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 Ponds at Foxhollow

Private Access To Laurel Lake, Enjoy Lake Life

10.0 out of 10, Exceptional, (14)
"The property was better than advertised. Everything anyone could need was provided and we could not have hoped for a better experience. Very large home and could easily accomodate 8 people or more. The Berkshires are magical and this home was great for out time there."
Private Access To Laurel Lake, Enjoy Lake Life

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

10.0 out of 10, Exceptional, (1)
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)
"Beautiful home perfect for our multi-generational family. We loved the separate spaces and easy walk to the town center. We can’t wait to come back!"
Enjoy comfortable elegance in this secluded grand home located in town

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

9.0 out of 10, Wonderful, (23)
"The property is great for a group of people lots of bedrooms. Lots of sitting rooms. The kitchen is great for a culinary event - we had a private chef one night. The upstairs den was very cozy-It was a cold weekend with lots of snow- we didn’t want to leave the house !And close to Lenox -and Miraval spaWe would definitely come back next year. "
Amore Estate - beautiful room with many places to explore and relax in.

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (67)
"Tom’s cottage was the perfect place for us to stay to enjoy the new year in quiet Lenox. It was centrally located which made exploring town easy and convenient. The check in and out process was super simple and Tom made himself easily accessible throughout the stay. "
Heart of Lenox Walk to Town Cozy Cottage!

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, (1786)
"It was very nice. Had a kitchen and 2 tvs!"
The price is NZ$227
includes taxes & fees
13 Mar - 14 Mar
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (925)
"Staff was exceptionally helpful and friendly."
The price is NZ$286
includes taxes & fees
1 Apr - 2 Apr
Jiminy Peak Mountain Resort

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is NZ$397
includes taxes & fees
13 Mar - 14 Mar
Berkshire Village Carriage House - Super Private!!

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

Peace and quiet on the lake

9.6 out of 10, Exceptional, (210)
"This was a cozy tucked away location that seemed far away from everything which was exactly what we wanted. The host was extremely communicative before and during the stay. The house had fresh linens and towels as well as basic cleaning supplies. It was cozy for a wintery weekend in. We enjoyed snowshoeing on the frozen lake! Pet-friendly was a huge plus! "
Peace and quiet on the lake

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (139)
"We have stayed at this property twice before and have been very pleased with the amount of bedrooms and sleeping available. The property is always very clean and is equipped with everything you need for cooking and dining.the property is a half way point for family members in several directions. "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
The price is NZ$1,857
includes taxes & fees
18 Mar - 19 Mar
Hancock Village Inn at Jiminy Peak

Private Estate, Heated Yearround Outdoor Pool

9.8 out of 10, Exceptional, (17)
"The home was beautiful and it was a gorgeous property too. It had all the right amenities in the kitchen. "
Private Estate, Heated Yearround Outdoor Pool

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

9.6 out of 10, Exceptional, (7)
"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!

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (14)
"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

BEAUTIFUL ESTATE! POOL, POND, ARCADE, GYM, TRAILS, BARN! ASK ABOUT REDUCED RATES

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! POOL, POND, ARCADE, GYM, TRAILS, BARN! ASK ABOUT REDUCED RATES

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!

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (19)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is NZ$621
includes taxes & fees
13 Mar - 14 Mar
Near Tanglewood: Historic Summer Retreat
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
9.2 out of 10, Wonderful, (522)
" I’ve place , clean, great bar and restaurant "
The price is NZ$189
includes taxes & fees
25 Mar - 26 Mar
Life House Berkshires

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1002)
"Excellent price point. Clean spacious room."
The price is NZ$164
includes taxes & fees
19 Mar - 20 Mar
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, (435)
"Lovely inn. Clean and friendly staff. Centrally located. Short walk to center of Lenox and to Tanglewood."
The price is NZ$162
includes taxes & fees
1 Apr - 2 Apr
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?

Enjoy comfortable elegance in this secluded grand home located in town: This highly rated holiday home rental in Lenox is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 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 garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Some other homes for rent in Lenox include Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate and Private Access To Laurel Lake, Enjoy Lake Life.

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 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.