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Guesthouse vacation rentals in Hudson Valley

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Top-rated guesthouse rentals in Hudson Valley

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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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
An inviting living area features wooden beams and warm tones. A comfortable sofa with decorative pillows faces a wood stove, while a well-equipped kitchen is visible in the background. Light filters through multiple windows, highlighting the natural wood cabinetry and charming kitchen appliances.
Guesthouse in Windham
5 out of 5 average rating, 141 reviews

Catskill Mts Artist Cabin: Fall Hiking, Dining…

Here now Beautiful Fall exploring, hiking, outdoor dining and farm mkts. Our storybook cabin is privately nestled in the heart of the Catskill Mtns, near a seasonal stream and lake, under open sky, surrounded by forest, Enjoy very nearby skiing (Windham Mt, Hunter Mt.) swimming, kayaking, hiking, dining, mkts. Experience true quiet, endless stars, indoor and outdoor wood fires, complimentary firewood, natural fabrics, authentic art/vintage design, full kitchen, rain shower, stone patio, grill…

Top guest favorite
Guesthouse in North Bennington
4.99 out of 5 average rating, 299 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, 229 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, 403 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 favorite
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.
Guesthouse in Accord
4.88 out of 5 average rating, 272 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 favorite
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.
Guesthouse in Woodstock
4.96 out of 5 average rating, 368 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 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, 150 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, 181 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, 106 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.

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
4.98 out of 5 average rating, 116 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, 191 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.

Popular amenities for Hudson Valley guesthouse rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Family-friendly guest house rentals

Superhost
A white Dutch door is framed by rustic wooden walls, showcasing a combination of horizontal and vertical planks. A small lantern hangs nearby, and a woven basket adorns the wall beside the door. A simple bench with a patterned cushion sits on the side.
Guesthouse in Southbury
4.94 out of 5 average rating, 356 reviews

Charming Guest Cottage with Modern Amenities

Guest favorite
A gentle brook flows through a landscape adorned with autumn leaves. Tall trees line the banks, their foliage transitioning to various shades of gold and orange. Smooth stones are scattered in the water, and the ground is covered with a carpet of fallen leaves.
Guesthouse in Williamstown
4.96 out of 5 average rating, 201 reviews

Brookside Cottage

Top guest favorite
A bright sitting room features a cozy sofa adorned with colorful pillows. A wooden sideboard stands against the wall, while a small side table holds reading materials. Natural light filters in through two windows, illuminating the room's warm, wooden flooring and vibrant area rug.
Guesthouse in South Salem
4.94 out of 5 average rating, 309 reviews

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt

Top guest favorite
The exterior of a Craftsman-style studio is shown, featuring a two-car garage with wooden doors. The building is accented with earthy tones of red and gray, while ambient lights illuminate the front in the evening glow. Surrounding trees enhance the natural setting.
Guesthouse in Margaretville
4.98 out of 5 average rating, 179 reviews

Sunny Arts & Crafts Loft

Superhost
The exterior of the Granary is highlighted, featuring a mix of red barn siding and natural stone. The two upper windows allow natural light inside, while a mint green double door adds a pop of color. Lush greenery and colorful flowers surround the entrance.
Guesthouse in Lenox
4.92 out of 5 average rating, 405 reviews

Restored 1735 Granary I King Bed + Views & Pool

Guest favorite
The exterior of the rustic cottage features a wooden facade and two sets of French doors. Chairs are positioned on a stone path leading to the entrance, surrounded by a manicured garden area with pebbles and greenery. Nearby trees provide a natural backdrop.
Guesthouse in Stroudsburg
4.94 out of 5 average rating, 218 reviews

Cozy guest cottage with indoor fireplace

Top guest favorite
The exterior of the chalet is shown in twilight, with soft light emanating from a window. The rustic wooden structure features a sloped roof and is surrounded by snow-covered ground and trees in the background.
Guesthouse in Granville
4.91 out of 5 average rating, 944 reviews

Moon Valley Country Retreat no clean fee pets yes

Guest favorite
A charming courtyard is surrounded by greenery and blooming flowers. A shaded area features a comfortable seating arrangement with neutral-colored cushions. Additional seating is available in the background under canopies, providing an inviting space for relaxation.
Guesthouse in Troy
4.93 out of 5 average rating, 655 reviews

Whimsical Carriage House & Private Courtyard

Guest house rentals with a patio

Guest favorite
A bright sleeping area features a spacious bed with light bedding, positioned beneath a vaulted ceiling. Floor-to-ceiling windows provide views of the woods, while a small desk and chair are set against one wall for workspace. A television is mounted for entertainment.
Guesthouse in Greenwich
4.95 out of 5 average rating, 105 reviews

The Cottage in Greenwich

Top guest favorite
The entrance features a welcoming porch with two wicker chairs positioned on a stone path. A variety of lush plants and flowers surround the area, enhancing the inviting appearance of the home with its cheerful yellow exterior.
Guesthouse in Cobleskill
4.99 out of 5 average rating, 107 reviews

