Guesthouse vacation rentals in Hudson Valley

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Top-rated guesthouse rentals in Hudson Valley

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Top guest favorite
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.
Guesthouse in Woodstock
5 out of 5 average rating, 415 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 favorite
The entrance to the guest house displays a dark wood-paneled exterior with a black door featuring a grid window. A small window is positioned beside the door. Recessed lighting illuminates the covered porch area above.
Guesthouse in North Bennington
4.99 out of 5 average rating, 294 reviews

Birch House - lake, green trees + modern comforts

We're a little guest house near a lake in Vermont with green trees + modern comforts. Perfect for couples + individuals looking to relax + enjoy nature. Renovated, air conditioned space w/ cozy, minimalist vibes. A small modern cabin that's peaceful + private. Tucked into a quiet neighborhood. Main home is a separate building next door. Near Bennington College. 12 minutes to downtown Bennington. IG birchhousevt Please note that due to a severe allergy, it is difficult to accommodate animals

Top guest favorite
A cozy living space features a stylish leather couch and a flat-screen TV. A wooden barn door leads to the adjoining bedroom, while natural light enters through two windows adorned with simple coverings. A plant adds a touch of greenery, enhancing the atmosphere.
Guesthouse in Kingston
4.95 out of 5 average rating, 226 reviews

Campfire Cottage: Fireplace, fire pit & no chores!

Escape the city and unwind at this beautifully designed home. Just 90 minutes from Manhattan, this is the perfect place to relax and reconnect with nature, or work remotely. Enjoy downtown attractions, hiking, and the Hudson River Maritime Museum nearby. The home features a cozy living area, full kitchen, electric fireplace, and no chore list for checkout. The yard has a grill and fire pit facing the woods. Book today to retreat to your private house and enjoy the beauty of Upstate New York!

Guest favorite
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.
Guesthouse in Beacon
4.95 out of 5 average rating, 402 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.

Top guest favorite
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.
Guesthouse in Kingston
4.99 out of 5 average rating, 148 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.

Top guest favorite
The chalet stands amidst vibrant autumn foliage, showcasing a green exterior and a spacious deck. The well-maintained yard features a lush green lawn, with a variety of trees surrounding the property that enhance the natural setting.
Guesthouse in Windham
4.99 out of 5 average rating, 178 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.

Top guest favorite
A welcoming living area features a green sofa positioned next to large glass doors that open to a view of the outdoor surroundings. A round side table is placed nearby, and natural light fills the space, highlighting the warm wooden walls and floor.
Guesthouse in New Milford
4.98 out of 5 average rating, 102 reviews

Luxury in the Litchfield Hills

Enjoy this gut-renovated two-floor post-and-beam luxury cottage just outside Kent, CT. Just 9 minutes from downtown Kent and close to the best of Litchfield County, our cottage sits on a serene 3.5 acre property that backs up to protected woodlands. We painstakingly brought the rustic space into the present, with a new kitchenette; bathroom with a massive, spa-like shower; new HVAC; and hotel-like accommodations. Close to Kent School, Canterbury, and great for a romantic getaway.

Top guest favorite
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.
Guesthouse in Delhi
4.97 out of 5 average rating, 169 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 beside it. 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. We are very excited to announce that our cabin has a huge upgrade as of Spring '25. We now have a full bathroom with running water! Note that cabin has a kitchenette, not full kitchen.

Top guest favorite
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.
Guesthouse in Waccabuc
4.99 out of 5 average rating, 113 reviews

French Guest House in Waccabuc

A mini Versailles just outside of NYC - located on a private and gated eight acre estate with its own lake in Waccabuc, NY. Surrounded by 18C statuary, manicured gardens and fountains, it’s equivalent to staying in a 5-Star European luxury hotel suite (house designed by David Easton) with its heated stone floors and heated towel rack, luxury linens, gold taps and serene private entrance. (.7mi from Waccabuc Country Club, 60 min from NYC by car or train - Katonah train St)

Top guest favorite
A sunlit open space features a light-colored wooden floor and white walls. Two large windows invite natural light, while a patterned area rug adds warmth. A small table and chairs are arranged nearby, creating a versatile area for dining or work.
Guesthouse in Cold Spring
4.99 out of 5 average rating, 189 reviews

Modern+bright forest escape - near village & train

Modern, efficient, and elegant private flexible garden apt. Guesthouse can be used as a studio apartment, or as a private personal retreat space for art/work/rest/meditation. Hiking trails available right out the door, and just a few minutes walk to Cold Spring's vibrant Main Street and Metro North train station to NYC and beyond. Comfortable bed, all modern amenities. Private patio. Native pollinator gardens and forest surround. Solar orientation brings in natural light.

Guest favorite
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.
Guesthouse in Pound Ridge
4.94 out of 5 average rating, 98 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.

Superhost
A rustic cabin is nestled among lush green trees, with a red umbrella shading a small seating area in front. A circular stone patio encircles firewood stacked neatly beneath a large window, enhancing the serene outdoor surroundings.
Guesthouse in Saugerties
4.9 out of 5 average rating, 124 reviews

Fireside Cabin Retreat near Woodstock & Saugerties

Wind down fireside after a day of hiking The Catskills, dining in nearby Woodstock or Saugerties (10 mins drive) or just BBQ-ing by the cabin. Located off a quiet road on our 7 acre property, you will have privacy in the woods. We will provide firewood and everything you need to get the fire roaring. Wifi is high speed. Dog friendly dogs are welcome! PS: We finished our bathroom renovation in Feb 2025. Come be among the first to enjoy it :)

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