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, (120)
"Very comfortable property in a lovely setting "
The price is NZ$420
includes taxes & fees
9 May - 10 May
The Ponds at Foxhollow

Imagine Being Lakeside This Summer! Book Now!

10.0 out of 10, Exceptional, (14)
"Enjoyed the property."
Imagine Being Lakeside This Summer! Book Now!

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

10.0 out of 10, Exceptional, (17)
"Perfect house for our family reunion. Everything was perfect."
The Kemble- Built by a US Secretary of State in Lenox

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.6 out of 10, Exceptional, (42)
"Absolutely no complaints. Great place to stay, great host! Happy 2025 wishes from our family to everyone reading this post! "
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

10.0 out of 10, Exceptional, (1)
"My friends and I stayed at this adorable and HUGE home in this lovely condo complex to spend the weekend at Ski Butternut which was only like 10 minutes away. The host even left us 2 bottles of wine! It had FIVE bathrooms which is unheard of, like anywhere, and the beds were the fancy adjustable kinds. TVs and cable in every bedroom. The fireplace was so luxurious. When the living room TV was giving us some connection issues I think it was a total of like 7 minutes to contact the host/co-host...
Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (65)
"Great location for access to both Tanglewood and Lenox center. "
Enjoy comfortable elegance in this secluded grand home located in town

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (70)
"Going to the Berkshires this is a great place to stay. It is within walking distance to over 8 restaurants in downtown Lenox. Great gas stove and comfortable bed. Owner makes sure your stay is great. Would stay here again. "
Heart of Lenox Walk to Town Cozy Cottage!

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1800)
"Great property"
The price is NZ$210
includes taxes & fees
6 May - 7 May
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (928)
"Staff was exceptionally helpful and friendly."
The price is NZ$251
includes taxes & fees
29 Apr - 30 Apr
Jiminy Peak Mountain Resort

Deluxe Queen Room with 2 Queen Beds

2.0 star property
The price is NZ$242
includes taxes & fees
29 Apr - 30 Apr
Deluxe Queen Room with 2 Queen Beds

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (61)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (43)
"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!

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (187)
"Wonderful getaway, lovely hosts, great location, overall a fabulous place to relax and recharge. "
The Clearing - Quiet - Close To Nature

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (14)
"Near Jacob's Pillow!"
Pristine Home In Becket Woods

Lakeside Oasis Just You, The Lake & The View!

9.8 out of 10, Exceptional, (70)
"Perfect location for a peaceful, scenic vacation."
Lakeside Oasis Just You, The Lake & The View!

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

9.8 out of 10, Exceptional, (28)
"We had a great time staying at Lars place. The hot tub was very relaxing and the location was just what we were looking for to get away for a few days."
The Meadows House @ Otis Ridge w/ 7-person hot tub

Near Tanglewood: Historic Summer Retreat

9.4 out of 10, Exceptional, (20)
"Beautiful house in a quiet location. Perfect for our trip to go see The Norman Rockwell museum , Stockbridge Christmas holiday lights only about 25 minutes away. "
Near Tanglewood: Historic Summer Retreat

Comfortable Berkshires retreat on mtn resort, SISO

10.0 out of 10, Exceptional, (3)
"Hosts were very responsiveHouse was clean and well maintainedExcellent locationOverall great stay"
The price is NZ$809
includes taxes & fees
29 Apr - 30 Apr
Comfortable Berkshires retreat on mtn resort, SISO

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (9)
"Lots of cozy relaxation by the fire and fun meals at the spacious dinning table. We had plenty of room to spread out and enjoy ourselves. "
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Very kinda hosts, and wonderful house."
The price is NZ$1,735
includes taxes & fees
29 Apr - 30 Apr
Hancock Village Inn at Jiminy Peak
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

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (573)
"Excellent stay at this beautiful property!"
The price is NZ$193
includes taxes & fees
8 May - 9 May
Berkshires Untold

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1002)
"Friendly staff , nice room and great view."
The price is NZ$192
includes taxes & fees
29 Apr - 30 Apr
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, (442)
"Lovely location!"
The price is NZ$142
includes taxes & fees
1 May - 2 May
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?

Private Access To Laurel Lake, Enjoy Lake Life: This highly rated holiday home rental in Lenox is located near the beach, and has a fireplace, a balcony 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. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Lenox?

With 44 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.