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

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Lenox holiday rentals

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,222 reviews)
"Large , clean suite .well equipped kitchen. Comfortable stay! Would definitely return."
United States
ulla
The price is £88
includes taxes & fees
22 Nov - 23 Nov
Berkshire Mountain Lodge
A covered outdoor seating area with two chairs and a view of a grassy landscape.

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 £230
includes taxes & fees
25 Oct - 26 Oct
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
A living room with a sofa, armchairs, a coffee table, and a television.

3. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (11 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
United States
Patricia O.
The price is £462
includes taxes & fees
26 Oct - 27 Oct
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A modern living room with a sofa, armchair, coffee table, and TV.

4. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.6 out of 10, Exceptional, (4 reviews)
"house was very clean, spacious and well equipped with everything we needed. Great communication with the host. Perfect location for our trip to Tanglewood."
United States
neil s.
The price is £440
includes taxes & fees
2 Nov - 3 Nov
Spacious Central Berkshires Home for Groups
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

5. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,777 reviews)
"We had an amazing stay."
United States
Luke
The price is £75
includes taxes & fees
1 Nov - 2 Nov
Vacation Village in the Berkshires
A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

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

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is £517
includes taxes & fees
2 Nov - 3 Nov
Ellie’s Overlook, best view in the Berkshires!
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

7. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (34 reviews)
"We were on a girls backpacking trip and this was the perfect location right off the trail to clean up, get some great rest and grab dinner. The people are so friendly in Dalton and this place had everything we needed!"
United States
Allie T.
The price is £267
includes taxes & fees
26 Oct - 27 Oct
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

8. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.0 out of 10, Wonderful, (9 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is £115
includes taxes & fees
30 Oct - 31 Oct
Cozy 1-bedroom studio in serene Great Barrington with AC
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

9. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is £511
includes taxes & fees
11 Nov - 12 Nov
Secluded Family Home in Serene Stockbridge Woods
A staircase with a wooden handrail and a white wall with a light switch.

10. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 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 £211
includes taxes & fees
26 Oct - 27 Oct
Leaf-Peeper Paradise in the Berkshires
A bedroom with a bed, a nightstand, a lamp, a chair, and a dresser.

11. Mayas Shangrila

Mayas Shangrila
2.0 star property
Richmond
The price is £853
includes taxes & fees
24 Oct - 25 Oct
Mayas Shangrila
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

12. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is £183
includes taxes & fees
27 Oct - 28 Oct
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

13. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is £160
includes taxes & fees
27 Oct - 28 Oct
NEW RENO - Chalet-style farm loft near Tanglewood
A dining area with a wooden table, black chairs, and a vase with green plants.

14. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is £258
includes taxes & fees
27 Oct - 28 Oct
Sweet Cozy Victorian in Housatonic. Close to everything.
A white two-story house with a porch, surrounded by trees and a hill.

15. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is £342
includes taxes & fees
18 Nov - 19 Nov
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A spacious living room with a dining area, a kitchen, and a large window.

16. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is £168
includes taxes & fees
15 Nov - 16 Nov
1800s Carriage house in Berkshires / Hudson Valley
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

17. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
The price is £180
includes taxes & fees
27 Oct - 28 Oct
Berkshires Apartment at the Stephentown Hotel
A Country Inn with a large, welcoming entrance and a parking area.

18. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is £183
includes taxes & fees
27 Oct - 28 Oct
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

19. 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, (10 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is £283
includes taxes & fees
27 Oct - 28 Oct
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A bedroom with a wooden bed, a window with a view of trees, and a red chair.

20. Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Sand Lake
10.0 out of 10, Exceptional, (1 review)
"The cabin was just what we needed! A gorgeous fall day, trees only visible from the window. The cabin had a comfortable bed, plenty of blanket and a chair. A rocker was on the porch. From this cabin, you turn right from the door and walk straight to the Bessie Woods trail. The common area had everything we needed, clean, comfortable. If you want to relax, this is pretty special!"
United States
Trena
The price is £141
includes taxes & fees
23 Oct - 24 Oct
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
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

Brook Farm Inn

Brook Farm Inn

10/10 Excellent
"Overall, it was a pleasant experience. Loved being in a home instead of a hotel."
Kathleen 1-night trip
Posted 3 hours ago
Brook Farm Inn

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, apart-hotels, 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 £75 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 Berkshire Scenic Railway Museum, 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?

Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++: This highly rated holiday home rental in Lenox is located on a lake, and has an indoor pool, a fireplace 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 patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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 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 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.