Guesthouse vacation rentals in Dutchess County

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Dutchess County

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Top guest favorite

A charming red guesthouse features a sloped roof and white trim. A set of stairs leads to a second-story entrance, flanked by landscaped gardens. The pathway is paved with stone and bordered by greenery, with a gravel area visible near the entrance.

Guesthouse in Rhinebeck

4.99 out of 5 average rating, 116 reviews

Country Suite Near Omega Inst and Rhinebeck

We designed our guesthouse with the comfort seeking guest in mind. Enjoy our extra comfy plush beds, soft and fresh bed linens, luxurious towels, and complimentary essential oil infused bath amenities for your ultimate getaway. Complimentary snack and beverage selections provided for your enjoyment in our efficient kitchenette which can accommodate light meals. Our second floor guesthouse offers a newly installed ductless HVAC to provide the ultimate comfort air-conditioning or heating as needed. Many of our guests comment on our relentless pursuit of cleanliness. Some features included are: kitchen with microwave, toaster oven, refrigerator/freezer, electric tea kettle, and Keurig coffee maker. Also, oversized shower, dimmable lighting, keyless access, internet, smart TV, blackout window treatments, heating and air conditioning. Kitchen is for light meal preparation only, no stove. Complimentary snacks, beverages, and bath amenities provided. Echo Dot with Amazon Alexa in suite for guest use. Please note: entrance includes one flight of stairs to enter and exit the country suite. Available promptly by Airbnb messaging, text or phone for any questions or needs during your stay. The guesthouse is within walking distance to the Omega Institute for Holistic Studies, 8 miles to the charming and historic town of Rhinebeck, and central to many pursuits in the Hudson Valley. Walk or run around the lake for a 3.5-mile outing. 90 miles from NYC along Taconic State Pkwy. 15 mins from Amtrak's Rhinecliff station. 25 mins from Metro North's Poughkeepsie station. Walk or run around the lake for a 3.5 mile outing. Our guesthouse is a separate structure from our main home on the property. Each building is separated by around 30 feet.

Superhost

Guesthouse in Rhinebeck

4.81 out of 5 average rating, 31 reviews

Charming Rhinebeck Cottage with Wood Burning Stove

Located on 4 acres in the Hudson Valley and minutes away from great breweries, food and scenery, this sweet cottage is perfect for a couple getaway, bard families, omega students or fair ground visitors. Extremely accessible by train & car and 1.4 hours from the city. The perfect place to relax by the outdoor fire pit or cozy up next to the wood burning stove. The cottage is 600 sqft and suitable for 2-4 guest (1 bed and 2 daybeds). Simple amenities include cooking utensils and bath basics

Guest favorite

Guesthouse in Kingston

4.95 out of 5 average rating, 206 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!

Superhost

A modern kitchen features stainless steel appliances, including a refrigerator and oven. Open shelving holds various kitchenware, while a small dining table with four chairs is present. Soft lighting illuminates the space, highlighting the warm wood flooring and light-colored cabinetry.

Guesthouse in Dover Plains

4.88 out of 5 average rating, 112 reviews

Spilt Milk Cottage - Hudson Valley, NY

Completely renovated 1BR + den cottage inside a circa 1800's dairy barn. Come stay in a perfect WFH base with easy access to the Metro North train and everything the Hudson Valley has to offer. Master bedroom features a full size massaging and adjustable bed with plenty of storage and an office nook. The den is perfect for cuddling up and watching movies or the queen size foldout works as a 2nd bed. Highspeed internet, and a well equipped kitchen to cook up all those locally sourced goodies!

Guest favorite

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, 140 reviews

Sherwood Barn - close to ski mountain

Our guests stay on the SECOND floor of the barn in a 1200 Sq Ft, fully reno'd apt that sleeps 6. Located about 1 hour from NYC you will find peace and serenity in the middle of nature on this 4 acre estate (that also contains our main home) where you can get away from it all. unwind this way or visit local attractions like Thunder Ridge Ski Mountain, snowshoe/ X Country skiing, hike/bike/running trails, restaurants and local cafe's. Great oasis to kick back and spend time with family.

