House holiday rentals in Lenox

An inviting living space features a blue sofa adorned with colorful cushions, complemented by an orange wall. Framed artwork is displayed prominently, with a stylish hat resting on a black basket. A doorway leads to additional rooms, enhancing the room's spacious feel.

4.97 out of 5 average rating, 102 reviews

Nerd Preservation Sanctuary

Nerdscapist, geekmantic country home; perfect for oddballs who wish for a crafty, private, hilarious country retreat. Featuring a bad art print collection from the glorious MA Museum of Bad Art (Or Mass MOBA). Original bad art and sculpture. Much scope for the imagination's doofiest crevices. Redonkulously close to all the local fun: tiny drive to 5 lakes, Jacob's Pillow, Tanglewood 17 mi, Otis ski, 1/2 hr to Butternut Ski & Tubing Pittsfield & Great Barrington, hour to Berkshire E & Mass MOCA.

An open kitchen and dining area feature a wooden dining table surrounded by black chairs. The space is illuminated by natural light from large windows, with a breakfast bar visible in the background. A neutral color palette adds warmth to the inviting layout.

4.94 out of 5 average rating, 120 reviews

Net Zero home with rustic Berkshire charm

Be a part of the solution in our centrally located solar home that sits on a safe and quiet street just a walk, ride, or drive from downtown Pittsfield! Warm up your day on the screened-in sun porch. Warm up your toes on the heated tile floors! Enjoy custom concrete counters and wood floors in this open kitchen concept. Grill out on the rear patio while your dogs roam in the enclosed backyard. Hiking trails abound and playgrounds are just a stroll away. We are emissions free! How cool is that?!

4.97 out of 5 average rating, 193 reviews

A cozy living room features floral-patterned armchairs and a sofa, complemented by a low coffee table. A lamp provides soft lighting, and artwork hangs on the walls, enhancing the warm decor. A textured rug covers the floor, adding comfort to the space.

Home in Catskill

Cheerful Catskill Village Cottage

Bright and airy Catskill village refuge - a wildflower and wildlife haven in the thick of things. Historic house set on a quarter acre of trees and wildflowers, but blocks from Main Street, Catskill. Walk to Foreland, The Lumberyard, the incredible village cemetery, Thomas Cole House, restaurants and shops. Olana State Historic Site is right across the bridge! Cottage has a full kitchen, clawfoot tub, penny tile shower, front porch, dining room and large living room. Truly peaceful and lovely.

A single-story wooden lodge with a green metal roof is set amidst a grassy area. The exterior is lined with windows, allowing natural light to fill the interior. Surrounding trees provide a backdrop, and a paved driveway leads to the entrance, enhancing accessibility.

4.87 out of 5 average rating, 311 reviews

Dancing Horse Lodge

Dancing Horse Lodge is located in the heart of the Berkshire Mountains in Pittsfield, MA, minutes from Tanglewood, Barrington Stage, Jacobs Pillow Ballet, Kripalu Yoga, Shakespeare and Co. and skiing at Bosquet and Jiminy Peak. It is a light and bright residence located on a 20-acre horse farm with nature views out of each window. It is surrounded by miles of woods, great for hiking and cross country skiing. Close to all amenities yet affords beautiful, quiet country living. Come and enjoy!

4.95 out of 5 average rating, 159 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.

5 out of 5 average rating, 100 reviews

The charming exterior of a renovated farmhouse features a spacious front porch with a red bench and hanging flower baskets. Large windows allow natural light to fill the entryway, while lush green grass and trees frame the property.

Home in Canaan

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

Welcome to our little slice of heaven upstate. Located just a 5-minute drive to the MA border, a stay at our home in Canaan, NY means access to the best of both Columbia County and the Berkshires. In the summer, enjoy the private Adams Point Beach on Queechy Lake and easy access to Tanglewood. In the winter, explore 4 different local ski resorts and curl up by the cozy wood stove. In between, enjoy the peaceful pond views and secluded location on a dirt road. We can't wait to welcome you!

A charming outdoor seating area is situated under a spacious pergola, designed with warm lights. Comfortable seating is set on a stone patio, with a grill nearby, surrounded by a grassy yard. Soft clouds and a gentle twilight sky provide a serene backdrop.

4.97 out of 5 average rating, 237 reviews

Berkshire 4 season home

The house is located in the heart of the Berkshires. It's less than 10 miles from Tanglewood, Kripalu, Jacob's pillow Dance, Monument Mountain, Beartown state forest, Norman Rockwell Museum, Shakespeare & Co., Ski Butternut, Lee Prime outlets. Located 1.5 miles from the turnpike exit for easy travel, 3 miles from Laurel lake, walking distance to a public golf course and downtown Lee where you will find great restaurants. There is Cable internet that is fast and reliable if you have to work.

