Bed and breakfast holiday rentals in Columbia County

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.

Family · Location · Hiking

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.

Family · Value · Sleep quality

Hudson, NY, 1br on 2nd floor - 2 queen - full bath

1BR with private full bath - 2 queen size beds - On second floor FREE private parking. - Check-in: 4pm until 12am / Breakfast is not included - We currently do NOT provide transportation - Same Day: Allow 2 hour prep. time - Private staircase - FREE WIFI - Built in 1848 - HISTORIC - TAKE HEED: Be good with winding stairs (have no mobility issues) - Work remote! Private back porch doors. Smoking on porch. No pets. Kitchen not included. Wares provided. Microwave/Fridge & Ice Compartment

Value · Location · Hospitality

Ground floor king bedroom in vintage farmhouse BnB

Wilder House Berkshires is a bed and breakfast located in the historic village of Sheffield. This ground-floor master bedroom is newly updated while preserving the charm of our 220-year-old farmhouse. Our lovingly designed common areas create fun and intimate opportunities for connection. Just 10 minutes from Great Barrington, the Berkshire School, Twin Lakes Connecticut, the Appalachian Trail, and epic waterfalls, our guests enjoy beautiful accommodations in a walkable village setting.

Walkability · Hiking · Hospitality

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.

Location · Family · Shared spaces

Hudson holidays? That extra cozy room here…

Need an extra room for the holiday family event or just want to get away? I have 2 rooms upstairs. Guest can spread out to second room to draw or write. Drive a rural river road 20 minutes to art openings /farmers markets/ dining in HUDSON Hudson is now the “ northern most art neighborhood of MANHATTAN. 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.

Location · Indoor spaces · Breakfast

Arnold Farmhouse (second room) (Italianate)

Beautiful airy room with room to sit and table to work on. The bathroom with a shower is just down the hall. Private entrance into house. Enjoy the porch, garden, honey bees; walk around the farm/fields. Larkin Hill is a stones throw, as well as the Valatie Kill & Kinderhook Creek. Excellent loops for cyclists. Get some real fresh air - good for couples or solo. If you are staying more than 1 night, we would provide a nutritious breakfast on the full days here, at your request.

Value · Family · Kitchen

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.

Location · Family · Back garden

Arnold Farmhouse (Italianate - private bath)

Room with an attached bathroom and private entrance. Enjoy the porch, garden, honey bees, the old farm & fields, situated on the Valatie Kill in a quaint hamlet. The AH Bike Trail is just around the corner. If you come by bike, we can safely store the bike in the garage opposite the barn. Larkin Hill, Kinderhook Creek & Hunt Club are close. Schodack Island state park is 15 min. Van Buren house is 15 also. It is a wonderful spot to get some real fresh air.

Location · Family · Sleep quality

Serene Suite: Hudson & Berkshires, Walk to Brewery

A peaceful, highly rated private suite in the heart of historic Hillsdale, where the Hudson Valley meets the Berkshires. Walk to shops, restaurants, a brewery, cooking school, grocery, wine and liquor store. Minutes to Hilltown, the Harlem Valley Rail Trail, scenic hikes, and beautiful drives, with galleries, antiques, live music, and cultural gems nearby. A serene, perfectly located home base for spring dining, exploring, and unwinding.

Family · Location · Biking

Standard Suite at Shaker Mill Inn

The Shaker Mill Inn is a unique family and pet friendly Inn that can be a comfortable and safe alternative to the traditional hotel and B&B. There is a self-check-in/check-out process. Each room has a private entrance, and is equipped with a kitchen or kitchenette, so that you can enjoy breakfast in the privacy of your room. The rooms and grounds are spacious, which will make for a relaxing visit to the Berkshires.

Location · Hospitality · Indoor spaces

Suminski Innski - Room 4 Queen bed/shared bath

The Suminski Innski is a 3-storied 19th century mansion, perched right on the Hudson River. A great place for writers, artists, musicians, hikers, and friends. Room 4 is a beautiful big room with a queen bed and a garden view. Fresh breakfast is provided every morning! Join us on the front porch by Hudson river to watch the sun set in the Catskill mountains, or on the patio for a barbecue.

Value · Family · Solo travel