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.

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Top guest favorite

Guesthouse in Sheffield

5 out of 5 average rating, 17 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

4.94 out of 5 average rating, 17 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.

Guest favorite

Guesthouse in Great Barrington

4.95 out of 5 average rating, 126 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 Red Hook

4.94 out of 5 average rating, 93 reviews

Private Cottage, Walk to Restaurants and Shops

Beautifully renovated modern cottage in the village of Red Hook has modern amenities, hardwood floors, and an open floor plan. The cooks kitchen has an island and high-end appliances. Walls of windows and doors bring in lots of light and there's a private patio out back. Bathroom has large walk-in shower. Bedroom has a king bed (or two twins) and a recliner for reading. A 3 minute walk from center of Red Hook and Bard Shuttle. 10 minute drive to both Bard College and Rhinebeck.

Superhost

Guesthouse in Great Barrington

5 out of 5 average rating, 3 reviews

Poolside Long Pond Bungalow!

Welcome to your peaceful oasis in the Berkshires! The charming studio features an open layout with a plush bed, reading chair, and convenient workspace boasting high speed internet. Enjoy the refreshing in-ground pool and spacious patio, perfect for lounging under the sun. The full bathroom ensures all your needs are met, while a coffee bar adds a touch of luxury to your mornings. Complete with air conditioning, this idyllic retreat is the perfect getaway. Book your stay today!

Top guest favorite

Guesthouse in Hudson

5 out of 5 average rating, 28 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. I’m also open to home swapping in Manhattan and Provincetown, Ma.

Superhost

Guesthouse in Valatie

4.89 out of 5 average rating, 75 reviews

Hudson Berkshire Lake Log Cabin

The Hudson Berkshire Martin VB Log Cabin This cute historic cabin was the Martin Van Buren hunting lodge back in the day. The cabin has been completely restored - maintaining the the vibe of the old while incorporating modern The cabin has an open kitchen with separate dining area and living room. There is separate bedroom and bathroom. The log cabin has a private open-field backyard surrounded by trees - ideal idea breakfast, lunch or even a barbecue

Guest favorite

Guesthouse in Germantown

4.96 out of 5 average rating, 198 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 Tivoli

4.92 out of 5 average rating, 177 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 Germantown

4.99 out of 5 average rating, 219 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).

Top guest favorite

Guesthouse in Stuyvesant Falls

5 out of 5 average rating, 30 reviews

The Falls at Lindenwald Cottage

Take it easy at this unique and tranquil getaway. Enjoy the sound of the water as you are a stone's throw away from the Stuyvesant Falls. Great for hiking, cycling, wining, and dining. Conveniently located as you are close to Hudson (12 min), Kinderhook (5 min), and Chatham (15 min). Thinking of a city escape, this is your place!