Superhost

A well-lit hallway features rustic exposed beams and a wooden floor, with decorative artwork framed on the walls. A patterned runner rug runs along the length of the corridor, leading to a staircase at the end, adding warmth to the space.

Guesthouse in Rhinebeck

4.89 out of 5 average rating, 123 reviews

Rustic and Elegant Converted Barn

Two large Hotel -like suites plus a coffee/mini bar. This dramatic and handsome converted 19th century barn serves as my guesthouse. Guests enter at the front barn door and climb the stairs to your accommodations on the second floor- which has two air conditioned bedrooms, each with a bath en suite. The downstairs of the barn is not part of the accommodations but will also not be in use by anyone else while you’re enjoying a serene stay just outside the charming Village of Rhinebeck.

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

4.94 out of 5 average rating, 397 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, gourmet kitchen appliances, & 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

Guesthouse in Stanfordville

4.93 out of 5 average rating, 179 reviews

Eco Cottage in the Woods

The cottage is light and airy, surrounded by forest. You may see birds and deer from the bedroom or living room. The queen bed is divided from the living room by a bookcase wall. There is a sofa bed in the living room which faces a patio overlooking the woods. We have a 16x36 unheated gunite pool, professionally maintained. The cottage works well for a couple or a couple with children. 2 night minimum required. Pets welcome. Pet owners passing through may stay 1 night.

Top guest favorite

A tranquil garden features a winding stone pathway surrounded by colorful flowers, including vibrant yellow daylilies and purple blooms. Lush greenery and various plants create an inviting atmosphere, while a covered pergola is nestled within the foliage, offering a shaded seating area.

Guesthouse in Beacon

4.97 out of 5 average rating, 173 reviews

Beacon Modern victorian+garden—steps to mainstreet

Hey there! Welcome to style and ease at our GUESTHOUSE in the heart of the creative and vibrant Beacon NY. Central air and heat (new!). Retreat to your 1000 square foot GH with your own private entrance, 2 bedrooms, (King sized bed!), queen bed, and plush queen pull out sofa in the living room (with door for privacy), and microwave, toasteroven, kettle, mini fridge, glasses, plates/utensils (no stove or kitchen sink). Streaming tv, WiFi, workstation, garden!

Superhost

The kitchen features modern cabinetry and sleek countertops with ample workspace. A brick wall adds character, while natural light filters in through a window. A cozy dining area is visible in the background, enhancing the overall inviting ambiance.

Guesthouse in Marlboro Township

4.86 out of 5 average rating, 42 reviews

Charming 1850's Guest House in Nature

Welcome to our charming 1850's guesthouse, situated on almost 6 acres of stunning natural beauty. This quiet getaway is perfect for anyone seeking a peaceful escape from the hustle and bustle of everyday life. The property is truly a nature lover's paradise. Stroll through the woods or spend a lazy afternoon canoeing in the creek outside your door. Book your stay today and experience the perfect blend of old-world charm and modern-day amenities!

Guest favorite

A modern cabin with a wood exterior is nestled among lush, green trees. The structure features multiple large windows and a wrap-around porch, providing an inviting space to connect with nature. The surrounding area is filled with tall grass and greenery.

Guesthouse in Tivoli

4.91 out of 5 average rating, 169 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.

Superhost

A large lawn area is featured, bordered by mature trees providing shade. The private cottage is visible in the background, with a stone pathway leading to a raised patio area. Flower pots and greenery are present in the foreground, adding to the tranquil outdoor setting.

Guesthouse in Stormville

4.98 out of 5 average rating, 172 reviews

Hudson Valley Cottage with Pond Access

Light and airy cottage situated on the private eighteen acre property surrounded by beautiful mature trees, large lawn area and quick two minute walk to a beautiful large 3 acre pond. Perfect spot for a relaxing weekend in the Hudson Valley; only 60 miles from Manhattan. The cottage has it's own private back yard, with a patio and a fire pit. Perfect place to disconnect and relax. Enjoy your Hudson Valley getaway!