Guest house holiday rentals in Columbia County

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.

Black Bear Bungalow, Minutes from Tanglewood

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.

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 ~ special events/requests may also be considered! This is new construction and we are still working on furnishings, window coverings, plants, etc. Price reflects this work-in-progress ;-)

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.

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.

Modern village studio with a forest view

Enjoy a stylish experience at this centrally-located home in the Village of Catskill, New York. You’ll be conveniently nestled on a village street while looking out on a wooded forest hillside behind this stand alone retreat, only a 7 min walk to the town of Catskill and an 11 min drive from Hudson and Hudson’s Amtrak station. Equipped with deep soaking tub, working fireplace, full kitchen, back deck, amazing natural light, and so many more details for the design inclined.

New-Modern! Guest House with Shared Pool

Tucked away on 10 peaceful acres in the Berkshires/Hudson Valley, our guesthouse is a cozy, design-forward escape surrounded by nature. Sip coffee on the deck or curl up with views of pastures and woods. In autumn, enjoy brilliant foliage and crisp air. In winter sleep in and relax or head to Jiminy Peak or Bousquet for skiing, snowshoe nearby trails, or explore Lenox, Chatham, and Great Barrington. A perfect setting to rest, recharge, and savor the beauty of the season.

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. 

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).

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!