Guest house holiday rentals in Columbia County

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.

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.

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.

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.

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.

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.

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.

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.

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).