Lenox vacation rentals

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Top-rated vacation rentals in Lenox

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Guest favorite

Home in Lee

4.89 out of 5 average rating, 235 reviews

Cozy Berkshires Cottage

Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)

Sep 22 – 29

R2,397 ZAR per night

Guest favorite

Loft in Great Barrington

4.99 out of 5 average rating, 296 reviews

The Old Red Barn

Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

May 26 – Jun 2

R2,957 ZAR per night

Guest favorite

Treehouse in Tyringham

5.0 out of 5 average rating, 228 reviews

Gingerbread House Tower in the Berkshire Hills

Escape to this newly renovated, off-beat retreat for a magical stay. Part of Tyringham’s Gingerbread House located on the Santarella Estate in the Berkshires, Western Mass. This one-of-a-kind loft with tower bedchamber offers guests a fairytale experience. The open concept living space filled with plants brings the outdoors inside and offers ample room to relax. If looking for activity, guests can spend the day on the grounds, walking nearby trails, or exploring the many nearby Berkshire towns.

Aug 30 – Sep 6

R6,351 ZAR per night

Superhost

Apartment in Lee

4.78 out of 5 average rating, 106 reviews

Cozy Berkshire Cottage Style Apartment

Stay in a cozy Berkshires apartment! All windows allow views to the peaceful surrounding state forest and yard. Watch humming birds, oriols, deer, squirrels, opossums, racoons, woodchucks, and many more... The house is set back from the road, easily accessible, yet private. The cottage is a duplex: the Airbnb apartment is on the left side of the cottage. • Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Stockbridge, Lenox, MA Turnpike • Ideal for lovers of nature & the Berkshires

May 9 – 16

R1,805 ZAR per night

Guest favorite

Guesthouse in Becket

4.93 out of 5 average rating, 258 reviews

Country Cabin

Lovely private country setting. Listen to owls and coyotes at night, birds during the day. When it rains you can enjoy the sound on the metal roof. I only accept advance reservations of 2 nights or more. (You may reserve a single night booking within 5 days of the request.) The space is for 2 adults but I allow for flexibility, so don't hesitate to ask. Seasonal/weekend rates may apply. I live on the property with my partner and the cabin would not otherwise be on the real estate market.

Dec 18 – 25

R2,341 ZAR per night

Guest favorite

Guest suite in South Lee

4.92 out of 5 average rating, 190 reviews

Sunny Riverside Apartment

The Berkshires are a perfect spot for a getaway week or weekend. You will enjoy this cozy 2-story apartment, easily accessible to all that the region has to offer. The apartment has a fully equipped kitchen, dining space, living area, and two bedrooms, overlooking the Housatonic River. Every town in South County is 5-15 minutes drive, and in 50 minutes you could be at The Clark Museum or Mass MOCA in North County. Several ski areas are nearby, and Kripalu is just an easy 10 minute drive.

Nov 2 – 9

R2,474 ZAR per night

Guest favorite

Home in Lee

5.0 out of 5 average rating, 230 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.

May 27 – Jun 1

R6,648 ZAR per night

Guest favorite

Guesthouse in Lenox

4.95 out of 5 average rating, 280 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Sep 8 – 15

R2,811 ZAR per night

Guest favorite

Farm stay in Pittsfield

4.99 out of 5 average rating, 105 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or take a walk on our hiking trail.

Sep 7 – 14

R2,264 ZAR per night

Guest favorite

Guesthouse in Stockbridge

4.96 out of 5 average rating, 175 reviews

Modern studio with views of the treetops

Our Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a brand new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

Sep 12 – 19

R3,495 ZAR per night

Guest favorite

Guest suite in Austerlitz

4.86 out of 5 average rating, 137 reviews

Rustic-Modern Studio - Near Hudson, Chatham, & GB

Get a small rustic-modern cabin feel in this cozy and self-sufficient space. 10 minutes from Chatham, 15-20 minutes from Great Barrington, Lee, Lenox, Kripalu Center for Yoga & Health, Catamount Ski Resort, TangleWood Institute and seconds away from a beautiful hike up Harvey Mountain in Austerlitz, NY. The wood-stove will keep you warm in the winter months and the large field and creek in the backyard will relax you in the summer.

Sep 19 – 26

R1,704 ZAR per night

Guest favorite

Apartment in Lenox

4.88 out of 5 average rating, 170 reviews

Station House 1E Private Room & Bath

Our place is a central location in Berkshire County, short drive to restaurants and shops; art and culture, skiing and hiking also close by. You’ll love this former train station( next to the Housatonic RR tracks) which is on three acres between a chapel, the scenic Housatonic River and October Mountain. Our place is good for couples, solo adventurers, and business travelers.

