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Places to stay near Brotherhood, America's Oldest Winery

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Top-rated vacation rentals near Brotherhood, America's Oldest Winery

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Guest favourite
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, 374 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 favourite
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, 108 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!

Guest favourite
A charming two-story cottage is surrounded by vibrant landscaping, featuring a mix of colorful flowers. The exterior is painted in green with maroon shutters adorning the windows. A wooden staircase leads to the upper entrance, while a welcoming front door is accented by a small planter.
Guest suite in Montgomery
4.94 out of 5 average rating, 545 reviews

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 6 people

Top guest favourite
A two-story white house is framed by lush green trees. The front porch features red rocking chairs and hanging flower baskets. An American flag is displayed on the porch. A pathway leads to the entrance, which is highlighted by white railings and steps.
Home in Cornwall-on-Hudson
4.99 out of 5 average rating, 117 reviews

Your West Point Academy Home Away from Home

Make yourselves at home in this lovely, privately-owned residence as you attend West Point Academy events and tour scenic Hudson Valley. Build in 1900 and renovated in 2019, this house combines historic charm (original wood floors) with modern conveniences. The home's location is a twelve-minute drive to West Point's Washington Gate and within walking distance to the restaurants and shops of Cornwall. Enjoy 4th of July fireworks and weekly summer concerts with ease relaxing on the front porch!

Top guest favourite
A charming cabin is nestled among vibrant trees displaying autumn foliage. A wooden staircase leads to the entrance, flanked by natural stone walls. Outdoor seating arrangements are visible on the deck, offering a peaceful retreat in a wooded setting.
Cabin in Fishkill
4.96 out of 5 average rating, 126 reviews

Secluded Hilltop Cabin near Beacon & Cold Spring

3 private acres atop small mountain. Feels like you're way upstate - check out the reviews! Hi-speed WiFi. Next to forest preserve and hiking trails. Furnished deck w grill overlooks Mt. Beacon sunsets. Loft w/queen and twin mattresses + pull out couch & twin-size mattress day bed on the porch. Perfect for 2, comfortable for 3, but 4 is probably max comfort since it's a small space. Please note that the road heading up there is steep. A car with AWD is ideal but a sedan will make it up too!

Top guest favourite
The sleeping area features two spacious beds, each with coordinating linens in calming green tones. Warm light is provided by two bedside lamps, enhancing a cozy ambiance. A decorative ottoman and a circular rug add texture and comfort to the inviting space.
Guest suite in New Windsor
4.96 out of 5 average rating, 263 reviews

Sunny Artistic Loft Morning Muffins Clean Comfy

Exceptional quality - safe & secure environment. Perfectly located for- -Storm King Art Center -USMA - Woodbury Common - DIA Beacon - Morning muffins/cookies - Coffee bar, teas, hot cocoa - 2 Super comfy queen sized beds. - Huge bathroom - Heated Jacuzzi bathtub - Seated shower - Private driveway. Private entrance. Park at door. - Writing desk. - Wifi - Singles/double -Local hiking -Historical sights -Vineyards -No cooking allowed. Inquire about extra guests. Relax. Enjoy. Book now.

Guest favourite
A lakeside retreat is showcased, featuring a rustic exterior with dark wood accents. Adirondack chairs are arranged near the water's edge, alongside colorful kayaks resting on the peaceful lake. Lush greenery surrounds the property, reflecting in the calm water.
Home in Putnam Valley
4.98 out of 5 average rating, 105 reviews

Waterfront Lake House

Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

Top guest favourite
Cabin in Greenwood Lake
4.88 out of 5 average rating, 241 reviews

The Greenwood Lake A-Frame: Perfect Lakefront View

Escape to a hip and cozy A-Frame cottage nestled right on Greenwood Lake, NY. Just over an hour drive from New York City, soak in the serene lake view, the quiet, and this unique retro modern A-Frame space. Perfect for a romantic couple’s getaway! Kick back and relax, listen to some tunes, read a great book, write your novel, sip your coffee, get creative, do some yoga stretches and enjoy time away from your day-to-day. Easy access to nearby beach, hikes, skiing. STR Permit #P25-0226

Guest favourite
Chalet in Napanoch
4.95 out of 5 average rating, 248 reviews

Catskills Aframe, Water View, Goat Sanctuary

This charming Aframe is tucked into the Catskill mountains, with spectacular seasonal views of the Rondout Reservoir. This house is cozy with rustic charm and is the perfect getaway nature-lovers. Outdoor enthusiasts will love the many hiking trails and waterfalls just a short drive away. A sanctuary for goats, animal lovers can visit with over 30 rescues during their stay. Art materials and yoga mats are provided to round out a perfect escape for you to unwind, rest, relax and heal.

Top guest favourite
A view of the exterior of the property is framed by lush greenery, featuring a stone wall with a potted plant. Beyond, expansive views of the lake and surrounding mountains are visible beneath a clear sky.
Home in Greenwood Lake
5 out of 5 average rating, 208 reviews

Spectacular Lake Views from Every Room & Garden

Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features a seasonal waterfall cascading into a lily pond with fish and frogs. The shaded patio offers panoramic views and a gas grill. During the winter months, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy ambiance of our living room, with exposed wooden ceilings, a welcoming fireplace, a smart TV, a record player and board games.

Guest favourite
A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.
Cabin in Sherman
4.96 out of 5 average rating, 427 reviews

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

Top guest favourite
A cabin with a red metal roof is nestled among tall trees beside a gently flowing creek. The structure features large windows, allowing natural light to fill the interior while offering views of the surrounding greenery.
Home in Livingston Manor
4.96 out of 5 average rating, 401 reviews

Modern creekside cabin in the Catskills

Welcome to our peaceful little cabin, designed for full immersion in nature. Lounge by the creek with the firepit or hammock, gaze out XL windows, or cozy up by the fire in the living room - every detail invites you to slow down. Tucked on a quiet road just minutes from hiking trails and Willowemoc fly fishing, we’re also only a winding 15-minute drive to charming Livingston Manor, a quintessential Catskills town, and less than 2 hours from NYC.

Popular amenities for vacation rentals near Brotherhood, America's Oldest Winery