Lenox Holiday Rentals from €125: Search Short-Term Rentals

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Holiday Rentals in Lenox

"Very comfortable property in a lovely setting "

"Beautiful home perfect for our multi-generational family. We loved the separate spaces and easy walk to the town center. We can’t wait to come back!"

"The property was better than advertised. Everything anyone could need was provided and we could not have hoped for a better experience. Very large home and could easily accomodate 8 people or more. The Berkshires are magical and this home was great for out time there."

"Fantastic, large house with tons of places to explore in the house and on the property. We came for a long weekend with 3 families and both the adults and kids felt quickly at home and really enjoyed our stay. We cannot wait to some back!"

Indoor pool, outdoor pool, pool umbrellas

"Absolutely outstanding! After a day of skiing at Jiminy my son & I checked into vacation village. Quick and efficient check in at the front desk by the gentleman working. Drove around to our bldg. unloaded our gear, changed into our swim trunks, grabbed a couple of cold ones and walked across the road to the hot tub! Just what the Dr. ordered! Our unit was clean & comfortable, slept great & were up and out early in the morning."

includes taxes & fees

3 Mar - 4 Mar

"Staff was exceptionally helpful and friendly."

includes taxes & fees

1 Apr - 2 Apr

"Property was very nice Kirchen could use some additons -starting with a ladle "

includes taxes & fees

2 Mar - 3 Mar

"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."

"The home was beautiful and it was a gorgeous property too. It had all the right amenities in the kitchen. "

"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...

"We have stayed at this property twice before and have been very pleased with the amount of bedrooms and sleeping available. The property is always very clean and is equipped with everything you need for cooking and dining.the property is a half way point for family members in several directions. "

"This was a cozy tucked away location that seemed far away from everything which was exactly what we wanted. The host was extremely communicative before and during the stay. The house had fresh linens and towels as well as basic cleaning supplies. It was cozy for a wintery weekend in. We enjoyed snowshoeing on the frozen lake! Pet-friendly was a huge plus! "

"The property was great for our group of 8. Slept everyone comfortably, with plenty of places to hangout and lounge all together. We had planned to cook in for a couple meals, so it was a hugely pleasant surprise to see that the kitchen was stocked with every cooking utensil, serving dish, and glassware that you could possibly need. We were maybe even more prepared than in my own kitchen at home. Also very well located. Had an excellent stay and would come back!"

"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...

includes taxes & fees

4 Mar - 5 Mar

"This place was awesome... I was 15 minutes away working late... and I was too tired to drive home... I actually scheduled the wrong night and realized it after I got confirmation. But I messaged the renters and they just happened to have a cabin vacancy... they gave me the directions.. the key code and we worked everything out afterwards. The set-up is genius... the common area building has all the plumbing in it. Bathroom and showers with an open very well built living room with a kitchen. My...

includes taxes & fees

2 Mar - 3 Mar

"We had fun! Game room great! Spacious and comfortable. Never got to enjoy outdoors, so maybe another trip in the future!"

"The house was perfect for us. Spacious, clean, comfortable. Beds comfortable. Bathrooms really nice. The road in the development is dirt, a 4wd is needed as stated. It was muddy and rutty on arrival, then snow and ice , but do-able. Great house. Would recommend "

"The cabin is quiet, tidy, and comfortable. It is within driving distance of several hiking trails and was a great place to spend a long weekend. The host was friendly and communicative, and made sure that we had everything we needed for a nice stay. "

"There is a game room that provided lots of fun. The linens were luxurious, the kitchen had every utensil. The yard is fenced in, the hot tub was great, we loved it!"

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"Great place for a quick stay but the heater was like a truck going off."

includes taxes & fees

9 Mar - 10 Mar

"Staff was super nice, the rooms were really nice and clean."

includes taxes & fees

9 Mar - 10 Mar

"Our one night at The Constance recently (February 2025), was fantastic! The inn is warm and welcoming, spotlessly clean, and beautifully decorated with lots of vintage charm and all the comfy, modern conveniences one would expect. We absolutely loved it! Each staff member we had contact with (Logan, Brenda and Stacy) was professional and friendly. Communication was efficient and timely. As we were in Lenox off-season, the inn was exceptionally quiet, with only two other rooms booked during...

includes taxes & fees

3 Mar - 4 Mar

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 €125 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.

Recent reviews of Lenox properties

5/5 Excellent

Dr.’s Orders

"Absolutely outstanding! After a day of skiing at Jiminy my son & I checked into vacation village. Quick and efficient check in at the front desk by the gentleman working. Drove around to our bldg. unloaded our gear, changed into our swim trunks, grabbed a couple of cold ones and walked across the road to the hot tub! Just what the Dr. ordered! Our unit was clean & comfortable, slept great & were up and out early in the morning."

