Family-friendly holiday rentals in Columbia County

Bucolic Berkshires House

UNIQUE, bright, open space with a great kitchen and thoughtfully decorated. Near MANY exciting destinations such as skiing, cultural and arts destinations, vineyards, antiquing, you name it, in both the Berkshires and Hudson Valley. Located on an unpaved road and adjacent to a beautiful park and a nearby lake. There's so much to do, but if you'd prefer to take a more relaxed approach to your get-away then shop the wonderful local food stores and farms and enjoy cooking and our lovely house.

A Victorian "Lady"

Enjoy an old-fashioned vacation right across the street from the Hudson river. Watch the tides, boats, and barges pass by. Dining, kayaking within walking. Historic Hudson, Olana just 10 min. drive. This is a house to relax, use as a base for other activities. It is not intended as a place to party.. It is a quiet neighborhood. I expect my guests to respect that. There is a weekend special. If you book friday/saturday or saturday/sunday the price is $350.00 for the 2 nights. Thanks

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

Modern Barn on 12 acres w Sauna, FirePit+swimming

Escape to our recently renovated guest house on a 12-acre property, 15min from Hudson. Take in the rural setting through oversized glass doors. Infared Sauna is within running distance of the swimming pond for a cold plunge. Located in a park like setting of rolling hills & colorful sugar maple trees. Fully equipped kitchen, memory foam mattress and all the amenities. In home Massage/Yoga available. XC ski from the house! 45min to downhill.

The City Farmers Upstate. Farm house with hot tub

Beautiful farm house in Columbia County, Less than 2 hours from NYC. 4 bedrooms ,an office that can convert to having 2 twin beds, and a gorgeous dining room. Can sleep up to 10 people. The house is surrounded by 9 acres of beautiful land with a creek. Located in the beautiful Columbia County. Nearby the town of Hudson. 10 min to Lake Taghkanic, 15 min to Catamount Ski

Beautiful cottage at the foot of the Birkshires

Come stay with us in our beautiful cozy cottage, on a small lot located in the heart of Copake Falls, walking distance to Taconic State Park. Enjoy great farm to table dining, ski the Berkshires (just under 10 minutes to Catamount Resort), hike to Bash Bish Falls, bike the Harlem Valley Rail Trail, and swim in the spring fed iron ore pit during the open season.

Your own private Berkshires retreat

My place is close to restaurants and dining, family-friendly activities, nightlife Tangelwood, Jacobs Pillow, Mahaiwe Arts Center, Arlo Guthrie Center. You’ll love my place because of the privacy, the views, the location, the ambiance, the outdoors space. My place is good for couples and families (with kids). It has new geo-thermal central heat and AC.

The old sawmill from 1771

The oldest house in town, fully renovated. Beautiful two-story living room with leafy, private back deck for meals outside. Kitchen with stone counters, gas cook top, and dishwasher; two bathrooms with warm floors. Floorboards upstairs a foot wide; queen size bed with view over the trees, creek and porch.

Cozy cabin in the Hudson Valley!

Our cool, cozy rustic cabin sits on 4+ acres with a creek bordering the back field. When you're ready to venture out, Rhinebeck, Hudson and Tivoli are just a short drive away. Three bedrooms, wood burning stove, cabin-y furnishings for a laid-back stay. The whole house is yours to enjoy.