Lenox Holiday Rentals

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Holiday Rentals in Lenox

Fridge, microwave, oven, stovetop
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, (12)
"Generous facility, nicely located, accommodating host."
Fox Hollow Luxury Ranch Laurel Lake
Exterior
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (15)
"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
Exterior
The Winthrop Estate - 12K SF 32 Acres
10.0 out of 10, Exceptional, (2)
"Absolutely stunning property - truly incredible stay. Recommend to anyone looking for a large group getaway. Fast WiFi, commercial grade kitchen and plentiful supplies make it easy for large groups. beautiful property and room for activities on a huge lawn. Highly recommend."
The price is NZ$7,539
per night
13 Jun - 14 Jun
The Winthrop Estate - 12K SF 32 Acres
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Private kitchen
Amore Estate - sleeps 12 in beds
9.6 out of 10, Exceptional, (8)
"Great space for a group of friends! House has a lot of character. Beautiful property and great location! Easy access to downtown Lenox and surrounding area. We really enjoyed our stay!"
Amore Estate - sleeps 12 in beds
Property entrance
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (857)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is NZ$264
per night
23 May - 24 May
Jiminy Peak Mountain Resort
7 bedrooms, iron/ironing board, cots/infant beds, travel cot
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (183)
"We rented the house to celebrate mom’s 70th birthday. We wanted a quiet, simple place where we could spend time together, visit, and spend time outdoors. That’s exactly what we got. We all fished and kayaked and enjoyed the peaceful scenery. Thank you."
Peace and quiet on the lake
Interior
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Fridge, microwave, oven, stovetop
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (7)
"My wife and young daughters live in central CT, and the drive to Becket was both scenic and relatively short at around an hour and a half. The property offers great privacy in a remote wooded setting in the heart of the always beautiful Berkshires. We brought our dog along, and we all were able to relax by the fire, read our favorite books, as well as peruse interesting titles on the impressive bookshelf built into the living room wall—a book lover’s delight. We admired the openness and light...
Pristine Home In Becket Woods
Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (195)
"We’ve stayed at the cabin with our dog four times and always enjoy our peaceful stay. It’s cozy, clean and private. Also, the Sherwood Shoppe - just down the road - is a wonderful place for breakfast, homemade chili and much more."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Fridge, microwave, oven, stovetop
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, (2)
"Be aware they will not proactively provide you with a local host name or contact info. It was very difficult to get Vacasa support to help me get this info to resolve wifi issue - like hours long to get them to just give me the property managers info and even then, they wouldn't give it to me, just had them contact me. Otherwise, amazing pool and great location. Outdated indoors but clean to the extent that it could be. Utensils were dirty and tons of flies in the house upon arrival - like 50...
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Property grounds
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (4)
"Perfect place to relax and have dogs as part of a mini vacation. Very clean, organized, and provided helpful local information. Will definitely stay there again."
Serene Acreage - Pond - Hiking Trails Nearby
Fridge, microwave, oven, stovetop
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (8)
"The pictures simply do not do this place justice, it’s an incredible home. Our friend group was cozy all weekend! We loved the hot tub/pool, the really interesting artwork, the driving range mat and basketball hoop. Plenty of towels and kitchen supplies. The in law apartment (which we didn’t use as sadly part of our group was unable to join us) is attached to the main home and is so cute. We had a small issue upon arrival and the hosts were immediately responsive with us troubleshooting and...
Private Estate, Heated YEARROUND Outdoor Pool
TV, fireplace, DVD player, books
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
"This house was the perfect get away house for out family! The place was clean and the kitchen well stocked! We had wonderful large family dinners and enjoyed heading into town for meals and fun too. We had the best hikes with are wonderful dog that we got to include, it was a very special week. Great location and the most peaceful and amazing views from the deck and the dock. Would stay here again for sure! Thank you for sharing your home."
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (203)
"Very clean, tastefully decorated place perfect for our weekend getaway for two. Enjoyed the reading nooks and kitchen amenities, comfortable bed and peacefulness of this carriage house!"
Berkshire Village Carriage House - Super Private!!
Interior
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (6)
"My wife and I were looking for a nice little getaway within reasonable driving distance and came across this great property. As soon as we saw the big windows in the living room we were sold. Definitely getting added to our short list of places to go back to."
Berkshires Cabin 2 Mi to Appalachian Trail!
Exterior
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, (4)
"We had a great time. Place is amazing. Highly recommend. We had four different families and we never felt cramped. Lovely open main room allowed us to stay connected. Bedrooms were nice and spacious, good bed options. Nice decor."
Quintessential 6-BR Berkshires Lodge
Interior
Rockspring by AvantStay | Huge Berkshires Estate
8.8 out of 10, Excellent, (10)
"We stayed with friends and family and had plenty of room. The separate game room is great! The house was as pictured and described. It is close to a few ski mountains and Great Barrington. We would happily stay at RockSpring or a different AvantStay again!"
Rockspring by AvantStay | Huge Berkshires Estate
Lake
Berkshire Lake access
10.0 out of 10, Exceptional, (41)
"Living space is bigger than the pictures, plenty of room for everyone, well stocked kitchen, everything we needed!"
Berkshire Lake access
Outdoor dining
Moose Lodge by AvantStay | Luxe Berkshires Escape
10.0 out of 10, Exceptional, (11)
"We had a wonderful time at the Moose Lodge. It was perfect for our family. Very clean, everything we needed and the property managers were extremely communicative. Thank you!"
Moose Lodge by AvantStay | Luxe Berkshires Escape
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See all available properties in Lenox
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.

Other types of properties in Lenox you may be interested in

Lobby
Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, (240)
"Lovely room and bar"
The price is NZ$180
per night
28 May - 29 May
Life House Berkshires
Front of property
The Lenox Collection
3.5 star property
8.6 out of 10, Excellent, (202)
"Everyone was very nice. We only wished the breakfast started at 7:30. "
The price is NZ$178
per night
3 Jun - 4 Jun
The Lenox Collection
Exterior
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1003)
"Room was very clean. Staff was helpful and available. "
The price is NZ$189
per night
20 May - 21 May
The Yankee, Trademark Collection by Wyndham
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Lenox holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Lenox. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Lenox. Seeing all the best attractions is bound to make you fall in love with Lenox. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Lenox short-term rentals, that won’t be hard to do.

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?

Fox Hollow Luxury Ranch Laurel Lake: This highly rated holiday home rental in Lenox is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Lenox?

With 45 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 Kennedy Park, or simply take in cultural attractions like Ventfort Hall Mansion and Gilded Age Museum and Shakespeare and Company. While here, Tanglewood Music Center and Wyndhurst Golf & Club 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.

Recent reviews of Lenox properties
Expedia verified reviews