House holiday rentals in Lee

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Popular amenities for Lee house rentals

House rentals with a pool

Superhost
Home in Wilmington
4.87 out of 5 average rating, 171 reviews

Adams Farm-"The Little Farmhouse"

Catherine (Lou)Rating, 5 stars4 months ago
We had an amazing stay! The house is lovely and very comfortable, perfect for going skiing at mount snow and cross country skiing and prospect mountain. We were really glad to have picked it. The house is spacious, we all had a lot of room to ourselves, and the kitchen had everything we needed. The farm is gorgeous. Great grocery stores nearby. Sharon was amazing - so helpful when a winter storm threatened to make it hard for us to drive home. She offered us extra time or even another night discounted, which was really generous. She also communicated with friends to help us determine if the road back to NYC had been cleared. We are so grateful for her help! We hope to return in warmer weather to enjoy the farm even more.
Guest favourite
Home in Hudson
4.96 out of 5 average rating, 156 reviews

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

ChristopherRating, 5 stars3 weeks ago
Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!
Guest favourite
Home in Rhinebeck
4.89 out of 5 average rating, 143 reviews

4Br Mountain Brook House on 130 acres w/ trails

DanielaRating, 5 stars3 weeks ago
Rick's House (Hemlock House) was a wonderful getaway! We unfortunately didnt hit the best weather but the house was perfect for a cool and rainy long weekend both indoors and out. The open first floor with huge kitchen was great for hanging out and cooking with alot of cozy nooks to read and relax. There was a lot of various outdoor spaces and decks to lounge on as well and the hot tub was perfect for the cooler cloudy weather. The bedrooms were all comfy and each room having its own bathroom was another plus. We all loved the sounds of the creek and being able to walk around the trails in the back. The House is in a fantastic location - only 10 minutes from Rhinebeck which has everything you need and is great for walking around, shopping and dining. Rick was informative and provided a great guidebook with clear instructions and local resources and recommendations. Thanks for a lovely stay!
Top Guest favourite
Home in Great Barrington
4.99 out of 5 average rating, 72 reviews

Stunning luxury home with pool

StephanieRating, 5 stars2 weeks ago
Beautiful home! Extremely clean upon arrival and excellent communication. Everything in the house was clearly labeled and directions for check-in and check-out were very clear. Sadly it rained our entire stay so we could not enjoy the pool or the beautiful backyard, but we still had a lovely stay. We hope to come back soon!
Guest favourite
Home in Ghent
4.88 out of 5 average rating, 318 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

JasonRating, 5 stars2 weeks ago
Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.
Guest favourite
Home in Saugerties
5 out of 5 average rating, 152 reviews

Upstate Modern Scandinavian Barn in the Catskills

Zoe StarRating, 5 stars3 weeks ago
We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***
Superhost
Home in Lee
4.96 out of 5 average rating, 81 reviews

Berkshire Vacation Home in Lee

KazRating, 5 stars4 months ago
Great house setting and we enjoy our stay. In the future, we will be racing at Berkshire East to Catamount, we will be be sure to look at this house before we will look elsewhere!. Thank you for sharing great house.
Top Guest favourite
Home in East Chatham
5 out of 5 average rating, 15 reviews

Stylish Rural Sanctuary with POOL!

CharlieRating, 5 stars2 months ago
A truly amazing experience. I wholeheartedly recommend staying at Amanda & John’s home. You won’t find a better, more cared for, more beautifully appointed home. Everything you could ask for and more. Super kind, responsive hosts and every detail is considered. Great WiFi, too. If you’re looking for an experience in a spacious landscape, in quietude, with stars up above, this is the place.

Weekly house rentals

Guest favourite
Home in Becket
4.96 out of 5 average rating, 80 reviews

Nerd Preservation Sanctuary

KaitlanRating, 5 stars1 week ago
Taryn's place is perfect for the quirky individual who is looking for eye catching and unique decor that you would not expect in a rural setting. The books, games, music selections were perfect for us and of course the "bad art" with the hilarious descriptions made for such a fun interactive experience. My only critique, which really is not the hosts fault is that my dog was able to slip through some spots of the backyard, so if you have an adventurous small doggo who cannot help but explore the beautiful surroundings on their own, please make sure they are supervised in the back yard area. My dog is about 16lbs, so if you have a medium or larger dog you might be okay with the fencing. Thank you Taryn and Bryan for the experience, I would definitely stay again.
Guest favourite
Home in Pittsfield
4.95 out of 5 average rating, 21 reviews

Whispering Woods Guest House

JanetteRating, 5 stars2 months ago
Taylor was an amazing host! Her home was super comfortable! We would absolutely stay again if we are in the area! Thank you for the amazing stay!
Guest favourite
Home in Great Barrington
4.97 out of 5 average rating, 32 reviews

Charming Cottage - Walk To Town

AmandaRating, 5 stars2 months ago
Perfect location for a few friends that came for a birthday party. Was perfect. I didn’t worry about them at all, and I knew they had a quality stay
Top Guest favourite
Home in Great Barrington
4.99 out of 5 average rating, 95 reviews

Private Home in The Berkshires (New Hot Tub!)

