Vacation rentals in Berkshire County

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Top-rated vacation rentals in Berkshire County

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Guest favorite

A private dock extends into the calm lake, featuring a sliding board and a set of stairs leading into the water. A rustic playhouse sits nearby, complemented by a wooden bench. Colorful Adirondack chairs surround the area, offering serene views of the surrounding nature.

Cottage in Becket

4.94 out of 5 average rating, 197 reviews

The Yellow • 1,750ft² (170m²), 2-level cottage • Open concept with 180° view from living room • 3 bedrooms (all queen size beds), 2 full baths • Fully equipped kitchen • Private dock & firepit • Canoe & 2 kayaks • 50" smart TV and 4 Google Smart Speakers • 1 Gigabit Wi-Fi 'gorgeous with amazing views' • Workspace with laptop stand upstairs • Additional full size bed upstairs • Additional queen size sofa bed downstairs • Additional twin trundle downstairs • Washer and dryer with laundry detergent

Top guest favorite

A spacious deck features several lounge chairs and a table, inviting relaxation. A bright red umbrella provides shade. The tranquil lake extends in the background, with a private dock visible along the shoreline, framed by lush greenery.

Home in Pittsfield

4.97 out of 5 average rating, 115 reviews

Berkshire Lake- Modern and Updated-close to skiing

Lakefront Home for Rent. This home has been 100% remodelled! With a beautiful spot directly on Pontoosuc, the new kitchen, bathrooms, fireplace, and glass enclosed family room all benefit from the idyllic scenery. The home has 5 bedrooms and a convertible playroom with a futon for even more space. 2 bedrooms have bunk beds plus a full size bed in them. 2 bedrooms have king size beds and 1 has a queen. The master suite has an en-suite bathroom and a balcony overlooking the lake. Many upgrades!

Guest favorite

A serene waterfall cascades over rocky formations into a clear pool, surrounded by lush greenery. Large boulders and smooth stones create a natural setting, while tranquil waters reflect the vibrant foliage overhead.

Apartment in Copake Falls

4.91 out of 5 average rating, 323 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Guest favorite

A spacious wrap-around deck is shown, adorned with comfortable seating. Lush green trees frame the area, while panoramic mountain views are visible in the background, complemented by a sky filled with scattered clouds.

Home in Canaan

4.93 out of 5 average rating, 29 reviews

Secluded Mountain and Lake View in Canaan, NY

Overlooking Queechy lake, this spacious home with a cook's kitchen and wrap-around deck is a great get-away for family and friends. Within an easy 20 minute drive you will find delicious farm fresh foods, renowned arts venues, swimming, kayaking, skiing, and hiking trails. Ideally situated between the Berkshires to the east and Hudson Valley to the west, whether you are seeking cultural attractions or natural escapes, you will be in the perfect place to soak up the best the area has to offer.

Guest favorite

A wooden dock extends over a tranquil lake, surrounded by lush trees and colorful foliage. The water reflects the blue sky and fluffy white clouds, creating a peaceful outdoor setting. This image highlights the natural beauty and serenity of the area.

Cottage in Becket

4.78 out of 5 average rating, 163 reviews

Tranquil Lake Cottage on 3 Acres with Large Deck

Tranquil 3-Acre Getaway in Becket, MA Escape to our charming 1,504 sq. ft. retreat on 3 acres in a private lake community. This historic home offers timeless appeal with a spacious 350 sq. ft. deck surrounded by lush trees. Take a 5-minute stroll to the lake. Key Features: Expansive Deck: Ideal for outdoor dining and relaxation. Lake Access: Enjoy water sports steps away. Modern Amenities: Features HDTV for streaming. Book your Becket escape today and experience the beauty of the Berkshires!

Guest favorite

Home in Great Barrington

4.96 out of 5 average rating, 24 reviews

Luxury Redo: Hot Tub, Playroom, Sleeps 12

Creamery: Fully Renovated 5 Bedroom Home, sleeps 12 with large screened porch, outdoor patio with seating, sun umbrella, hot tub, fire pit and billiards! Amenities also include: Central AC, all new kitchen appliances, washer/dryer, 4 Smart tvs, fiber internet + good cell service, propane fireplace, blue stone outdoor patio with seating, billiards table, playroom, high quality linens included, Front porch with seating, superior central location: less than 10 to GB, less than 10 to Catamount!

