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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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A spacious loft area features high ceilings accented by exposed wooden beams. A queen size bed is fitted with a soft blanket, while a colorful area rug complements the white furniture. A dining table with chairs and a cozy sitting area are visible in the background.

Guesthouse in Warwick

4.94 out of 5 average rating, 392 reviews

Rustic Loft Space with Distinctive Artistic Charm

Beautiful spacious and bright artist loft on the second floor of a newly renovated Warwick barn behind our 1893 Warwick Village home. More information The space We offer our furnished live and work artist loft on a daily or weekly basis. The loft : -is 400 sqf -is located on the second floor -has nicely designed bathroom -has a very comfortable queen size bed -has high speed internet access -is very tidy and clean The neighborhood: -one blocks from the NJ Transit bus to Manhattan. -great restaurants and cafés nearby This loft is wonderful is perfect for 2-4 visitors. You are in the middle of lovely village neighborhood, but get the comfort of a cozy retreat. Guests will have access to the entire SECOND FLOOR space. Situated in the lower Hudson Valley, the town of Warwick is just over an hour’s bus ride New York City. Explore its numerous orchards and wineries, head to the drive-in movie theater, or grab a bite from one of the village restaurants. The loft is just one block from the NJ Transit bus that leaves from Port Authority.

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, 392 reviews

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

PRIVATE Modern/Rustic Apt WALK TO TOWN 5 * Rating "premiere" 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

A cozy living area features a leather sofa adorned with colorful throw pillows and a wooden coffee table. A black armchair complements the seating arrangement, while vibrant artwork hangs above the sofa. Natural light enters through two windows with light-filtering shades.

Guesthouse in Mount Tremper

4.97 out of 5 average rating, 346 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, cathedral ceiling, sleeps two adults comfortably. Due to allergies, we do not allow pets. This includes service animals. We use fragrance free laundry detergent. No smoking or vaping. This listing is not suitable for children or infants.

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, 259 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 charming guest house is nestled among lush trees, featuring a sloped roof and large windows. The exterior is painted in warm brown tones, blending with the natural surroundings. A gravel driveway leads to the entrance, providing access to a serene rural landscape.

Guesthouse in Bearsville

4.98 out of 5 average rating, 540 reviews

Relax on the Ridge - 2 miles from Woodstock

Stay and relax in a private guest house on a 5+ acre picturesque property overlooking historic Woodstock, N.Y. The cottage is nestled away high on a private road in a quiet country setting, yet conveniently only 2 miles from Woodstock and 10 miles from Phoenicia! Relax on the grounds while watching our Tennessee Mountain, Cashmere & Kiko goats—drive into town to enjoy shops, restaurants, & the unique artistic culture of Woodstock—explore the many beautiful trails that the Catskill Park offers.

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, 352 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 round dining table with two transparent chairs is positioned near large windows that offer views of vibrant autumn foliage. A small vase with flowers decorates the table. Light enters through the open door, enhancing the bright and airy ambiance.

Guesthouse in Mahopac

4.95 out of 5 average rating, 238 reviews

Lakeview Guesthouse with Sauna

Art and light filled spacious studio with panoramic views overlooking lake Mahopac perched on a steep hill. A short 5 min walk down the hill to swimming/paddleboarding/canoeing. Walkable to an on-the-lake restaurant/ dining/ takeout options + boba tea! Drivable to farm fresh food markets, restaurants and art museums. Cedar dry Sauna on property for use. Nearby towns and hikes include Fahenstock Park, Pound Ridge, Cold Spring, Beacon, Ridgefield, or walk up the hill to trails of Volz park!

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, 153 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! A project over 3 years in the making. (Stayed tuned for new pics)

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

5 out of 5 average rating, 135 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, 165 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 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, 169 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.

A modern cabin is nestled among lush greenery, featuring a wooden exterior and a wrap-around porch. Large windows provide views of the surrounding trees, while the gentle slope of the land leads to a grassy area in the foreground.

Guesthouse in Tivoli

4.91 out of 5 average rating, 181 reviews

Tivoli Star Gazing Cabin

Down a long driveway, set amongst 100 year old trees and meadows, the cabin offers time in the quiet country though only minutes to the lively village of Tivoli. With a wrap around porch for morning coffee, fire fly viewing or star gazing. It has a soaking tub, with a hand held shower. The cabin is part of our family compound of a main house and a small garden hut. Each property has an independent outdoor space for relaxing and privacy.

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Hudson Valley guesthouse rentals

Free parking on premises

Air conditioning

Family-friendly guest house rentals

A quaint cottage is surrounded by lush greenery, featuring a striking red front door. Sunflowers rise in the foreground, adding a touch of color. The wooden deck extends towards the peaceful landscape, showcasing the cottage's inviting exterior.

Guesthouse in Mount Tremper

4.92 out of 5 average rating, 358 reviews

Cozy Catskill Cottage Perfect Getaway for Two

Top guest favorite

A serene pond reflects the cloudy sky, surrounded by lush greenery and tall grasses. The still water enhances the tranquil atmosphere of the landscape, with distant buildings nestled among the trees, completing the rural setting.

