House vacation rentals in Lenox

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.

4.93 out of 5 average rating, 136 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?!

ValueLocationHeating

4.95 out of 5 average rating, 191 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 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, 253 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.

FamilyValueWifi

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.

4.95 out of 5 average rating, 240 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!

ValueFamilyAccuracy

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, 106 reviews

Berkshire Vacation Home in Lee

Our spacious home is situated in a secluded neighborhood in Lee, MA (Berkshire County) and has 5 bedrooms & 2.5 baths. There is a fully equipped open concept kitchen/dining room and 2 living rooms with TVs and gas fireplaces. There is central air/heat, and a sun room that leads out to a deck overlooking our in-ground pool. Tanglewood, Antimony brewery, Balderdash winery, Hilltop Orchards, Laurel Lake, Highlawn Farm, outlets, golf, and Lenox & Stockbridge are all within a 20 minute drive.

LocationFamilyCheckout

4.91 out of 5 average rating, 188 reviews

A wrap-around porch features a small table with two colorful chairs, overlooking a serene lake framed by lush trees and greenery. The view showcases calm water, complemented by distant hills under a clear blue sky.

Home in Canaan

Berkshire Lakefront House with Amazing Views

Enjoy the culture of the Berkshires & Hudson - 15 min from Tanglewood, Norman Rockwell Museum, Shakespeare & Co, PS21, McHaydn Theatre, Mount Greylock, Jiminy Peak Resort, zipline parks, Bousquet & more. Restaurants & market within driving distance and a membership-only beach within a short walk or drive. Great lake views with wrap-around porch. The lake is family-friendly. We welcome couples, solo adventurers, and families. Sorry, no "Group Bookings" - book & pay via one account only.

FamilyLocationOutdoor spaces

5.0 out of 5 average rating, 119 reviews

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.

Home in Becket

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.

ValueLocationNearby

4.93 out of 5 average rating, 136 reviews

Home in Becket

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 -Naumkeag Pumpkin Show/Christmas Lights -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch

ValueLocationQuiet

4.96 out of 5 average rating, 311 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.

ValueFamilyParks

5.0 out of 5 average rating, 39 reviews

Cozy cottage on peaceful pond

This little slice of heaven is located on the serene Richmond Pond. Right down the street from Balderdash winery and a 15 minute drive to charming downtown Lenox and Tanglewood. In Lenox you can find great dining, shopping, and there is plenty of hiking and biking around this area. This cozy cottage has everything you need for a Berkshire retreat. In the fall cozy up next to the fireplace inside or out take a break and unwind at this Peaceful oasis.

LocationFamilyBeach

4.95 out of 5 average rating, 176 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,

This recently renovated waterfront home is perfectly situated close to many Berkshire attractions for an ideal getaway. Lake views are stunning year around. The fire-pit at shore offers a unique outdoor gathering option. Warm and welcoming interior with three levels of living for families and friends (up to 8 people). Area offers family-friendly hiking. Enjoy the whimsical decor and mid-century style furnishings. Cook in the well-equipped kitchen.

LocationFamilyCondition

A serene bedroom features a spacious bed dressed in soft linens and a colorful quilt. A cozy couch is positioned against the wall, offering a relaxation spot. Natural light is let in through multiple windows, highlighting the light blue paneled walls and white furniture.

4.97 out of 5 average rating, 143 reviews

Stylish Mid-century Modern Berkshires Cape

Stylish and design forward, yet entirely comfortable for families and kids. Fully renovated 4 bedroom, 2.5 bath home located in the heart of the Berkshires. Enjoy the large, sunny yard and deck with lots of seating and a large dining table - perfect for al fresco dinner and drinks! The house is decorated in mid century modern style with gorgeous design touches throughout!

LocationFamilyGetting around

Popular amenities for Lenox house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with free parking

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.

4.93 out of 5 average rating, 61 reviews

Home away from home: Minutes to Tanglewood.

FamilyLocationBackyard

5.0 out of 5 average rating, 9 reviews

Historic Haven at 93 Church St.

LocationFamilyNearby

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, 38 reviews

Sunny House in Downtown Lenox

FamilyValueHiking

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.

4.95 out of 5 average rating, 40 reviews

The Aviary Hosted by Leo and Jacqueline

FamilyValueWifi

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.

4.89 out of 5 average rating, 56 reviews

Spacious Central Berkshires Home for Groups

LocationFamilyIndoor spaces

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.

