Holiday rentals in Summit

The A-Frame on Pudding Hill

Escape to the charming town of Stamford and unwind at The A-Frame on Pudding Hill. Nestled on 5 wooded acres, this A-frame offers a secluded and serene retreat for friends, families, and couples alike. Take in stunning views of foliage, hike nearby trails, and cozy up by the crackling fire for family game night or karaoke. With endless activities like indulging in a wood-burning hot tub or channeling your inner child with our new rope swing. The A-Frame on Pudding Hill is the perfect getaway.

Lovely Farm Cottage & Majestic Waterfall

The Sparrow House is a beautiful farmhouse with a private trail to a majestic 120' waterfall. With vintage wallpapers, eclectic antiques, a cozy fireplace, an outdoor cedar sauna, a large fenced in yard surrounded by honeysuckle vines and a spectacular mountain view, the house is a perfect getaway spot in unspoiled nature and still-wild forests of the Catskills. The waterfall is a truly magical place and considered a sacred site. The house is not appropriate for loud groups or parties. 🙏🦋🙌

Thyme Cottage-Winter Getaway

Our cottage is located in an idyllic mountain setting surrounded by spectacular & breathtaking views. The 7 acre property boasts a serene pond stocked with koi, carp & gold fish that can be viewed from the wrap-around porch. It is conveniently located within close proximity to numerous options for dining and activities such as boating, fishing, hiking, & antiquing at local shops and flea markets. Thyme Cottage is perfect for couples, solo adventurers or anyone looking for tranquility.

The Mill House: An Enchanting Stream-Side Retreat

Nestled in the heart of the Catskills and just a 2.5-hour drive from NYC, escape to the perfect fall retreat where you can reconnect with nature and enjoy the serene beauty of the season. This historic gem underwent a recent restoration, 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.

Spacious cabin w/mountain views & woodstove

NOTE: Click “Show More” to read the full description. Home with stunning views perfectly situated between Roxbury and Stamford! Drink your morning coffee at the bar on the deck overlooking the mountains, curl up with a good book in the reading nook, or explore the farms, mountains, and countryside of the beautiful Western Catskills. Cabin is situated on five beautiful acres at the end of a private drive. Beautiful sunrises over the mountains, with wide-open stargazing after dark.

Fern Valley Cabin w/ Sauna

Get away from it all in this secluded off-grid cabin. Inspired by traditional lean-tos and modern Swedish design. This minimal space features a wall of windows that makes you feel like you are sleeping in the trees, while staying cozy and dry. There is also a traditional Norwegian Sauna and stream cold plunge for your relaxation and pleasure. **For winter bookings** This experience is not for everyone, you should be prepared for roughing it. please fully read the other notes.

Little Red Cabin Near Windham & Hunter w/ Hot Tub

Nestled in the woods, our 3 bedroom cabin offers the perfect escape from the hustle and bustle of everyday life. The cozy interior features a warm, inviting atmosphere with all the amenities you need for a comfortable stay. The spacious living room is the perfect place to unwind after a long day of exploring the great outdoors, complete with a cozy fireplace and outdoor hot tub that offer stunning views of the surrounding landscape. Follow us on IG @thelittleredcabinny

Little Green Lake House

Owned and styled by an artist couple with the dream of creating a place for others to escape, reflect, and feel reinvigorated by nature, this rustic lake house sits right on the banks of Summit Lake in the Catskill Mountains. This thoughtfully renovated 1940s cabin is perfect for couples seeking a romantic weekend, small families wanting a restorative break, writers and artists looking for inspiration, or anyone in need of a quiet, peaceful sanctuary.

An Upstate NY getaway treasure!

Take it easy at this unique and tranquil getaway. For several hundred years our family has been a part of the Cooperstown community and we look forward to sharing it with you! On over 20 acres of land , you can explore the beautiful landscape of water and woods. Just over the hill from Otsego Lake. Only 3.9 miles (8 min) to Cooperstown’s Main Street in the spring, summer and fall and 5.7 miles (10 min) in winter.

"Far from the Madding Crowd" Cozy Cabin Retreat

Cabin Clack is a quiet, stream-side retreat bordering 1000 acres of wild trails in NY State Forest. The cabin is a historic hunting cabin from circa 1935. The cabin is good for a couple, solo adventurers, or families (with kids). We welcome pets, and they will love exploring the secluded forest and the freedom of our virtually traffic-free dead-end road. There is a spring fed pond you can swim in.

Tiny Cabin in The Catskill Mountain

Enjoy and relax roaming our 4 acres, amazing sunset views, and mesmerizing magic star gazing when the sun goes down. Our cabin offers one beautiful cozy bedroom comfortably sleeping two + two childrens , with one full bathroom. fully laundry with washer and dryer. The cabin is good for a couple, solo adventurers, or families (with kids) just be careful there is a steep latter going up the bedroom.

Lady Viola (w/balcony hot tub)

Wander in this stunning Purple Victorian adorned with vintage curiosities on 1.6 bucolic acres. Get lost in the backyard, exploring it’s many vignettes: fire pit, apple orchard, wooded areas, and many places to sit and relax. Enjoy 2400 sq ft of indoor space inclusive of a chef’s kitchen, spacious bedrooms, and a variety of seating. Walk to downtown Cobleskill in 5 minutes.