Cottage vacation rentals in Town of Shandaken

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Top-rated cottage rentals in Town of Shandaken

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Guest favorite
An open-plan kitchen and dining area features a large wooden table surrounded by several chairs. A modern kitchen with dark cabinetry and stainless steel appliances is seen in the background. A wood stove is positioned near the window, which offers views of the snowy outdoor scenery.
Cottage in Saugerties
4.94 out of 5 average rating, 378 reviews

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.

Top guest favorite
The great room features large glass doors that frame views of the lake, allowing natural light to fill the space. A comfortable sectional sofa is arranged with a tufted coffee table in the center. A stone fireplace adds a cozy touch, complemented by a telescope for observing the scenery.
Cottage in Livingston Manor
5.0 out of 5 average rating, 107 reviews

Gorgeous Waterfront w/ Hot Tub and Game Level

Hi, I’m Anna. I’m so glad you’re here, and I’d love to welcome you to The Glass House! Here are a few things I think you’ll especially enjoy about the house. Highlights – You’ll love the: Peaceful waterfront setting – tucked away on the lake, yet just minutes to town Year-round hot tub – the perfect way to unwind after hiking, or exploring Family-perfect layout – two spacious levels with a game/media room and screened porch Kayaks & life vests – easy, safe access to the water for all ages

Top guest favorite
A stone patio is surrounded by vibrant flowers and greenery, featuring a wooden table with four chairs. The cottage's large window provides a view of the inviting outdoor space, where additional potted plants add a touch of color and natural beauty.
Cottage in Chichester
4.99 out of 5 average rating, 645 reviews

Garden Cottage In The Catskills

This quaint, relaxing cottage sits among Flowering Gardens in spring & summer, incredible Fall Foliage in autumn, & a Wonderland in Winter. Enjoy a peaceful cozy & private space with nature at your doorstep, an outdoor fire pit, stargazing, & your own stone patio at the edge of the woods. We love to share our garden, come pick your own! We are in the heart of The Catskill Mountains, 2 miles from the vibrant town of Phoenicia, in the hamlet of Chichester near the Stony Clove Creek.

Guest favorite
Cottage in Halcott Center
4.98 out of 5 average rating, 370 reviews

Cozy Cottage with Stunning Mountain Views

Welcome to Halcott Cottage! Featuring gorgeous mountain views, less than two and a half hours from NYC, and ten minutes from Belleayre Ski Center, this cozy and private cottage is perfect for a romantic couples retreat, two couples, a small family, or a group of friends looking for a relaxing and quiet escape in the historic Catskills. The cottage is a short drive to Phoenicia, Woodstock, Andes, and Margaretville for shopping, dining, antiquing, skiing and exploring.

Top guest favorite
A charming cottage exterior features light blue siding with white trim and a front door painted in a soft green. Large windows allow natural light to illuminate the inviting entryway. Lush greenery and colorful blooms enhance the tranquil surroundings.
Cottage in Phoenicia
4.94 out of 5 average rating, 235 reviews

Phoenicia Getaway

Welcome to Phoenicia, the greatest little town in the Catskills. Our little home is nestled on a peaceful block among quaint fishing cottages. The Esopus Creek runs nearby and is home to some of the country's best fly fishing. The mountains, lakes and streams are breathtaking all year round, and the peace of nature is easy to find. We can't wait to be your home away from home, and share the wonder of the Catskills with you. License #2022-STR-007

Top guest favorite
A cozy living area showcases a brown sofa adorned with decorative pillows, complemented by a patterned area rug. A rocking chair sits nearby, and a wooden table holds a stack of books. Natural light enters through two windows featuring bamboo shades.
Cottage in Phoenicia
4.95 out of 5 average rating, 345 reviews

Cozy Catskill Cottage on the Pantherkill

Cozy Cottage nestled in the Catskill Mountains minutes away from village of Phoenecia. This is a great secluded spot and easy to get to and conveniently located near great restaurants, skiing, hiking, tubing, fishing, swimming holes, Village of Woodstock. This small cottage feels bigger than it is while remaining cozy and intimate. Great getaway spot for couples or a solo retreat into the beautiful Catskill Mountains. License #2026-STR-AO-084

Top guest favorite
The exterior view showcases a blue cabin with a welcoming deck leading to several outdoor planters. Expansive mountain views create a scenic backdrop under a partly cloudy sky, with rich green foliage framing the scene.
Cottage in Fleischmanns
4.94 out of 5 average rating, 155 reviews

Private Cabin with Views, WIFI, 9 min to Belleayre

Scenic 2BR Catskills cabin just 2 hours from NYC! Enjoy stunning mountain views from the private deck, fast & reliable WIFI for remote work, and easy access to Belleayre skiing, lake swimming, & tons of hiking trails. Peaceful and private—perched above a quiet road with regular visits from deer, turkeys, bunnies, and songbirds. Perfect for family getaways, ski trips, or a scenic work-from-home stay. Follow us @berushka_cottage for more!