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.

4.93 out of 5 average rating, 242 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!

The living room features a spacious leather sectional sofa facing a TV, with a wooden coffee table placed in front. A wood stove is positioned nearby on a black hearth, and a large window allows natural light to illuminate the space, adorned with plants and decorative items.

4.91 out of 5 average rating, 276 reviews

Cozy Berkshires Cottage

Stay in a cozy, newly remodeled Berkshires 1920's cottage! We've added bedrooms and a bathroom with a soaking tub upstairs, expanded the first floor bathroom and added a laundry room. The cottage is set back from the main road, easily accessible yet private. -Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. -Ideal for couples, adventurers, business travelers, and furry friends (pets). -Note: Stairs to the 2nd floor are steep: guests are responsible for child safety.

A serene view of a winding driveway surrounded by vibrant perennial gardens. Colorful flowers grow abundantly along the path, leading to a scenic landscape of rolling hills and distant mountains under a partly cloudy sky.

4.98 out of 5 average rating, 139 reviews

Hidden Oasis in the Mountains by Evergreen Home

Evergreen Home Vacation Rentals invites you to this hidden oasis in the heart of the Berkshires. This attractive 5-bedroom home features a large, fully-outfitted kitchen, Tuft & Needle mattresses, and stunning mountain views. Relax in the hot tub, enjoy the perennial gardens, or gather on the stone patio by the fire pit. Just 7 minutes to Bousquet Mountain and minutes from Lenox and Tanglewood, this is the perfect retreat for family and friends. Experience luxury and comfort—book today!

4.96 out of 5 average rating, 100 reviews

HOT TUB! Spring Time! Berkshires! Dog-Friendly!

Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Patio w/ Hot tub, fire pit, canoe use -Acre wooded/secluded lot -Ski Otis Ridge 15 min or Butternut 30 min -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Naumkeag Lights -Appalachian Trail hiking -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch -Generator on site

4.99 out of 5 average rating, 306 reviews

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.

Popular amenities for Lenox house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 33 reviews

A charming two-story home is set amidst lush greenery, featuring a spacious front porch with seating. The house is flanked by trees, and a large lawn is visible in front, complemented by a gravel driveway leading towards an attached garage.

Home in Lanesborough

Berkshire Mountain House

4.96 out of 5 average rating, 174 reviews

A spacious cedar hot tub sits peacefully outdoors, surrounded by a natural setting of trees and open space. Bubbles rise from the water, creating a relaxing atmosphere. Clear blue skies are visible above, enhancing the tranquil environment.

Home in Hudson

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

4.89 out of 5 average rating, 182 reviews

A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.

Home in Rhinebeck

4Br Mountain Brook House on 130 acres w/ trails

4.99 out of 5 average rating, 89 reviews

A bright living room is highlighted by a grand piano and a modern gas fireplace, both set against a light brick wall. Large windows provide natural light, and wooden flooring adds warmth. A comfortable dark sofa and armchairs are arranged around a glass coffee table.

Home in Great Barrington

Stunning luxury home with fire pit

4.89 out of 5 average rating, 351 reviews

A tranquil swimming pond is framed by lush greenery and surrounded by wooden decking. Two lounge chairs are positioned on the deck, providing a relaxing spot to enjoy the natural scenery. A shaded area with wooden slats offers a cool retreat beside the water.

Home in Ghent

Modern Barn on 12 acres w Sauna, FirePit+swimming

4.92 out of 5 average rating, 102 reviews

Home in Hudson

Hudson River Sunset Getaway

5 out of 5 average rating, 112 reviews

A bright living area features large windows that invite natural light. The space includes a dark sofa, a vibrant yellow armchair, and a soft, patterned area rug. A coffee table is centrally placed, accompanied by a small side table with a decorative lamp.

Home in Taghkanic

Sunbeam Lodge: Pool+Sauna, 50 Acres, ‘70s Oasis

4.9 out of 5 average rating, 230 reviews

A pathway lined with lush greenery leads to a bungalow with a screened-in porch, featuring outdoor seating. The soft sunlight filters through the foliage, creating a serene entrance to the welcoming space.

Home in Williamstown

Hollywood Bungalow in the Berkshires #C0191633410

Weekly house rentals

Superhost

A charming outdoor balcony is depicted, featuring a round wooden table topped with a vase of flowers. Expansive views of lush greenery and distant hills are showcased under a bright blue sky with scattered clouds.

