A town hall with a central dome and columns, surrounded by trees and people.

Lenox Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Lenox vacation rentals

Lobby

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,151 reviews)
"Clean & comfortable stay"
United States
Robert
The price is AED 292
AED 409 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
Smart TV, books

2. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Lenox
The price is AED 826
AED 1,165 total
includes taxes & fees
24 Sep - 25 Sep
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
4 bedrooms, travel crib, WiFi, bed sheets

3. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
The price is AED 1,868
AED 3,206 total
includes taxes & fees
18 Oct - 19 Oct
Stylish Mid-century Modern Berkshires Cape
Lobby

4. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,668 reviews)
"Love this place for a weekend getaway."
United States
Jacob
The price is AED 349
AED 431 total
includes taxes & fees
27 Sep - 28 Sep
Vacation Village in the Berkshires
Exterior

5. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (40 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveler
The price is AED 1,690
AED 3,143 total
includes taxes & fees
28 Sep - 29 Sep
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
TV

6. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is AED 1,054
AED 2,143 total
includes taxes & fees
28 Sep - 29 Sep
Treetop Hideaway in Tyringham
Miscellaneous

7. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is AED 1,157
AED 2,603 total
includes taxes & fees
28 Sep - 29 Sep
Ellie’s Overlook, best view in the Berkshires!
Interior

8. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (26 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is AED 744
AED 1,163 total
includes taxes & fees
25 Sep - 26 Sep
Riverside Retreat in the Berkshires
Property grounds

9. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (39 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
The price is AED 840
AED 1,849 total
includes taxes & fees
24 Sep - 25 Sep
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
3 bedrooms, iron/ironing board, WiFi, bed sheets

10. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is AED 1,554
AED 2,687 total
includes taxes & fees
28 Sep - 29 Sep
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Outdoor spa tub

11. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AED 588
AED 1,445 total
includes taxes & fees
29 Sep - 30 Sep
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
TV, fireplace, printers

12. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"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 AED 2,079
AED 4,661 total
includes taxes & fees
24 Sep - 25 Sep
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Beach nearby, sun loungers, beach towels

13. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is AED 768
AED 1,206 total
includes taxes & fees
28 Sep - 29 Sep
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Interior

14. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 536
AED 1,374 total
includes taxes & fees
28 Sep - 29 Sep
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Outdoor dining

15. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
10.0 out of 10, Exceptional, (1 review)
"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...
United States
hannah w.
The price is AED 582
AED 740 total
includes taxes & fees
5 Oct - 6 Oct
Cozy Camper tucked into the woods
Coffee/tea maker, fridge, microwave, oven

16. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is AED 813
AED 1,216 total
includes taxes & fees
24 Sep - 25 Sep
Home in Great Barrington
Outdoor dining

17. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (7 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveler
The price is AED 911
AED 1,970 total
includes taxes & fees
29 Sep - 30 Sep
NEW RENO Historic Creamery in Berkshires w/hot tub
Outdoor dining

18. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is AED 2,310
AED 4,027 total
includes taxes & fees
29 Sep - 30 Sep
Hancock Village Inn Near Jiminy Peak
House (3 Bedrooms) | Interior

19. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is AED 823
AED 2,035 total
includes taxes & fees
24 Sep - 25 Sep
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"Clean room comfortABLE"
Gary 3-night trip
Posted 8 hours ago
Berkshire Mountain Lodge

Frequently asked questions

Can I find a vacation rental in Lenox?

Yes, we offer vacation rentals in Lenox near Berkshire Scenic Railway Museum, or you can go with a more remote option if you're looking for extra privacy while you relax. 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's the top vacation rental that Lenox has to offer?

Amore Estate - beautiful room with many places to explore and relax in.: This highly rated vacation home rental in Lenox offers an outdoor pool, a barbecue grill, 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 you can cook with friends or family. Another good choice for your trip to Lenox is Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++.

How many vacation rentals are there in Lenox?

With 42 Expedia vacation rentals, you're sure 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 Lenox Mountain, or simply take in cultural attractions like Ventfort Hall Mansion and Gilded Age Museum and Shakespeare and Company. While here, Lenox Library and Tanglewood Music Center are other places worth a visit.

What are vacation rentals like in Lenox?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Lenox. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for families.