardens are awesome. Located near Hunter Mountain Festivals, Woodstock & Katterskill Falls.

Guest suite in Tannersville

4.75 out of 5 average rating, 103 reviews

La Villa Catskills: Studio

Welcome to our home, nestled in Catskill Park! We are 20 min to Windham Mnt, 10 min to Hunter Mnt, 5 min to Kaaterskill Falls, 3 min to North-South Lake & plenty Catskill gems! Enjoy a family friendly stay or romantic getaway in nature & relax on the private wrap around porch after a nearby hike or day at the slopes! Relish the views of Upstate NY at the fire pit on our 2 acre lawn, next to our fountain lake, with scenic mountain views at day or at night under the stars. #LaVillaCatskills on IG

4.97 out of 5 average rating, 204 reviews

Home in Round Top

Escape in the Catskills w/hottub

Escape to the Catskills: Your Mountain Retreat No Cleaning Fee! Immerse yourself in the breathtaking beauty of the Catskills. Our cozy retreat offers the perfect blend of relaxation and adventure, whether you're seeking a romantic getaway, a peaceful remote work haven, or an exciting outdoor adventure. Unwind in the hot tub while enjoying stunning world-class panoramic views. Conveniently located near charming towns with unique shops, delectable dining options, and hidden antique treasures.

4.98 out of 5 average rating, 237 reviews

Cabin in Tannersville

Cabin by the woods, Hunter Mountain & Kaaterskills

Our cozy little cottage is tucked away adjacent to the woods. This single floor 650sf apartment is a perfect place to unwind, build a bonfire, & enjoy the nature that surrounds you. Wake up in the morning to watch deer while enjoying your coffee on the porch. Main St. Tannersville is only an 8 min walk; with its nice selection of restaurants & shops. Hunter Mountain & Kaaterskill Falls are within a 10 min drive . Woodstock, Saugertise, Windham, Catskill & Kingston are within a 35 min drive.

4.96 out of 5 average rating, 283 reviews

Cottage in Catskill

1930's Cottage charm cozy air cond. near hiking

1 bedroom 1930's guest cottage with a living room. Near many hiking trails. Window air conditioner brand new, ceiling fans in living room and bedroom. Separate windowed bedroom with new full size mattress. Full size gas stove, microwave, fridge, Keurig coffee maker, toaster and large tiled counter and sink. Full bath off bedroom with large clawfoot tub and shower combination and sink and brand new toilet. Wifi , flat screen Smart TV. Vintage cast iron fireplace with electric insert.

4.89 out of 5 average rating, 193 reviews

Apartment in Windham

Cozy Hideaway Windham, Hunter ,Pool,Pickleball.

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

4.98 out of 5 average rating, 177 reviews

Guest house in Cairo

Tomte Cottage in the Catskills!

Stay in the heart of the Catskills! 2 Bedroom Cottage with private entrance. One bedroom has a queen bed the other a twin/full bunk bed, suited for up to 5 guests! Cottage has full kitchen and bath w/shower. Wi-Fi and a 50 inch smart tv. Located 18 minutes to Windham and 30 to Hunter for skiing or snowboarding. Whether you are looking for a quiet weekend retreat or family weekend skiing trip, hiking or just exploring, this is the place for you! Self check in for your convenience.

4.96 out of 5 average rating, 108 reviews

Home in Cairo

Modern Mountain Retreat: Great for slopes & trails

Surrounded by trees with exceptional mountain views, this two-bedroom retreat has been carefully thought out to allow you to take in the scenery without having to give up modern conveniences. There's so much to discover in this rural area of NY, including Windham Mountain and Hunter Mountain, which are just 20 mins and 30 mins away, respectively. So if you're looking for a cozy spot after hitting the slopes, or a tranquil home to relax and curl up with loved ones, this is it.

4.89 out of 5 average rating, 552 reviews

Tiny home in Palenville

Plant House- Woodstock/Kaaterskill/Ski, NYC Bus

Two hours from NYC, close to skiing (hunter mountain) , Kaaterskill falls, Woodstock, Hudson, Saugerties. Book us and make Hudson Getaways your base station for all kinds of adventures. Enjoy facilities of a bigger house in a tiny form factor. Heat/AC, Queen bed, Hot shower, Kitchenette, Fridge, Towels, linens, soap,coffee etc. *Hudson Getaways is a small woman owned business. We offer discounts to our social media followers, to returning guests and during slow seasons.

