House holiday rentals in Lenox

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Popular amenities for house rentals in Lenox

House rentals with a pool

Guest favourite
Home in Saugerties
4.94 out of 5 average rating, 70 reviews

Perfect Family Retreat•Pool•Volleyball•Firepit

JustinRating, 5 stars2 weeks ago
Highly recommend Sarah’s house. We stayed in the spring and it was beautiful. Spacious outdoor area with lots to do. There was plenty of space, lots of activities and stuff for our kids to play with; super family friendly. Also very close to all the towns we wanted to visiting and natural attractions up in Hudson River valley. We would stay again thank you !
Guest favourite
Home in Woodstock
4.86 out of 5 average rating, 211 reviews

Lux Woodstock Pool/ Pvt/Fireplaces /4 mins 2 town

JoshuaRating, 5 stars2 months ago
Yanna's house exceeded all expectations. Immaculate throughout the spacious layout offered plenty of room for two families with children. My 10yo son said the bed was the most comfortable bed he ever slept in. Master bedrooms far enough apart so adults can have some privacy. Large kitchen with dining table perfect to cook and hang out. We skied at Belleayre both days (easy drive on 28) and less than 10 min from Woodstock if you want to go out. Also very close to a large grocery store. Would love to stay there again!
Top guest favourite
Home in Saugerties
4.98 out of 5 average rating, 160 reviews

Spacious Staycation near HITS & the Hudson

McKennaRating, 5 stars6 months ago
My group loved our stay at Alan and Cara’s place for the Sheep & Wool festival. Great space for a large group; we especially loved how comfortable the living room couches were and how there was space for everyone there to gather. The place was immaculately clean. We’d love to come back again!
Superhost
Home in Stanfordville
5 out of 5 average rating, 5 reviews

The Round House w/ Heated Pool

JonathanRating, 5 stars5 months ago
An amazing location when you want to get slightly off the grid for peace and tranquility. Everything you need to truly slow down, dial out and get peace, quiet and rest. An amazing spot for a weekend getaway. If you want to find yourself amongst serene surroundings and a quiet, private wooded area, this is the place. Just enough modern amenities to be comfortable, but just basic enough to make you slow down. Tanner the host was the most responsive and helpful host of any of the airbnbs we've ever stayed. Truly went above and beyond at every turn to make our stay as comfortable as possible. More than accommodating with every request.
Guest favourite
Home in Woodstock
4.86 out of 5 average rating, 132 reviews

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!

HelaRating, 5 stars1 month ago
Beautiful home with amazing views. The house was very clean and spacious, the views were amazing. Susanna was very responsive and gave clear instructions. We had a very relaxing weekend and enjoyed very much staying at the house. We would love to come back.
Guest favourite
Home in New Paltz
4.93 out of 5 average rating, 134 reviews

Harrison Field Heated Pool UponRequest 10Acres

AlannaRating, 5 stars6 months ago
We had a great weekend celebrating our parents anniversary. The house was plenty big for all of us and the grounds are beautiful. Nathan was quick to respond when we had trouble navigating the AC and made sure we enjoyed our stay!
Guest favourite
Home in Colonie
4.97 out of 5 average rating, 37 reviews

Adorable house with pool

CassieRating, 5 stars2 weeks ago
Perfect for our Easter family gathering! We especially enjoyed spending time in their delightful backyard cooking on their gas grill and admiring their exquisite flowering trees!
Guest favourite
Home in Preston-Potter Hollow
4.91 out of 5 average rating, 33 reviews

Catskill Home w/ private Pool, Sauna,Mountain view

ThomasRating, 5 stars1 week ago
Our group really enjoyed our stay at JunkO and Ryo’s place! It was def one of the better ones and we’ve been to 30+ upstate. The recently renovated open concept house is roomy, squeaky clean, and decorated and furnished beautifully. The windows and new sliding doors provide a full panoramic view of the mountains while you sit and eat. The sauna downstairs is also very relaxing and gets hot quickly. They provide robes, spa towels, slippers, and has its own private shower a few steps away. Beds are super comfy and there’s no shortage of linens, towels or anything you may need. Kitchen was also fully stocked. Location is 10-15 mins from anything and everything. Oh and it is VERY baby friendly With very little excess clutter, and they provided all the necessary items (crib,highchair,child gates, tub etc) Don’t hesitate to stay here, We look forward to visiting again soon.

