Lenox Vacation Rentals

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Tonight
Jan 15 - Jan 16
Tomorrow
Jan 16 - Jan 17
This weekend
Jan 16 - Jan 18
Next weekend
Jan 23 - Jan 25

Our top choices for Lenox vacation rentals

Smart TV, books

Vacation Home in Lee

Sun Filled Lenox Retreat - Minutes to Tanglewood!
9.4 out of 10, Exceptional, (3 reviews)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
$412 nightly
The price is $460
Jan 19 - Jan 20
Total with taxes and fees
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Fridge, microwave, oven, stovetop

Vacation Home in Lee

Spacious 5-bedroom house in charming Lee with WiFi
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
$771 nightly
The price is $861
Feb 12 - Feb 13
Total with taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi
Smart TV

Apartment in Pittsfield

Chic corporate apartment in wonderful Pittsfield with AC, WiFi
2.0 star property
2.0 out of 10, (1 review)
"THIS. PLACE. IS. A. DUMP. Do NOT STAY HERE under any circumstances."
United States
Michael
$183 nightly
The price is $204
Jan 16 - Jan 17
Total with taxes and fees
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Exterior

Camping in Williamstown

Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (7 reviews)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
$166 nightly
The price is $186
Jan 19 - Jan 20
Total with taxes and fees
Huttopia Berkshires
Dining

Mobile Home in Chatham

Sugar Shack - 300 square feet of pure sweetness.
2.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
$320 nightly
The price is $361
Jan 26 - Jan 27
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
Terrace/patio

Mobile Home in Chatham

BLUSH: Boutique TINY home*private spa*walk to town
10.0 out of 10, Exceptional, (6 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
$320 nightly
The price is $361
Jan 20 - Jan 21
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
Lobby

Condo in Williamstown

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2,209 reviews)
"I great place to stay!!"
United Kingdom
Maricel
$126 nightly
The price is $141
Jan 19 - Jan 20
Total with taxes and fees
Vacation Village in the Berkshires
Exterior

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (989 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
$212 nightly
The price is $237
Jan 19 - Jan 20
Total with taxes and fees
Jiminy Peak Mountain Resort
Interior

Vacation Home in Sherwood Forest

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$337 nightly
The price is $376
Jan 21 - Jan 22
Total with taxes and fees
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Smart TV, books

Vacation Home in Sherwood Forest

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
9.6 out of 10, Exceptional, (10 reviews)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
$345 nightly
The price is $386
Jan 21 - Jan 22
Total with taxes and fees
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Outdoor dining

Chalet in Becket

Little Longbow Lakefront Chalet
9.8 out of 10, Exceptional, (21 reviews)
"Absolutely perfect quiet get away to relax and recharge will be back! "
United States
Dana V.
$431 nightly
The price is $482
Jan 16 - Jan 17
Total with taxes and fees
Little Longbow Lakefront Chalet
Property grounds

Cabin in Hinsdale

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (35 reviews)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
$411 nightly
The price is $459
Jan 20 - Jan 21
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Dining

Apartment in Lanesborough

Charming Apt in 18th c Berkshire Farmhouse
9.4 out of 10, Exceptional, (40 reviews)
"Patrick was super nice and his farmers market/ cafe is great. Got to cut my own flowers from his field for free! I would definitely stay there again if in the area."
United States
Patricia A.
$189 nightly
The price is $208
Jan 16 - Jan 17
Total with taxes and fees
Charming Apt in 18th c Berkshire Farmhouse
House (3 Bedrooms) | Interior

Cottage in Stephentown

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
$499 nightly
The price is $554
Jan 19 - Jan 20
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Pool

Apartment in Hancock

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"The host communicated everything and ensured we had all the necessary information for our arrival. The room was super clean and everything was new. Really enjoyed our stay and had plenty of room and closets for storage. Would definitely stay again and truly a premiere host!! Angelica "
United States
Jeffrey R.
$247 nightly
The price is $276
Jan 19 - Jan 20
Total with taxes and fees
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Exterior

Apartment in Hancock

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
10.0 out of 10, Exceptional, (1 review)
"The one-bedroom aparment is spacious, very clean, nice and funtional furniture and a perfectly well equipped kitchen area. Our 2 grandchildren had a fun time. And the apartament is footsteps from the ski lifts - a real treat! I highly recommend it!Ps. And the owner is always at hand, very helpful, and concerned that all is perfect for the guest's stay."
United States
Antonio S.
$247 nightly
The price is $276
Jan 19 - Jan 20
Total with taxes and fees
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Desk, iron/ironing board, WiFi, bed sheets

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
9.2 out of 10, Wonderful, (5 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
$180 nightly
The price is $202
Jan 16 - Jan 17
Total with taxes and fees
The Brooks Motel: Exceptional Suite
Living area

Apartment in Adams

Penthouse Apartment on Park Street
2.0 star property
9.6 out of 10, Exceptional, (14 reviews)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
$219 nightly
The price is $245
Jan 16 - Jan 17
Total with taxes and fees
Penthouse Apartment on Park Street
Interior

Condo in Hancock

UNIQUE - 1BR Country Condo @ Jiminy Peak
10.0 out of 10, Exceptional, (14 reviews)
"lovely place to stay"
United States
Nancy P.
$348 nightly
The price is $389
Feb 8 - Feb 9
Total with taxes and fees
UNIQUE - 1BR Country Condo @ Jiminy Peak
Fridge, microwave, oven, stovetop

Cabin in Sand Lake

Taborton Harvest Timber Trails Unique cabin experience
10.0 out of 10, Exceptional, (1 review)
"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.
$165 nightly
The price is $183
Jan 16 - Jan 17
Total with taxes and fees
Taborton Harvest Timber Trails Unique cabin experience
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Clean, very nice bed and linens, pool, jacuzzi, in room fireplace. Balcony right outside of living room. The breakfast was ok, they offered a lot but not top quality. The waffles were very good and the bacon. Overall excellent stay. Conveniently located to everything."
James 2-night trip
Posted 2 days ago
The Yankee, Trademark Collection by Wyndham

Find out more about Lenox

Everything you need to know about Lenox vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Lenox vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Lenox vacation 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 low season months. For more hustle and bustle, you may prefer to visit Lenox in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $141 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Lenox rentals

At Expedia, we put the best Lenox vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Lenox?

Yes, we offer vacation rentals in Lenox near The Bookstore, 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 Enjoy comfortable elegance in this secluded grand home located in town.

How many vacation rentals are there in Lenox?

With 43 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 Housatonic River, 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.