Guesthouse vacation rentals in Columbia County

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Top-rated guesthouse rentals in Columbia County

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Guest favorite

Guesthouse in Hudson

4.98 out of 5 average rating, 66 reviews

Stylish, New Carriage House on Warren St!

Enjoy your stay at this adorable, newly-renovated, 2- bedroom Carriage House located in the heart of Hudson. Restaurants, galleries, antiques shops and bar are just steps away! This Carriage House is a free-standing 2-story, located on Warren Street. It offers a parking pass directly behind building in a municipal parking lot. The Amtrak station is a 12-15 minute walk away. The Carriage is located behind the main building which houses a gift shop and a wine bar, Sisters Hudson and Bar Bene.

Guest favorite

Guesthouse in Germantown

4.95 out of 5 average rating, 351 reviews

Art Studio at Pear Farm

Sophisticated large studio has gorgeous light and Catskill Mountain Views Formally an artist studio, it has undergone an elegant renovation. The luxurious bathroom features premium tile and a glass walled shower The kitchen is new, nicely equipped and has a full sized refrigerator. Enjoy outdoor grilling and dining on the private deck. The studio is located on 65 pristine acres fronting directly on the Hudson River. 5 minutes to Germantown. 10 minutes to Tivoli, Hudson or Bard College.

Guest favorite

Guesthouse in Germantown

4.97 out of 5 average rating, 186 reviews

Loblolly Cottage

Loblolly Cottage is a peaceful retreat set among towering pines on our property in Germantown NY. This guest suite harkens back to an authentic 1930s Adirondack cabin that features a reclaimed barn wood interior with vaulted ceilings and antique beams. Outside enjoy our fantastic deck with a Cabana kitchen and fire pit. A short stroll will lead you to the heart of the hamlet where you will find an array of shops and restaurants. Loblolly Cottage is a unique one-of-a-kind vacation experience.

Guest favorite

Guesthouse in Chatham

5 out of 5 average rating, 17 reviews

Idyllic and cozy guesthouse

Cozy back guesthouse in beautiful, sleepy Spencertown, NY. Ideally located to take advantage of some of the best of both the Hudson Valley and the Berkshires. Just twenty minutes to Hudson, NY; Tanglewood; Great Barrington and West Stockbridge, MA. Closer still is the charming village of Chatham. Or, forget the commute all together and hunker down in peaceful Spencertown. The guesthouse hosts a lovely view of the Austerlitz Hills, and is tucked back far from the road. A home away from home.

Guest favorite

Guesthouse in Great Barrington

4.95 out of 5 average rating, 91 reviews

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

Guest favorite

Guesthouse in Hudson

5 out of 5 average rating, 16 reviews

Serene, Stylish cottage - near Hudson- New Listing

Serene and stylish attached cottage on 10 acre wooded property. Private entrance, dedicated parking. Located on a country road with great biking, lovely farm and mountain views. Close to Hudson, with its many restaurants, galleries, farmers market, antique stores. Nearby excursions to Hudson River estates, nature trails, waterfalls, lakes. The space is designed for simplicity and relaxation. The yard has a hammock and chairs for lounging under a pair of old Chestnut trees

Guest favorite

Guesthouse in Germantown

4.96 out of 5 average rating, 193 reviews

Luxe Guest House Retreat

Welcome to the Guest House nestled in the woods. We designed this lush and light-filled studio with peace and luxury in mind. Situated across from apple orchards, it sits ten minutes from Hudson and ten minutes from Germantown, you get the best of both worlds: country living with two amazing destinations close by. Ideal for a romantic getaway, or to be close to the sights and sounds but can retreat to natural beauty. A true sanctuary from the City.

Guest favorite

Guesthouse in Germantown

4.98 out of 5 average rating, 183 reviews

The Loft

This beautiful loft apartment is located in the heart of Germantown- just 0.3 miles from Otto's Market (groceries and deli), 3 minute walk to Gaskins Restaurant, "A charming eatery serving a locally-sourced menu of classic American fare in a rustic dining room." We offer tea & coffee in the loft, parking, yard access, wifi, basic amenities, full kitchen and a smart TV that has a fire stick with access to Amazon Prime and Netflix (no cable).

Guest favorite

Guesthouse in Tivoli

4.93 out of 5 average rating, 147 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.

Guest favorite

Guesthouse in Germantown

4.97 out of 5 average rating, 242 reviews

Peaceful, Private, Secluded Guesthouse on Hilltop.

We are on the top of one of the highest points in Southern Columbia county. The dirt driveway is a quarter of a mile long and once you arrive at the top you will find the guesthouse nicely situated away from the main house. Completely private setting, including parking and patio overlooking a natural woodland. A perfect place to relax or explore the area. We are 15 minutes from Rhinebeck or Hudson with lots to do in between.

Guest favorite

Guesthouse in Hudson

5 out of 5 average rating, 27 reviews

Serene one bedroom guest house with fireplace.

Serene 900 square foot guest cottage located eight miles from Hudson, City center. The guest house is located near the main house and has a private entrance and partially screened-off stone patio—Sunny, bright, cheerful interior with king-size bed. The bathroom has a shower, heated floors, and a washer and dryer. The kitchen has a microwave, refrigerator, coffee maker, toaster, and electric tea kettle.

Superhost

Guesthouse in Hillsdale

4.82 out of 5 average rating, 22 reviews

Hudson valley and The Berkshires Cottage

Welcome to your luxury cottage escape. Located in the heart of the Hudson Valley in Hillsdale, NY sits a calm, stylish 1 bedroom cottage; perfect for a couple or a solo vacationer looking for solitude. We believe you’re here to completely relax, that’s why we have no requirements when checking out, just turn the lights off and lock the door!