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Holiday houses in Stephentown Center

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Top-rated holiday rentals in Stephentown Center

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Cabin in Stephentown

4.86 out of 5 average rating, 267 reviews

Cabin in the woods w cedar Hot Tub + private pond

The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.

Guest favourite

Rental unit in Petersburg

4.87 out of 5 average rating, 171 reviews

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Space is 14 x 28 feet and includes living/dining/work space, bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed with pull out twin mattress. High def TV, wifi, private deck, kitchenette has mini fridge, microwave, toaster oven, hot kettle for tea and and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

Guest favourite

Cottage in Williamstown

4.89 out of 5 average rating, 179 reviews

Cute Cozy Comfy Cottage in the Berkshires

A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 pull out couch.. Dog friendly for up to 2 dogs .More than one dog will have to be an additional fee of 50.00 each pet. My cottage sits on 13 privately owned acres. Partially fenced in.3 miles down the road from Jiminy Peak ski resort & summer activities and a short drive to Ramblewild adventure park. Hiking, boating, museums, shopping, restaurants- all sorts of activities in the Berkshires. Two minute ride to Bloom Meadows!

Guest favourite

Rental unit in Canaan

4.99 out of 5 average rating, 147 reviews

Mountain View Getaway

Come relax & enjoy panoramic mountain and pond views. Marvel at the dramatic lighting effects on Mercer Mt from sunrise-sunset from your private deck or bright living room. Fully equipped kitchen, grill on the deck, short scenic drive to a wide variety of restaurants & endless cultural venues in the surrounding quaint villages of Berkshire County Mass and Columbia County NY. Near hiking trails, skiing, apple picking & farm stores. Queechy Lake swimming, NYS boat launch for car top boats.

Guest favourite

Cabin in Canaan

4.99 out of 5 average rating, 247 reviews

Rustic Barn Studio Apartment

Built from a saved, moved, & reconstructed 1850s- era barn from a former local dairy farm, this upstairs studio space features views of the Berkshire Mountains and walking paths on the 5 acre grounds. 20 mins from Jiminy Peak. 20 mins from Tanglewood Music Center. The space has a queen bed, sofa, kitchen area with fridge, sink, oven, stove, microwave, Keurig and coffee, toaster, and cooking essentials. **EV Charging Station coming sometime summer of 2023. We'll update when available.

Guest favourite

Guest suite in Hancock

4.81 out of 5 average rating, 176 reviews

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.

Guest favourite

Earthen home in West Sand Lake

4.97 out of 5 average rating, 178 reviews

The Hobbit House at June Farms

Enjoy 120-acres of beautiful farmland while you stay in your very own Hobbit house! Nestled in the hills of Hudson Valley, June Farms is a gorgeous animal sanctuary. During your stay, you will be able to meet our Shire horses, Scottish highland cows, Gloucestershire spotted pigs, Nigerian dwarf goats, many chickens and ducks! From June 1 - Labor Day, the bar & restaurant is open most days for you to enjoy (check our calendar to be sure). We look forward to meeting you!

Guest favourite

Farm stay in Pittsfield

4.99 out of 5 average rating, 170 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

Guest favourite

Farm stay in Hoosick

4.95 out of 5 average rating, 169 reviews

Airbnb @ Sweet & Savory Farmette

Welcome to the AirBnB situated on a small working farm. You are welcome to tour the grounds to say hello to all the animals. This place is for the birds! No really you will enjoy watching chickens, ducks, emus, geese, guinea fowl, and peafowl. The farm is also home to a herd of beautiful alpaca and resident llama, curious goats, and barn cats. There are working livestock guardian dogs who watch over the herd who will greet you from behind the fence.

Yurt in Stephentown

4.91 out of 5 average rating, 113 reviews

Off Grid Yurt Right By The Best of The Berkshires

This is an off grid yurt with a woodstove for heat and an off grid kitchen - no running water or electricity - water can be heated on the woodstove. You'll have a comfy bed and futon. We love it when it rains. Staying inside, listening to the rain on the yurt and playing games is a highlight of our trips there. Cooking outside and enjoying a campfire & toasting marshmallows is also fun!

Guest favourite

Loft in East Nassau

4.99 out of 5 average rating, 172 reviews

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!

Guest favourite

Home in Averill Park

4.95 out of 5 average rating, 154 reviews

Cozy, peaceful lake house close to Jiminy Peak

My fabulous, peaceful lake house is located on beautiful quiet 3rd Burden Lake complete with a large private porch, dock, a canoe and one kayak. The house has incredible views throughout . Great kayaking, hiking, fishing,close to MASS MOCA. 25 minutes to Troy, Chatham and Albany. Very close to Jimney Peak for skiing in the wintertime.

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Popular amenities for Stephentown Center holiday rentals

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Other great holiday rentals in Stephentown Center

Guest favourite

Holiday home in Williamstown

4.98 out of 5 average rating, 90 reviews

ALL welcome: Lovely 1 BR studio, Berkshires beauty

Guest favourite

Home in Williamstown

4.97 out of 5 average rating, 29 reviews

New Berkshire home - 3 bed, 2.5 bath w/views

Guest favourite

Cabin in East Nassau

4.95 out of 5 average rating, 39 reviews

Cozy Country Cabin: Skiing,Hiking, fishing.

Cottage in Hancock

4.85 out of 5 average rating, 75 reviews

Berkshire Cottage Queen Bd-Jiminy Peak 3 mi

Guest favourite

Home in Old Chatham

4.97 out of 5 average rating, 36 reviews

The Red House

Guest favourite

Rental unit in Nassau

4.92 out of 5 average rating, 84 reviews

A Haven of Rest Beautiful Historic Tranquil Suite

Guest favourite

Home in Sand Lake

4.95 out of 5 average rating, 19 reviews

Mandalyn Farmhouse

Guest favourite

Farm stay in Nassau

4.99 out of 5 average rating, 72 reviews

Private 1830 farm house perfect for a country stay

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