4.98 out of 5 average rating, 101 reviews

Flat in Round Top

🏔O'Clarke Mountain House - The Catskills

Enjoy a slice of hosts (Bridgitte and Kevin's) ideal Catskill Mountain vacation rental. This 2bd 2ba apartment has an outstanding kitchen, bathrooms, cozy living room, and a perfect dining table to enjoy all your meals. This is our first home, and we will be your neighbors living on the other side of the duplex, we will respect your privacy and let you enjoy your well-earned time away from home. We hope to introduce you to our favorite shops, hikes, and restaurants nearby.

5 out of 5 average rating, 304 reviews

Flat in Freehold

Mountain View Retreat~Sunny Hill Golf / Skiing

Welcome to Sunny Hill Road ! We are located in a small community of private homes in an open space overlooking the mountains. This one bedroom unit has everything you need to enjoy your stay in the Catskills. Relax on the private deck or inside with amazing views from every window. The kitchen is fully equipped and ready to cook a full meal and then enjoy it in the dining room overlooking the mountains. It is quiet and restful here, amazingly beautiful in all four seasons!

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Other great holiday rentals in Round Top

4.98 out of 5 average rating, 62 reviews

Cabin in Catskill

Modern Cabin in the woods

MichaelRating, 5 stars1 month ago

Sahar's listing was exactly what i was looking for to get away for a weekend. I stayed at the Sol cabin which was located right next to the start of the hiking trail. The cabin itself is clean and the kitchen has everything you need to make a simple meal. The property is very private and I really enjoyed my stay. Would recommend to family and friends.

4.96 out of 5 average rating, 27 reviews

Tent in Catskill

Mountain View Camping - The Old Catskill Game Farm

MorganRating, 5 stars1 week ago

Absolutely beautiful campsite, waking up to mountain views and listening to local wildlife at night is something youll never appreciate until you can really see it. this campsite was clean, well structured and really came with anything i could have needed

4.93 out of 5 average rating, 27 reviews

Home in Catskill

Chic Stream-side Chalet • Mountain View • Catskill

AlexaRating, 5 stars3 weeks ago

We had a great stay, the house was beautifully decorated and we enjoyed the hot tub and soaking tub. Views were stunning too!

4.98 out of 5 average rating, 65 reviews

Home in Cairo

Couples' Mountain Escape |HotTub|GameRoom|MtnViews

KristinRating, 5 stars1 week ago

Enjoyed a fun and peaceful stay. Janet and Bernard were communicative and helpful, and the house has an amazing indoor bathtub and relaxing outdoor hot tub. Game room downstairs was also fun! I had some issues with allergy/asthma triggers--my fault for not noticing that the house is listed as "pet friendly" and has carpets in the bedroom (everything was EXTREMELY clean, but I'm just really sensitive to residual allergens). Although the house is located on a street with other nearby houses, the hot tub and back porch have fences to maintain a private atmosphere. I recommend dining and hiking in the Hudson area, which is a short ride away. Overall, a very relaxing and enjoyable place to stay, with fantastic hosts!

5 out of 5 average rating, 37 reviews

Cabin in Saugerties

Luxury A-Frame Cabin w/ Hot Tub

ChrisRating, 5 stars6 days ago

Fil & Ellie’s place was the perfect stay for our getaway. Their home is amazing. We were very impressed by the amenities, the cleanliness and attention to detail. This place has everything you’ll need for a great stay. The hosts were also very helpful in answering our questions and assisting us with check-in. I would highly recommend staying here if you have the chance.

4.97 out of 5 average rating, 39 reviews

Home in East Jewett

Creekside Couple's Retreat w/Hot tub, Sauna & More

JessicaRating, 5 stars2 days ago

My boyfriend and I stayed here for 2 nights, wishing we booked for longer. From the second we walked through the door we were super relaxed. The whole house is decorated for a very cozy feel and the house was super clean. We did not leave once we got there until check-out and never felt bored or like we needed to get out of the house. This house has everything you need to cook, relax there is also plenty of things to do. We loved the air hockey table and I spent most of my time in the hot tub which is right next to the river. If you book this place you won’t be disappointed!

5 out of 5 average rating, 26 reviews

Flat in Purling

The Purling Perch

SanjedaRating, 5 stars2 weeks ago

I had such a wonderful stay at Paul’s place! The house was beautiful, very clean and cozy. It had everything I needed for a relaxing getaway. The surrounding area was equally stunning, with mountains all around, making it the perfect place to unwind. Paul was incredibly kind, even leaving out some treats! I would absolutely stay here again!