Holiday houses in Cherrytown

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Top-rated holiday rentals in Cherrytown

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Top Guest favourite

Cottage in Kerhonkson

Beautiful stream side cottage in the woods

Stunning fully renovated 1970 partial A frame cottage in the woods! Set privately on four acres with a stream and meandering stone walls, the cottage is modern yet rustic, with a mid century decor. Main floor has living room with beautiful floor to ceiling stone fireplace (gas operated), kitchen, bathroom, and an office with a desk and twin bed. Second floor has master bedroom with queen size bed and a separate loft area with desk. Great place to relax in nature - a perfect couple's getaway!

FamilyValueGetting around

4.88 out of 5 average rating, 275 reviews

Top Guest favourite

A contemporary house is displayed, featuring a sleek exterior of wood and metal. Expansive windows offer a view of the surrounding trees. A spacious deck extends from the structure, providing a seamless transition to the outdoor environment.

Home in Accord

Accord River House

Welcome to our house in the woods! 12 acres surrounded by trees and above a series of waterfalls along the Stony Kill, which runs all the way from Minnewaska State Park through our property and into downtown Accord. You can sit in a hammock outside, soak in our hot tub while listening to the river, or chill out inside with some tunes or the TV projector. Budding entomologists will enjoy the endless procession of bugs, ants, spiders, ticks, and other creepy-crawlies that is part of River House.

ValueFamilyWalkability

4.99 out of 5 average rating, 107 reviews

Top Guest favourite

A charming cabin stands surrounded by trees, illuminated by soft string lights. A fire pit with glowing embers is positioned in front, with a charcoal grill nearby. The cabin features large windows, allowing for views of the serene wooded landscape.

Cabin in Kerhonkson

Cozy Cabin | Fire pit + Hiking + Pets Welcome

Imagine yourself on a screened porch, gas fireplace glowing, string lights warm overhead, peering into the woods — our guests' favorite space. Take a leisurely walk under the towering trees in the quiet wooded acre surrounding our cozy, alpine-inspired cabin with contemporary bohemian touches. Sleep upstairs under deep-set skylights, observe wildlife out our large picture windows, or daydream on the hammock. On a clear night, stargaze through the tall trees while toasting marshmallows fireside.

FamilyValueOutdoor spaces

4.96 out of 5 average rating, 655 reviews

Superhost

Home in Kerhonkson

Mid-Century Hudson Valley Retreat with Fire pit

Beautiful Mid-Century home on 2.5 acres of former farmland in Kerhonkson with 3 bedrooms and 1 bath. The interior is stylishly furnished, a well-stocked kitchen, unique wood cabinetry, and comfortable accommodations for relaxing after a day outdoors. Hiking at Minnewaska, Sundown Wild Forest, and rock climbing at The Gunks are all easy to access. Visit the villages of Stone Ridge, High Falls, or New Paltz. Enjoy great restaurants and sip wine, bourbon, or cider at a local vineyard or distillery

FamilyLocationParks

4.81 out of 5 average rating, 122 reviews

Top Guest favourite

Home in Kerhonkson

Fall Farmhouse: Private, Firepit & Fireplace

Super private, pet-friendly 13 acre solar powered*, modern farmhouse 2 hours from NYC in Catskills. ✔ Large backyard w/ firepit ✔ Dogs allowed** ✔ 229Mbps wifi ✔ Screen-in porch w/ outdoor dining ✔ 65” Smart TV with Apple TV in living room ✔ 50” Smart TV with Apple TV in guest bed ✔ Bluetooth sound system ✔ Memory foam mattresses ✔ Back deck w/ BBQ grill ✔ Indoor fireplace ✔ Onsite parking 10 mins → Vernooy Falls 20 mins → Minnewaska State Park, Mohonk Preserve & Ashokan Rail Trail

ValueLocationAccuracy

4.97 out of 5 average rating, 193 reviews

Top Guest favourite

A spacious game room is displayed with a large pool table and a green sectional sofa. Soft, round bean bags provide additional seating. Large garage doors open to a scenic view featuring blooming trees and a well-maintained outdoor space.

Home in Kerhonkson

Grateful Woods Farmhouse w/ Hot Tub & Firepit

The Farmhouse is part of the Grateful Woods family! It sits on 7 acres at the top of the hill & offers a beautiful view of our farm just across the road. In addition to its own amenities like a hot tub, firepit, and game room, guests enjoy full access to everything Grateful Woods has to offer—scenic trails, peaceful walks through the pastures, and time with our friendly animals, including goats, Highland cows, chickens, & horses. (Search Grateful Woods to view our full listing of all units.)

