House holiday rentals in Lee

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Popular amenities for house rentals in Lee

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 stars2 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, 141 reviews

4Br Mountain Brook House on 130 acres w/ trails

DanielaRating, 5 stars2 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!
Guest favourite
Home in Woodstock
4.92 out of 5 average rating, 243 reviews

Little owl Japanese teahouse: pool is OPEN

JaneRating, 5 stars1 week ago
My husband and I had a wonderfully relaxing time at the Little Owl Teahouse. It’s a cozy and well-outfitted cabin with a super comfy bed and a great leather reading chair. Drank lots of the delicious mountain well water. Made breakfast in kitchen — love the pans and electric cooktop. Short drive to Woodstock for dinner. And oh the beauty of the surroundings - scenic views everywhere. Our two little doggies were happy to romp in the fenced in yard. Little too chilly when we were there but pool looks so appealing. Lisa is a proactive and super responsive host.
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 stars2 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.***
Guest favourite
Home in Lee
4.96 out of 5 average rating, 80 reviews

Berkshire Vacation Home in Lee

EileenRating, 5 stars4 months ago
had a great family get together with our kids and grandkids! The space was perfect for all of us and a great location for skiing at both Bousquet and Butternut! Many restaurants in the area and kitchen well stocked for making family dinners. - easy access to everything - Thank you Jon for the use of your house - made our weekend great!
Guest favourite
Home in Woodstock
4.98 out of 5 average rating, 146 reviews

Woodstock Historic Artist Estate- The Museum House

EmilyRating, 5 stars2 weeks ago
We had the best weekend at the house with our two young children and dog. We loved the house, we loved exploring the property and close by water. We couldn't be closer to town. I can't wait to go back again!

Weekly house rentals

Top guest favourite
Home in Canaan
4.96 out of 5 average rating, 54 reviews

Private Retreat: Hot Tub! Movie Room! Pool Table!

MusserRating, 5 stars5 days ago
This was a bit of a last minute decision to come to the Berkshires and I was grateful that Tiffany could accommodate some quick changes. The house is just as described--lots of space, nice setting, pool table was fun (and cool in the basement), and I appreciated that our two dogs could be included. Even though the house is in NY, it is not far from the hiking trails and museums. We would like to come back--a lot more to see and do in this area.
Superhost
Home in Lee
4.89 out of 5 average rating, 19 reviews

Centrally Located Historical Home

AdaRating, 5 stars9 months ago
We stayed for three nights at this beautiful house. It is ideal for two adult couples with two bedrooms and two bathrooms, both bedrooms have queen size beds. The bedrooms are upstairs, and there is a powder room on the first floor. The house is very clean, fully equipped kitchen, nice view from the open porch. It is on a quiet street, but very close to the center of the town. Tanglewood is 13 min drive, many major Berkshire attractions are a short drive away. Lucas is very prompt in responding to any questions, all check in/check out instructions were clear. We enjoyed our stay a lot!
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 stars2 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 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
Guest favourite
Home in Becket
4.96 out of 5 average rating, 26 reviews

New Shaw Pond Skytop Retreat in the Berkshires

NancyRating, 5 stars5 months ago
We stayed here on our way to Stowe to break up our long drive with an 8 and 2 year old. It ended up being a wonderful mini trip that we didn't want to leave. The house exceeded our expectations in terms of quality, cleanliness, and amenities. And the location was excellent - about 10 to 12 min to the nearest grocery store and downtown with restaurants, Edith Wharton's estate about 20 min away, and Great Barrington/Stockbridge were easily accessible for day trips. We plan to come back for skiing, and to take advantage of the lake activities in the summer. The only downside was the busy road, as mentioned in the listing, but the traffic quieted down in the evening and it didn't affect our sleep at night with the bedrooms located in the back of the house (husband is a very light sleeper; we did bring and use sound machines just in case).
Guest favourite
Home in Guilford
4.94 out of 5 average rating, 47 reviews

Vermont Mirror House

GeorgeRating, 5 stars1 day 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.
Top guest favourite
Home in Lenox
5 out of 5 average rating, 26 reviews

