Bed and breakfast holiday rentals in Columbia County

4.97 out of 5 average rating, 33 reviews

Beautiful Room in Hartfield House - The Berkshires

Hartfield House is a wonderful old home situated in the beautiful farming community of Sheffield Massachusetts, minutes from both the Catamount and Butternut ski resorts. We are only a few miles from the village of South Egremont and downtown Great Barrington, both with their share of amazing restaurants. We are in the heart of the Berkshire mountains, known for their lakes and trails, while also being close to Stockbridge, Tanglewood and numerous museums, galleries and points of interests.

Cabin in Sheffield

4.77 out of 5 average rating, 71 reviews

The Brook House at Race Brook Lodge

Cozy, private brookside bungalow sleeps four. Bright studio living space with queen and two twin beds, full kitchen, breakfast nook. Beyond the shady porch, enjoy rolling lawn, hammocks, abundant hiking. The Brook House is situated on the grounds of Race Brook Lodge, with breakfast, swimming pool, lawn games, and great hiking right on the property, including direct access to Race Brook Falls. Also just steps away from the Stagecoach Tavern Restaurant and Barnspace and DCSC performance spaces.

Private room in North Chatham

4.93 out of 5 average rating, 340 reviews

Arnold Farmhouse (Italianate - private bath)

Private entrance to room with an attached bathroom. Enjoy the porch, garden, honey bees, the old farm/fields., situated on the bank of the Valatie Kill in the quaint hamlet. The AH Bike Trail is just around the corner, Larkin Hill, Kinderhook Creek & Hunt Club. We are 30 minutes from Albany or Hudson on excellent roads. Schodack Island is 15 min. Van Buren house is 15 also. Jiminy Peak Ski is a 30 min. It is a wonderful to get some real fresh air - good for couples, solo, and business.

4.98 out of 5 average rating, 47 reviews

Sheffield Lodge - Ramblewood Master

The Sheffield Lodge is a warm and inviting rustic Bed and Breakfast secluded from city life nestled in a pine forest. Enjoy your home-away-from-home where there is always friendly service, delicious breakfasts, afternoon treats. The lodge features an inviting fireplace, large screen TV, game table for board games or cards and a quiet reading/living room, and ample parking. Outdoor recreation is within minutes in every direction. There are museums, shops and many great restaurants nearby.

4.95 out of 5 average rating, 41 reviews

Private room in Red Hook

Dilas room , private bathroom, jacuzzi

This spacious bedroom is perfect for two people. If you want to get away for a romantic weekend , also perfect if you have a young child . In the bedroom I have a comfortable Chase ! It has a comfortable king bed and Attached to a large, private bathroom with a jacuzzi, 2 sinks and a shower. The house is very large and there is plenty of common space you are welcome to use. The property has a lot of land with outdoor seating areas, a terrace, a pool -- all of which you are welcome to use.

Cabin in West Stockbridge

4.98 out of 5 average rating, 92 reviews

Modern Cabin near Tanglewood

Welcome to West Stockbridge in the Berkshires! This newly renovated modern cabin is nestled amongst the trees and located just 3 miles from the famous Tanglewood and Kripalu. Right down the street is main street where you can peruse the shops, grab a gourmet coffee, or listen to more music at the Foundry. There are restaurants, hiking trails, waterfalls and lakes less than a mile away. We are 5 minutes from the turn pike for easy directions! Come hang and enjoy all the activity and beauty.

Private room in Hudson

4.84 out of 5 average rating, 779 reviews

Hudson, NY, 1br - 2 queen - June sale

Free private parking. - Now: Late Check-in: Until 12am / Mutual Agreement - Please allow 1 hour prep. Private staircase - FREE WIFI - Built originally in 1848, one window facing crescent driveway - Be good with winding stairs (have no mobility issues) - Sunny big room. Perfect to work remote. Private back porch doors. 2 double mattress queen beds. Smoking on porch. No pets. Kitchen not included. Wares provided. Full bathroom. Microwave & Silent Fridge Same price: 1 to 4 guests!

