Holiday houses in Stephentown Center

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Top-rated holiday rentals in Stephentown Center

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

A tiny home features a private hot tub on the deck, illuminated by soft LED lights. The structure is surrounded by natural wood paneling, with doors leading into the cozy interior, where warm light spills out, creating an inviting ambiance.

Tiny home in Chatham

4.99 out of 5 average rating, 371 reviews

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

Sept. SPECIAL(Mon-Thurs): Includes Prosecco, s’mores kit, firepit supplies. Blush is a romantic boutique tiny home getaway in Chatham, NY—just 2.5 hrs from NYC. 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

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Superhost

A tranquil exterior view of a single-story house, framed by lush greenery and vibrant flowers. A gravel path leads to the front door, which is flanked by a small set of stairs. Two satellite dishes are visible on the roof among the trees.

Home in Stephentown

4.82 out of 5 average rating, 90 reviews

A Magic Spot: Booking year round.

Springtime at The Magic Spot! It's beautiful. In the woods, with birds and tulips (1200), lilacs and lots of rare lilies. Perfect for families. Art and books in every room. Excellent kitchen. A perfect vacation house. Hiking/birding/guided mushrooming. Nearby State Park for swimming. Near Tanglewood, Mass Moca, Clark Art Inst. IMPORTANT: Weekday BASE PRICE $200 for 2 bedrooms. Additional bedrooms $50 per room . Summer weekends $300/entire house. Discounts available. We say: "Welcome Home!"

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Top Guest favourite

A mid-century A-frame house is set within a lush landscape, surrounded by trees displaying autumn colors. A spacious driveway leads to the entrance, and a large deck with railings extends along the front, offering an inviting outdoor space.

Chalet in Averill Park

4.94 out of 5 average rating, 101 reviews

A Hidden Sparrow

/\ Keeping it cozy, yet modern. Our take on hygge minimalism. A Hidden Sparrow is a classic mid-century A-frame nestled on 60+ acres for hiking and has a picturesque creek that flows in the front of the property. With fresh upgrades, tasteful aesthetic and comfy accommodations, A Hidden Sparrow is an idyllic sanctuary offering complete privacy for your next getaway. This all season escape is the perfect place to disconnect from your typical dwelling and enjoy everything nature has to offer. /\

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Guest favourite

An open living space with a high wood-beam ceiling is displayed. A large stone fireplace serves as a focal point, surrounded by comfortable seating. A kitchen island with stools offers additional space. Large windows allow natural light to fill the room, enhancing the inviting atmosphere.

Farm stay in New Lebanon

4.95 out of 5 average rating, 273 reviews

Barn Stay at Shadowbrook Farm

Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

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Guest favourite

Cabin in East Nassau

4.97 out of 5 average rating, 101 reviews

Luxury Cabin - Fall Foliage & Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit and chairs, Webber Grill, radiant floor, WFH space, and EV charging!

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Guest favourite

An open living space features a large sectional sofa surrounding a central glass coffee table. A decorative chandelier hangs from the exposed wooden beams. Natural light streams in through multiple floor-to-ceiling windows, revealing views of the surrounding greenery.

Barn in East Chatham

4.96 out of 5 average rating, 111 reviews

Luxury Barn Retreat Near Hudson & the Berkshires

Set on eight private acres where New York meets the Berkshires, this architect-designed retreat combines dramatic contemporary design with warmth and comfort. Soaring ceilings, a chef’s kitchen, designer interiors, peaceful outdoor spaces and nearby lake access create the perfect escape. Ideal for couples, families with children or close friends, it’s a short drive from Hudson, Chatham, Great Barrington, Tanglewood and countless other destinations for shopping, dining, hiking and more.

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Top Guest favourite

Guesthouse in Averill Park

4.95 out of 5 average rating, 22 reviews

Cozy Weekend Getaway Averill Park/Crooked Lake

Escape to this cozy 2-bedroom (Queen), 1-bath retreat. Nestled just minutes from Crooked Lake House making it the perfect stay for wedding guests, as well as those looking for a weekend full of fun at nearby Jiminy Peak Ski Resort! Enjoy a warm, inviting atmosphere with a working fireplace, ideal for cozy evenings after a day on the slopes or exploring the area. The fully ready kitchen is ready for home-cooked meals, and the in-unit laundry ensures you can pack light for your stay!

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Top Guest favourite

A red cabin with a welcoming front porch is set against a backdrop of vibrant greenery. The landscaped yard features small plants and flower beds, complemented by a stone pathway leading to a well-maintained patio area.

Cabin in Stephentown

5.0 out of 5 average rating, 28 reviews

Stylish Mountain Cabin Close To Cherry Plain Park

Escape to our charming cabin, tucked away in the heart of the Berkshires! Surrounded by scenic hiking trails and just moments from the lake, this cozy retreat is the perfect place to slow down & soak in the beauty of summer. Spend your days swimming, kayaking, or exploring the trails, then unwind on the porch as the sun sets through the trees. With access to outdoor adventure, local restaurants, & peaceful relaxation, our cabin offers the perfect blend of comfort & summer escape.

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Top Guest favourite

A wooden structure with a deck extends into the greenery, framed by tall hop poles. The building features a large front porch, inviting outdoor seating, and an entrance accentuated by surrounding trees and a grassy area leading up to it.

Apartment in Petersburg

4.9 out of 5 average rating, 229 reviews

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Open space includes living/dining/work space & bedroom; bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed (extra twin mattress beneath). HD TV, wifi, private deck, kitchenette with mini fridge, microwave, toaster oven, hot tea kettle and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

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Top Guest favourite

Home in New Lebanon

5.0 out of 5 average rating, 23 reviews

Modernized 1860s Getaway w/ Queechy Lake Passes*

Unwind in our quiet, spacious, light-filled, rural home without leaving modern conveniences behind. Located in Historic Lebanon Springs, our newly restored antique home is near both Hudson Valley restaurants and shops and the Berkshire's vast outdoor activities. We took great care to save this home's historic details while creating a fully modernized, comfortable retreat. Every room is thoughtfully curated with local antiques, artwork, and many unique touches you'll enjoy.

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Guest favourite

Tiny home in New Marlborough

4.94 out of 5 average rating, 190 reviews

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

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Superhost

Cabin in Stephentown

4.86 out of 5 average rating, 313 reviews

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.

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