Lenox Vacation Home Rentals from CA $86: Search Top Private Vacation Homes for Rent

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Find vacation rentals that suit your style

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Lenox vacation homes

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

1. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

CA $853 total

includes taxes & fees

Nov 9 - Nov 10

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

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

New Lebanon

Joanna P.

CA $275 total

includes taxes & fees

Nov 9 - Nov 10

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

3. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

CA $298 total

includes taxes & fees

Nov 9 - Nov 10

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

4. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

CA $868 total

includes taxes & fees

Nov 9 - Nov 10

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

5. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

Christine C.

CA $560 total

includes taxes & fees

Nov 9 - Nov 10

A dining area with a wooden table, black chairs, and a vase with green plants.

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

Housatonic

Eric H.

CA $417 total

includes taxes & fees

Nov 9 - Nov 10

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

7. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

CA $425 total

includes taxes & fees

Nov 9 - Nov 10

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

8. Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

William C B.

CA $406 total

includes taxes & fees

Nov 12 - Nov 13

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

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

Stockbridge

Anonymous traveller

CA $1,165 total

includes taxes & fees

Dec 1 - Dec 2

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.

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

Sherwood Forest

Brian C.

CA $508 total

includes taxes & fees

Nov 9 - Nov 10

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

11. Home in Great Barrington

Great Barrington

Janet G.

CA $456 total

includes taxes & fees

Nov 9 - Nov 10

A modern living room with a sectional sofa, wooden beams, a large window, and a view of the outdoors.

12. Beautiful and Private Home Centrally Located in the Berkshires

West Stockbridge

CA $1,789 total

includes taxes & fees

Nov 16 - Nov 17

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

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

Sherwood Forest

Frank M.

CA $532 total

includes taxes & fees

Nov 15 - Nov 16

A wooden deck with a table and chairs, surrounded by a white railing.

14. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Stephen L.

CA $668 total

includes taxes & fees

Nov 10 - Nov 11

A cozy living room with a sofa, a fireplace, and large windows.

15. Luxury Barn Near Hudson With New Private Sauna

East Chatham

Michael T.

CA $955 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

16. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Stephentown

Robbie S.

CA $787 total

includes taxes & fees

Nov 9 - Nov 10

17. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

CA $730 total

includes taxes & fees

Nov 9 - Nov 10

A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

18. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington

Roberta

CA $1,772 total

includes taxes & fees

Nov 20 - Nov 21

A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

19. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington

Mary R.

CA $942 total

includes taxes & fees

Nov 16 - Nov 17

20. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham

Jess S.

CA $465 total

includes taxes & fees

Nov 9 - Nov 10

View all properties

Learn more about Lenox

Tucked in the Berkshires, Tanglewood's summer concerts attract music lovers who spread picnics across the lawn at sunset. Gilded Age mansions like The Mount and Ventfort Hall offer tours, while downtown's boutiques and farm-to-table restaurants welcome hikers in boots.

See all hotels in Lenox

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

Top reviews in Lenox

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

We stayed at the Devonfield Inn in mid-October during peak foliage season. The hotel is a wonderful historic home built in 1800 with much of its historic character preserved. Our hosts were so welcoming and made us feel at home. The room was very comfortable and breakfast was fantastic. In the morning, we got a special surprise to see a bear on the patio drinking from the fountain and robbing the bird feeder. Overall we highly recommend the Devonfield. We will definitely go back.

Lise

A crowded outdoor event with tents and people gathered in a grassy area.

Chambery Inn

Lee

10/10 Excellent

Val

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

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Excellent

Michael

A lodge with a large building and a dock by a lake, surrounded by forest.

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

10/10 Excellent

Laraib

A hotel patio with outdoor seating and a fire pit.

Hilton Garden Inn Lenox Pittsfield

Pittsfield

10/10 Excellent

Pete

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

Andrea

A spacious hotel lobby with multiple seating areas, large windows, and a television.

Hampton Inn & Suites Berkshires-Lenox

Lenox

10/10 Excellent

Smadar

A white house with a balcony, green shutters, and a front door with a decorative glass panel. There are two large flower pots on the steps.

Hampton Terrace Inn

Lenox

10/10 Excellent

Loved everything about the Hampton Terrace Inn...this is my second time staying here. The inn itself is comfortable and homey, the location is easy access to Tanglewood and many area attractions, we loved being able to come back from touring for a dip in the pool (open 24/7), our room was terrific, breakfasts were delicious and there was lots of choice, Stan was our genial host and he made sure that everything was to our satisfaction. I’ll be staying at this inn when I go back to the...

Ruth

Quality Inn Lee - Lenox South

Lee

10/10 Excellent

Dale

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

The Whitlock

Lenox

8/10 Good

We had a late arrival, which worked out with self checkout. Left the next morning after 9am, didn't see a single staff member during our whole stay, Was a bit of a challenge getting luggage up to the top floor without an elevator but we probably should have realized that when we booked. Nice property, nice big room with separate area for visiting. TV channel choices, which included streaming services, was excellent. Overall a good experience, just didn't see anyone there.

James

Lenox Vacation Rentals

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Lenox vacation homes

1. Sun Filled Lenox Retreat - Minutes to Tanglewood!

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

3. 1800s Carriage house in Berkshires / Hudson Valley

4. Secluded Family Home in Serene Stockbridge Woods

5. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

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

7. Leaf-Peeper Paradise in the Berkshires

8. Real Estate: Therapy - Lake, Laundry, Love it

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

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

11. Home in Great Barrington

12. Beautiful and Private Home Centrally Located in the Berkshires

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

14. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

15. Luxury Barn Near Hudson With New Private Sauna

16. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

17. Comfortable Berkshires retreat on mtn resort, SISO

18. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

19. Cozy. Clean. Free bagel shop. 3 Fireplaces.

20. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Learn more about Lenox

Top reviews in Lenox

Devonfield Inn B&B

10/10 Excellent

Explore a world of travel with Expedia