The 10 best holiday rentals in Lenox, USA | Booking.com
Skip to main content

Holiday Rentals in Lenox

Find the holiday rentals that appeal to you the most

Holiday Rentals for every style

Find the right holiday rental for you in Lenox

The best holiday rentals in Lenox

Check out our pick of great holiday rentals in Lenox

Show hotels on map

Filter by:

Review score

The Cornell Inn, Lenox & The Berkshires

Lenox

Located on four acres, this bed and breakfast features traditional exteriors and stunning, updated designer rooms and bathrooms which are all equipped with cable TV, high-speed internet, and coffee...

B
Beth
From
United States
We loved the kindness message and the staff was wonderful! Food was great and highly recommend taking a walk in Kennedy Park.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 562 reviews
Price from
US$138.88
1 night, 2 adults
Check availability

Brook Farm Inn

Lenox

Situated within 3 km of Tanglewood and 3.1 km of Cranwell Spa & Golf Club, Brook Farm Inn features rooms with air conditioning and a private bathroom in Lenox.

V
Virginie
From
United States
Beautifully arranged. A lot of details and love were put into this b&b. The breakfast was simple but absolutely delicious and homemade. We loved every minute of it. We will go back in summer
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 44 reviews
Price from
US$208.10
1 night, 2 adults
Check availability

The Constance by The Lenox Collection

Lenox

Set in Lenox, 2.4 km from Tanglewood Musical Center, The Constance by The Lenox Collection offers accommodation with a fitness centre, free private parking, a garden and a terrace.

C
Corinna
From
Germany
Beautiful hotel with lovely and very helpful staff
Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 498 reviews
Price from
US$183
1 night, 2 adults
Check availability

Whistler's Inn

Lenox

Boasting a garden and views of mountain, Whistler's Inn is a bed and breakfast set in a historic building in Lenox, 3 km from Tanglewood Musical Center.

J
Joanne
From
United States
Very welcoming and personable. Breakfast was fresh & delicious.
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 143 reviews
Price from
US$160.20
1 night, 2 adults
Check availability

Gateways Inn

Lenox

Located in Lenox and only 2.4 km from Cranwell Spa & Golf Club, Gateways Inn provides accommodation with quiet street views, free WiFi and free private parking.

C
Christopher
From
United Kingdom
Gateways was the perfect place for our stay. It's a beautiful old house in the heart of Lenox with friendly, caring staff who will ensure your stay is memorable. It exceeded expectations in every way.
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 18 reviews
Price from
US$208.95
1 night, 2 adults
Check availability

The Dewey by The Lenox Collection

Lenox

This bed and breakfast in the scenic Berkshires boasts uniquely styled guest rooms, each with a private bathroom. Hiking and bicycle trails in Kennedy Park are just 1 mile away.

A
Andrea
From
Austria
A beautiful night in a museum. The house is incredible and you can use all the areas. The room was very cozy, spacious and clean. loved it. Breakfast (besides the fresh blueberries) was nothing to remember but the feeling of staying in such a historical, well kept building made up for it 100%.
Scored out of 10, guest rating 6.9
Pleasant - What previous guests thought, 74 reviews
Price from
US$166
1 night, 2 adults
Check availability

Shaker Mill Inn

West Stockbridge (Near Lenox)

Set within 6.3 km of Tanglewood Musical Center and 6.6 km of Tanglewood, Shaker Mill Inn offers rooms with air conditioning and a private bathroom in West Stockbridge.

m
meira
From
Israel
Unbelievable clean, beautiful, and outstanding place. I am very particular re cleanliness in hotel rooms so I was amazed by this outstanding suite we got. Absolutely 💯 lovely greenery around. Big windows. Kitchenette equipped with numerous products one wouldn't expect at all in a B/B. In the hallway there is a big dvd library, box games and books. We ride 🏍 it was raining all day and night, the morning we left, there were 4 towels on the bike 🏍 just for drying it before we leave!
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 87 reviews
Price from
US$136
1 night, 2 adults
Check availability

Devonfield Inn

Lee (Near Lenox)

Situated just 6.1 km from Cranwell Spa & Golf Club, Devonfield Inn features accommodation in Lee with access to a garden, a shared lounge, as well as a shared kitchen.

L
Lesley- Ann
From
South Africa
We had the most wonderful time at this beautiful inn set in stunning surroundings and gardens. On our holiday this was the only place where we actually met and interacted with the owners , Doug and Jim. Our room was comfortable, clean and had everything we needed. Lovely leather chairs and decor. The bed was comfortable with nice linens. We were invited to the cheese and wine evening and it was great. Lovely wines and cheeses and a great way to meet other guests. We so enjoyed the piano and a few songs from Doug. Breakfast was a feast .. fruit, yogurts , eggs . Delicious and a different menu each morning. Home baked cakes .. yummy. Saturday we sat in the gardens and enjoyed a lovely afternoon of music , it was so nice to see locals join the afternoon too. We wish we could have stayed longer.. Doug and Jim you run a beautiful Inn, your commitment and hard-work tells the story. Thank you!
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 14 reviews
Price from
US$369
1 night, 2 adults
Check availability

Stockbridge Country Inn

Stockbridge (Near Lenox)

Featuring a garden and views of mountain, Stockbridge Country Inn is a bed and breakfast situated in a historic building in Stockbridge, 1.5 km from Norman Rockwell Museum.