Mill Creek Guest House

Top guest favorite
A rustic black barn is showcased, featuring wooden doors and exterior lighting. A paved driveway leads up to the entrance, bordered by a well-maintained lawn and trees. The surrounding natural landscape enhances the barn's secluded charm.
Guesthouse in Brewster
4.94 out of 5 average rating, 160 reviews

Sherwood Barn - close to ski mountain

Top guest favorite
A lush green field extends towards the horizon, framed by clusters of trees. The sky is filled with varying shades of clouds, reflecting a soft light from the setting sun. The peaceful rural landscape evokes a sense of tranquility.
Guesthouse in Gardiner
4.99 out of 5 average rating, 183 reviews

Red Barn Retreat - Shawangunk Mountains Getaway

Superhost
A vibrant living area features a bright orange sectional sofa complemented by decorative pillows. A round mirror and geometric wall art are displayed above. A large window allows natural light, enhancing the warmth of the space. Two dark poufs and a colorful area rug add texture.
Guesthouse in Cobleskill
4.85 out of 5 average rating, 160 reviews

upstate caverns b&b

Top guest favorite
Guesthouse in Honesdale
4.93 out of 5 average rating, 119 reviews

Cozy Guesthouse by the Lake

Top guest favorite
A spacious loft area features a queen-size bed with decorative pillows and a comfortable futon sofa positioned against a wooden wall. Natural light enters through large windows, illuminating a colorful area rug that spans the floor. A fan is mounted on the ceiling.
Guesthouse in Wurtsboro
4.9 out of 5 average rating, 102 reviews

Hiker’s Haven, a Cozy Cabin above Bashakill Refuge

Top guest favorite
A light-filled living room features a gray sectional sofa with a colorful throw pillow. A wooden console table stands beside a lamp, while natural light enters through two large windows adorned with white trim, providing views of the surrounding greenery. Vintage art pieces are displayed on the walls.
Guesthouse in Sharon
4.95 out of 5 average rating, 128 reviews

Cottage with a Waterfall View

Guest house rentals with a washer and dryer

Guest favorite
A spacious bedroom features a large bed with neutral bedding, complemented by a comfortable, modern seating area. Natural light fills the room through multiple windows, and built-in shelves showcase books and decorative items, adding functionality and style to the space.
Guesthouse in Mamaroneck
4.9 out of 5 average rating, 166 reviews

Your Modern Guest Wing Near NYC

Guest favorite
A cozy living area features a comfortably upholstered sofa paired with a stylish armchair. A cowhide rug lies on the warm hardwood floor, while a contemporary side table and a console table provide functional space. Art is displayed on the walls, enhancing the room's decor.
Guesthouse in Saugerties
4.86 out of 5 average rating, 148 reviews

Private Guesthouse in Saugerties

Guest favorite
A spacious wooden deck features a round table with green chairs and an umbrella providing shade. Inviting views of the surrounding mountains and lush trees create a serene backdrop, encouraging outdoor relaxation and dining.
Guesthouse in Arlington
4.94 out of 5 average rating, 116 reviews

Cottage with a View

Guest favorite
A modern kitchen features sleek white cabinetry and stainless steel appliances, including a gas stove and refrigerator. An island with black countertops is centered in the space, complemented by three black stools. Large windows provide natural light, enhancing the bright and airy atmosphere.
Guesthouse in Red Hook
4.94 out of 5 average rating, 102 reviews

Private Cottage, Walk to Restaurants and Shops

Superhost
A charming cottage is depicted, featuring a dark exterior with bright pink doors. Two pink chairs and a small table are positioned outside on a gravel area, surrounded by potted plants. Trees frame the backdrop, contributing to a serene setting.
Guesthouse in Dover Plains
4.87 out of 5 average rating, 126 reviews

Spilt Milk Cottage - Hudson Valley, NY

Top guest favorite
A spacious guesthouse and main house are visible, both surrounded by greenery. The guesthouse, featuring a peaked roof and front porch, is set beside the main house, which includes a symmetrical design and large garage doors. A gravel pathway leads to both structures.
Guesthouse in Fort Plain
4.99 out of 5 average rating, 576 reviews

Starhaven: Baseball HoF, Mineral Mining & More

Top guest favorite
A charming red exterior features white window treatments and a rustic door. Decor elements include a wooden wagon wheel and an artistic iron wall hanging. Lush greenery and flowers are visible in the garden area, enhancing the welcoming entryway.
Guesthouse in Newtown
4.98 out of 5 average rating, 108 reviews

Guest Suite at Wisteria Gardens

Guest favorite
A cozy living area features mid-century modern furniture, including an orange armchair and a sleek glass coffee table. A gallery wall displays various artworks, complemented by natural light from two windows. A small dining area with a round table and four chairs contributes to the inviting layout.
Guesthouse in New Haven
4.92 out of 5 average rating, 329 reviews

Square 6ix

Destinations to explore