Lenox Holiday Rentals

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Our top choices for Lenox holiday rentals

9.4 out of 10, Exceptional, (3)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is NZ$783
includes taxes & fees
5 Jan - 6 Jan 2026
Sun Filled Lenox Retreat - Minutes to Tanglewood!
8.0 out of 10, Very good, (2)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is NZ$1,676
includes taxes & fees
12 Jan - 13 Jan 2026
Spacious 5-bedroom house in charming Lee with WiFi
2.0 out of 10, (1)
"THIS. PLACE. IS. A. DUMP. Do NOT STAY HERE under any circumstances."
United States
Michael
The price is NZ$350
includes taxes & fees
8 Jan - 9 Jan 2026
Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Camping in Williamstown

Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is NZ$387
includes taxes & fees
25 Jan - 26 Jan 2026
Huttopia Berkshires
10.0 out of 10, Exceptional, (9)
"Huny House was the most artistically created space we stayed in on our entire trip! We were sooo impressed and appreciated the attention to detail!"
Canada
Patti S.
HunnyHAUS: Deluxe TINY*private spa*walk to town
2.0 star property
10.0 out of 10, Exceptional, (3)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is NZ$641
includes taxes & fees
12 Jan - 13 Jan 2026
Sugar Shack - 300 square feet of pure sweetness.
3.0 star property
8.8 out of 10, Excellent, (2184)
"Awesome for ski"
United States
Lazar
The price is NZ$218
includes taxes & fees
25 Jan - 26 Jan 2026
Vacation Village in the Berkshires

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (987)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is NZ$411
includes taxes & fees
26 Jan - 27 Jan 2026
Jiminy Peak Mountain Resort
The price is NZ$591
includes taxes & fees
12 Jan - 13 Jan 2026
3-bedroom house in beautiful Berkshires, close to amenities!
9.4 out of 10, Exceptional, (40)
"It’s a nice comfortable apartment with a good kitchen. We were traveling to see a concert and some art at Mass MOCA. Patrick is a friendly and welcoming host."
United States
Roy
The price is NZ$356
includes taxes & fees
2 Jan - 3 Jan 2026
Charming Apt in 18th c Berkshire Farmhouse
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is NZ$418
includes taxes & fees
3 Jan - 4 Jan 2026
Berkshires Apartment at the Stephentown Hotel
2.0 star property
9.6 out of 10, Exceptional, (13)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
The price is NZ$419
includes taxes & fees
2 Jan - 3 Jan 2026
Penthouse Apartment on Park Street
9.8 out of 10, Exceptional, (35)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
The price is NZ$814
includes taxes & fees
7 Jan - 8 Jan 2026
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is NZ$640
includes taxes & fees
5 Jan - 6 Jan 2026
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is NZ$672
includes taxes & fees
5 Jan - 6 Jan 2026
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
10.0 out of 10, Exceptional, (2)
"Cozy home on the lake."
United States
Terry O.
The price is NZ$661
includes taxes & fees
28 Dec - 29 Dec
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
7.0 out of 10, Good, (2)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
The price is NZ$547
includes taxes & fees
28 Dec - 29 Dec
Charming 3-bedroom Cabin for nature lovers
10.0 out of 10, Exceptional, (13)
"Loved the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven "
United States
Joanna R.
The price is NZ$314
includes taxes & fees
28 Dec - 29 Dec
Taborton Harvest Boulder Pines Cabin in the woods
10.0 out of 10, Exceptional, (1)
"Beautiful house! It was a big house and we loved all the rooms and how they were decorated! When we first arrived the heat wasn’t working and the host had someone there with the half hour fixing the problem. Beautiful quite area as well "
United States
Gabrielle T.
The price is NZ$1,922
includes taxes & fees
19 Jan - 20 Jan 2026
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
10.0 out of 10, Exceptional, (3)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is NZ$2,274
includes taxes & fees
4 Jan - 5 Jan 2026
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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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Top Lenox Hotel Reviews

Find out more about Lenox

Everything you need to know about Lenox holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Lenox holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Lenox holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Lenox holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Lenox. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Lenox holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Lenox holiday rentals we have selected for you start as low as NZ$218 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Lenox rentals

At Expedia, we put the best Lenox holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Lenox rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Lenox holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Lenox. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Amore Estate - beautiful room with many places to explore and relax in.: This highly rated holiday home rental in Lenox offers an outdoor pool, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Lenox?

With 42 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 Shakespeare and Company and Tanglewood Music Center. While here, Lenox Library 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.