Guest house holiday rentals in Hudson Valley

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Top-rated guest house rentals in Hudson Valley

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Top guest favourite
A spacious master suite features a wooden accent wall and vaulted ceiling. A large bed with decorative pillows is positioned centrally, flanked by nightstands. In the background, a private bathroom is visible with modern fixtures and a wooden sink. Natural light filters through nearby windows.
Guest house in Woodstock
5 out of 5 average rating, 433 reviews

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star

PRIVATE Modern/Rustic Apt WALK TO TOWN 5 * Rating "PREMIER" NO EXTRA CHARGES! 1000 sq ft Pet Friendly n/c Park Master King Suite &I can put up 2cots /crib Full Kitchen Cathedral Living Room w/Mountainview. 1 1/2 Bath Deck for Outside Dining w/Mountainview WOOD FIREPLACE ondeck Wi-Fi Wash/Dryer Gas BBQ Steps to CTR of Town Green & NYC Bus-stop, THE COLONY, Yum Yum, Goodnight , Garden Cafe, Silvias, Bread Alone, Mud Club, Station Bar, shops . Cemetery's Bubbling Stream, PrivatePlayground

Top guest favourite
A modern living space is featured with a gray sofa adorned with yellow cushions. A round turquoise ottoman complements a patterned area rug on warm wood flooring. The room includes an open kitchen area visible in the background, with light streaming through the windows.
Guest house in Hudson
4.97 out of 5 average rating, 104 reviews

Stylish, New Carriage House on Warren St!

Enjoy your stay at this adorable, newly-renovated, 2- bedroom Carriage House located in the heart of Hudson. Restaurants, galleries, antiques shops and bar are just steps away! This Carriage House is a free-standing 2-story, located on Warren Street. It offers a parking pass directly behind building in a municipal parking lot. The Amtrak station is a 12-15 minute walk away. The Carriage is located behind the main building which houses a gift shop and a wine bar, Sisters Hudson and Bar Bene.

Top guest favourite
The exterior of the Equestrian Suite is showcased, featuring a two-story structure with a blend of brick and wood. A wrap-around balcony offers scenic views, and lush greenery surrounds the property, complementing the tranquil mountain setting.
Guest house in Beacon
4.95 out of 5 average rating, 416 reviews

Cozy Mountainside Suite - Minutes from Beacon

The Equestrian Suite at Lambs Hill is a private estate with panoramic views overlooking the Hudson River & downtown Beacon. This beautifully-designed luxury suite sits atop a barn home to Icelandic horses & miniature donkeys, & features an outdoor hot tub, red light therapy, gourmet kitchen, & wrap-around decks. 1 mile to Beacon's Main St, 2 miles to Metro North train station & DIA: Beacon. We can host a max of 2 guests & have some dangerous features for kids so guests should be adults only.

Guest favourite
A bright sleeping area features a spacious bed against a backdrop of a sloped ceiling. A wooden bench sits at the foot of the bed, with a patterned rug laid beneath. Shelves display various decorative items, and natural light floods in from large windows.
Guest house in Accord
4.88 out of 5 average rating, 282 reviews

Sweet Cottage on a Farm Road

Simple, airy, studio cottage next to my house, featuring a woodstove & enormous bathroom with a clawfoot tub. Perfect for writers/solo-travelers seeking solitude & peace and couples wanting quality time together. The cottage is on a scenic country road, walking distance to 3 farms, including 2 great farm-to-table restaurants: Westwind Pizza/Apple Orchard, Arrowood Brewery, & Hollengold Farm. A stone's throw are Stonehill Barn and Inness. 15 min drive to the incomparable Minnewaska State Park.

Top guest favourite
A cozy living area features a stone fireplace with a wood fire burning inside. A colorful couch adorned with various patterns is complemented by a stylish chair. Natural light enters through large windows, and a rustic table is visible in the background.
Guest house in Woodstock
4.97 out of 5 average rating, 382 reviews

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.

