Vacation rentals in Shokan

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Top-rated vacation rentals in Shokan

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Guest favorite
A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.
Home in Woodstock
4.94 out of 5 average rating, 379 reviews

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.

Top guest favorite
The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.
Cabin in Saugerties
5 out of 5 average rating, 116 reviews

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

Top guest favorite
A charming 1950s cottage exterior features a rustic wooden facade with a welcoming front door highlighted by a window and shutters. Lush greenery surrounds the entrance, with flowerbeds and decorative stones adding character. A gravel path leads to the main door, creating a cozy appeal.
Guesthouse in Olive
4.99 out of 5 average rating, 155 reviews

The Lily Cottage Guesthouse

Tuck up in a thoughtfully renovated 1950s one bedroom cottage, perfect for a solo or a couples Catskill getaway! Situated in a quiet hamlet, nights in are lit by starlight and serenaded by peepers. Perfectly hemmed in by the Ashokan Reservoir, hiking, and the rail trail. The interior features a mix of vintage furnishings along with modern comforts. A 20 minute drive takes you to Rosendale, Kingston, or Woodstock for shops, breweries and excellent dining. Town of Olive Registration # STR-22-23

Top guest favorite
A bright and open living space features a spacious blue sofa and a dining area with a white table surrounded by wooden chairs. Large windows bring in natural light, while a modern kitchen is visible in the background, providing a seamless flow to the outdoor deck.
Home in Mount Tremper
4.98 out of 5 average rating, 115 reviews

Woodstock Hideaway

Escape to our cozy 3-bedroom, 2.5-bathroom home in the Catskill Mountains! Ideal for families, couples, or friends seeking a relaxing break. Unwind in front of the fireplace, whip up culinary delights in our chef's kitchen or grill out on the back deck. Relax and enjoy breathtaking mountain views by the firepit. Minutes away from hiking, swimming and ski slopes, offering endless outdoor adventures. Explore nearby Woodstock, known for its entertainment, shopping, and farm to table dining options.

Top guest favorite
A sunlit living area features large windows offering panoramic views of the mountains and autumn foliage. A marble-topped table holds a vase of white flowers and candles, while various seating options, including plush cushions and wooden chairs, invite relaxation amidst a serene atmosphere.
Home in Mount Tremper
4.95 out of 5 average rating, 119 reviews

Sunset Mountain View Retreat · 11 min to Woodstock

Florentine is a sunset-facing, mountain-view retreat on 15 private acres, 11 min to Woodstock—quiet, solar-powered, and designed by architect Barry Price with loft-size windows and golden walnut floors. Cook and gather in the chef’s kitchen, work on 520 Mbps Wi-Fi, then unwind by the fireplace or screened porch as sunset settles over the mountains. Early check-in/late check-out when available. Minutes to Woodstock/Phoenicia cafés & trails; easy to Belleayre, Hunter & Windham. Permit #21N-224.

Guest favorite
Home in Woodstock
4.99 out of 5 average rating, 117 reviews

Catskills Woodstock Nature Retreat Views & Privacy

❤️A beauty in scenic nature with scenic rides to charming historic towns, Woodstock, Kingston, Phoenicia, Saugerties, Hunter & Belleayre ski and many outdoor adventures & dining options nearby. 🥾 😊 PinkyHouse, where friends and family gather for a lovely time and fond memories, welcomes you to its bright, sweet, peaceful, and private setting on 3.5 acres of green & forest with a brook and view of mountains. Enjoy your relaxing getaway here! 😊 🥾🚙⛰️ * No Pets & No-smoking xoxox anne 😊

Top guest favorite
The exterior of a green cottage is presented, featuring a sloped roof with burgundy trim. Two comfortable chairs sit on the porch, alongside a small table. Lush greenery surrounds the property, enhancing the inviting setting.
Guesthouse in Mount Tremper
4.97 out of 5 average rating, 373 reviews

Artful and Serene Woodstock Getaway

Please read description thoroughly before booking. Relax with a comfortable mix of rustic and elegant in this colorful studio with loft bedroom in the Catskill Mountains of NY. Midway between lovely towns, Woodstock and Phoenicia. Full kitchen and bath, closet, cathedral ceiling, sleeps two adults comfortably. Due to allergies, we do not allow pets. This includes service animals. Not suitable for children or infants. No smoking or vaping. We use fragrance free laundry detergent.

