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Our top choices for Lenox vacation rentals

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
$316 nightly
The price is $353
Jul 10 - Jul 11
Total with taxes and fees
stylish Berkshires Retreat

Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
8.0 out of 10, Very Good, (1 review)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
$575 nightly
The price is $642
Jul 12 - Jul 13
Total with taxes and fees
Spacious Central Berkshires Home for Groups

Enjoy comfortable elegance in this secluded grand home located in town

Enjoy comfortable elegance in this secluded grand home located in town
Lenox
10.0 out of 10, Exceptional, (80 reviews)
"Amazing property, close to town "
United States
Tricia E.
$686 nightly
The price is $766
Jul 19 - Jul 20
Total with taxes and fees
Enjoy comfortable elegance in this secluded grand home located in town

BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 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.
$285 nightly
The price is $321
Jul 9 - Jul 10
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,420 reviews)
"Property is great and stay was great"
United States
Isha
$142 nightly
The price is $158
Jul 16 - Jul 17
Total with taxes and fees
Vacation Village in the Berkshires

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Cummington
10.0 out of 10, Exceptional, (1 review)
"Staff was super friendly, host was also amazing!"
United States
Connor
$129 nightly
The price is $136
Jul 7 - Jul 8
Total with taxes and fees
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

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
$181 nightly
The price is $201
Jul 7 - Jul 8
Total with taxes and fees
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

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, (38 reviews)
"Gorgeous place.Great stay.Will diff be backG"
United States
Gerard C.
$391 nightly
The price is $437
Jul 8 - Jul 9
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

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, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
$389 nightly
The price is $434
Jul 7 - Jul 8
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

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, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$400 nightly
The price is $446
Jul 13 - Jul 14
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (8 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
$262 nightly
The price is $295
Jul 9 - Jul 10
Total with taxes and fees
Downtown | Waterfront | Walk to Shops

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Hancock
9.8 out of 10, Exceptional, (8 reviews)
"A great, comfy suite! We had a great stay! "
United States
Wendy D.
$237 nightly
The price is $265
Jul 7 - Jul 8
Total with taxes and fees
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
$167 nightly
The price is $187
Jul 7 - Jul 8
Total with taxes and fees
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (13 reviews)
"Location was very good-close to campus. Host was responsive. Accommodations were just right"
United States
Dan R.
$251 nightly
The price is $282
Jul 7 - Jul 8
Total with taxes and fees
2-Bdr Apt In Town, By the Water

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
$321 nightly
The price is $359
Jul 16 - Jul 17
Total with taxes and fees
Real Estate: Therapy - Lake, Laundry, Love it

Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (16 reviews)
"This was a dash away and perfect! "
United States
Linda R.
$165 nightly
The price is $183
Jul 7 - Jul 8
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Hancock
9.0 out of 10, Wonderful, (17 reviews)
"Great stay! Perfect location by the pool and nicely renovated as advertised!"
United States
Matthew B.
$237 nightly
The price is $265
Jul 7 - Jul 8
Total with taxes and fees
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (18 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
$280 nightly
The price is $312
Jul 29 - Jul 30
Total with taxes and fees
Cozy Riverside Berkshires Retreat

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
United States
John F.
$237 nightly
The price is $265
Jul 7 - Jul 8
Total with taxes and fees
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (14 reviews)
"Our stay was beautiful! The check in process was super easy and the building was easy to access. The apartment was very clean and it was a lovely stay."
United States
Margaret C.
$252 nightly
The price is $281
Jul 26 - Jul 27
Total with taxes and fees
Penthouse Apartment on Park Street
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

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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?

Imagine Being Lakeside, Kayaks/Fishing/EV Charger: This highly rated vacation home rental in Lenox is located near the beach and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. Make the most of the garden in this rental home to help you unwind. 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 45 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.