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Guesthouse vacation rentals in Hudson River

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Top-rated guesthouse rentals in Hudson River

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, 140 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, 297 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

Guest favorite
A detached red barn is surrounded by a grassy yard, with patches of snow visible on the ground. The property features a gravel driveway leading to the barn's double garage doors. Mature trees line the background, offering a natural setting.
Guesthouse in Lenox
4.9 out of 5 average rating, 284 reviews

The Coach House | Modern 2BR Loft + Views & Pool

Restored coach barn with 25-ft cedar ceilings, skylights, and mountain views—part of House on Golden Hill, a historic Lenox farmhouse compound. This airy 2BR + loft retreat blends rustic charm with modern ease. Enjoy a full kitchen, cozy living space, and outdoor area. Set beside a stream with seasonal pool access, it’s perfect for families, couples, or creative escapes. Centrally located and just minutes to downtown Lenox, Tanglewood, and trails—your Berkshires base for rest and inspiration.

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 sleeping area is highlighted by a spacious bed dressed in neutral linens. An inviting cushion rests on the bed, while warm light emanates from two bedside lamps. A wooden bench sits at the foot of the bed, and decorative greenery adorns the walls.
Guesthouse in Cummington
5 out of 5 average rating, 139 reviews

Cozy Hilltown Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

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, 367 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, 180 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 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, 115 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, 190 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, 100 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.

Popular amenities for Hudson River guesthouse rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Family-friendly guest house rentals

Guest favorite
A comfortable living area features a sleek black sofa opposite a large television displaying streaming options. A contemporary glass coffee table sits in front of the sofa. Soft lighting creates a cozy atmosphere in the space with large windows providing abundant natural light.
Guesthouse in Brooklyn
4.91 out of 5 average rating, 165 reviews

Amazing Views & Rooftop Deck - Safe - Parking Incl

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, 178 reviews

Sunny Arts & Crafts Loft

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, 942 reviews

Moon Valley Country Retreat no clean fee pets yes

Superhost
A small red cabin is nestled under large trees, surrounded by lush greenery and autumn foliage. The backdrop features distant mountains, creating a serene and natural setting. Soft light filters through the leaves, enhancing the peaceful atmosphere of the landscape.
Guesthouse in Manchester
4.8 out of 5 average rating, 237 reviews

Glamping Cabin with Private Pond and Mountain View

Top guest favorite
The entrance features a white door with a windowpane design, framed by light blue siding. A decorative lantern hangs beside the door. A small potted plant rests on a blue chair, while a welcome mat adorned with black dogs is placed at the threshold.
Guesthouse in Northampton
4.99 out of 5 average rating, 381 reviews

Mill River Cottage (pet friendly!)

Superhost
A beautiful retreat is set amidst lush greenery, featuring a wooden structure with a welcoming entrance. A stone pathway leads through the garden, and the building is surrounded by various plants, enhancing the natural ambiance of the setting.
Guesthouse in Brattleboro
4.91 out of 5 average rating, 563 reviews

Mahalo Temple Retreat

Guest favorite
A charming, restored cottage is depicted, with a sloping roof and a mixture of large and smaller windows. Surrounded by greenery, the serene landscape includes trees in the background, creating a peaceful, secluded atmosphere.
Guesthouse in New Berlin
4.89 out of 5 average rating, 164 reviews

Cozy, Comfortable Country Cottage

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

Guest house rentals with a patio

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

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 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.
Guesthouse in Philipstown
4.99 out of 5 average rating, 113 reviews

Historic 1 bedroom home in Cold Spring, NY

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, 158 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

Guest house rentals with a washer and dryer

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

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

Top guest favorite
A spacious studio is illuminated by natural light from large windows. The bright room features a mix of furnishings, including a white sofa, a dining table, and a variety of shelving units. Warm wood flooring complements the inviting layout.
Guesthouse in Northampton
4.93 out of 5 average rating, 285 reviews

Large Studio – Walk to Town

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

Top guest favorite
A spacious living area features modern seating arrangements with natural light streaming through large glass windows. A small table is set by the window, overlooking the garden. Polished wooden floors and decorative items add warmth to the inviting atmosphere.
Guesthouse in Marlboro Township
4.97 out of 5 average rating, 173 reviews

Refined, serene and like no other, Marlboro, VT.

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
An outdoor deck showcases a round table surrounded by three metal chairs. A small vase with white flowers is positioned at the center of the table. Lush greenery and tall trees provide a tranquil backdrop, with a partially cloudy sky overhead.
Guesthouse in Millerton
4.98 out of 5 average rating, 113 reviews

Loft in the Pines

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