Holiday rentals in Round Top

Guest suite in Palenville

4.93 out of 5 average rating, 198 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.

4.97 out of 5 average rating, 205 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.

4.96 out of 5 average rating, 233 reviews

Cabin in Maplecrest

The Cabin - Ski House near Windham

The Cabin is set back, secluded, unbelievably cozy and wonderfully romantic. It's a place to reconnect and recharge, to listen to the river and hear the wind through the trees and indulge in slow lunches and long walks and truly marvel at the Catskills. There's hiking in the summer, skiing in the winter, mountain fresh air and dark, starry nights. This is a house, and you can treat it as such. But if you let go, and give in to the energy of a space created with love, this will feel like home.

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.

Guest suite in Tannersville

4.85 out of 5 average rating, 114 reviews

La villa Catskills: 1 Bedroom Apt

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. Take in nature at our 2 acre property & enjoy the views of Upstate NY, all year round! Relax at a family-friendly stay or romantic getaway after a hike or day at the slopes. Grill with scenic mountain views from a private balcony or enjoy a toasty fire pit by the fountain lake, under the stars. #LaVillaCatskills on IG

4.89 out of 5 average rating, 196 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.

4.96 out of 5 average rating, 205 reviews

Chalet in Round Top

Welcome to the Shangri-La Chalet!

A Chalet-style home in the Catskills, ideal to SKI, HIKE, WORK REMOTELY; PLAY or simply get away. Lots of GAMEROOM activities; a large airy "GREAT ROOM" for gatherings by the FIREPLACE then wander to private bedrooms. OUTDOOR wrap-around split-level DECKS (nearly 3,000 sq. ft!) with all the accoutrements for outdoor GRILLING & DINING AL FRESCO and a dip in the HOT TUB! WIFI is 200 DOWNLOAD /10 UPLOAD On-site AMPLE PARKING Longer stays welcomed & discounted! NOT SUITABLE FOR MINORS.

4.96 out of 5 average rating, 109 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, 556 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, 305 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!

4.99 out of 5 average rating, 441 reviews

Bungalow in Cairo

Riverfront-swim & float the river-20 min to Hudson

Modern Scandinavia-style riverfront bungalow on 8 acres. Sit on your deck with twinkle lights for coffee/dinner filled w sounds & views of a rushing river; walk across the river into your own private swimming spot! Perfect for a nature retreat, hiking, swimming, fishing (stocked every April), skiing, work w mountain views or write that novel you have always wanted to finish. 2 hrs from the George Washington Bridge. Level 2 EV charger. Hate has no home here-all are welcome.

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Other great holiday rentals in Round Top

4.88 out of 5 average rating, 8 reviews

Cabin in Hunter

Moritz - Cozy Modern with a Perfect View

CharlesRating, 5 stars3 weeks ago

Wonderful place to stay in Hunter! Loved the view from this super comfortable and spacious (for one or a couple) modern cabin. The hosts have great taste in design and were very responsive and friendly when I needed help with something. Great WiFi, great kitchen and bath and comfortable bed. There’s a lovely view of the mountains through a large window but it’s so cleverly designed that you never feel a lack of privacy. I highly recommend a stay here.

5 out of 5 average rating, 30 reviews

Home in Leeds

Panorama Catskills - Luxury Mountain Escape

inbarRating, 5 stars2 weeks ago

I had a lovely stay at this beautiful home. The house is charming, comfortable, and set in a peaceful, scenic location — perfect for a relaxing getaway. The hosts were thoughtful and communicative, which made the experience smooth and enjoyable. Thank you for a wonderful stay!

5 out of 5 average rating, 63 reviews

Cabin in Cairo

The Catskill Equestrian Cabin

AbbyRating, 5 stars3 days ago

We stayed here for a long weekend girls' trip and had the best time! The space was absolutely beautiful. Everyone room was thoughtfully decorated with stylish, cozy touches that made it feel like a home away from home. It was the perfect backdrop for a fun and relaxing getaway with a view of the mountains. Communication with the host was amazing from the start. Eman was incredibly responsive, helpful, and made sure everything went smoothly before and during our stay. It really made the whole experience stress-free and enjoyable. Highly recommend this place to anyone looking for a chic, comfortable spot with top-notch hospitality. We’d come back in a heartbeat! Definitely the best airbnb I have stayed in.

4.98 out of 5 average rating, 65 reviews

Home in Cairo

Couples' Mountain Escape |HotTub|GameRoom|MtnViews

KristinRating, 5 stars3 weeks 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!

4.85 out of 5 average rating, 73 reviews

Tiny home in Saugerties

Peaceful Catskills Cabin Glamping Retreat

RudyRating, 5 stars1 month ago

Had a peacful time with my wife at this tiny home. It was a perfect getaway from the busy city. Loved everything about it.

4.98 out of 5 average rating, 42 reviews

Home in East Jewett

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

JennRating, 5 stars5 days ago

Lovely stay! The place was spotless, beautifully decorated, and clearly designed with care. Everything felt thoughtfully chosen, and the amenities were great—comfortable bedding, quality toiletries, and a well-stocked kitchen. Would definitely stay here again!

5 out of 5 average rating, 26 reviews

Flat in Purling

The Purling Perch

SanjedaRating, 5 stars4 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!