Lenox Holiday Rentals

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Holiday Rentals in Lenox

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (16)
"We were a big group..16 adults and 7 children. The families with children were well situated with nearby or adjacent rooms. Everyone had comfortable rooms which afforded privacy and quiet times. Each room had its own beautiful newly renovated bathrooms ( with great water pressure). The living and dining rooms were large and comfortable. The dining table was a loooong table with benches all around which easily sat our crowd. The backyard was gorgeous with beautiful views of the distant mountains....
The Kemble- Built by a US Secretary of State in Lenox

Amore Estate - beautiful room with many places to explore and relax in.

9.4 out of 10, Exceptional, (21)
"Fantastic, large house with tons of places to explore in the house and on the property. We came for a long weekend with 3 families and both the adults and kids felt quickly at home and really enjoyed our stay. We cannot wait to some back!"
Amore Estate - beautiful room with many places to explore and relax in.

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (40)
"We have stayed here twice and it is a great spot, located a few minute drive north of downtown Lenox. The house is cozy yet spacious and is great for our family to stay in while visiting family in the area. We used the kitchen to cook a meal during one of the stays and we had everything we needed. There is an air hockey table in the basement which the kids enjoyed. The house is on a main road, but it was still easy enough to pull in and out of and the noise of the road did not bother us at all....
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1757)
"It had a great pool and hot tub. also right near the ski area, jiminey Peak."
The price is NZ$380
includes taxes & fees
26 Jan - 27 Jan
Vacation Village in the Berkshires

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (33)
"We had a wonderful stay for our mother’s birthday with her 4 children and 10 of her 12 grandchildren. There was plenty to do for everyone especially with a 75 year difference in ages!!"
The Freeman - Newly Renovated 14K SF Estate on 40 Acres

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods

Peace and quiet on the lake

9.6 out of 10, Exceptional, (203)
"The house was great with plenty to do in the area. It was warm, comfortable, and just what we were looking for a quick weekend away. Would definitely return.Thanks,-Mike"
Peace and quiet on the lake

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (209)
"The Cabin Had All The Amenities You Would Need and With A Quiet and Serene Area. For Me It Was Relaxing Stay!"
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (235)
"Very lovely place to stay. Everything was clean and the owner made everything simple."
The price is NZ$399
includes taxes & fees
26 Jan - 27 Jan
Berkshire Village Carriage House - Super Private!!

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (923)
"Staff was exceptionally helpful and friendly."
The price is NZ$365
includes taxes & fees
26 Jan - 27 Jan
Jiminy Peak Mountain Resort

Serene Acreage - Pond - Hiking Trails Nearby

10.0 out of 10, Exceptional, (6)
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby

Private Estate, Heated Yearround Outdoor Pool

10.0 out of 10, Exceptional, (15)
"We had a wonderful stay. Would most definitely book again! "
The price is NZ$5,825
includes taxes & fees
19 Feb - 20 Feb
Private Estate, Heated Yearround Outdoor Pool

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (42)
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Berkshires Cabin 2 Mi to Appalachian Trail!

9.8 out of 10, Exceptional, (11)
"The hosts were extremely responsive and helpful, providing us with hiking ideas, questions regarding the house and suggesting best shopping spots for incidentals. The living room was cozy, seating five comfortably. The kitchen was well stocked so cooking a Thanksgiving meal was a pleasure. We thoroughly enjoyed ourselves."
Berkshires Cabin 2 Mi to Appalachian Trail!

Berkshire Lake access

10.0 out of 10, Exceptional, (51)
"Very spacious yet comfy home. Joni is a very kind compassionate person to communicate with. We would definitely not hesitate to reserve this home again. "
Berkshire Lake access

Beautiful Estate w/pool, gym, pond, trails, arcade! Perfect for family/friends!

9.6 out of 10, Exceptional, (85)
"We had fun! Game room great! Spacious and comfortable. Never got to enjoy outdoors, so maybe another trip in the future!"
Beautiful Estate w/pool, gym, pond, trails, arcade! Perfect for family/friends!

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"Beautiful, well-stocked home with a lovely lake view. "
Quintessential 6-BR Berkshires Lodge

The Meadows House @ Otis Ridge w/ 7-person hot tub

9.8 out of 10, Exceptional, (26)
"We enjoyed it! Five of us stayed for a quiet weekend away. The house was clean, comfortable, and as advertised. There was plenty of space and beds for us to use. The hot tub was great. I would definitely recommend it to others! "
The Meadows House @ Otis Ridge w/ 7-person hot tub

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"From beginning to end, could not have dreamed of a better island getaway, in the Berkshire’s none-the -less. Bill was a wonderful host. Very friendly, responsive and helpful. Super welcoming. The home was simple, quaint, and super cozy. Perfect for a nice long relaxing weekend for both the dogs and people. The views from the sun room were lovely. The deck/patio area had a beautiful view of the water. The fire pit was a nice perk in the evening. Surrounded by water, the place felt so private....
Private Island - Largest Fresh Water Reservoir in Mass....
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Lenox you may be interested in

Life House Berkshires

3.5 star property
9.0 out of 10, Wonderful, (479)
"I love this place! The staff is friendly, helpful and accommodating. The lobby and rooms are updated and gorgeous! There is an onsite bar and restaurant.Great location, minutes from restaurants and shopping (Lee Outlets, Marshall's and quaint boutiques)."
The price is NZ$190
includes taxes & fees
4 Feb - 5 Feb
Life House Berkshires

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1002)
"Had a great time at this hotel. The rooms are comfortable. The staff is very friendly. Ended up spending Friday and Saturday night hanging out in the bar in the hotel where Carl and George kept us entertained. We had a lot of unexpected fun (I’m not one to hang out in a bar but felt at home)"
The price is NZ$202
includes taxes & fees
2 Feb - 3 Feb
The Yankee, Trademark Collection by Wyndham

The Constance, The Whitlock, & The Dewey By The Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (423)
"Great location. Easy walk to restaurants "
The price is NZ$246
includes taxes & fees
28 Jan - 29 Jan
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I find a holiday rental in Lenox?

Yes, there are holiday rentals in Lenox close to The Bookstore, or you can select a more secluded option if you're looking for a relaxing stay. 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 are some of the best holiday rentals that Lenox has to offer?

Berkshire Village Carriage House - Super Private!!: This holiday home rental outside of Lenox is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind.

How many holiday rentals are there in Lenox?

With 46 Expedia holiday rentals, you're guaranteed 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 Pleasant Valley Wilderness Sanctuary, or simply take in cultural attractions like Shakespeare and Company and Tanglewood Music Center. While here, Lenox Mountain Reserve and Lenox Library are other places worth a visit.

What are holiday rentals like in Lenox?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Lenox. Holiday rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a family getaway.