A large white house with multiple chimneys, surrounded by lush greenery and trees.

Lenox Vacation Rentals

Dates

November 2026

December 2026

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Our top choices for Lenox vacation rentals

1. Berkshire Mountain Lodge

Pittsfield

Charline

AED 397 total

includes taxes & fees

6 Dec - 7 Dec

A living room with a sofa, armchairs, a coffee table, and a television.

2. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

AED 2,206 total

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with a dining area, built-in shelves, and a large window.

3. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Lenox

AED 1,112 total

includes taxes & fees

10 Nov - 11 Nov

4. Vacation Village in the Berkshires

Williamstown

Marcos

AED 370 total

includes taxes & fees

8 Nov - 9 Nov

A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

5. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

AED 2,257 total

includes taxes & fees

9 Nov - 10 Nov

A dining area with a wooden table, chairs, and a ceiling fan.

6. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

AED 1,106 total

includes taxes & fees

8 Nov - 9 Nov

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

7. Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

Eric H.

AED 1,083 total

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

8. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Dalton

Marcia O.

AED 1,106 total

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

9. NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

Joanna P.

AED 719 total

includes taxes & fees

8 Nov - 9 Nov

A sandy beach with a lake and forest in the background.

10. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Great Barrington

Kristin O.

AED 1,111 total

includes taxes & fees

8 Nov - 9 Nov

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

11. Cozy 1-bedroom studio in serene Great Barrington with AC

Great Barrington

bob i.

AED 425 total

includes taxes & fees

14 Nov - 15 Nov

A two-story house with a front porch, surrounded by a garden with various plants and rocks.

12. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge

Anonymous traveler

AED 3,028 total

includes taxes & fees

1 Dec - 2 Dec

A white two-story house with a porch, surrounded by trees and a hill.

13. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

Christine C.

AED 1,494 total

includes taxes & fees

9 Nov - 10 Nov

A spacious living room with a dining area, a kitchen, and a large window.

14. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

AED 778 total

includes taxes & fees

8 Nov - 9 Nov

A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

15. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Hinsdale

Kyle R.

AED 1,540 total

includes taxes & fees

10 Nov - 11 Nov

A cozy living room with a large window, wooden walls, and a television.

16. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Hancock

Maura D.

AED 781 total

includes taxes & fees

8 Nov - 9 Nov

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

17. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Brian C.

AED 1,312 total

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

18. Home in Great Barrington

Great Barrington

Janet G.

AED 1,186 total

includes taxes & fees

9 Nov - 10 Nov

A hot tub with a string of lights above it, set against a dark night sky.

19. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

Frank M.

AED 1,375 total

includes taxes & fees

8 Nov - 9 Nov

A bedroom with a wooden bed frame, a large window, and a painting of mountains on the wall.

20. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Hancock

patricia f.

AED 781 total

includes taxes & fees

8 Nov - 9 Nov

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Find vacation rentals that suit your style

Top Lenox Hotel Reviews

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

Devonfield Inn B&B

Lee

10/10 Excellent

Anonymous traveler

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

Brook Farm Inn

Lenox

10/10 Excellent

roberta

The Inn at Stockbridge

Stockbridge

10/10 Excellent

Kevin

A two-story building with a sign reading "Chambéry Inn".

Chambery Inn

Lee

10/10 Excellent

Elaine

A snow-covered outdoor area with a patio, seating, and a covered dining area.

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Excellent

Lawrence

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

10/10 Excellent

Sheila

Two Adirondack chairs facing a river with a forested hill in the background.

The Yankee Inn

Lenox

10/10 Excellent

We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!

Colleen

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

Courtyard by Marriott Lenox Berkshires

Lenox

10/10 Excellent

Alyssa

A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

Hilton Garden Inn Lenox Pittsfield

Pittsfield

10/10 Excellent

A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

South Lee

10/10 Excellent

I love this place and have stayed here before. Even with the precautions for COVID-19, my kids and I still had a great time. The check-in was smooth and safe. The room was clean and sanitized. In fact, we had to "break the seal" on the door to enter and the seal was evidence of the cleaning that was done. Of course, the arcade and movie theatre were closed, but that was no surprise. The pools were open and reservations required to ensure everyone could be safe and still have fun. Lots of...

David

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

Berkshires Untold

Lenox

10/10 Excellent

High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, there is a free bottle of still water but since it was not marked i wasn’t sure what it was or if it was free. There is a fun wardrobe with robes but no place but the floor to put your suit case. Oh...

Jill

Berkshire Mountain Lodge

Pittsfield

10/10 Excellent

Elliott

Quality Inn Lee - Lenox South

Lee

10/10 Excellent

Anonymous traveler

A large house with a covered patio area featuring outdoor seating and a fire pit.

The Whitlock

Lenox

10/10 Excellent

LOVED The Whitlock. Location, quality and vibe can't be beat. The outdoor gardens and patio were unexpected bonuses that are as cared for as the interior spaces. The restaurant menu was limited but the offerings were truly inspired and delicious (better than other restaurants we experienced during the trip). The bartender made a mean spicy margarita and was friendly and informed. The one low point was the complimentary continental bkfst that doesn't live up to other Whitlock experiences....

Jeff

A large, two-story building with a symmetrical facade, multiple windows, and a well-maintained lawn.

Gateways Inn & Restaurant

Lenox

10/10 Excellent

Richard

Frequently Asked Questions

Can I find a vacation rental in Lenox?

Yes, we offer vacation rentals in Lenox near Berkshire Scenic Railway Museum, or you can go with a more remote option if you're looking for extra privacy while you relax. The gardens and museums are just a few reasons why tourists like Lenox. The live music and entertainment venues are some other things you might like to check out during your trip.

What's the top vacation rental that Lenox has to offer?

Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++: This Lenox vacation home rental is located on a lake and has an indoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Lenox?

With 42 Expedia vacation rentals, you're sure to find just the right place for your Lenox stay.

What can I see and do in Lenox?

Enjoy the outdoors at The Mount and Lenox Mountain, or simply take in cultural attractions like Ventfort Hall Mansion and Gilded Age Museum and Shakespeare and Company. While here, Lenox Library and Tanglewood Music Center are other places worth a visit.

What are vacation rentals like in Lenox?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Lenox. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for families.

Lenox Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Lenox vacation rentals

1. Berkshire Mountain Lodge

2. Sun Filled Lenox Retreat - Minutes to Tanglewood!

3. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

4. Vacation Village in the Berkshires

5. Secluded Family Home in Serene Stockbridge Woods

6. Leaf-Peeper Paradise in the Berkshires

7. Sweet Cozy Victorian in Housatonic. Close to everything.

8. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

9. NEW RENO - Chalet-style farm loft near Tanglewood

10. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

11. Cozy 1-bedroom studio in serene Great Barrington with AC

12. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

13. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

14. 1800s Carriage house in Berkshires / Hudson Valley

15. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

16. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

17. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

18. Home in Great Barrington

19. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

20. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Find vacation rentals that suit your style

Top Lenox Hotel Reviews

Devonfield Inn B&B

10/10 Excellent

Frequently Asked Questions

Can I find a vacation rental in Lenox?

What's the top vacation rental that Lenox has to offer?

How many vacation rentals are there in Lenox?

What can I see and do in Lenox?

What are vacation rentals like in Lenox?