4.91 out of 5 average rating, 22 reviews

Centrally Located Historical Home

The exterior of the rustic chalet features a brown wooden facade with a peaked roof. An American flag is displayed in front of the entrance, which is flanked by two windows. A small bistro table and chair sit on a gravel path, surrounded by lush greenery.

4.93 out of 5 average rating, 84 reviews

Little Longbow Lakefront Chalet

A large, light blue Victorian house is set amidst a lush green yard, with a variety of trees and landscaped bushes. Outdoor seating is provided by adirondack chairs, and a red shed is visible in the background, all under a clear blue sky.

4.94 out of 5 average rating, 34 reviews

The Aviary Hosted by Leo and Jacqueline

A charming Victorian house with a pointed roof is surrounded by vibrant foliage. Colorful flowers in shades of pink and green bloom in the foreground, adding life to the entrance. Clear blue skies are visible above, enhancing the inviting appearance of the property.

4.97 out of 5 average rating, 31 reviews

Sunny House in Downtown Lenox

Superhost

Home in Stockbridge

5 out of 5 average rating, 3 reviews

Secluded + Modern | Enclosed Patio | Woodland Zen

A newly renovated home is showcased amidst a wide expanse of lush green grass, surrounded by trees and open spaces. Bright blue skies feature soft, white clouds, creating a serene setting for relaxation.

5 out of 5 average rating, 29 reviews

Meadowbrook Cottage

4.99 out of 5 average rating, 74 reviews

The exterior of a historic red house is surrounded by lush green grass and trees. A stone path leads to the front entrance, while flowering plants add a touch of color to the landscape. The sky is clear with some clouds, creating a serene outdoor setting.

Home in Old Chatham

The Red House

4.97 out of 5 average rating, 69 reviews

Winter Wonderland 15 minutes to Jimmy Peak

Private house rentals

4.85 out of 5 average rating, 39 reviews

A modern eat-in kitchen is highlighted by wooden beams and a rustic kitchen island. Wooden cabinetry complements the black appliances, while natural light pours in through sliding glass doors. A gray rug enhances the space, creating a functional and welcoming atmosphere.

Home in Sheffield

Cozy Cottage Route 7 Sheffield

Superhost

A spacious living room is presented, featuring a large, dark sectional couch with various cushions. A 60-inch 4K TV is positioned on a low media console, opposite the couch. Natural light filters through sheer curtains into the room, complemented by a soft area rug and a potted plant.

4.83 out of 5 average rating, 64 reviews

Spacious & Family-Ready Home w/ Fenced Yard in Lee

4.97 out of 5 average rating, 31 reviews

A charming house is nestled among autumn foliage, displaying warm earthy tones. A winding stone pathway leads to the entrance, framed by a well-maintained stone wall and lush greenery. Colorful leaves adorn the surrounding trees, creating a serene and inviting landscape.

Home in Great Barrington

Seekonk Hill

A bright and inviting living room is featured, showcasing a light-colored sofa with decorative pillows. Two blue chairs are positioned around a wooden coffee table, while stylish ottomans provide additional seating. Natural light pours in through large windows, highlighting the soft area rug and green plants.

4.95 out of 5 average rating, 91 reviews

BB's Central Berkshire Home

5 out of 5 average rating, 39 reviews

The living room features a bright and airy design with large windows that provide natural light. A soft sectional sofa offers ample seating, facing a cozy fireplace surrounded by stone. Decorative art pieces and a wooden ceiling enhance the room's warmth and character.

Home in Great Barrington

Hilltop Ski and Sun Chalet with Hot Tub

A cozy bedroom features a decorative iron bed with soft pillows adorned with floral patterns. A wooden dresser stands beside the bed, while soft lighting from lamps adds a warm glow to the space. Patterns from the curtains complement the room's inviting atmosphere.

4.88 out of 5 average rating, 16 reviews

Whistler's Inn/The Garden Room (#9)

4.98 out of 5 average rating, 51 reviews

A charming home is set in a serene neighborhood, featuring a white exterior and red shutters. Bright autumn leaves blanket the ground, while colorful trees are seen in the front yard. The house includes a small set of stairs leading to its entrance.

Home in Bethlehem

Cozy Renovated Home Near Albany

A quaint lakeside cottage features large windows for scenic views and a deck with outdoor seating. A grill is positioned nearby for easy outdoor cooking. The property is framed by lush greenery, enhancing the natural setting by the water's edge.