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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Guest favorite

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.

Guest favorite

Guesthouse in Millerton

4.98 out of 5 average rating, 93 reviews

Loft in the Pines

Loft in the Pines: Get away to your own private retreat, walkable to Main St, Millerton, NY & Harlem Valley Rail Trail. Beautiful 1 bedroom escape with two decks for your relaxation. Perfect for couples or families. Close to great hiking & skiing. Easy walk to antique shops & delicious restaurants or put your feet up and relax! 1.5 baths, living room with flat screen TV, dining room & fully equipped kitchen & expansive deck to take in the view. Rent with House in The Pines for a larger group

Guest favorite

Guesthouse in Kingston

4.94 out of 5 average rating, 172 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

Guesthouse in Dover Plains

4.89 out of 5 average rating, 104 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

Guesthouse in Brewster

4.94 out of 5 average rating, 126 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.

Guest favorite

Guesthouse in Rhinebeck

4.89 out of 5 average rating, 122 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

Guesthouse in Beacon

4.94 out of 5 average rating, 381 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.

Guest favorite

Guesthouse in Beacon

4.97 out of 5 average rating, 159 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!

Guest favorite

Guesthouse in Fishkill

4.87 out of 5 average rating, 82 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!

Guest favorite

Guesthouse in Carmel Hamlet

4.88 out of 5 average rating, 69 reviews

Sweet lil' house among the boulders LONG TERM STAY

This cozy modern bungalow is set adjacent to our home with a separate entrance from the driveway on 8 acres isolated on a back country road with no neighbors visible anywhere. You are a bike ride away from Fahnestock Park, the Appalachian Trail, the Zen Monastery, White Pond and a small country deli. It's a 20 minute drive to Cold Spring with antiques and restaurants, 15 minutes to Carmel with first run movies, bowling, restaurants and a mall.

Guest favorite

Guesthouse in Tivoli

4.93 out of 5 average rating, 153 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.