4.96 out of 5 average rating, 385 reviews

Private room in Athens

Brick Row House in the Woods, private 2nd floor

Looking for the best price to stay in a historic Hudson Valley townhouse? Just 15 minutes from Hudson, NY is a private second-floor suite above an artist’s studio—bedroom, living room and bathroom all to yourself. Hosted by a top-rated Superhost known for her glowing reviews and exceptional hospitality, you'll enjoy a continental breakfast, easy self-check-in, and spotlessly cleaned rooms. The sunlit space and garden is perfect for meditation, journaling, studying, or simply unwinding.

4.95 out of 5 average rating, 216 reviews

Townhouse in Hudson

Palazzo Hudson: Luxury Home with Pool, Spa, Sauna

Welcome to Palazzo Hudson! The only private vacation home in the town of Hudson with a chef's kitchen, seasonal in-ground pool, deluxe sauna, cedar hot tub & a separate poolhouse library lounge. A home for all seasons, you'll experience inspiration and relaxation from the warm, light-filled rooms, curated art, books, music, luxury spa features, and outdoor deck, patios, and gardens. A quick stroll to the restaurants, bars, cafes, and shops of Warren Street and the Upper Depot District.

Private room in Pine Plains

4.7 out of 5 average rating, 10 reviews

The Smithfield Room

The Inn at Pine Plains is a great basecamp for exploring the Hudson Valley, The Berkshires, and the Litchfield Hills. We're near restaurants and dining, hiking, farms, art and culture, polo fields, horseback riding, distilleries, Millerton NY, Rhinebeck NY, Red Hook NY, Hudson NY, Millbrook NY, Sharon CT, Wassaic NY, and Lakeville CT. Our rooms each have unique character, comfortable charm, and simple elegance. Couples, solo adventurers, and business travelers are all welcome.

5 out of 5 average rating, 9 reviews

Private room in Red Hook

Mountain View Queen Suite w pool and patio

Enjoy your weekend in the Hudson Valley at this peaceful and centrally-located private Mountain View suite. This is a private home & shared entryway. Your Suite is entirely private. Bard College 3.5 miles away. Dutchess County Fair grounds 3 miles away. Many Historic Landmarks w in 20/30 min drive. Performing Art centers w in 15 min drive. Rhinebeck & Red Hook many restaurants & theatre’s 5-10 mins. Hiking trails, Apple picking, and Tree Farms all close by.

Private room in Schodack Landing

5 out of 5 average rating, 3 reviews

Weekend room of one’s own plus “study” with view.

Have a room of your own.Share cozy quiet home/ drive a rural river road 20 minutes to art openings /farmers markets/ dining in Hudson. Rapidly expanding culture hub: Berkshires, Mass MOCA, Bard. Bath room shared, spotless: claw foot tub, shower spray handle. Enjoy view of Schodack Island State Park/3 mikes up the road - wildlife preserve. Use my home as a base to explore : Hudson, Berkshires, Adirondacks, the Catskills, more!

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Popular amenities for bed & breakfast rentals in Columbia County

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Family-friendly bed & breakfast rentals

Hotel room in Athens

Stewart House - Room 1 Queen

SenaitRating, 5 stars60 months ago

The Stewart House is a super stylish location. The decor is wonderful, and there are so many thoughtful touches that they provide. The historic nature of the house makes it a special place to stay as well. The River Grill right across the street is connected to the hotel. It has a wonderful vibe, over looks the river, and we thoroughly enjoyed the live music on Friday evening. Definitely make a point of stopping by the River Grill during your stay!

Private room in Red Hook

4.85 out of 5 average rating, 27 reviews

Nanas beautiful B/R Queen bed and private bathroom

TaraRating, 5 stars20 months ago

Dila and her home are both incredibly wonderful. She's extraordinarily easy to communicate with, and she's thought of every detail you might need when arriving to and staying at her place. Dila is warm and welcoming, and the way she's arranged and kept her home is absolutely charming, sweet, pristine, and lovely. I would stay with her anytime, and hope to again soon.

4.77 out of 5 average rating, 137 reviews

Suminski Innski - Room 2 Queen bed/shared bath

SophiaRating, 5 stars10 months ago

Tim was a very kind, easygoing, and communicative host. The home had a ton of character and the outside spaces were so beautiful--lots of little animals running around and beautiful foliage! Loved the chill vibe of the place, the views, and the activities around the space like badminton. Definitely plan to go back!