Guest favorite

A spacious yard is surrounded by tall trees, featuring several adirondack chairs arranged around a central fire pit. The charming house is visible in the background, showcasing a blend of traditional and modern architectural elements.

Home in Great Barrington

4.91 out of 5 average rating, 33 reviews

Spacious hideaway mins from town

The perfect getaway spot for family and friends. Our home is a spacious, private retreat on 3 acres. Surrounded by tall trees, you'll be able to enjoy nature yet are only 10 mins from town, 5 mins from skiing, and 5 mins from shopping. With a fully fenced in backyard, it's perfect for families to enjoy time together - kicking a ball, building a snowman, or making s'mores by the fire pit - and we've got baby gear too. Whether for a weekend or longer, you've found your home away from home.

Guest favorite

A winter scene depicts a charming town square with snow-covered ground, featuring a building adorned with a glowing Christmas tree in its window. Vintage cars are parked in front, while small groups of people are visible, creating a festive atmosphere against a twilight sky.

Apartment in Stockbridge

4.96 out of 5 average rating, 104 reviews

Historic,Famous,Iconic, Unforgettable Berks Escape

PICTURE IT...You can put yourself in the "famed" Norman Rockwell Main Street at Christmas Painting! That's Right,Cozy, Intimate,Magical and all to yourself.Fully equipped with all the comforts of home. Small Town Charm,Big time Historic setting in the heart of Downtown Stockbridge! Spend your afternoon sipping Tea or Wine looking out the iconic picture window Norman Rockwell installed himself. The one where the Christmas Tree Glows in a room that was Norman Rockwell's Studio from 1953-1957

Top guest favorite

A spacious deck is illuminated by warm string lights, creating a cozy outdoor atmosphere. A shaded area features a grill and a table with four chairs, inviting gatherings. The surrounding woods are visible in the evening light, enhancing the natural setting.

Home in North Adams

5 out of 5 average rating, 109 reviews

Berkshires Retreat! in the woods, yet in town!

We are happy to share our piece of heaven in the Berkshires! Newly renovated 4-bedroom 2-1/2-bathroom vacation rental nested in 2.7 acres of woods, yet conveniently located in the city of North Adams. A 5 minute walk from Windsor Lake, a 15 minute walk to MASS MoCA, and a close drive to many restaurants. The house is kid friendly, basketball hoop, soccer goal, and games. We are close to ski resorts, as well hiking and biking trails, including Mount Greylock. PET FEE. PERMISSION NEEDED.

Guest favorite

A well-lit bedroom features a black wooden bed with a plush blanket layered over crisp white linens. A small bedside table holds a lamp, and framed photos adorn the walls. A window with a blackout shade allows natural light while a wooden chair adds a touch of warmth.

Home in Sheffield

4.91 out of 5 average rating, 117 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Only one rental is rented at a time. Rental #1 has 2 bedrooms, FULLY EQUIPPED KITCHEN and is SUPERCLEAN! (SEE THE 1 BEDROOM LISTING #2!) We are conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. Queen size beds. High Speed WiFi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

Top guest favorite

Home in Great Barrington

5 out of 5 average rating, 13 reviews

Great Barrington Ranch. Sleeps 10,Hot Tub, 5 acres

Easy living Ranch nestled on 5+ acres and just 0.8 miles from GB Main St. Sleeps 10 | Wi-fi | Outdoor Hot TUB| Central Air and Heating | Cable| Screened in Porch | Fire Pit | Nestled by trees and tucked at the end of a long private driveway. Tons of flat yard space provide fresh views while sitting on the large front porch or sipping your favorite drink in the ultra-comfortable screened in back porch.Cap off the night sharing stories and making memories by the outdoor firepit.

Guest favorite

Bungalow in Great Barrington

4.91 out of 5 average rating, 117 reviews

Idyllic Berkshires Getaway

Secluded large ranch in the country on 8 acres with pastoral scenic views, only 7 minutes drive from the center of Great Barrington and Lake Mansfield Beach, 10 minutes to Ski Butternut, 12 minutes to Stockbridge, 20 minutes to Lenox and Tanglewood . Kids playroom and a spectacular jungle gym, perfect for entertaining inside by the fire or outside on the patio with the bbq with beautiful views surrounded by pine trees. Perfect for fall foliage, skiing, spring and summer!