Vacation rentals in Cheshire

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Top-rated vacation rentals in Cheshire

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Top guest favorite

A cozy outdoor seating area is highlighted by a stone fire pit, with flames dancing above a bed of volcanic rocks. In the background, a high-definition TV displays a sports event. Barstools and a wooden structure suggest a welcoming spot to relax.

Apartment in Petersburgh

4.88 out of 5 average rating, 186 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.

Top guest favorite

An open door reveals the entryway of a rustic cabin. A patterned rug leads into a softly lit interior, where a cozy bed is visible in the background, framed by natural wood accents and windows that invite the outside in.

Cabin in Cummington

4.98 out of 5 average rating, 215 reviews

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Guest favorite

A panoramic view of a snow-covered mountain, featuring illuminated ski runs that carve down the slopes. The surrounding trees are blanketed in snow, while a cozy cluster of buildings can be seen at the mountain's base, glimmering softly in the evening light.

Apartment in Lanesborough

4.89 out of 5 average rating, 127 reviews

Cozy Rustic Apt. in 18th c. Berkshire Farmhouse

This cozy rustic studio is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built in the 1700’s, this centuries old farmhouse has since been converted into four separate cute suites. Newly updated kitchen, bathroom and furniture. Enjoy exploring the sprawling 19 acre property you will be staying on which includes seasonal flower fields, thousands of berry bushes, fruit trees, creek, and walking trails full of wildlife. Follow us on IG @SecondDropFarm

Superhost

A weathered wooden bench is positioned amidst green grass and ornamental plants. A decorative pillow with a patterned design is placed on one side of the bench, enhancing the outdoor seating area.

Home in Dalton

4.89 out of 5 average rating, 145 reviews

The Yellow House

The Yellow House in the Berkshires is the perfect place for a getaway, just 2. 5 hours from NYC and 2 hours from Boston. This historic small town offers many activities including Jacob's Pillow, hiking trails, skiing, Mass MoCA, and The Clark Art Institute. It is close to Tanglewood in Lenox and the Norman Rockwell Museum in Stockbridge. Located steps away from The Stationery Factory, which houses a food market, gallery spaces, artisan shops, coffee shop, and the Shire Brewhouse & pub.

Top guest favorite

The entrance of a light green house is shown, featuring a welcoming door with multiple glass panes. A wooden welcome mat lies at the foot of the door, while a pathway leads through a well-maintained grassy area beside it.

Guest suite in Williamstown

4.96 out of 5 average rating, 239 reviews

Berkshire Guest Suite

Welcome to our guest suite in the beautiful Northern Berkshires, home to many great cultural venues, including The Clark, Williamstown Theatre Festival and Mass MoCA. The newly updated private suite offers a queen pillow-top mattress, bathroom with stall shower, coffee bar and an outdoor seating area with mountain views. Located in a quiet neighborhood at the base of Mt. Greylock, we are a short walk to a local farm stand, and a few minutes drive to downtown Williamstown and North Adams.

Top guest favorite

A bright living room features a plush sofa and comfortable chairs on a colorful area rug. Large windows offer scenic views of the surrounding landscape, and natural light fills the space. A wooden dining table is visible in the background, along with a decorative plant.

Home in Cheshire

5 out of 5 average rating, 53 reviews

The Berkshires Hummingbird House

Enjoy beautiful lake view sunsets from the comforts of your living room. This bright and airy 3 bedroom home sits on an acre overlooking Cheshire Lake and is mere steps to the Ashuwillticook Rail Trail bike path. Centrally located in the Berkshires, this convenience allows for short drives to hikes at Mt Greylock Reservation, arts venues MASS MoCA, the Clark and Tanglewood, numerous ski areas, shopping/dining options, and countless other outdoor activities and cultural attractions.

Guest favorite

A quaint cottage is nestled among trees, featuring a welcoming front porch with several potted plants and outdoor seating. The light-colored exterior is complemented by blue accents on the chairs, while the wooden deck extends invitingly, creating a serene outdoor space.