A verified traveller stayed at Vacation Village in the Berkshires

Posted 1 day ago

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

5/5 Excellent

"Our one night at The Constance recently (February 2025), was fantastic! The inn is warm and welcoming, spotlessly clean, and beautifully decorated with lots of vintage charm and all the comfy, modern conveniences one would expect. We absolutely loved it! Each staff member we had contact with (Logan, Brenda and Stacy) was professional and friendly. Communication was efficient and timely. As we were in Lenox off-season, the inn was exceptionally quiet, with only two other rooms booked during our one-night stay. We got to meet the other guests in the dining area after dinner, and stayed chatting with them long into the evening. The inn offered free snacks (small bags of pretzels, chips, trail mix, etc), fresh fruit (apples), granola bars, super-cute hot chocolate bar, tea and coffee, all self-serve, 24 hours a day! In our room, a beautiful glass decanter was filled with water along with two drinking glasses. An elegant touch! We really appreciated the Eco-friendly liquid soap, lotion, shampoo and conditioner dispensers, and each product had a beautiful scent and felt luxurious. The continental breakfast was fresh and beautifully presented (self-serve) in the dining area from 7:00 am - 9:00 am: hard boiled eggs, bagels, (gluten-free bagels as well), croissants, fresh fruit, yogurt, granola, orange and cranberry juice, tea, coffee. Delicious! Plenty to do in the area, within walking distance of the inn. Can't wait to return! Highly recommend! "

A verified traveller stayed at The Constance, The Whitlock, & The Dewey By The Lenox Collection

Posted 3 days ago

5/5 Excellent

Cozy New England Inn

"This was my first stay at the Williams Inn and I found it the coziest hotel I've stayed at! The furnishings are lovely and the lobby area very inviting (especially in the winter when the fire is always going). There's also - unfortunately, I didn't discover this until the end of my stay - a little nook area off to the side with books, games, and complimentary fruit water. The rooms were lovely and clean. The bathroom and shower were mostly clean except for some black spots near the bottom of one part of the shower wall and floor. The air unit for the most part actually kept the room temperature well controlled (which seems to be rare these days). In all, our little group enjoyed our stay and would definitely like another visit."

A verified traveller stayed at The Williams Inn

Posted 3 days ago

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

5/5 Excellent

"Great stay again. My family has been going here 3 years in a row, and its always a great experience "

A verified traveller stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

Posted 5 days ago

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All accommodation types in Lenox

Inns in Lenox

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?

Enjoy comfortable elegance in this secluded grand home located in town: This highly rated holiday home rental in Lenox is located in a rural location, and has a fireplace, a patio 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 garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Some other homes for rent in Lenox include Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate and Private Access To Laurel Lake, Enjoy Lake Life.

How many holiday rentals are there in Lenox?

With 45 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 Kennedy Park, or simply take in cultural attractions like Ventfort Hall Mansion and Gilded Age Museum and Shakespeare and Company. While here, Tanglewood Music Center and Wyndhurst Golf & Club 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.

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Holiday Rentals in Lenox

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Check prices for these dates

Holiday Rentals in Lenox

The Ponds at Foxhollow

The Ponds at Foxhollow

Enjoy comfortable elegance in this secluded grand home located in town

Enjoy comfortable elegance in this secluded grand home located in town

Private Access To Laurel Lake, Enjoy Lake Life

Private Access To Laurel Lake, Enjoy Lake Life

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

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

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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

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

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

Private Estate, Heated Yearround Outdoor Pool

Private Estate, Heated Yearround Outdoor Pool

Pristine Home In Becket Woods

Pristine Home In Becket Woods

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Peace and quiet on the lake

Peace and quiet on the lake

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Hancock Village Inn at Jiminy Peak

Hancock Village Inn at Jiminy Peak

Cabin in the woods

Cabin in the woods

BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, LIBRARY, BARN, TRAILS ON 60 ACRES!

BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, LIBRARY, BARN, TRAILS ON 60 ACRES!

Quintessential 6-BR Berkshires Lodge

Quintessential 6-BR Berkshires Lodge

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Other types of properties in Lenox you may be interested in

Life House Berkshires

Life House Berkshires

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

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

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

Find out more about Lenox

Find out more about Lenox

Recent reviews of Lenox properties

Recent reviews of Lenox properties

Vacation Village in the Berkshires

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions