House holiday rentals in Lee

4.95 out of 5 average rating, 187 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.

LocationFamilyLong stay

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, 328 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!

FamilyLocationView

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.

4.98 out of 5 average rating, 248 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.

FamilyLocationBiking

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.

4.9 out of 5 average rating, 282 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.

ValueLocationBackyard

A bright living area features a yellow couch and two accent chairs, inviting relaxation. A patterned area rug centers the space, while natural light filters through large windows. A staircase is visible in the background, along with decorative plants and artwork adorning the walls.

4.96 out of 5 average rating, 228 reviews

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

LocationFamilyAccess

A spacious living area features a modern sectional sofa adorned with various cushions, positioned around a round coffee table. Exposed wooden beams and high ceilings create an open atmosphere. A staircase leads to an upper level, and natural light illuminates the well-equipped kitchen visible in the background.

4.88 out of 5 average rating, 107 reviews

Stonebridge Cabin: Modern Amenities, Enjoy Nature!

Our quiet, peaceful and nestled in the woods, is a meticulously updated modern retreat offers the quiet comfort of a home away from home. Only 5 minutes from town and in the heart of the Berkshires, this cozy cabin is a perfect escape from everyday life. Enjoy the fully appointed trappings of modernity—high-speed internet, a beautifully updated and well-stocked kitchen, hot tub, brand new stylish and comfortable furnishings, TV room, and more! Find us on social media: @stonebridgecabin

LocationValueHeating

The exterior of a Craftsman-inspired home is showcased against a colorful sunset sky. Natural materials create a warm facade, with a prominent stone chimney and large windows enhancing the inviting atmosphere. Lush landscaping surrounds the property, highlighting its connection to nature.

4.98 out of 5 average rating, 138 reviews

Lovely Berkshire Home

"We are located in the heart of America's cultural epicenter known as the Berkshires. Known as the "Gatehouse" to upscale Erskine Park, this truly one of a kind Craftsmen inspired home is filled with unique features and materials seldom found including eucalyptus and Brazilian Cherry flooring, Jerusalem stone and porcelain plank tiles. Inviting color and intriguing design elements make this an extraordinarily pleasing home. Every detail has been thoughtfully considered within. Dreamy!"

FamilyValueHeating

4.99 out of 5 average rating, 313 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 relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

LocationValueAccuracy

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.

5.0 out of 5 average rating, 113 reviews

Cozy lakehouse

Relax with family or friends at this sweet cottage on Center Lake in the Berkshires. This lakeside cottage is charming and rustic. Enjoy a beautiful day on the lake swimming, fishing off the dock and kayaking. Grill dinner on your private deck and watch the stars come out in the evening Or enjoy all that the Berkshires have to offer, Jacob’s Pillow (15 min), Berkshire Theater (20 min), Tanglewood (30 min). There are plenty of nearby hiking trails and charming towns to explore.

ValueFamilyCondition

4.97 out of 5 average rating, 103 reviews

A welcoming living area is seen through an arched doorway. Two patterned chairs sit beside a small table, illuminated by soft light. A bookshelf filled with books lines the wall, while a traditional rug adds color to the wooden floor. An antique clock stands nearby.

Home in Ashfield

An 18th century farmhouse

Built in 1785 this antique Cape was carefully restored to its original design about 20 years ago. The house is set on a quiet road in the middle of fields, woods, gardens, and hiking trails. it is secluded with easy access to the natural world. The rooms are book-lined and filled with family objects. It is close to Berkshire East for skiing and snowboarding in the winter and whitewater rafting and swimming in the summer. Mass MoCA and the Clark Museum are within an easy drive.

ValueLocationCheck-in

4.96 out of 5 average rating, 307 reviews

The spacious living room features large windows that provide scenic views of the mountains and lake. A comfortable sectional sofa is complemented by a decorative throw and cushions. The ceiling is elevated with wooden beams, and stylish decor enhances the inviting atmosphere.

Home in Monterey

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

LocationValueBarbecue

4.95 out of 5 average rating, 131 reviews

HOT TUB! Dog & Family Friendly in the Berkshires!

Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Freshly painted & new floors for 2026! -Patio w/ Hot tub, fire pit, canoe use -Acre secluded lot -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Appalachian Trail hiking -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch

LocationValueComfort

Popular amenities for Lee house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A comfortable living room features a large sectional sofa and a wooden coffee table. A reclining chair is positioned nearby, while a flat-screen TV is mounted on the wall. Natural light enters through glass doors, which open to the outdoor area. Soft colors and warm tones create a cozy ambiance.

4.93 out of 5 average rating, 102 reviews

Berkshire Vacation Home in Lee

LocationFamilyKitchen

4.89 out of 5 average rating, 376 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

LocationFamilyCleanliness

The exterior shows a modern home embraced by lush greenery. A wooden deck with a railing wraps around the entrance, complemented by well-maintained landscaping featuring shrubs and plants. Trees provide a natural backdrop, enhancing the tranquil rural setting.

4.92 out of 5 average rating, 106 reviews

Berkshire Getaway Ranch 3 acres + saltwater pool

ValueLocationKitchen

4.87 out of 5 average rating, 116 reviews

Berkshires Lodge | Pool, Hot Tub & Fire Pit

FamilyLocationBackyard

4.92 out of 5 average rating, 111 reviews

Home in Hudson

Hudson River Sunset Getaway

LocationFamilyNearby

4.98 out of 5 average rating, 106 reviews

A spacious hot tub is positioned under a wooden pavilion, surrounded by string lights. Water cascades gently inside, with soft lighting reflecting on the surface. In the background, a tranquil view of the lake and nearby seating areas can be seen, inviting relaxation.