Cabin in Cheshire

4.89 out of 5 average rating, 164 reviews

Private Paradise in the Berkshires

Your own private and romantic getaway behind a small orchard. A sweet running brook and outdoor shower! A short drive to all Berkshire cultural events -- Tanglewood, Jacob's Pillow, theatre festivals and more. Great dining nearby. Perfect for 2! Under COVID-19 regulations in Massachusetts, I am required to allow at least 24 hours between guests. It's a drag, but it is intended to keep us all healthy! Please forgive any inconveniences this might create in your trip plans.

Top guest favorite

A wooden sign with the text 'BITTERSWEET FARM' is displayed prominently. Below the sign, a flower bed contains vibrant orange and yellow marigolds, adding a touch of color to the entrance. The surrounding grassy area is well-maintained, enhancing the welcoming appearance of the farm.

Farm stay in Pittsfield

4.99 out of 5 average rating, 222 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 favorite

A wooden sign displays the name 'Ashuwillticook Rail Trail' against a backdrop of lush greenery and a serene water view. The sign features clear lettering, and nearby information boards are visible, providing details for visitors. The scene conveys a peaceful outdoor setting.

Guest suite in Adams

4.85 out of 5 average rating, 102 reviews

Quaint Suite in Center of Adams

Pet Friendly mother-in law suite within a beautiful Victorian home in the center of Adams. The quaint town sits at the base of Mount Greylock with hiking and bike trails within minutes of your accommodations. Restaurants, grocery store and a 9 hole golf course are in walking distance. MASS MOCA is just a short 6 mile drive. Tanglewood music center is a 35 minute drive. Beautiful deck with gas firepit and grill. We would love you to be our guest.

Guest favorite

Bright living space features high, wooden ceilings and large windows allowing natural light. Comfortable seating arrangements are provided by several couches and chairs, complemented by an area rug. Access to a deck is offered through two glass doors, enhancing the spacious feel of the room.

Home in Cheshire

4.81 out of 5 average rating, 152 reviews

Large Secluded Berkshire Home

Rustic Berkshire Retreat Relax in this cozy home on 3.5 private acres in Cheshire with scenic mountain views. Just 5 minutes to downtown Adams and the Susan B. Anthony Birthplace, and under 25 minutes to MASS MoCA, Williams College, Mt. Greylock, and Pittsfield. Tanglewood and Jiminy Peak are within 45 minutes. Note: Sand Mill Road bridge construction in August 2024 may add about 5 minutes to travel times.

Superhost

An ironing board is positioned against a wall, featuring a patterned cover. A turquoise laundry basket stands nearby, while a small window allows natural light into the space. The floor showcases a decorative tile design, adding visual interest to the room.

Apartment in Adams

4.85 out of 5 average rating, 136 reviews

full apartment in adams self check in

nice apartment on first floor in adams mass near mt greylock(URL HIDDEN) also 2 miles to greylock glen at the base of the mountain for hiking & biking trails 5 miles from mass moca 5 miles from mcla 12 miles from clart art & williams college 10 miles mt greclock peak 18 miles from jiminy peak , a ten mlle bike trail about 1000 feet from house also 23 miles & 40 minutes to tanglewood

Guest favorite

The exterior of a rustic wooden house is framed by vibrant greenery and blooming flowers, including azaleas and irises. A decorative weather vane adorns the rooftop, and large windows reflect the surrounding landscape under a partly cloudy sky.

Apartment in Plainfield

4.95 out of 5 average rating, 272 reviews

Sunny carriage house apartment

Our sunny apartment is located midway between Northampton and the Berkshires, in a lovely rural setting. The kitchen, bath and studio living area are in a private apartment, surrounded by 12 acres of open fields. The kitchen is well equipped and includes all the makings for tea and coffee. Orange juice, oatmeal, English muffins and homemade granola are also provided!