Aug 24 – 31

R1,409 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Lenox vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Lenox's top sights

Kripalu Center For Yoga & Health122 locals recommend

The Mount, Edith Wharton's Home167 locals recommend

Ventfort Hall Mansion and Gilded Age Museum19 locals recommend

Chocolate Springs Cafe23 locals recommend

Haven67 locals recommend

The Olde Heritage Tavern20 locals recommend

Other great vacation rentals in Lenox

Superhost

Home in Dalton

4.88 out of 5 average rating, 113 reviews

The Yellow House

Oct 28 – Nov 4

R2,262 ZAR per night

Guest favorite

Home in Lenox

4.96 out of 5 average rating, 170 reviews

Lenox - Walk to Town - Berkshire Home

May 16 – 23

R6,600 ZAR per night

Guest favorite

Home in Canaan

5.0 out of 5 average rating, 134 reviews

Country Cottage

Feb 27 – Mar 6

R2,963 ZAR per night

Guest favorite

Guest suite in Valatie

4.98 out of 5 average rating, 230 reviews

Guest Suite in Old Chatham Hunt Country

Sep 27 – Oct 4

R1,755 ZAR per night

Guest favorite

Home in Lenox

4.93 out of 5 average rating, 208 reviews

Heart of Lenox Walk to Town Cozy Cottage!

Sep 12 – 19

R8,232 ZAR per night

Guest favorite

Tiny home in Chatham

4.99 out of 5 average rating, 182 reviews

Tiny House on 70 Private Acres in Hudson Valley

Sep 27 – Oct 4

R2,947 ZAR per night

Guest favorite

Loft in East Nassau

4.99 out of 5 average rating, 153 reviews

Dog Friendly Farm Spring bird watching

Aug 29 – Sep 5

R3,077 ZAR per night

Guest favorite

Cottage in West Stockbridge

4.98 out of 5 average rating, 107 reviews

Historic 1810 Farmhouse - Fully Renovated

Jul 19 – 26

R6,653 ZAR per night

Show all

Other great vacation rentals in Lenox

Guest favorite

Guesthouse in Stephentown

5.0 out of 5 average rating, 360 reviews

Dog Friendly Studio

Nov 24 – Dec 1

R3,676 ZAR per night

Superhost

Apartment in Lenox Dale

4.93 out of 5 average rating, 116 reviews

Charming 2BD apartment.

May 8 – 15

R2,814 ZAR per night

Guest favorite

Cottage in Great Barrington

4.98 out of 5 average rating, 126 reviews

Newly built cottage on working farm

Mar 8 – 15

R2,218 ZAR per night

Guest favorite

Guesthouse in Lenox

4.9 out of 5 average rating, 51 reviews

Lenox - Sunny cottage nestled in the garden

Dec 11 – 18

R2,414 ZAR per night

Guest favorite

Apartment in Canaan

5.0 out of 5 average rating, 86 reviews

Mountain View Getaway

Jan 11 – 18

R2,077 ZAR per night

Guest favorite

Guest suite in Great Barrington

5.0 out of 5 average rating, 45 reviews

Sweet 1-bedroom with salt water pool

Jun 8 – 15

R2,579 ZAR per night

Guest favorite

Home in Lee

5.0 out of 5 average rating, 35 reviews

GreenHouse

Sep 10 – 17

R2,755 ZAR per night

Guest favorite

Home in Becket

4.94 out of 5 average rating, 36 reviews

Nerd Preservation Sanctuary

Nov 14 – 21

R1,774 ZAR per night

Show all

Quick stats about vacation rentals in Lenox

Total rentals
240 properties
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
100 properties are a good fit for families
Total number of reviews
6.6K reviews
Nightly prices starting at
R192 ZAR before taxes and fees

Frequently Asked Questions

Are there pet-friendly vacation rentals in Lenox?
Four-legged friends are welcome in Lenox. Choose from more than 50 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Lenox?
Yes! Work meets play with ease at over 130 vacation rentals in Lenox featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Lenox vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 60 vacation homes with pools in Lenox, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Lenox have a gym?
Absolutely! We offer over 10 house rentals with a gym in Lenox. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly apartment rentals in Lenox?
Lenox has more than 10 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Lenox have a bbq area?
Absolutely! We offer over 40 house rentals with a bbq area in Lenox. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in hotel rentals in Lenox?
Experience the best of Lenox with our hotel rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do hotel rentals in Lenox have wifi?
Absolutely! We offer over 40 hotel rentals with wifi in Lenox. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Lenox have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Lenox. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Lenox?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with a bbq area, over 80 homes with wifi, over 70 homes with air conditioning, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

Lenox vacation rentals

Top-rated vacation rentals in Lenox

Vacation rentals for every style

Apartments

Houses

Hotels

Popular amenities for Lenox vacation rentals

Stay near Lenox's top sights

Other great vacation rentals in Lenox

Home in Dalton

Home in Lenox

Home in Canaan

Guest suite in Valatie

Home in Lenox

Tiny home in Chatham

Loft in East Nassau

Cottage in West Stockbridge

Other great vacation rentals in Lenox

Guesthouse in Stephentown

Apartment in Lenox Dale

Cottage in Great Barrington

Guesthouse in Lenox

Apartment in Canaan

Guest suite in Great Barrington

Home in Lee

Home in Becket

Quick stats about vacation rentals in Lenox

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there pet-friendly vacation rentals in Lenox?

Are there vacation rentals with a dedicated workspace in Lenox?

Are there Lenox vacation rentals on Airbnb with pools?

Do house rentals in Lenox have a gym?

Are there family-friendly apartment rentals in Lenox?

Do house rentals in Lenox have a bbq area?

How much does it cost to stay in hotel rentals in Lenox?

Do hotel rentals in Lenox have wifi?

Do apartment rentals in Lenox have air conditioning?

What are the most popular amenities for House Rentals in Lenox?

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