ValueFamilySleep quality

4.98 out of 5 average rating, 101 reviews

Top Guest favourite

A charming cabin exterior is framed by a well-maintained lawn and lush trees. A stone pathway leads to the front door, flanked by modest garden beds with various plants. Natural wood siding and a dark roof create a warm, inviting appearance.

Cabin in Accord

Hidden cabin on 2 wooded acres

Retreat to a beautiful cabin and get lost on two wooded acres. Reconnect with nature in your own way - hike around nearby Lake Minnewaska, or another of the dozens of incredible trails in the area. Explore infinity under a blanket of stars and share stories gathered around the firepit. When you’re called inside, grab a book and settle in by the fireplace. Then cook a meal in our well-equipped kitchen or on the grill, and enjoy it on the patio overlooking the property.

FamilyLocationComfort

4.98 out of 5 average rating, 201 reviews

Top Guest favourite

Home in Kerhonkson

Luxe modern A Frame, Hot tub and new heated pool

Experience the luxury of this black double A-frame, finished to the highest standards and nestled in the woods for ultimate privacy. The main bedroom features a soaring ceiling and spa-like en-suite with walk-in shower, tub, bidet, double sink, and heated floors. The sunny second bedroom also has an en-suite. Enjoy a chef’s kitchen, double-sided fireplace, hot tub, and a new pool available June. Pets must be disclosed and approved prior to booking.

FamilyLocationBiking

4.97 out of 5 average rating, 120 reviews

Guest favourite

A serene saltwater pool is framed by lush greenery, providing a tranquil escape. Comfortable lounge chairs are positioned around the patio, inviting relaxation. The setting is peaceful, surrounded by trees that enhance the private atmosphere.

Home in Kerhonkson

A Very Cozy House With a Very Big Yard

The perfect spot to unwind with family, friends, and pups. Spend the day hiking, visiting farms, or trying local restaurants, then come home to the yard for kid-and-dog frolicking, “Squirrel TV” through long windows. Soak in the claw-foot tub or the jetted spa tub, then gather by the fire with wine and board games. Swim and make s’mores in summer, watch snow fall in winter, and enjoy peaceful views in every season, relax, play, laugh, repeat.

ValueLocationHospitality

4.94 out of 5 average rating, 414 reviews

Guest favourite

A modern kitchen features sleek white cabinetry and stainless steel appliances, including a gas stove and refrigerator. A black island is enhanced by a minimalist pendant light above, while natural light floods in through large windows, illuminating a simple green plant centerpiece.

Home in Kerhonkson

ENTER HOME - Minimalistic style warm & inviting

ENTER our HOME, an inviting, comfortable space filled with natural light and clean lines inspired by Nordic design. Enjoy a fully equipped new kitchen with Bosch appliances, including a washer and dryer. Our home is designed to embrace the beautiful nature around you and bring a sense of peace and comfort to your stay. ENTER HOME is ideal for individuals, couples, or families with children. AC is provided in both bedrooms only.

ValueFamilyHospitality

4.96 out of 5 average rating, 193 reviews

Top Guest favourite

The cabin's exterior showcases a peaceful environment, surrounded by trees. A spacious deck features a wooden dining table with colorful umbrellas providing shade. Planters filled with flowers and greenery are arranged around the deck, enhancing the natural setting.

Cabin in Kerhonkson

Mai Cabin

Mai Cabin located in Kerhonkson, Upstate, Catskills area. About 2 hrs drive from New York city. It's just a 10-minute drive to Minnewaska State Park and Mohonk Preserve, 15 mins to High Falls and Stone Ridge. 30 mins to Ashokan Reservoir. There are many farm stands, breweries, galleries, restaurants only mins away. Rock climbing, hiking/ biking trails ( bring your bike) and a Old Rail Trail just a few minutes away.

FamilyValueHospitality

4.94 out of 5 average rating, 176 reviews

Guest favourite

The exterior of a serene, handcrafted Japanese folk house is depicted, featuring wooden eaves and a unique slatted window design. Stacked firewood rests on the ground, surrounded by natural landscaping and tall trees, under a clear blue sky.

Home in Accord

Little Minka - Japanese House in the Woods

Little Minka. A serene Japanese folk house nestled on 10 acres of private woodland and streams. Embracing the Wabi-Sabi, Little Minka is unique, handcrafted using Japanese traditional carpentry joinery methods. Soaring ceilings, shoji, and tatami complete the interior. Outside there's a fire pit, open cooking area. We have Japanese bathroom products in partnership with sowakanyc that guests can experience.

ValueFamilyLayout

4.96 out of 5 average rating, 162 reviews