
House vacation rentals in Lenox
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Top-rated house rentals in Lenox
Guests agree: these houses are highly rated for location, cleanliness, and more.

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.

Boulder Tree House
Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

HEAVEN ON EARTH - Hudson Riverfront Home
Voted one of the Most Romantic AirBnB's Near NYC (Time Out NY). Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access yr round. Enjoy your private sauna & steam shower inside & hot tub on covered lower deck. Kayaks/SUP/Fishing Poles provided. Enjoy brunch, dinner or high tea on the Gazebo suspended over the Hudson with a private chef. Explore Hudson, Woodstock....also only 30 mins to Hunter/Skiing/Snowboarding!

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.

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.

Hillside Views in Hudson Valley
Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

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.

HOT TUB! Berkshires: Dog & Family Friendly!
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 -Generator on site

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.

Chatham on the Creek. Pet friendly. F Trump
This is a recently renovated 120-year-old house. There are no neighbors in sight. The backyard is a wooded area. There is a stream, fire pit, table, and chairs. The garage has been converted into a game room with ping pong, pool, couches and a bar. Across the road is farmland. It's less than one mile off the Taconic State Parkway exit, and about a half hour to both Catamount and Jimminy Peak (ski resorts). Twenty minutes from Hudson.

Private Home in The Berkshires (New Hot Tub!)
Leave your worries and stress behind and enjoy all the beautiful Berkshires have to offer! This fully remodeled home is ready to serve as your new favorite vacation spot! Whether you’re looking to enjoy a laid back getaway or an adventurous stay, look no further. You’re a short 10 minute drive to Ski Butternut, less than 15 minutes to Catamount, and about 20 minutes away from Tanglewood Music Center!

Cozy Modern Sugar House with spectacular views.
This beautiful Vermont home sits on 25 acres with spectacular views. We moved this sugar house structure to this land and had an architect adapt it to its surroundings. It has three walls of windows that display the amazing views. The house is surrounded by Mount Anthony hiking trails and a gorgeous pond. The location is a 5 minute drive to town or a lovely 20 minute walk.
Popular amenities for Lenox house rentals
House rentals with free parking

The Lenox Cottage

Mountain Farmhouse Getaway

Waterfront oasis in heart of Berkshires

Sunny House in Downtown Lenox

Meadowbrook Cottage

Historic Stone Church in The Berkshires

Berkshire Lakefront Lighthouse Getaway

Cozy Vermont mini-house
House rentals with a pool

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

4Br Mountain Brook House on 130 acres w/ trails

Highwoods Haven | saltwater pool and hot tub

Modern Barn on 12 acres w Sauna, FirePit+swimming

Hudson River Sunset Getaway

Luxury Prvt Estate w/Hot Tub+Gameroom nr Rhinebeck

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

Summer Paradise - Pool, Fire-pit, Nursery!
Weekly house rentals

Spectacular Berkshire Retreat on Private Lake

Stunningly Designed Luxury Home w/ Pool & Hot Tub

Wildflower Cottage near Hudson w/ Fire Pit & AC

Bucolic Pet Friendly Oasis | 10 min to Tanglewood

Private Lakehouse in the heart of the Berkshires

4BDR Elegant Berkshires Escape | Beaver Creek

Pixley Forest | 15 Mins To Tanglewood • Fireplace

Shatemuc, a magical getaway on the Hudson River
When is the best time to visit Lenox?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$62,345 GYD | G$66,948 GYD | G$69,040 GYD | G$57,533 GYD | G$59,626 GYD | G$69,040 GYD | G$88,915 GYD | G$80,756 GYD | G$70,505 GYD | G$67,785 GYD | G$65,902 GYD | G$66,320 GYD |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Quick stats about house rentals in Lenox

Total vacation rentals
Explore 100 vacation rentals in Lenox

Nightly prices starting at
Lenox vacation rentals start at G$12,553 GYD per night before taxes and fees

Verified guest reviews
Over 3,610 verified reviews to help you choose

Family-friendly vacation rentals
90 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
100 of Lenox vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Lenox rentals

4.9 Average rating
Lenox stays are highly rated by guests—averaging 4.9 out of 5!
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- Hunter Mountain
- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Mount Snow Ski Resort
- Windham Mountain
- Butternut Ski Area and Tubing Center
- Thacher State Park
- Bash Bish Falls State Park
- Hunter Mountain Resort
- Kent Falls State Park
- Taconic State Park
- Bousquet Mountain Ski Area
- Zoom Flume
- Mohawk Mountain Ski Area
- Ski Sundown
- June Farms
- Norman Rockwell Museum
- Opus 40
- Naumkeag
- Berkshire Botanical Garden
- Millbrook Vineyards & Winery
- Hancock Shaker Village





