Lenox Holiday Rentals

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Holiday Rentals in Lenox

The Ponds at Foxhollow
3.0 star property
8.6 out of 10, Excellent, (132)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
United States
michelle
The Ponds at Foxhollow
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
United States
Stephanie R.
The Kemble- Built by a US Secretary of State in Lenox
Amore Estate - beautiful room with many places to explore and relax in.
9.2 out of 10, Wonderful, (31)
"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."
United States
Jacquie S.
Amore Estate - beautiful room with many places to explore and relax in.
Tranquil Lakeside Escape in the Berkshires
10.0 out of 10, Exceptional, (1)
"perfect location to go everywhere in the Berkshires"
United States
Edward G.
Tranquil Lakeside Escape in the Berkshires
Enjoy comfortable elegance in this secluded grand home located in town
10.0 out of 10, Exceptional, (75)
"We stayed for a weekend at this beautiful home. It was very clean, and a perfect location - walking distance to Lenox and a very short drive toTanglewood. We really enjoyed our stay! "
United States
lindsramm
Enjoy comfortable elegance in this secluded grand home located in town
Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2093)
"Great place!"
United States
Nicole
The price is AU$174
includes taxes & fees
2 Nov - 3 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (983)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
The price is AU$240
includes taxes & fees
26 Oct - 27 Oct
Jiminy Peak Mountain Resort
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
Huttopia Berkshires
Taborton Harvest Boulder Pines Cabin in the woods
10.0 out of 10, Exceptional, (12)
"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 AU$286
includes taxes & fees
28 Oct - 29 Oct
Taborton Harvest Boulder Pines Cabin in the woods
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
9.0 out of 10, Wonderful, (2)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AU$401
includes taxes & fees
3 Nov - 4 Nov
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
Spacious 5-bedroom house in charming Lee with WiFi
8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is AU$1,114
includes taxes & fees
29 Oct - 30 Oct
Spacious 5-bedroom house in charming Lee with WiFi
Spacious 6BR Near Jiminy Peak – Hot Tub, Game Room & Ski Lift Ticket Discount
10.0 out of 10, Exceptional, (15)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is AU$1,731
includes taxes & fees
28 Oct - 29 Oct
Spacious 6BR Near Jiminy Peak – Hot Tub, Game Room & Ski Lift Ticket Discount
Peace and quiet on the lake
9.6 out of 10, Exceptional, (226)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
United States
Anika J.
Peace and quiet on the lake
Comfortable Berkshires retreat on mtn resort, SISO
8.8 out of 10, Excellent, (6)
"Kind and responsive host."
United States
Javier
The price is AU$761
includes taxes & fees
23 Oct - 24 Oct
Comfortable Berkshires retreat on mtn resort, SISO
Amazing Estate! Ring in the New Year at Bellavista Country Estate! NYE now open!
9.6 out of 10, Exceptional, (93)
"What a lovely property. Laurie was so kind and helpful checking us in, and the house was so fun. Would absolutely stay here again. "
United States
Daniel R.
Amazing Estate! Ring in the New Year at Bellavista Country Estate! NYE now open!
Taborton Harvest Timber Trails Unique cabin experience
10.0 out of 10, Exceptional, (1)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
United States
Georgia M.
The price is AU$284
includes taxes & fees
6 Nov - 7 Nov
Taborton Harvest Timber Trails Unique cabin experience
Charming 3-bedroom Cabin for nature lovers
7.0 out of 10, Good, (2)
"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...
United States
John O.
The price is AU$458
includes taxes & fees
23 Oct - 24 Oct
Charming 3-bedroom Cabin for nature lovers
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
9.8 out of 10, Exceptional, (19)
"Very friendly hosts, great location. "
United States
Dan M.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
The Lakeshore House
10.0 out of 10, Exceptional, (1)
"Excellent stay!"
United States
KEITARO A.
The price is AU$1,226
includes taxes & fees
3 Nov - 4 Nov
The Lakeshore House
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
9.8 out of 10, Exceptional, (70)
"Beautiful location, very spacious, comfortable and clean."
United States
Aubrey G.
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near 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.
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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 favourite 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 depend 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 AU$174 per night. Entering your travel dates in the search wizard might find you 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 Housatonic River, 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.