DanielleRating, 5 stars3 weeks ago
Great stay! This is our second time staying at Bradley’s place and it was exactly the same as last time, in a good way. Place was clean, great neighborhood, very quiet!
Guest favourite
Home in Lanesborough
4.96 out of 5 average rating, 51 reviews

Historic Stone Church in The Berkshires

ZacharyRating, 5 stars3 weeks ago
Our stay at Hinterland Hall was a wonderful, unique experience. The property has been carefully restored and tastefully staged. The surrounding area includes some great hikes, like Mount Graylock to the north and Monument Mountain to the south.
Guest favourite
Home in Becket
5 out of 5 average rating, 54 reviews

Berkshires! Canoe Use, HOT TUB, Private

JonasRating, 5 stars1 week ago
Memorable stay in The Berkshires! Nicole's place was cozy and welcoming a great place to relax and unwind after long days of sightseeing and shopping. At night the backyard would be lit by the soft glow of string lights and made for the perfect scene to end every day in the hot tub.
Top Guest favourite
Home in Pittsfield
4.98 out of 5 average rating, 40 reviews

Cozy Cottage on Peaceful Pond, Close to Winery

RogerRating, 5 stars1 week ago
Was a wonderful place to stay. Relaxing and restful, the view of the pond was beautiful, and there was easy access to towns like Great Barrington and Lenox if you are so inclined.
Superhost
Home in Hillsdale
4.75 out of 5 average rating, 4 reviews

Private Getaway on large acreage

MichaelRating, 5 stars1 month ago
Beautiful, well-appointed, rustic cabin. Perfect place to unwind and disconnect. Very clean and bright. Highly recommend.

Private house rentals

Guest favourite
Home in Washington
5 out of 5 average rating, 22 reviews

Modern Berkshire Mountain Home

TomRating, 5 stars1 month ago
Ideal spot to catch up with family and see the Berkshires area. The furnace heat in the house came on like a charm and the laundry downstairs made our clothes washing a dream.
Top Guest favourite
Home in Monterey
5 out of 5 average rating, 21 reviews

Berkshires Retreat | Fenced Yard + Near Tanglewood

CharmaineRating, 5 stars2 months ago
Home is very beautiful. Jim and Susan were very responsive when needed we felt right at home everything was right at our fingertips when needed. We came for a weekend girls getaway and this home helped us achieve that peace we needed. Very spacious we will be back again.
Top Guest favourite
Home in Hillsdale
5 out of 5 average rating, 51 reviews

Cambridge Hill Farmhouse - Sauna - Swimming Pond

janetRating, 5 stars3 days ago
This was a perfect vacation home for our family trip. Spacious house with beautiful indoor and outdoor spaces, a well equipped kitchen, luxurious and extremely comfortable furnishings and a location that makes visits to surrounding charming towns so easy.
Top Guest favourite
Home in Canaan
5 out of 5 average rating, 66 reviews

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

MichelleRating, 5 stars1 week ago
We had a wonderful stay at James and Lissy’s house! It was perfectly located for getting around the Berkshires. The house was clean, beautiful, and cozy. When we needed to communicate with James and Lissy they were incredibly responsive and helpful. Every year, my friends from high school and I meet up for a reunion in the Berkshires (we have been doing this annually), and the hope is to stay in this very Airbnb next year, if possible/ available! It was an exceptional Airbnb experience!
Guest favourite
Home in Great Barrington
5 out of 5 average rating, 11 reviews

Valley Vista atop Jug End

PanosRating, 5 stars1 week ago
Nice place. Great layout. Easy to navigate. Host was very communicative. We would stay there again.
Guest favourite
Home in Becket
4.92 out of 5 average rating, 77 reviews

Little Longbow Lakefront Chalet

JensRating, 5 stars3 months ago
We went in February. Even with snow no problem to drive to the house. It is perfectly located. Remote but still close enough to everything. It is close to nice hikes. We would love to come back in the Summer or so as it has its own lake access. Kitchen is perfectly equipped if you like to cook. I always like if you have a separate dinning table - to eat, work, talk. All very clean with personal touches. We can just recommend the place highly. And Jaclyn was a great host - she gave us some flexibility with checkout but also was vey responsive. Thanks a lot!
Top Guest favourite
Home in Lenox
5 out of 5 average rating, 22 reviews

Sunny House in Downtown Lenox

MarkRating, 5 stars2 weeks ago
We loved this place. Everything is as described. It’s within walking distance of the main section of Lenox with restaurants and such, but still a block back into a lovely neighborhood so it felt secluded. No traffic or sounds of people. Very quiet.
Guest favourite
Home in Guilford
4.92 out of 5 average rating, 49 reviews

Vermont Mirror House

GeorgeRating, 5 stars1 week ago
I was planning on my proposal and wanted somewhere special. The window house was exactly that. Private, peaceful, super clean, amazing views and wildlife. Taylor and Marla were EXTREMELY good at communicating and getting back in a timely manner. If you and your significant other are looking to get away, this is the place. It’s sublime.

Quick stats about house rentals in Lee

  • Total rentals

    100 properties

  • Nightly prices starting at

    $99 NZD before taxes and fees

  • Total number of reviews

    5.7K reviews

  • Family-friendly rentals

    80 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. Lee
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