Holiday rentals with a fire pit in Zena

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

Timberwall Ranger Station | Your Upstate Base Camp

The Timberwall Ranger Station is the perfect home base for your peaceful upstate escape. Located minutes from Woodstock, Saugerties, and Kingston, this breathtaking hand-built cabin is close to all the Catskills and Hudson River Valley have to offer. The cabin is a restful place year-round: for enjoying spring birdsong at breakfast; swaying away an afternoon in a breezy summer hammock; starry skies and luscious wines around an autumn campfire; a cozy winter morning amidst freshly fallen snow.

Woodstock Dog Friendly Cozy Cottage in Town + Yard

Charming Country Escape – Pet-Friendly & Walk to Village Green! Enjoy country charm and modern comforts in this newly updated 2-bed, 1.5-bath home. Just 2.5 blocks from the Village Green, it’s the perfect getaway for city folk with dogs. Relax in the private backyard with waterfall sounds or stroll to shops, restaurants, and trails. Features include a cozy woodstove, updated kitchen & bath, queen beds, and a master bedroom with an en-suite plus a balcony. You and your pet will love it here!

Modern Catskills Cabin

SISTER PROPERTY OF 5-STAR RATED, COZY CATSKILLS CABIN (ALSO IN SAUGERTIES): 10 minutes from the charming towns of Saugerties and Woodstock, this super-cozy, Tonga has every modern convenience, overflows with style, and comfortably sleeps up to four. The tiny house/cabin feels a million miles away, yet is close to area restaurants, breweries, music venues, ski resorts and other attractions. Think of it as the perfect private getaway with creature comforts aplenty and lots of peace and quiet.

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.

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Pick Herbs at a Quirky Stone Cottage with BBQ and Fireplace

Snuggle by a roaring fire. Eat in a corner nook or at a rustic wooden counter by a window. This quaint, whimsical home has a private deck w/bbq, a garden with a hammock and fire pit. A full size Murphy bed with a full kitchen (except for an oven). You will have access to the entire guest house. A short drive to the beautiful, eclectic, funky town of Woodstock. Art & culture, restaurants, hiking & biking all nearby. Electric heat, ceiling fan, a standing ac unit and single person shower.

Red Maple Spa & Studio on the Sawkill Stream

Steam, Stream, & Dream just 3 miles from the heart of Woodstock, NY, under 15 minutes to uptown Kingston. Enjoy our custom-designed 400 sq ft studio and spa for a romantic getaway, family vacation, or solitary retreat. Private entrance, spacious deck, gourmet chef's kitchen, 2 person Roman soaking tub, steam room, and cedar accents. Take advantage of our lovely 3.5 acre meadow and woods, plus private access to 2 huge refreshing swimming holes! Queen bed, full sofa bed, twin air mattress.

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.

Hillside Views in Hudson Valley

Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

Spacious, Private, Close to Town, Work From Home

Spacious, modern ranch-style house on 1.9 acres, atop a hill, with plenty of natural sunlight. Designed and decorated for a relaxing time in Woodstock, the home has an open and flowing layout. Conveniently located minutes from the center of town, it's perfect for those who want convenience to shopping and restaurants. A perfect home for a family getaway, work-from-home alternative or company retreat in the Catskills / Hudson Valley. Outdoor fire pit in the front yard!

Retro-Chic Cabin in Woodstock - Sauna

Perfect upstate escape! Whether you're planning a romantic couples getaway, a fun trip with friends, a family vacation, or even a much-needed solo escape, The Retro Chic House offers the ideal stay for a memorable local Upstate Experience. This stunning renovated property is designed to cater to a variety of preferences and is guaranteed to provide you with an unforgettable stay. Located 8 mins to Woodstock, 12 mins to Saugerties, & picturesque drive to Hunter!