
House holiday rentals in Lanesborough
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Top-rated house rentals in Lanesborough
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Popular amenities for house rentals in Lanesborough
House rentals with a pool

Berkshire Mountain House
This property was fantastic. It was great for adults and kids. The inground pool and hot tub were used all day and night. The house had many amenities for everyone. We have 3 grand children, (ages 5-7), the hosts had all kind of spaces and toys for them to utilize. Excellent place for kids inside and out! House was very well appointed and very user friendly. We loved our family time there and would not hesitate to return. Thank you!!!

Adams Farm-"The Little Farmhouse"
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.

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres
Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!

Berkshire Mountain home views, pool, Queechy Lake
The house was very spacious, the kids ranging from 6-10 loved the games, especially cue ball and fuzz ball. The adults loved the fact there was a lower half where the kids can watch movies and play, while the adults did grown up chatting in the living space. A memorable ski weekend that everyone enjoyed to the fulliest and sad it went so fast. We look forward returning one day in the spring or summer to see a different aspect of the area. Thank you!

Bougie B’s Mountainside Getaway
Absolutely beautiful space. Spotlessly clean. Full kitchen amenities plus a little coffee station. Fabulously comfortable beds and living room furniture. Deliciously soft towels. Just an overall great experience and peaceful stay!!

Modern Barn on 12 acres w Sauna, FirePit+swimming
Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

Stylish Rural Sanctuary with POOL!
We had a wonderful stay at this beautiful property! The location is close to plenty to do and great dining but also feels very private. The home is absolutely beautiful as pictured. The pool was a real treat to have and half of the pool is a shallow end which was a bonus for us traveling with a child. The beds are very comfortable which is always a huge plus when traveling. The hosts were responsive with any questions that came up. We would happily stay again!

Hollywood Bungalow in the Berkshires #C0191633410
We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.
Weekly house rentals

Cozy Log Cottage in Berkshires on 1.6 Acres!
My time at Maggies’s home was rainy and overcast. However, the home was warm and comfortable. All was , as it was stated upon booking. Maggie was responsive to my communications. The Berkshires and MASSMOCA are pretty wonderful. So was our stay.

Berkshire Lakehouse - 3 bedrooms - sleeps 5
Wonderful place on the lake with a great host. Janice was very responsive, offered an early check-in and set up a baby gate. Great place for dogs and kids.

Whispering Woods Guest House
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!

Cambridge Hill Farmhouse - Sauna - Swimming Pond
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.

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove
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!

New Berkshire home - 3 bed, 2.5 bath w/views
2nd year staying there. Trina is great and as usual the house was perfect! we'll see you next year!

Cozy Berkshire lake house
The house was very clean, comfortable, and cozy. It had everything we needed. We were a group of 7 and it was perfect. After skiing, it was a short drive back to the house. The hot tub overlooking the lake was an added bonus. I would highly recommend.

The Berkshires Hummingbird House
Karen’s place is amazing. She is so thoughtful in providing all the little things that you wish you had. First aid kit , Kleenex. Paper towels. Plenty of toilet paper! Beds were amazing. Sheets were amazing. The best equipped Airbnb I’ve ever stayed in. She was so helpful with local Recommendations as well! Thanks Karen! We will be back !
Private house rentals

Private Retreat: Hot Tub! Movie Room! Pool Table!
We had a wonderful time and this house is completely amazing. There is absolutely nothing missing! When Tiffany said, "all you need to bring are clothes" she wasn't joking. The person who designed the house was a genius with the master bedroom on one side of the house, the 2nd bedroom on the other side and the 3rd on the 2nd floor. Privacy inside as well as outside. It was a hiking trip for the family and included Kennedy Park, Olivia Outlook and the Great Monument Mountain. After spending the day hiking, the hot tub, playing pool and watching a movie in the theater just ended a perfect day. We didn't realize how close we were to MA and it was bonus to explore Western Mass as well. Thank you Tiffany for sharing your home with us.

Luxury retreat with sauna on 20 acres
We had an amazing stay! We reached out because we were desperate and need to find a place to stay, the host was so supportive and amazing!! Thank you so much and we will definitely come back!!

Mountain Escape - hike, bike, museums, and more!
We rented Amar's place for a 3 day getaway to enjoy the Berkshires area. We had 7 adults in our party and found Amar's place to be perfect for our needs. It's a beautiful home in a quiet town with all the amenities that one would hope for. Amar was extremely responsive and even proactive with communication and was a very gracious host. I would highly recommend his place

Majestic lake front house
We had a great time at Francois & Ann's oasis by the lake. It was so relaxing to wake up, look at the lake, and listen to birds chirp. If you are looking for isolation, this place does the trick, We didn't see anyone all week on the lake or at the other cabins until the day we left. The lake has excellent fishing. With little effort, we caught several decent-sized bass and pickerel right off the dock. The location is ideal. You feel like you are out in the country, but are close to great restaurants in Kinderhook and only 25 minutes from Hudson or Albany. It's also only an hour from Mass Moca and 90 minutes to Cooperstown. Francois and Ann were very communicative and quickly responded to questions and comments.

An 18th century farmhouse
What a beautiful, idyllic getaway Susan offers for her guests. A kind welcoming soul who provides a stay that brings you back in history – we had the most lovely time!

The Red House
We went to Chatham for a wedding near by and could not have asked for better accommodations for a weekend out of the city. Hope to go back!

Magical Retreat Cottage - Waterfalls Everywhere
Gene’s house is a place of peaceful quiet and beauty. It’s well appointed and comfortable, with wireless and all the various conveniences, but it’s far more than that. The separation between the interior and the beautiful meadow and forest outside dissolves through Gene’s use of windows and glass doors, and the calming sound of falling water can be heard in every room. His use of color and symmetry create an environment that allows you to decompress, and as a result, you can’t help but to connect with the beauty of the forest. The waterfalls are wonderful to sit by; it was too early in the season for a swim in a cold mountain stream, but that’s just me. The design and setting of the home is a reflection of Gene. If you visit, I recommend that you get to know him a bit. His kind attentiveness makes him a first-rate host, but it’s part and parcel of his uncommon connection to the world around him. Gene was more than a host to us- he became a true friend. We will be back.

Berkshire Retreat: Huge Home W/Hot Tub & Yard
John was the best host! He was super responsive and the photos/ description were spot on! Had a great weekend there and only a 4 minute drive to Jiminey Peak! Definitely will stay again!
Quick stats about house rentals in Lanesborough
Total rentals
50 properties
Nightly prices starting at
$116 SGD before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
20 properties have a pool
Destinations to explore
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- Stratton Mountain
- Saratoga Race Course
- Six Flags New England
- John Boyd Thacher State Park
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Taconic State Park
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Zoom Flume
- Bash Bish Falls State Park
- Stratton Mountain Resort
- Saratoga Spa State Park
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Beartown State Forest
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Naumkeag
- Hildene, The Lincoln Family Home
- Brignole Vineyards