Home in Athens

Hudson Valley Lake · Hot Tub · Dock · Games · View

FamilyLocationView

4.98 out of 5 average rating, 105 reviews

A spacious white cottage is set against a vibrant green lawn, framed by blooming white flowers. Expansive trees surround the property, overlooking rolling hills that stretch towards a tranquil river in the distance under a clear blue sky.

Home in Coxsackie

Hudson River estate guest cottage

LocationFamilyOutdoor spaces

4.95 out of 5 average rating, 109 reviews

Home in Athens

Lake House close to Skiing & Indoor Hot Tub

LocationFamilyCheckout

Weekly house rentals

4.89 out of 5 average rating, 125 reviews

A charming cottage is illuminated from within, showcasing a welcoming porch with steps leading down to a spacious grassy yard. The exterior features light blue siding and a deck equipped with a grill, set against a backdrop of trees and a fenced yard.

Home in Stockbridge

Rabbit Run in the heart of Stockbridge Village

ValueFamilyBathroom

An open-concept kitchen and dining area is presented, featuring a large island with eight wooden stools and sleek white cabinetry. A dining table with black chairs is set against a backdrop of large windows that allow natural light to illuminate the space.

4.99 out of 5 average rating, 117 reviews

Modern and spacious Berkshires 5bdr retreat.

ValueFamilyBackyard

4.99 out of 5 average rating, 248 reviews

A cozy living room features a brown sofa positioned centrally, paired with an ottoman. Striped armchairs flank the space, with two lamps providing soft illumination. Warm wood paneling and large windows contribute to a welcoming ambiance, complemented by a decorative area rug underneath.

Home in Colebrook

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

LocationValueCheck-in

4.95 out of 5 average rating, 175 reviews

The tranquil lake reflects a soft sunrise, showcasing a palette of warm hues and gentle ripples. A dock and small boats are visible on the water, framed by the serene landscape of trees along the shore.

Home in Otis

Idyllic family retreat - spacious lake home,

LocationValuePool

5.0 out of 5 average rating, 3 reviews

Pond House at Middle Way Farm • Sunset Views

LocationBathroomOutdoor spaces

5.0 out of 5 average rating, 33 reviews

Cozy cottage on peaceful pond

FamilyLocationDecor

A bright living room features a comfortable white sofa and a plush armchair beside a coffee table on a patterned rug. Large windows allow natural light to illuminate the space, while a television is positioned against a wooden accent wall. A potted plant adds a touch of greenery.

4.88 out of 5 average rating, 51 reviews

Spacious Central Berkshires Home for Groups

FamilyLocationCheckout

4.98 out of 5 average rating, 43 reviews

A warm fire burns within a stone fire pit, with flames flickering against the evening sky. The serene lake reflects the fading light, while a wooden dock is visible in the distance, surrounded by tall reeds and lush greenery.

Home in Lenox

Lakefront Retreat -Private Dock,creek,and Fire pit

LocationFamilyOutdoor spaces

Private house rentals

A well-lit living area is furnished with two light-colored sofas and a round coffee table. Soft curtains frame large windows, allowing natural light to brighten the space. A bookshelf filled with books is visible, alongside a cozy area rug that enhances the inviting ambiance.

5.0 out of 5 average rating, 26 reviews

Charming Berkshires Getaway

FamilyLocationComfort

5.0 out of 5 average rating, 20 reviews

An inviting kitchen features a central island with barstools and warm wood accents. Large windows allow natural light to fill the space, highlighting the modern appliances and tasteful decor. A dining area with additional seating is visible in the background, promoting a sense of openness.

Home in Lenox

Spacious Lenox Farmhouse | Retreat Near Tanglewood

FamilyLocationBackyard

4.93 out of 5 average rating, 55 reviews

A spacious kitchen area is presented with light-colored cabinetry and a modern countertop. A wooden table, designed to accommodate ten, is centered in the room. Open shelves display glassware, and stainless steel appliances are visible, enhancing the functional layout.

Home in Lenox

Home away from home: Minutes to Tanglewood.

LocationFamilyCheckout

5.0 out of 5 average rating, 11 reviews

4BDR Elegant Berkshires Escape | Beaver Creek

FamilyLocationQuiet

A spacious living area features rich wooden paneling and a coffered ceiling. Comfortable seating arrangements are provided on a sectional sofa and ottoman. A stone fireplace adds warmth, while a large window presents views of the outdoors. A television is mounted on the wall for entertainment.

5.0 out of 5 average rating, 24 reviews

Entire Historic Farmhouse, 5 BR

LocationFamilyHospitality

A tranquil lake reflects a charming red house set against a backdrop of lush green trees and blue sky. The surrounding nature provides a serene atmosphere, inviting peaceful contemplation and relaxation.

4.94 out of 5 average rating, 88 reviews

Spectacular Berkshire Retreat on Private Lake

LocationFamilyCleanliness

The exterior of the house features a classic design with white siding and green accents. Large windows line the front, providing ample natural light. A pathway leads up to the entrance, surrounded by a green lawn and views of the Berkshire Hills in the background.

4.96 out of 5 average rating, 25 reviews

Berkshire Hills country retreat

FamilyLocationWalkability

A rustic chalet is situated among lush greenery, overlooking a peaceful lake. A wooden dock extends into the water, with tall grasses framing the shoreline. The home is partially visible, surrounded by trees and natural landscape.