Lakefront Retreat -Private Dock,creek,and Fire pit

LizRating, 5 stars1 month ago
Had a beautiful, relaxing stay with friends at George's place right on the lake. Loved sitting on the deck watching trout swim in the stream and deer passing by. The house is in a perfect location, short drive to both downtown Lenox and Lee. In addition, the house is right down the street from High Lawn farm which makes delicious ice cream and cheese. Can't wait to visit again!
Guest favourite
Home in Becket
5 out of 5 average rating, 53 reviews

Berkshires! Canoe Use, HOT TUB, Private

SuelyRating, 5 stars3 weeks ago
Beautiful, peaceful and private. Nicole was very to super attentive, they also left a birthday balloon on the kitchen table since it was my daughter birthday. The house has everything you will need. It looks small but actually very accommodative! FYI : Nighttime can be very windy around 9-10 pm we were unable to stay outside for too long, but it also probably depends on the weather and the dates, but that didn’t ruin our stay😁 we had a lot of fun on the hot tub and the kayak 🩷🌈🌳…

Private 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.
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.
Guest favourite
Home in Pittsfield
4.95 out of 5 average rating, 20 reviews

Whispering Woods Guest House

James H, JrRating, 5 stars5 months ago
Taylor's space was exactly as described. Decorated so cute and extremely clean. Excellent amenities including well-appointed kitchen, snacks, coffee, tea, robes and slippers. Water pressure (including hot water) more than adequate. Tons of info available for "out of towners" if necessary. Communication was top notch.... accommodating, friendly and practically instantaneous. Would highly recommend. Thank you Taylor and Robert!!!
Top guest favourite
Home in Canaan
5 out of 5 average rating, 64 reviews

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

JillianRating, 5 stars2 weeks ago
We had a slight delay to our trip due to health issues but Lisena and James were very understanding, flexible and caring. Very flexible with our check in and out during our stay since we unfortunately had to shorten it. We are looking forward to planning another night soon. Thank you for sharing your beautiful home with us. We visited the general store right down the road, definite must see, very cute friendly family owned store and was impressed with finding all local milk and products and also gluten free options for baking etc. we also went to Stockbridge to explore the town and to hilltop orchard.
Top guest favourite
Home in Hillsdale
5 out of 5 average rating, 50 reviews

Cambridge Hill Farmhouse - Sauna - Swimming Pond

RebekahRating, 5 stars2 weeks ago
My stay at Danielle’s was so lovely, the swimming pond was so special and just created a beautiful atmosphere around the backyard. The place itself had so much character in the kitchen was greatly stocked. The sauna was lovely and could not get over the view that it had it was raining for most of my trip, but it didn’t take away from the beauty of the place. We were very grateful for how accommodating Danielle was for our arrival and departure. A heads up for anyone that is over 6 foot you will have to duck your head for every bathroom haha would not stop us from booking again though! Such a real gem!
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!
Guest favourite
Home in Becket
5 out of 5 average rating, 14 reviews

Private Lakehouse in the heart of the Berkshires

AaronRating, 5 stars7 months ago
I want to say thank you to Christopher and his family for allowing my friends and me to stay in their home. it was clean, beautiful, serene and exactly what it was described to be. Christopher, your suggestions on golf courses for my friends and me were exceptional. I hope we were as good of guests as you were hosts!
Top guest favourite
Home in East Jewett
4.97 out of 5 average rating, 36 reviews

Creekside Couple's Retreat w/Hot tub, Sauna & More

ValeriyaRating, 5 stars2 weeks ago
We had the most relaxing and enjoyable stay! I cannot express how beautiful this home and property is, truly a gem hidden away in the woods. The location is a dream—completely surrounded by trees, with nothing but the sound of birds and the running creek. It felt like our own private retreat from the world. The cabin itself was beautifully maintained, super clean, and had everything we needed for a relaxing stay. Our favorite were the hot tub and wood fired sauna! The host Diana is incredible—friendly, responsive, and clearly put a lot of care into making this space special. If you’re looking for a peaceful escape in nature, this place is everything.

Quick stats about house rentals in Lee

  • Total rentals

    100 properties

  • Nightly prices starting at

    ₹5,143 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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