Guesthouse vacation rentals in Columbia County

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.

Family · Location · Quiet

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.

Location · Value · Cleanliness

Hudson Berkshire Lake Log Cabin

The Hudson Berkshire Martin VB Log Cabin This cute historic cabin (we have been told) was the Martin Van Buren hunting/fishing 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.

Family · Value · Getting around

Athens Cottage

Welcome to your perfect Hudson Valley escape. This cozy two-bedroom cottage is nestled in the charming riverside village of Athens, NY, offering small-town charm, scenic beauty, and a relaxing home base for your stay. Inside, you’ll find a thoughtfully furnished space filled with natural light, comfortable bedrooms, and all the essentials for a stress-free getaway. Whether you’re sipping coffee in the morning or unwinding after a day of exploring, the cottage feels warm and inviting.

Location · Family · Amenities

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.

Location · Family · Layout

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.

Value · Location · Long stay

Modern Farmstay Cabin in the Woods

Escape to our newly remodeled 500-sq-ft cabin in the woods that offers peace and quiet on a homestead with flower fields, chickens, an organic garden, and wooded trails. Relax on the cedar deck with an outdoor shower or enjoy the spacious, stylish interior with a luxurious shower. Just 5 minutes from Hudson’s Warren Street, it’s the perfect escape in nature with a quick drive to the best shops and restaurants in the valley.

Location · Family · Hiking

Serene one bedroom guest house.

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. 

Location · Sleep quality · Decor

Josey's WineFarm Vineyard Cottage

1 of 3 guest cottages available for rent More dates open soon (feel free to make a request)! Weekly & monthly discounts available. This cottage is nestled between the Catskills & Berkshires on a Farm Winery property. The winery tasting room is open Saturdays and Sundays from April/May to October/November (closed Labor Day Weekend) ~ special events/requests may also be considered!

Location · Laundry · Wifi

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).

Value · Family · Accuracy

Guest House near hiking trails and excellent cafés

Studio guesthouse is all yours. In a quiet valley near walking and hiking trails. Close to Tanglewood, the Stockbridge Bowl, and Kripalu. 10 minutes to downtown West Stockbridge and No. 6 Depot Roastery and Cafe. 15 minutes to Great Barrington. The guest house is on owner's property and there is a dog on the premises. Absolutely no pets or children under 18.

Value · Location · Indoor spaces

The Loft at Honey Hollow in the Catskills

Welcome to our newly renovated private guesthouse. Tucked into a peaceful wooded setting in the northern Catskills, you're just minutes from top hiking and skiing. Enjoy an open-concept living space with a full kitchen, comfy furnishings, sleeper sofa, and a loft with a king-size bed. Perfect for couples, families, or a quiet work-from-nature getaway.

Family · Location · Backyard