Guesthouse in Stephentown

5 out of 5 average rating, 418 reviews

Dog Friendly Studio

A fisherman is seen casting a line across the tranquil Farmington River, surrounded by lush greenery and mist rising from the water. Towering trees provide a natural frame, creating a serene outdoor setting.

Guesthouse in Barkhamsted

4.89 out of 5 average rating, 103 reviews

Farmington River Carriage House Pleasant Valley CT

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, 139 reviews

Private Guesthouse in Saugerties

A charming cottage exterior is framed by lush greenery, featuring large front glass doors and a sloped roof. Potted flowers adorn the entrance, while a shaded sitting area with comfortable chairs is visible beside the pathway, inviting relaxation in a serene setting.

Guesthouse in Stormville

4.97 out of 5 average rating, 175 reviews

Hudson Valley Cottage with Pond Access

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

4.9 out of 5 average rating, 911 reviews

Moon Valley Country Retreat no clean fee pets yes

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

4.94 out of 5 average rating, 400 reviews

Cozy Mountainside Suite - Minutes from Beacon

Top guest favorite

A spacious studio apartment features hardwood floors and warm, recessed lighting. A comfortable queen bed is complemented by a cozy seating area and a study desk. A partial view of the kitchen is visible, showcasing the granite counters and modern appliances.

Guesthouse in Saratoga Springs

4.99 out of 5 average rating, 172 reviews

CHARMING CARRIAGE HOUSE-GREAT LOCATION!

Guest house rentals with a patio

Top 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, 185 reviews

Brookside Cottage

A dark wooden barn is surrounded by lush greenery, showcasing a set of stairs leading to the second floor. A paved patio area features a table and chairs, inviting outdoor relaxation among the tranquil natural setting.

Guesthouse in Brewster

4.94 out of 5 average rating, 146 reviews

Sherwood Barn - close to ski mountain

Top 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

4.95 out of 5 average rating, 184 reviews

Cozy guest cottage with indoor fireplace

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, 176 reviews

Red Barn Retreat - Shawangunk Mountains Getaway

Top guest favorite

A modern guesthouse features a dark exterior with large windows, surrounded by trees. A stone patio area is equipped with two outdoor chairs and a firepit, accompanied by neatly stacked firewood. Landscaping includes green grass and flowering plants, creating a serene outdoor setting.

Guesthouse in High Falls

4.97 out of 5 average rating, 35 reviews

Modern and warm guesthouse

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, 117 reviews

Cottage with a Waterfall View

Top guest favorite

A quaint cottage is nestled among vibrant green trees, showcasing newly blossomed flowers in the foreground. Sunlight casts gentle shadows on the lush lawn, with the spacious deck visible through French doors. The peaceful natural surroundings highlight the beauty of early spring.

Guesthouse in Woodstock

5 out of 5 average rating, 12 reviews

Modern & Private Cottage Minutes From Woodstock

An open living space is illuminated by natural light from multiple windows, featuring a cozy sofa, wooden coffee table, and a dining area with metal chairs. A spiral staircase leads to a loft space, while a door opens to a private outdoor deck.

Guesthouse in Accord

4.91 out of 5 average rating, 126 reviews

Tiny Horse Barn

Guest house rentals with a washer and dryer

Top guest favorite

A charming guesthouse with a red exterior is set against a backdrop of vibrant greenery and colorful flower beds. Various flowers in shades of orange, pink, and purple border the property, while tall trees provide natural shade. The tranquil setting invites relaxation in nature.

Guesthouse in Wallingford

4.98 out of 5 average rating, 701 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

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, 108 reviews

Cottage with a View

Top guest favorite

A covered patio area features two turquoise chairs and a round table positioned on a wooden deck. A small refrigerator and microwave are visible in the background. A decorative rug adds texture to the space, while a nearby hammock invites relaxation.

Guesthouse in East Meredith

4.98 out of 5 average rating, 136 reviews

Lily Pad by the Ponds

A modern, renovated barn is set against a backdrop of lush greenery. Two brightly colored lounge chairs and a reclining chair are positioned on the grassy area, inviting relaxation. Large windows reflect the surrounding trees, emphasizing the tranquil outdoor setting.

Guesthouse in Stockbridge

4.92 out of 5 average rating, 131 reviews

Modern barn in the heart of the Berkshires

Top guest favorite

The studio features a spacious sleeping area with a green quilted bedspread and decorative pillows. Colorful artwork adorns the walls, while large windows provide natural light and views of the outdoors. A foosball table is positioned nearby, enhancing the playful atmosphere.

Guesthouse in Mongaup Valley

4.99 out of 5 average rating, 413 reviews

Good Vibes Studio in the Woods

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, 117 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, 548 reviews

Starhaven: Baseball HoF, Mineral Mining & More

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, 105 reviews

Loft in the Pines

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