Holiday houses in Ruby

4.9 out of 5 average rating, 233 reviews

Tiny home in Kingston

Esopus Creek modern Tiny house Retreat!

Dare to break from the hustle and bustle culture and immerse yourself in the beauty and solitude of our modern spacious brand new Tiny house tucked away on a peaceful dead end st on our 13 acresbluestone property located 10 mins from Woodstock and Kingston.You will be steps away from waterfalls on the creek nature trails and a myriad of flora and fauna,sleeps up to 4-5 masterbedroom and loft has queen beds,loveseat with full bed, one bathroom with shower and updated regular toilet . Close to ski

4.93 out of 5 average rating, 216 reviews

Cabin in Kingston

Cabin 192

No cleaning fee and no 2-night minimum! Cabin 192 is a tiny home glamping experience located in lovely Kingston, NY. Cabin 192 takes you back to 1992 with: a vhs collection of classics, a Super Nintendo, Sega, and other fun activities. Warm and toasty in fall and winter and cool in summer you’re always comfortable at Cabin 192. Enjoy smores by the fire surrounded by trees in nature while also being able to enjoy a vibrant uptown district a 9-minute drive away! Minnewaska and Woodstock nearby!

4.85 out of 5 average rating, 149 reviews

Tiny home in Kingston

Cabin Noir where Modern meets Rustic, Hot Tub+View

Cabin Noir may be small, but it’s charm and character, is ideal for a romantic getaway. The perfect blend of modern comfort and rustic appeal. Enjoy an off-grid atmosphere without sacrificing the amenities of home. Unwind by the hot tub or gather around the fire, soaking in the tranquility sounds of the creek flowing at the foot of the mountain. The loft bedroom offers stunning views of all four seasons, and a hidden door leads to a secret nook where you can savor your morning coffee in peace.

4.94 out of 5 average rating, 211 reviews

Guesthouse in Kingston

Campfire Cottage: Fireplace, fire pit & no chores!

Escape the city and unwind at this beautifully designed home. Just 90 minutes from Manhattan, this is the perfect place to relax and reconnect with nature, or work remotely. Enjoy downtown attractions, hiking, and the Hudson River Maritime Museum nearby. The home features a cozy living area, full kitchen, electric fireplace, and no chore list for checkout. The yard has a grill and fire pit facing the woods. Book today to retreat to your private house and enjoy the beauty of Upstate New York!

4.98 out of 5 average rating, 116 reviews

Cabin in Saugerties

Sweet Saugerties A-Frame - 10 mins from Woodstock

This sweet A-Frame hideaway located in a wooded area between Saugerties and Woodstock will welcome you and warm your spirit with its charm. Featuring 2 bedrooms, each with Queen Beds, and a couch that folds out to a Full Bed, there's ample space for 4. But, it's also a serene escape for an individual or couple. An inspiring creative retreat, the home has beautiful views, and an electric piano. Quiet but 10 mins from great restaurants! 11 mins to HITS, 30 mins to skiing at Hunter Mountain.

4.94 out of 5 average rating, 301 reviews

Cottage in Saugerties

New:Cozy Barn-Style Retreat Minutes From Woodstock

Recently featured in Vogue as one of “The Best Airbnbs in Upstate New York for a Weekend Away From the City” - A cozy getaway upstate on 2 acres of beautiful Catskill land. It's only 8 minutes to Woodstock, 5 minutes to the village of Saugerties, and there’s hiking, skiing and swimming within minutes. The entire second floor has been newly renovated including the bathroom and both bedrooms. The first floor is an open layout with kitchen, living and dining areas leading to the backyard deck.

4.91 out of 5 average rating, 176 reviews

Cabin in Kingston

The Arts & Crafts House - Skylights/Deck/Bath Jets

Get away to a charming cabin in a lush glade just 10 min from quaint Woodstock and trendy Kingston. If you've never stayed in an Arts and Crafts house, here's your chance! Steps from soothing waterfalls, our enchanting house sleeps up to six and features two full luxury bathrooms and a modern kitchen. Fall asleep under skylights, unwind in the jacuzzi tub, and enjoy coffee (or yoga!) on the deck. Explore the nearby Catskill mountains, quirky shops, breweries, and farm-to-table restaurants.

4.96 out of 5 average rating, 238 reviews

Apartment in Kingston

DeMew Townhouse in Historic Kingston

DeMew Townhouse is beautiful duplex apartment located in a renovated 1850s building overlooking Hideaway Marina in the Rondout district of Kingston. The building boats a rich history: the main floor of the building served as a speakeasy during Prohibition. It has hand rubbed oak floors, a renovated kitchen and bath and 14 windows providing views of the Rondout. With a spacious open plan, the DeMew Townhouse is the perfect location from which to explore Kingston and the Hudson Valley.