4.84 out of 5 average rating, 25 reviews

Spacious Lenox Farmhouse | Retreat Near Tanglewood

LocationFamilyAccess

The exterior of the cottage features light grey siding and a charming front door adorned with seasonal wreaths. Large windows invite natural light, while the surrounding snow-covered landscape highlights the tranquility of the setting. A garage is visible on the side of the property.

4.95 out of 5 average rating, 21 reviews

The Lenox Cottage

FamilyLocationIndoor spaces

A spacious living room features a cozy sectional couch alongside a wooden coffee table. Two armchairs are placed next to a floor lamp, and natural light streams through two large windows adorned with sheer white curtains. A soft area rug complements the hardwood floors.

5.0 out of 5 average rating, 38 reviews

Cliffwood Cottage

LocationFamilyHiking

House rentals with a pool

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.

4.93 out of 5 average rating, 109 reviews

Berkshire Getaway Ranch 3 acres + saltwater pool

LocationValueTV

4.98 out of 5 average rating, 109 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

FamilyLocationCheck-in

4.98 out of 5 average rating, 136 reviews

The spacious kitchen features an island with a wood countertop and built-in storage. Mint green cabinetry offers a serene ambiance. Natural light flows through large windows, illuminating the dining area with a wooden table and cozy seating, creating an inviting space for gatherings.

Home in Ghent

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

FamilyLocationGrill

4.92 out of 5 average rating, 112 reviews

Hudson River Sunset Getaway

LocationFamilyOutdoor spaces

Superhost

A spacious outdoor area is surrounded by vibrant planters filled with blooming flowers. Comfortable seating is arranged around a fire pit, with a green umbrella providing shade. A pink flamingo float is set nearby, alongside a wooden hot tub and a stock tank plunge pool.

4.94 out of 5 average rating, 198 reviews

Hudson getaway w/ hot tub+ plunge pool on 20 acres

LocationFamilyCheck-in

4.98 out of 5 average rating, 112 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

LocationFamilyRiver

A spacious living area features a large sectional sofa with dark cushions, complemented by a wooden chair with patterned fabric. A modern ceiling fan hangs above, and a sleek fireplace is positioned nearby. Large windows invite natural light, providing a view of the greenery outside.

4.92 out of 5 average rating, 268 reviews

Casa Luna Country Retreat with Pool, Hudson, NY

FamilyLocationCleanliness

4.9 out of 5 average rating, 242 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

ValueLocationWalkability

House rentals with a hot tub

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, 108 reviews

Stonebridge Cabin: Modern Amenities, Enjoy Nature!

LocationFamilyTV

4.95 out of 5 average rating, 111 reviews

A bright living area features large glass doors that open to a wooden deck. Two green chairs flank a modern coffee table, while a basket sits in the corner. Natural light fills the space, illuminating the wooden floor and surrounding greenery outside.

Home in West Stockbridge

Berkshires-Enjoy The Peak, private home

FamilyValueTV

4.99 out of 5 average rating, 252 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

LocationValueOutdoor spaces

Superhost

4.89 out of 5 average rating, 152 reviews

Designer Home, Hot Tub, Private Yard, & Projector

FamilyLocationGrill

An outdoor area is illuminated by warm lights, featuring a hot tub nestled beneath a canopy. Comfortable seating is arranged nearby, surrounded by lush greenery. A wooden deck provides a relaxing space, with a partially enclosed yard that enhances privacy.

4.95 out of 5 average rating, 175 reviews

Vibing Hot Tub Cottage | Pet-Friendly | Hudson, NY

FamilyValueAccuracy

Superhost

A bright great room features large windows that offer expansive views of the surrounding valley. Vaulted wooden ceilings enhance the airy feel, while a comfortable gray sofa and a white couch are positioned to invite relaxation. Natural light fills the space, showcasing the warm wooden walls.

Home in Tyringham

Treetop Hideaway in Tyringham

LocationFamilyOutdoor spaces

4.82 out of 5 average rating, 146 reviews

4.85 out of 5 average rating, 215 reviews

An outdoor hot tub accommodates up to seven people, featuring a smooth surface and multiple jets. The setting includes lush green foliage in the background, with a clear sky above and natural light reflecting off the water's surface.

Home in Otis

The Meadows House @ Otis Ridge w/ 7-person hot tub

FamilyValueWifi