Vacation rentals with a washer and dryer in Lenox

4.95 out of 5 average rating, 433 reviews

A striking octagonal home is illuminated at dusk, showcasing wrap-around glass windows that blend with the surrounding woodland. The exterior features natural stone accents, and a warm glow from a light at the entrance creates a welcoming ambiance amidst a snowy landscape.

Chalet in Otis

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

4.94 out of 5 average rating, 140 reviews

An open living area showcases rustic wooden beams and a cozy gas fireplace. A modern gray sofa faces the fireplace, complemented by a glass coffee table with a vase of pink flowers. Natural light floods in from the glass doors, leading to the lush green outdoor space.

Home in Stockbridge

Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

4.96 out of 5 average rating, 113 reviews

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

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

Lush, colorful flowers surround the entrance of the cottage, adding a vibrant touch to the exterior. A combination of greenery and blooms creates a welcoming atmosphere. The cottage features large windows, allowing for ample natural light and offering views of the blooming landscape.

4.92 out of 5 average rating, 236 reviews

Heart of Lenox Walk to Town Cozy Cottage!

The cottage is a 2-minute walk to Church St., right in the heart of Lenox. Kennedy Park (1.5 miles) is a short stroll away for great hiking & biking, while multiple 5-star restaurants are all within a few minute walk. Tanglewood (2 miles), Kripalu (3 miles), Shakespeare & Co. (1 mile), Berkshire Theatre Festival & the Norman Rockwell Museum (7 miles), Butternut, Jiminy Peak (15 miles) & Bousquet (5 miles) ski area, Mahaiwe Performing Arts Center & Jacob's Pillow (14 miles) are all close by!

4.95 out of 5 average rating, 198 reviews

A wooden rocking chair sits on a quaint porch, next to vibrant flower pots filled with blooming plants. Green grasses and a hint of autumn foliage create a serene outdoor setting, inviting relaxation and peaceful moments.

Cottage in New Lebanon

The Writer's Cottage

The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and ironwork table.

An open living and dining area is showcased with a light wood floor and large windows. A teal sofa, accented with bright cushions, faces a coffee table on a patterned rug. A dining area with modern chairs is visible in the background, enhancing the welcoming layout.

4.93 out of 5 average rating, 237 reviews

The Berkshire Quintessential Cape downtown Lenox

Experience the best of the Berkshires in this charming, in-town, Lenox home! With stunning oak floors and white walls, this light-filled gem features high ceilings and abundant windows. Enjoy a cozy first-floor bedroom and full bath, while upstairs hosts two spacious bedrooms with a shared bath. The open-concept living and dining area, complete with a wood-burning fireplace, is perfect for gatherings. Just a short stroll to town, Tanglewood, and Canyon Ranch, this is your ideal getaway!

4.95 out of 5 average rating, 140 reviews

A dining area features a wooden table surrounded by four black chairs. A vase with greenery is centered on the table. In the background, a cozy seating area with a sofa is visible, illuminated by natural light from a nearby window.

Guesthouse in Housatonic

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

4.99 out of 5 average rating, 127 reviews

A charming two-story home is set on a landscaped plot with a gravel driveway. A wooden staircase leads to the entry, flanked by vibrant flower beds. The natural backdrop features lush trees and a striking granite ledge, creating a peaceful and inviting outdoor environment.

Home in Great Barrington

Granite Ledge, Modern home in a unique setting

Welcome to Great Barrington, the heartbeat of the Berkshires! This newly remodeled home that sits on 3.5 acres, is conveniently located 1 min from Butternutt Ski Mountain, and a 6 min drive from downtown main street Great Barrington. Convenient to restaurants, shops, farmers markets, art galleries, Tanglewood, Stockbridge, The Norman Rockwell Museum, Simon’s Rock, etc. Enjoy a vibrantly diverse restaurant scene and cultural events while still staying in a private setting.

4.99 out of 5 average rating, 288 reviews

A spacious kitchen is complemented by large windows that allow natural light to fill the area. An island with a countertop of mixed materials serves as a central gathering spot. A colorful rug lies on the concrete floor, while various kitchenware is neatly arranged on shelves.

Home in Lee

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 relax by the firepit- we hope you enjoy your stay and will visit us again.

A sunlit living area is furnished with a spacious sectional sofa and a round coffee table atop a patterned area rug. The hardwood floors and natural light from the multiple windows enhance the room's inviting feel, complemented by a decorative fireplace and wall art.

4.87 out of 5 average rating, 162 reviews

Spacious 4-Bedroom Colonial Gem in Downtown Lenox

Spacious 4-Bedroom Retreat in Lenox, MA Experience your perfect getaway in this beautifully renovated home in Lenox, MA. This charming 4-bedroom, 3-bathroom retreat offers 2,089 sq. ft. of space and is designed for a comfortable stay. The deck, BBQ grill, and cozy seating make for memorable gatherings. The Wi-Fi is fast for all your streaming needs, and there are 2 Wi-Fi HDTVs. Lenox, MA, is a picturesque town in the heart of the Berkshires. Book your stay today!

4.96 out of 5 average rating, 133 reviews

The bedroom features a spacious bed with a light grey coverlet, accentuated by decorative pillows. Natural light filters through two windows adorned with bamboo shades. A light-colored dresser and a cozy armchair add functionality, complemented by a soft area rug on the hardwood floor.

Apartment in Lenox

Lovely Downtown Lenox apt, walk to everything!

Experience the best of the Berkshires in a beautiful, spacious apartment right in the center Lenox. This updated space is filled with natural light and hardwood floors, great for families or friends looking to experience culture and countryside. Walking distance to Tanglewood, Shakespeare & Co, Kennedy Park, restaurants, and shopping. On second floor of a Historic building with a deck that has a birds eye view of town. 7 min to Bousquet Mountain.

A cottage entrance is framed by lush greenery, with a stone pathway guiding guests to a welcoming front porch. The wooden door features a round window, and large windows on either side allow natural light to illuminate the space, surrounded by vibrant flora.