Top guest favourite
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.
Guest house in Mount Tremper
4.97 out of 5 average rating, 371 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 favourite
A private cabin is nestled among lush greenery, showcasing a large deck with two Adirondack chairs positioned for relaxation. The cabin features large glass doors that open to the natural surroundings, enhancing the peaceful atmosphere.
Guest house in Kingston
4.99 out of 5 average rating, 162 reviews

Chic, Private Cabin with Stunning River Views

Private, fully renovated cabin with high-end finishes and stunning views of the Hudson River. All creature comforts including full kitchen, expansive living room, stylish bathroom and cozy bedroom, along with firepit and large deck to watch the eagles from. Nestled on a wooded corner of the owner's property but completely independent with separate driveway, parking and fenced yard for privacy. Just minutes from shopping/dining in Kingston, as well as world world class hiking and nature.

Guest favourite
A cozy living space features a gray sectional sofa adorned with textured pillows and a soft throw. A rustic wooden coffee table sits within reach, complemented by a gas fireplace framed in warm wood. Natural light floods the area through a skylight, enhancing the inviting ambiance.
Guest house in Windham
4.99 out of 5 average rating, 188 reviews

Alpine Chalet on Spectacular Property

Inspired by their travels in the Swiss Alps, the hosts of the Mountaintop Chalet invite guests to their peaceful alpine guesthouse atop a mountain in the Northern Catskills. Nestled on a quiet, private road, the Mountaintop Chalet is just an 8 minutes drive to downtown Windham, NY, 10 minutes to Windham Mountain and 18 minutes to Hunter Mountain. This tranquil yet accessible setting makes it the perfect escape for couples, families and friends. Follow on Insta at mountaintop_chalet.

Guest favourite
The exterior of the cabin is showcased, featuring a wooden facade with a steeply pitched roof. A welcoming porch with wooden railings surrounds the entrance, leading to a front door flanked by windows. Lush greenery surrounds the cabin, enhancing its secluded setting.
Guest house in Delhi
4.96 out of 5 average rating, 189 reviews

Catskills Peakes Brook Cabin-Creek, Pond & Privacy

Take a breath at Peakes Brook Cabin, our cozy and private cabin on a pond, with the brook steaming nearby. Our beloved property is perfect for couples needing to escape the city, decompress and deplug. You're minutes to charming Delhi and other Catskill villages, with nature all around, and our canoe ready for you. We are happy to welcome your doggies, but not your cats due to allergies. Please note that cabin has a kitchenette, not a full kitchen. Looking forward to hosting you!

Guest favourite
The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.
Guest house in Pound Ridge
4.94 out of 5 average rating, 118 reviews

A Lovely Cottage in the Woods

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

Top guest favourite
A cozy sitting room features exposed wooden beams and a brick fireplace. Two comfortable leather chairs are arranged around a wooden coffee table. Natural light enters through multiple windows adorned with sheer curtains, illuminating the space, which is enhanced by decorative touches like artwork and plants.
Guest house in Philipstown
4.99 out of 5 average rating, 134 reviews

Historic 1 bedroom home in Cold Spring, NY

This lovingly restored home, built in 1826,is located within the hamlet of Nelsonville within walking distance of the village of Cold Spring. This home has its own entrance and private courtyard and is attached to the owners main residence. Space is curated with antiques and is intended for a couple. This is cozy any time of the year. This home is near trailheads of spectacular hikes in the Hudson Highlands and at the base of Bull Hill.

Guest favourite
The exterior of the guest house is framed by manicured gardens, featuring two decorative statues positioned beside a pea gravel walkway. A small patio area includes a round table with two chairs, creating a serene spot for outdoor relaxation.
Guest house in Waccabuc
4.98 out of 5 average rating, 126 reviews

French Guest House in Waccabuc

A private, European-style retreat just 60 minutes from NYC. Set on an eight-acre gated French estate with its own lake, this guest house feels like a mini Versailles with 18th-century statuary, fountains and manicured gardens. Designed by David Easton, it features heated stone floors, a heated towel rack, luxury linens, gold fixtures, fast WiFi, and a private entrance. Minutes from Waccabuc Country Club and the Katonah train station.

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