L
Leslie
From
France
Very friendly owner and lovely country inn.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 12 reviews
Price from
US$309.47
1 night, 2 adults
Check availability

Chambery Inn

Lee (Near Lenox)

This historic Massachusetts bed and breakfast boasts free Wi-Fi access. Cable TV and an en suite bathroom are featured in every uniquely styled room. Ski Butternut is 13 miles away.

L
Lori
From
United States
Beautiful, huge room; stunning 4 poster bed w/ canopy.
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 36 reviews
Price from
US$249.99
1 night, 2 adults
Check availability
All holiday rentals in Lenox

Most booked holiday rentals in Lenox and surroundings in the past month

See all

These holiday rentals in Lenox and nearby have options with free cancellation

  • Chambery Inn

    Lee
    Free cancellation options available
    Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 36 reviews

    This historic Massachusetts bed and breakfast boasts free Wi-Fi access. Cable TV and an en suite bathroom are featured in every uniquely styled room. Ski Butternut is 13 miles away.

    From US$279.24 per night

  • Stockbridge Country Inn

    Stockbridge
    Free cancellation options available
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 12 reviews

    Featuring a garden and views of mountain, Stockbridge Country Inn is a bed and breakfast situated in a historic building in Stockbridge, 1.5 km from Norman Rockwell Museum.

    From US$499.57 per night

  • Berkshire Retreat- A stone's throw to downtown Lenox is located in Stockbridge, 6.4 km from Tanglewood Musical Center, 6.6 km from Tanglewood, as well as 11 km from Norman Rockwell Museum.

  • Stockbridge Home Walk to Town Beach!

    Stockbridge
    Free cancellation options available
    Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 3 reviews

    Stockbridge Home Walk to Town Beach! is situated in Stockbridge, 3.3 km from Tanglewood Musical Center, 3.6 km from Tanglewood, and 6.5 km from Norman Rockwell Museum.

  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 2 reviews

    Cozy Stockbridge Cabin - Walk to Beach and Lake! is set in Stockbridge, 4.7 km from Tanglewood Musical Center, 4.9 km from Tanglewood, and 5.1 km from Norman Rockwell Museum.

  • Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 3 reviews

    Situated 10 km from Tanglewood Musical Center, 10 km from Tanglewood and 10 km from Norman Rockwell Museum, Cordelia by AvantStay Amazing Backyard 10mins from Stockbridge features accommodation set in...

  • The Cottage

    Stockbridge
    Free cancellation options available
    Scored out of 10, guest rating 7.2
    Good - What previous guests thought, 57 reviews

    Situated in Stockbridge, 3.3 km from Norman Rockwell Museum, The Cottage has a private beach area, parking on-site and rooms with free WiFi access.

  • Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 2 reviews

    Situated in Stockbridge, 2.2 km from Norman Rockwell Museum and 8.5 km from Tanglewood Musical Center, Tranquil 3 BR Stockbridge House with Private Deck! offers air conditioning.

Highly rated holiday rentals in Lenox and nearby

  • Devonfield Inn

    Lee
    8.0+ review score
    Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 14 reviews

    Situated just 6.1 km from Cranwell Spa & Golf Club, Devonfield Inn features accommodation in Lee with access to a garden, a shared lounge, as well as a shared kitchen.

    From US$568.55 per night
  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 87 reviews

    Set within 6.3 km of Tanglewood Musical Center and 6.6 km of Tanglewood, Shaker Mill Inn offers rooms with air conditioning and a private bathroom in West Stockbridge.

    From US$251.33 per night

Enjoy breakfast in Lenox and nearby

Holiday rentals that guests love in Lenox

See all

  • Brook Farm Inn

    Holiday Rental in Lenox
    Avg. price/night: US$478.12
    Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 44 reviews
    Joe and Maureen were excellent hosts. The property is beautiful and very close to the village center (3 minutes by car). The cookies and fudge left for guests were wonderful and the breakfast was delicious!
    Guest review by
    Yania
    Family with young children

Research, refine and make plans for your whole trip

Hotels near Jiminy Peak Mountain Resort

Search and compare hotels close to Jiminy Peak Mountain Resort, a popular destination just outside Lenox.

Hotels near Empire State Plaza Convention Center

Hotels close to a popular local landmark.

Holiday Rentals in New York

Discover another destination in the United States.

Holiday Rentals in Las Vegas

Discover another destination in the United States.

Hotels in Lenox

More great accommodation options for your trip.

Hotels with Parking in Lenox

More great accommodation options for your trip.

Family Hotels in Lenox

Explore more great accommodation options in Lenox, starting with family hotels.

Cheap hotels in Lenox

More great accommodation options for your trip.

Accessible Hotels in Lenox

More great accommodation options for your trip.