Holiday rentals in Stephentown

Historic Stone Church in The Berkshires

<b>Hinterland Hall</b> was built in 1836 by the Saint Luke's Episcopal Parish and joined the National Register of Historic Places in 1972. Ripe with history and impeccable beauty, Ian & Jane purchased the old stone church in May of 2021, completing an extensive restoration process in accordance with the Massachusetts Historical Commission. It is with great pleasure that we open our doors to you for a wondrous stay. <b>Follow us @hinterlandhall</b> Please inquire about weddings & events.

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Cozy apartment near Jiminy Peak

Two cozy bedrooms with an efficient kitchen make this a great weekend getaway for 2 adults or family of 3 to use as a base to explore both north and south Berkshire county in every season. About a mile from Jiminy Peak Ski Resort, less than 5 minutes to Bloom Meadows, 15 minutes to both Williamstown and Pittsfield, and 30 minutes to Mass MoCA, the quiet, wooded mountainside surroundings let you enjoy nature at its finest while easily getting to the area's many cultural attractions.

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

Creekside Couple's Escape w/ Hot Tub Sauna & More!

Nestled beside a charming creek, our newly renovated cabin offers a peaceful escape where nature and comfort come together. Relax with your partner in the hot tub, on the covered deck, unwind in the wood-fired sauna, or sit by the fire in the gazebo. Enjoy the calming sounds of the creek and the outdoor views from every window. Discover nearby trails, quaint towns, lakes and waterfalls. Pet-friendly and ideal for couples looking for a unique getaway any time of year.

2 Bed Berkshire Getaway @ Stephentown Hotel

Welcome to the Stephentown Hotel in the heart of the Berkshire & Taconic Mountains. Completely remodeled two bedroom apartment, brand new everything! Located on the 2nd FL. Large apartment, private arcade with (x3) real arcade games, private kitchen, soaking bathtub, bright and spacious with plenty of windows, ductless ACs, plus a Washer Dryer in-unit. Located minutes to Jiminy Peak! Outdoor area w/ fire pits, BBQ, picnic tables, outdoor games, etc.

Chic Hudson Farmhouse w/ Fireplace & Porch

1873 Stylish & cozy Hudson Farmhouse w/ a wood burning stove & the perfect porch. 14 minute drive to Warren St This 3 bedroom + office home has been lovingly updated while maintaining the original details of this historic property. Located on over an acre of land, on a quiet street, this peaceful retreat is the perfect escape to unwind and relax. With high ceilings, tons of oversized windows, and an open layout, this house feels both airy & bright.

Boutique TINY home+private HOT TUB-walk to Main St

Blush at Art Park Homes is a romantic boutique tiny home getaway in Chatham, NY—just 2.5 hrs from NYC & Boston. Enjoy a private hot tub, firepit, dreamy loft lounge, plush queen bed, full kitchen & curated luxe design throughout. Tucked into a peaceful private oasis, yet only a 2-min walk to Main St. restaurants, brewery, shops & theater. Perfect for couples seeking a unique Hudson Valley getaway near hiking, galleries & great dining. @artparkhomes

Dog Friendly Farm

Welcome to The June Arthur Farm! This beautiful spot has a long agricultural history. It hasn't been in production for the past 40 years but we're slowly bringing it back to life. It's once again producing good, happy, Hudson Valley food: eggs, fruit, lamb, and beef. We hope you'll come visit us. Note for the skiers out there: We're 20 minutes from Jiminy Peak!

Rustic Cabin | Barrel Sauna | Private Pond

The Hemlock Hideaway is a freshly renovated, charming cabin tucked into 14 acres of quiet woodland in the Berkshire foothills, built for the kind of rest that's hard to find anywhere else. This is a genuine rustic escape: complete with antique furnishings, a wood-burning stove, mid-century stove, no television, and the sound of nature just outside your door.

The East Street Cabin

This adorable cabin is your perfect escape for rest and relaxation. This is a perfect place for people coming to the Berkshires for Tanglewood or any of the other wonderful things the area has to offer. The cabin is located down a path through the woods about 100 yards from the main house. We are excited to share our cabin with you.

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.