Guesthouse vacation rentals in Columbia County

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Columbia County

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

0 of 0 items showing

1 of 3 pages

Superhost

Guesthouse in Great Barrington

4.84 out of 5 average rating, 58 reviews

1-bed unit 3/4 mi. from GB dwntwn.

Detached 1-bed unit on peaceful open 5-acre land. Housatonic River flowing through property with Appalachian Mountain backdrop. Only 3/4 mile to downtown Great Barrington. Unit is detached from main house with separate entrance and deck. Feels a world away from everything with secluded feeling but walking distance to all the great spots in Great Barrington (Guidos, GB Bagels, Bistro Box, and Big Y with Tesla Supercharge Station). "Pets allowed" are only for small dogs. No cats or other pets.

Guest favorite

Guesthouse in Sheffield

5 out of 5 average rating, 14 reviews

Black Bear Bungalow, Sheffield Mass. U Will Love!

This private guest house with full kitchen, living area and large bedroom with Luxurious Queen bed and plenty of storage only 10 miles to Ski Resorts. Sheffield, Mass. is only 5 miles to Great Barrington with wonderful shops, restaurants and grocery stores. You will have a FULL SIZE kitchen in this wonderful guest house. The first level has a full size kitchen, living area with recliners and TV, large bath and laundry. Upstairs is a large bedroom with queen bed. This is a 2 person guest home.

Guest favorite

Guesthouse in Great Barrington

5 out of 5 average rating, 11 reviews

Berkshires Guest Barn

Come enjoy the Berkshires in a newly renovated post and beam barn. Located walking distance to Egremont, and a short drive to the charming town of Great Barrington, where you will find many shops and restaurants. In the mood for music? Take a short walk and you are at one of the best music venues in the Berkshires. This space is all one level and has two separate bedrooms and a day bed/ trundle. The kitchen does not have an oven but you can use the induction cook top to whip up easy meals.

Top guest favorite

Guesthouse in Old Chatham

4.93 out of 5 average rating, 15 reviews

Mountain View Retreat in Hudson Valley

Sweet retreat perfectly located for exploring Columbia County, the Berkshires or simply lazing on the lawn with a lemonade and a good book. Totally renovated in 2019, the guest cottage has an open layout with kitchen, living room, dining area and 2 bedrooms. It's set in a sunny, open meadow surrounded by woods with views of the Berkshire mountains. Walk down a grassy path to a pond complete with an ancient dock. For hiking, there's a spectacular park a mile down the road, Ooms Conservation.

Top guest favorite

Guesthouse in Chatham

5 out of 5 average rating, 19 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.

Top guest favorite

Guesthouse in Great Barrington

4.96 out of 5 average rating, 118 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.

Superhost

Guesthouse in Coxsackie

4.78 out of 5 average rating, 64 reviews

Eagles Perch / Hudson River! Pet Friendly!

The guest house is located on the Hudson River in the charming village of Coxsackie. The space has a fabulous sunrise view, two bedrooms, and a beautiful tiled bathroom with a tub. There is a small refrigerator, microwave and coffee maker. The location is within walking distance to a wine shop, restaurants and a coffee shop. The yard is lovely and there is a dock to sit on next to the water to enjoy the late afternoon sun. In summer months, access to the pool. Unrivaled location.

Guest favorite

Guesthouse in Germantown

4.97 out of 5 average rating, 74 reviews

The Guest House

Welcome to The Guest House at Gatherwild Ranch, one of 8 accommodations on 15 acres of in the Hudson Valley. This cabin is a renovated 1800's guesthouse, just behind the main farmhouse. It is a comfortable space with a private lawn, kitchenette , firepit, electricity and wifi and is cozy yet spacious. It has 2 entrances, with beautiful morning and evening sun and features a queen size bed with fresh linens and shares the main bathhouse with beautiful Moroccan tiled showers.

Guest favorite

Guesthouse in Germantown

4.96 out of 5 average rating, 196 reviews

Luxe Guest House Retreat (Sauna)

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 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.

Top 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.

Top guest favorite

Guesthouse in Germantown

4.99 out of 5 average rating, 206 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), And Universal Cafe. " farm to table global inspired classics." 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).