Guesthouse vacation rentals in Dutchess County

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouses in Dutchess County

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

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Guest favourite

Guesthouse in Kingston

4.94 out of 5 average rating, 135 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!

Dec. 6 – 13

$185 CAD per night

Superhost

Guesthouse in Dover Plains

4.88 out of 5 average rating, 85 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!

Dec. 27 – Jan. 3

$201 CAD per night

Guest favourite

Guesthouse in Verbank

4.98 out of 5 average rating, 43 reviews

Cozy Cabin Getaway in the Hudson Valley

Cozy wood cabin situated on a 20 acre property in the Hudson Valley. Large lawn area to explore and a hill leading down to our pond. Ideal place for couples or solo travelers looking to escape. Only an 1.5 drive from the city. Full equipped kitchen and bath and working wood-burning stove. Explore the many hiking trails nearby, or drive into the idyllic town of Millbrook, NY - host to antiques, restaurants, and bookstores to enjoy. Pets welcome for $50 fee. For more, follow @pondridgeny !

Sep. 6 – 13

$311 CAD per night

Guest favourite

Guesthouse in Kingston

5.0 out of 5 average rating, 87 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.

Jul. 31 – Aug. 7

$329 CAD per night

Guest favourite

Guesthouse in Beacon

4.94 out of 5 average rating, 367 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.

Dec. 19 – 26

$827 CAD per night

Guest favourite

Guesthouse in Stanfordville

4.92 out of 5 average rating, 164 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.

Sep. 1 – 8

$176 CAD per night

Guest favourite

Guesthouse in Poughkeepsie

5.0 out of 5 average rating, 23 reviews

Newly Complete Full Guest Suite!

Welcome to our fully renovated, brand new guest suite in the perfect part of town - walking distance from the rail trail! Safe, private indoor parking spot and separate keypad deadbolt entrance. The suite is located in a forested, quiet residential neighborhood just minutes from Vassar, less than 10 minutes to the Poughkeepsie train station, and less than 15 minutes from Marist college. The perfect stay for anyone visiting family, looking at colleges, or just needing to get away!

Jan. 10 – 17

$158 CAD per night

Guest favourite

Guesthouse in Beacon

4.96 out of 5 average rating, 128 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!

Apr. 20 – 27

$556 CAD per night

Guest favourite

Guesthouse in Fishkill

4.86 out of 5 average rating, 69 reviews

Hudson Valley Studio in the Village of Fishkill NY

This spacious studio is in a quiet cul-de-sac and under a half mile walk from the Village of historic Fishkill, NY. Also, only a 10 minute drive to Beacon, NY! It is a private dwelling that includes a full kitchen, 1 new Queen bed, 1 new pull out bed, and a separate room for laundry. Plenty of drawers and closet place caters to up to 4 guests for whichever Hudson Valley activity you're in town for. Come enjoy the atmosphere of this Hudson Valley studio!

Oct. 4 – 11

$189 CAD per night

Superhost

Guesthouse in Marlboro

4.88 out of 5 average rating, 24 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!

Mar. 11 – 18

$282 CAD per night

Guest favourite

Guesthouse in Stormville

4.99 out of 5 average rating, 159 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!

Dec. 2 – 9

$506 CAD per night

Superhost

Guesthouse in Rhinebeck

4.89 out of 5 average rating, 115 reviews

Rustic and Elegant Converted Barn

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 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.

Oct. 4 – 11

$463 CAD per night