Guesthouse vacation rentals in Columbia County

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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 Hudson

4.98 out of 5 average rating, 92 reviews

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.

Superhost

Guesthouse in Great Barrington

4.84 out of 5 average rating, 63 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

4.91 out of 5 average rating, 23 reviews

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.

Guest favorite

Guesthouse in Great Barrington

5 out of 5 average rating, 18 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

4.95 out of 5 average rating, 22 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, 142 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 Valatie

4.87 out of 5 average rating, 83 reviews

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.

Guest favorite

Guesthouse in Red Hook

4.94 out of 5 average rating, 101 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 Coxsackie

4.79 out of 5 average rating, 71 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 Catskill

4.89 out of 5 average rating, 19 reviews

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.

Top guest favorite

Guesthouse in Hudson

5 out of 5 average rating, 32 reviews

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.

Top guest favorite

Guesthouse in Germantown

4.99 out of 5 average rating, 238 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).