Top guest favorite
A spacious studio area features wooden beams above, with a large artwork displayed on the back wall. The floor is adorned with various rugs, and a kitchenette is visible, equipped with essential appliances. A chair is situated near a curtain-draped area, enhancing the room's functionality.
Home in Shokan
4.97 out of 5 average rating, 160 reviews

West Wing - a unique private space w/deck

This unique studio space with private entrance is a recent addition to our charming home, located on a quiet private road in the village of Shokan. Situated within minutes of the Ashokan Rail Trail, this bike and walking trail offers dramatic vistas of the Ashokan Reservoir. Woodstock & Phoencia with their stores, galleries and restaurants are only 15 minute drives . Local recreation includes hiking trails, kayaking and for those looking for relaxation there are renowned spas.

Guest favorite
A serene bedroom features a spacious bed adorned with decorative pillows and a soft throw. Nightstands with lamps are situated on either side. Natural light filters through two windows, complemented by light-colored curtains, creating a calm and inviting atmosphere.
Guesthouse in Olivebridge
4.95 out of 5 average rating, 192 reviews

The Ashokan Guest House

This newly renovated guest house is attached to a 120 year-old farmhouse which originally housed the workers building the Ashokan Reservoir. This quiet refuge sits on a lovely 3-acre lot in Catskill Park within .5 mile of Ashokan Reservoir. An outdoor adventure in our beautiful Catskill Mountains awaits any direction you go. This is the perfect location for couples or individuals looking for a retreat (it is not child-proofed). Near Kingston, Woodstock and Stone Ridge.

Top guest favorite
A charming guest house is nestled among lush trees, featuring a sloped roof and large windows. The exterior is painted in warm brown tones, blending with the natural surroundings. A gravel driveway leads to the entrance, providing access to a serene rural landscape.
Guesthouse in Bearsville
4.97 out of 5 average rating, 572 reviews

Relax on the Ridge - 2 miles from Woodstock

Stay and relax in a private guest house on a 5+ acre picturesque property overlooking historic Woodstock, N.Y. The cottage is nestled away high on a private road in a quiet country setting, yet conveniently only 2 miles from Woodstock and 10 miles from Phoenicia! Relax on the grounds while watching our Kiko goats—drive into town to enjoy shops, restaurants, & the unique artistic culture of Woodstock—explore the many beautiful trails that the Catskill Park offers.

Top guest favorite
The Treehouse is nestled among trees, elevated above a tranquil pond. Its wooden structure features large windows that provide views into the surrounding greenery, while the natural landscape is reflected in the pond's surface. The setting offers a secluded feel contrasting with the nearby wooded area.
Treehouse in Willow
4.96 out of 5 average rating, 845 reviews

Willow Treehouse - secluded, unique, romantic

The Willow Treehouse is settled among the trees, overlooking a small, swimmable pond, on a wooded property 15min away from the town of Woodstock. It is cozy, yet has all you need to cook dinner, enjoy reading, sit on the couch and stare outside the window, or swim. No WiFi and no cell service = fully disconnecting from daily life and true relaxation. Perfect for couples and solo adventurers (2 adults max). STR operating permit #21H-109

Top guest favorite
Home in Shokan
4.98 out of 5 average rating, 113 reviews

Historic Catskills farmhouse with sweeping views

Welcome to Juniper Grove - your country home in the Catskills. This 4 bed 2 full/2 half bath farmhouse has stunning views of the Ashokan Reservoir to enjoy from the classic farmhouse front porch. Relax under the stars in the new hot tub on the back stone patio. Sitting on 40 private acres, you are held by Mother Nature at every turn. Inside find all the modern conveniences & comforts to support your stay.

Popular amenities for Shokan vacation rentals

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