Weekly house rentals

Guest favourite
Home in Mount Tremper
4.9 out of 5 average rating, 224 reviews

Stunning Modern Barn minutes from Woodstock 21N195

Tracy,JRating, 5 stars4 weeks ago
A beautiful and thoughtfully reconstructed house. It has everything you could need to enjoy a very chill time at the house indoors and outdoors or even cook a meal in. Kid friendly.Beautiful light. Beautiful views. Very convenient location. Kind hosts. We have stayed at a few places around town but this was by far our favorite house.
Guest favourite
Home in Catskill
4.98 out of 5 average rating, 407 reviews

The Martin House, Catskills

McCaulRating, 5 stars2 weeks ago
Could not have found a better place for our trip to Hudson! The spot was gorgeous, spacious, well-located, etc.
Superhost
Home in Ulster Park
4.88 out of 5 average rating, 228 reviews

Entire lake house to yourself. Great for groups

Maggie FuentesRating, 5 stars2 weeks ago
Scott is amazing! The airbnb was incredible! Lovely placed filled for immense and loving memories. He allowed me a late Check-Out which was wonderful. Definitely recommend you guys coming more often!
Superhost
Home in Ancram
4.8 out of 5 average rating, 112 reviews

Secluded Post-And-Beam Retreat

SarahRating, 5 stars2 months ago
A lovely house in a private location. Our kids loved the games, watching movies on the projector, and watching deer from the window. The kitchen was well equipped and everything was comfortable.
Superhost
Home in Durham
4.84 out of 5 average rating, 134 reviews

Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI

Fur-EliseRating, 5 stars2 weeks ago
we stay for about a month and absolutely adored this place! 🥰
Guest favourite
Home in Mount Tremper
4.97 out of 5 average rating, 155 reviews

Perfect Abbey Road Retreat

MeganRating, 5 stars4 months ago
What a beautiful place to spend Christmas!! Before moving to Australia next year we wanted one more cold snowy holiday. While we didn’t have as much snow as we’d hoped, it was still an amazing stay. The house is so homey and comfortable. With two young neurodivergent kids it’s hard being in a new place and the kids room was absolutely essential to our time there. The mattress in the primary bedroom is heavenly, and the overall decor and vibe of the house were incredible with enough room for everyone to have their own space (MIL included!). The kitchen was perfectly stocked and felt like we were right at home. We made a day trip out to Hunter Mountain to go tubing and a trip down to Kingston to Aldi and Target as well. Noah and Brandon were absolutely amazing hosts, Noah was extremely responsive even before we booked, and made sure we had what we need as our trip got closer. I would absolutely make the trip again and am so thankful for the memories we made!
Guest favourite
Home in Wilmington
4.9 out of 5 average rating, 220 reviews

Wilmington A-Frame- Cozy and Convenient

AveryRating, 5 stars1 month ago
This spot is absolutely perfect to be on a quite spot to enjoy nature but still right within walking distance of the center of Wilmington. The cabin itself is beautifully appointed, gorgeous, and super comfortable. Due to rain we ended up spending most of our time inside relaxing and watching movies, and have zero regrets about it. The host was also extremely friendly, helpful and responsive. I'll definitely be coming back again and recommend this for a Wilmington get away weekend!
Guest favourite
Home in Lee
4.97 out of 5 average rating, 100 reviews

Stylish Mid-century Modern Berkshires Cape

LarryRating, 5 stars1 month ago
The home was very clean and as described with everything we needed for our visit. Chris was very clear with his check-in instructions and quickly responsive to questions as we got settled. I would stay here again.