Top guest favorite
A rustic cottage is surrounded by lush greenery, featuring a wrap-around deck illuminated by string lights. The wooden structure is complemented by various plants and shrubs, offering a serene and inviting atmosphere. The entry is adorned with a partially covered porch, enhancing the cottage's natural charm.
Cottage in Phoenicia
4.94 out of 5 average rating, 309 reviews

Charming creekside cottage in Phoenicia

Come relax in one of the prettiest places in the Catskills. Enjoy views of the Stony Clove, while sipping coffee on the wrap-around deck. The location is private and quiet, yet convenient to all the region's many attractions - hiking, skiing, antiquing, eating. When you are done exploring, enjoy a dip in one of the largest, deepest swimming holes in the area. Perfect for small families and couples. License Number: 2022-STR-AO-081

Top guest favorite
The inviting living area features a comfortable gray sofa adorned with accent pillows. A wooden coffee table is centrally placed, while a modern lamp and a cozy rug enhance the space. Large sliding doors open onto the deck, offering natural light and views of the surroundings.
Cottage in Chichester
4.94 out of 5 average rating, 149 reviews

Stream Come True | Hot Tub, Ski, Hike, Relax

Welcome to Flowing Water, a peaceful streamside cottage in the heart of the Catskills where the sound of rushing water and rustling trees melts stress away. Just minutes from Phoenicia and a short drive to Woodstock, Hunter, and Belleayre, it’s the perfect retreat for skiing, hiking, stargazing, or simply relaxing. Enjoy a hot tub or the firepit under the stars, a wood stove, streamside deck, and peaceful vibes year-round.

Guest favorite
Cottage in Olive
4.97 out of 5 average rating, 128 reviews

Perch Cottages #9: Creek access + Sauna + Mt views

A group of modern cottages with spectacular mountain views, and magical creek frontage on the Esopus Creek (with its own beach and swimming hole!) Completely renovated. Quick 2 HR drive from the city. ✔ Fishing and Swimming ✔ 1 Dog or Cat per cabin allowed ✔ Gas BBQ Grill ✔ 40” Smart TV ✔ Bluetooth sound system ✔ Memory foam mattresses ✔ Onsite parking 7 mins → Ashokan Rail Trail 25 mins → Belleayre Ski Resort

Top guest favorite
An aerial view showcases Amber Lake Cottage set against the backdrop of vibrant autumn foliage. The cottage features a spacious lawn leading to a dock on Amber Lake. Calm waters reflect the trees, while a rowboat rests nearby, indicating opportunities for outdoor activities.
Cottage in Livingston Manor
4.96 out of 5 average rating, 447 reviews

Catskills Modern Amber Lake Cottage

Featured in the NY Times, Amber Lake Cottage is nestled right on the bank of Amber Lake in Livingston Manor, NY. Just 2 hours from the bustle of your 9-5 in NYC, the home lets you catch your breath. Sleep in. Rowboat. Fix a drink by the fire. Dance to a record. Experiment with local produce in the chef's kitchen. See the stars above you. Hear quiet for the first time in months.

Top guest favorite
The interior space showcases exposed timber beams and a warm wood palette. A comfortable seating area is highlighted by a vibrant patchwork rug, while a staircase leads to the upper level. Shelving units display books, and a television is mounted on the wall.
Cottage in Woodstock
4.99 out of 5 average rating, 371 reviews

Grapevine Cottage

DESCRIPTION Enter our private backyard on 2 1/2 acres by crossing your own bridge far above the forest floor overlooking a stream and waterfall, then meander along a stone path, entering your grape arbor and vegetable garden into your cottage. The gardens where featured in THE Wall Street JOURNAL Sept 11-12 2021

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