Lenox Holiday Rentals

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Holiday Rentals in Lenox

Amore Estate - beautiful room with many places to explore and relax in.
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (18)
"There was plenty of room for four families. Beds were comfy. If you plan on cooking you might want to bring your own knives and pans. Teflon pans were scraped . Only metal utensil available to flip pancakes. "
Amore Estate - beautiful room with many places to explore and relax in.
The Kemble- Built by a US Secretary of State in Lenox
Exterior detail

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (16)
"We were a big group..16 adults and 7 children. The families with children were well situated with nearby or adjacent rooms. Everyone had comfortable rooms which afforded privacy and quiet times. Each room had its own beautiful newly renovated bathrooms ( with great water pressure). The living and dining rooms were large and comfortable. The dining table was a loooong table with benches all around which easily sat our crowd. The backyard was gorgeous with beautiful views of the distant mountains....
The Kemble- Built by a US Secretary of State in Lenox
The Winthrop Estate - 12K SF 32 Acres
Exterior

The Winthrop Estate - 12K SF 32 Acres

10.0 out of 10, Exceptional, (4)
"Everyone enjoyed the stay"
The Winthrop Estate - 12K SF 32 Acres
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Interior

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (37)
"The home was convenient to hiking, shopping and dining. It is on a busy street and can be a bit tricky getting in and out of driveway. Inside the home was warm and welcoming. The kitchen had all cooking pans and tools we needed to make meals. There is a great grocery store right down the road. The beds were comfortable and the bathrooms were clean. The hostess was very helpful and attentive when we had a question about the heat. Be aware the staircase to upstairs bedrooms and 2nd bathroom are...
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1750)
"Nice and quiet family get a way"
The price is HK$1,458
HK$1,677 total
includes taxes & fees
1 Jan - 2 Jan 2025
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is HK$1,470
HK$1,612 total
includes taxes & fees
5 Jan - 6 Jan 2025
Jiminy Peak Mountain Resort
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Interior

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.8 out of 10, Exceptional, (38)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (200)
"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"
Peace and quiet on the lake
Pristine Home In Becket Woods
Fridge, microwave, oven, stovetop

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"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
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (231)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is HK$1,135
HK$1,737 total
includes taxes & fees
30 Dec - 31 Dec
Berkshire Village Carriage House - Super Private!!
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (209)
"The Cabin Had All The Amenities You Would Need and With A Quiet and Serene Area. For Me It Was Relaxing Stay!"
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Private Estate, Heated Yearround Outdoor Pool
Fridge, microwave, oven, stovetop

Private Estate, Heated Yearround Outdoor Pool

10.0 out of 10, Exceptional, (14)
"Beautiful property, well-appointed, and comfortable for extended family of 12."
Private Estate, Heated Yearround Outdoor Pool
Serene Acreage - Pond - Hiking Trails Nearby
Terrace/patio

Serene Acreage - Pond - Hiking Trails Nearby

10.0 out of 10, Exceptional, (6)
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby
Berkshires Cabin 2 Mi to Appalachian Trail!
TV, fireplace, books

Berkshires Cabin 2 Mi to Appalachian Trail!

9.6 out of 10, Exceptional, (10)
"The hosts were extremely responsive and helpful, providing us with hiking ideas, questions regarding the house and suggesting best shopping spots for incidentals. The living room was cozy, seating five comfortably. The kitchen was well stocked so cooking a Thanksgiving meal was a pleasure. We thoroughly enjoyed ourselves."
Berkshires Cabin 2 Mi to Appalachian Trail!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (41)
"We had expectations of a peaceful rustic cabin in the woods, and this rental checked almost all of the boxes! The quaint town of Great Barrington was just close enough for convenience, but the house was rural enough to help us all relax and enjoy the quiet. We loved the dock and the firepit, and the house was well-stocked with firewood, towels, and toiletries. "
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Antique Farmhouse Totally Restored
Exterior

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (83)
"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "
Antique Farmhouse Totally Restored
Berkshire Lake access
Lake

Berkshire Lake access

10.0 out of 10, Exceptional, (48)
"The house worked was exceptionally clean and worked great for us. The landowner was exceptionally helpful in providing suggestions. We loved visiting the Norman Rockwell Museum and walking around Lenox. Thanks for everything!"
Berkshire Lake access
Beautiful 5-Star Private Estate! Inquire about our Early Booking Reduced Rates!
Fridge, microwave, oven, stovetop

Beautiful 5-Star Private Estate! Inquire about our Early Booking 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 5-Star Private Estate! Inquire about our Early Booking Reduced Rates!
Private Island - Largest Fresh Water Reservoir in Mass....
Outdoor dining

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"From beginning to end, could not have dreamed of a better island getaway, in the Berkshire’s none-the -less. Bill was a wonderful host. Very friendly, responsive and helpful. Super welcoming. The home was simple, quaint, and super cozy. Perfect for a nice long relaxing weekend for both the dogs and people. The views from the sun room were lovely. The deck/patio area had a beautiful view of the water. The fire pit was a nice perk in the evening. Surrounded by water, the place felt so private....
Private Island - Largest Fresh Water Reservoir in Mass....
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

The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1004)
"This hotel was awesome! We enjoyed the hot tub along with the fireplace in our room! "
The price is HK$753
HK$842 total
includes taxes & fees
2 Jan - 3 Jan 2025
The Yankee, Trademark Collection by Wyndham
Life House Berkshires
Lobby

Life House Berkshires

3.5 star property
9.0 out of 10, Wonderful, (455)
"The coziest best hotel in area! Staff was so wonderful, room was perfect! Lobby bar and lounge is so great."
The price is HK$687
HK$767 total
includes taxes & fees
1 Jan - 2 Jan 2025
Life House Berkshires
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Free WiFi, bed sheets

The Constance, The Whitlock, & The Dewey By The Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (415)
"It was amazing! The staff was incredible, the room was very clean and cozy, and overall was a great place to stay. Loved it here!"
The price is HK$1,205
HK$1,346 total
includes taxes & fees
23 Dec - 24 Dec
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?

Private Estate, Heated Yearround Outdoor Pool: This holiday home rental outside of Lenox offers a balcony, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of books in this rental home to help you unwind.

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 Pleasant Valley Wilderness Sanctuary, or simply take in cultural attractions like Shakespeare and Company and Tanglewood Music Center. While here, Lenox Library and The Bookstore 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.