Private house rentals

Top guest favourite
Home in High Falls
5 out of 5 average rating, 227 reviews

Mahali Petu - A Big Little House

DoraRating, 5 stars2 months ago
Excellent place to stay at. Truly luxurious with modern fixtures and appliances. Very clean and neat with tasteful decor. Great view in the winter, extremely peaceful and private. Driveway definitely requires AWD due to ice and snow in the winter. Tons of towels and toiletries provided. Patti and Bob were so helpful and courteous. Many great suggestions for places to eat and things to do. Very knowledgeable on the local trails. Wouldn't hesitate to return!
Top guest favourite
Home in Schenectady
4.99 out of 5 average rating, 206 reviews

Bright & Clean ~Tons of Upgrades ~Office Space

MaureenRating, 5 stars6 days ago
This is our second time staying here when we come to visit family. We love the location, quiet and just a couple minutes from our grandchildren. Easy access, cute cozy clean home nice kitchen amenities.
Superhost
Home in Windham
4.73 out of 5 average rating, 30 reviews

Beautiful, cozy and private house

AnushkaRating, 5 stars1 week ago
We loved our stay here!! It is very accessible to a lot of hikes in upstate. The place was super clean. You would find most amenities in the house for your stay. Loved it.
Top guest favourite
Home in Stone Ridge
4.96 out of 5 average rating, 145 reviews

Secluded Oasis w/ Fire Place In Stone Ridge

WayneRating, 5 stars1 day ago
Loved the location, wooded and quiet, and a short drive to Stone Ridge. The house was comfortable and the kitchen had everything needed to cook in-house. Jane met us at check in and answered any questions, very responsive host. There were hiking trails nearby and there was even a park pass available to use at nearby state parks.
Superhost
Home in Canaan
4.96 out of 5 average rating, 72 reviews

Peaceful Berkshire Getaway (A/C, Lake Access)

PaulRating, 5 stars10 months ago
Becky’s house was exactly as listed with plenty of space to relax and enjoy the area. Her gardens are beautiful and the house is convenient to the Berkshires without the stress of the downtown areas. We are extremely appreciative of all that was provided!
Guest favourite
Home in Greenville
4.87 out of 5 average rating, 244 reviews

Beautiful Fall cabin, North Catskills/Greenville

MaureenRating, 5 stars4 months ago
When I first pulled up to Kliment's, I literally teared up - that's how breath-taking his spot is. It was just what the doctor ordered... if doctors actually treated your mind, body, and soul and not just your body :) Seriously though, Kliment's place was an oasis for me: private, quiet, peaceful, with amazing views of the Catskill mountains. His home itself was beautifully decorated, simple yet super cozy, and had everything I needed and then some. (And the chickens were lovely company as well!) Kliment is one of the best Airbnb hosts I have ever had, hands down. With a very hectic schedule, Kliment was flexible, responsive, kind and patient with accommodating my many change requests and needs throughout my stay. Kliment is not just a wonderful host, but also a truly wonderful person - the world needs more people like him. In short: I can't recommend Kliment's home or him as a host enough! If you are hovering over the "Reserve Now" button, book it!!! You won't regret it! :)
Top guest favourite
Home in Craryville
4.92 out of 5 average rating, 113 reviews

The Gatehouse at Raspberry Ridge

JenniferRating, 5 stars2 weeks ago
If your looking for a great quiet stay while visiting Hudson or other local places this home is it. Very clean, super dog friendly. Close to the highways and hidden enough to really be apart of nature.
Top guest favourite
Home in Cheshire
4.81 out of 5 average rating, 152 reviews

Large Secluded Berkshire Home

BruceRating, 5 stars6 months ago
We thoroughly enjoyed our stay and the accommodations were exactly as stated, comfortable, roomy, very clean and convenient to amenities. The sleeping accommodations were perfect and the beds were comfortable even for older adults and children. The surroundings were incredibly picturesque, beautiful yard for outdoor activities and lovely mountainous views. The host was very accommodating to our needs and for that we are very thankful. We would definitely stay again.

Quick stats about house rentals in Lenox

  • Total rentals

    90 properties

  • Nightly prices starting at

    £45 before taxes and fees

  • Total number of reviews

    3.7K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

Destinations to explore

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  2. United States
  3. Massachusetts
  4. Berkshire County
  5. Lenox
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