4.91 out of 5 average rating, 117 reviews

Chalet in Ruby

Enchanting Upstate Cabin w Pool, Firepit

Welcome to our family-friendly haven in the heart of the beautiful Hudson Valley, just 10 minutes from Kingston, Saugerties, and Woodstock. Less than 2 hours from New York, our retreat offers an idyllic escape surrounded by enchanting forest views. Great for large groups, and year round stays with a heated pool and air conditioning in summer months. Just 40 mins away from skiing Hunter. Listing pics by @dirtandglass and @heypamcakes See more snapshots @theserenityhomes on IG. Ok

4.99 out of 5 average rating, 101 reviews

Cabin in Saugerties

Cozy Catskills Cabin

SISTER PROPERTY OF 5-STAR RATED, MODERN CATSKILLS CABIN (ALSO IN SAUGERTIES): Just 10 minutes from the towns of Saugerties and Woodstock, this perfectly-located, super-cozy, tiny house has every modern convenience, overflows with style, and comfortably sleeps two. “Kona” feels a million miles away, yet is close to area restaurants, stores, music venues, ski resorts, and other attractions. Think of it as the perfect cozy getaway with plenty of privacy, nature, and peace and quiet.

4.99 out of 5 average rating, 162 reviews

Guest suite in Woodstock

Woodstock retreat with hot tub and deck with view

Guest suite in home of long-time Woodstock artist and resident. Separate entrance off 2nd story deck with meadow and mountain views. Space has everything you need for a retreat away from it all – a meditation nook for 2, yoga mats to use inside or out on the deck, hot tub to soak cares away and relax after a day out and about in the beautiful Catskill mountains. Hot tub is in 3-acre backyard with privacy enclosure, so bathing suits are optional (we provide bathrobes.)

4.99 out of 5 average rating, 312 reviews

Treehouse in Wallkill

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

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Other great holiday rentals in Ruby

4.9 out of 5 average rating, 10 reviews

Home in Kingston

Dogwood Lane Estate

HannahRating, 5 stars5 months ago

Loved the place, stunning house with beautiful light, spacious yet cozy feel with the working fireplace and wonderfully set back location. Thank you for hosting us, our baby and dog!

4.92 out of 5 average rating, 52 reviews

Home in Saugerties

Serene forest retreat in picturesque modern cabin

AndersonRating, 5 stars2 weeks ago

Andrew had been super helpful and responsive. We loved his property so much that we are already planning for our next trip to stay once again in Andrew’s place. It is so close to Woodstock and there are so many things to explore in the area. Love the vibe.

4.92 out of 5 average rating, 25 reviews

Home in Saugerties

Country Charm with Modern Comfort in Saugerties

RobertoRating, 5 stars1 week ago

We had a wonderful stay at this home, it was the perfect place to decompress from city life and enjoy some peaceful downtime. Our main reason for visiting the area was to attend the Field & Supply Market in Kingston, and the location couldn’t have been better, just a quick and easy 25-minute drive each way. When we weren’t out, we spent most of our time indoors due to rainy weather, and the house was more than comfortable for two people. We especially enjoyed lounging in the living room on the large sofa overlooking the great lawn, and gathering in the kitchen, which offered another lovely view of the expansive yard through the bay window and Dutch door. Although our group ended up being smaller than planned, the house would have easily accommodated the five of us originally intended for the trip. We highly recommend this property to anyone looking for a relaxing stay in the area.

4.94 out of 5 average rating, 96 reviews

Home in Saugerties

Waters' Edge on the Esopus

SueRating, 5 stars5 days ago

Jane was the best hostess! We had a few questions and she responded promptly in a friendly manner. The house is so homey and easy to immediately relax. It was just what we needed. Kitchen was amazing. It was stocked with all we needed to cook all our meals. And the plus was the yummy homemade jam! Thanks again. We talked about making it an annual trip! Thanks, Jane for tip top hospitality.

5 out of 5 average rating, 20 reviews

Home in Kingston

Private Creekside escape 10min Woodstock/Kingston!

DoreenRating, 5 stars2 weeks ago

Lovely clean and modern home. Liked the location - quiet and peaceful but only a short drive to both Kingston and Woodstock. Was perfect for our group.

Bungalow in Saugerties

4.76 out of 5 average rating, 164 reviews

Waterfront Charming Cottage

ShakaylaRating, 5 stars1 month ago

My family and I had a nice relaxing stay. The house was clean and comfortable. The neighborhood was quiet and tranquil. Michael was a very responsive host, would definitely stay here again! 🙂

Tiny home in Haines Falls

5 out of 5 average rating, 4 reviews

Romantic tiny Pod for two/HotTub/LakeView/FirePit

ZenasRating, 5 stars6 days ago

A perfect get away This place exceeded all our expectations. Tucked away in a peacful, scenic location, it offered the perfect blend of rustic charm and modern comfort. Pure relaxation! The host was incredibly responsive and thoughtful, leaving helpful instructions. Whether you’re looking for a romantic escape or a quiet family retreat, this place is a gem. We are already planning our next stay! :)