4.87 out of 5 average rating, 227 reviews

Suminski Innski - Room 4 Queen bed/shared bath

Chitra F.Rating, 5 stars3 weeks ago

I love everything about Innski Suminski. It’s a laid back and casual and funky communal vibe. It’s like a beautiful friendly hostel with young and old and local and International guests. Innski is not for someone that wants a pristine cookie cutter hotel room with all the modern conveniences like a motel or hotel would have. Innski is an experience more than just a place to spend the night. My family and I loved it and didn’t want to leave. One of the best things about Innski is the Host, Tim Voell. Warm guy with a big heart.

4.88 out of 5 average rating, 164 reviews

Suminski Innski - Room 3 Queen bed/ shared bath

Rachel Rating, 5 stars8 months ago

The most magical place on planet earth! It is very special and was a such a joy to stay.

4.87 out of 5 average rating, 180 reviews

Suminski Innski - Room 1

ChristineRating, 5 stars9 months ago

The Suminksi Innski has its own vibe and attracts people who hopefully get it. No one builds homes like this anymore, and fills it with wonderful eclectic art. It felt like a privilege to stay there and take in the sounds of the Hudson River, the birds, and the train that transports you to another time and place. Tim is a great host - wonderful to sit on the porch and chat with him, the Bard students and families, and the all characters that pass by. I would highly recommend!

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Bed and breakfast rentals with breakfast

4.71 out of 5 average rating, 7 reviews

The Inn at Silver Maple Farm - Cottage Room

MaxineRating, 5 stars2 months ago

A perfect stay! Everything was wonderful, and I would love to stay again. Warm common area with comfy furnishings and a fireplace with an outstanding library! Rooms are so thoughtfully designed! Lovely Beekman Bros. Toiletries, Extending magnifying mirror in bathroom, comfy bedding, and a delicious breakfast made for a wonderful stay. Have already recommended to family and friends.

SabrinaRating, 5 stars14 months ago

The Inn at Silver Maple Farm - King Maple

Chloe and her husband Sean, were both very kind and eager to please. Their property was very well maintained and you can tell they take a lot of pride in what they do. There were many sweet touches throughout our stay and the room/house was immaculate. We especially loved the treats, coffee/tea, and water that were always available. Although we felt it was further than anticipated to eateries, we truly enjoyed our time at SMF and would recommend anyone to stay there especially if they want to cozy up with a great book by the fire.

4.94 out of 5 average rating, 77 reviews

Sheffield Lodge - Monument Room

JessicaRating, 5 stars4 months ago

Susan is an incredible host running a charming lodge. The decor is beautiful and everything is easily accessible. The peaceful environment inside and outside the lodge makes this place a must visit. Delicious breakfast every morning and pet friendly. We couldn’t ask for a better experience.

4.93 out of 5 average rating, 73 reviews

Sheffield Lodge - Greylock Room

JamesRating, 5 stars9 months ago

A beautiful location tucked away from the road. Susan clearly enjoys what she does and goes above and beyond to accommodate—plus spoiling us with a lavish breakfast every morning!

5 out of 5 average rating, 14 reviews

Sheffield Lodge

MirandaRating, 5 stars18 months ago

Susan graciously accommodated us during the busy holiday season and her house was spacious enough for our group of two families with kids. The house is easy driving distance to Butternut for skiing as well as other spots in the Berkshires. Breakfasts were made from scratch and included multiple options. Susan was also kind enough to quickly reach out when we'd left behind an item of sentimental value—we really appreciated it.

MarioRating, 5 stars24 months ago

The Inn at Silver Maple Farm - Silver Maple

We had a great stay at Chloe's inn. Everything was just right, with many thoughtful touches. Good local recommendations and easy access to Lenox/Tanglewood area attractions. Will come again!

5 out of 5 average rating, 3 reviews

The Inn at Silver Maple Farm - Upper Lodge

HeidiRating, 5 stars26 months ago

We loved The Silver Maple Farm stay! The historic renovations are stunning. We felt at home and we’re sorry to only stay one night! Chloe and Sean were great hosts! Delicious and generous breakfast was another highlight.