Family-friendly holiday rentals in Lanesborough

A quiet private property located close to amenities, the city of Hudson, and nature. It is a beautiful and comfortable home filled with creative and tangible care. We enjoyed cooking in the kitchen and spending time on the property over a long weekend stay.

John went out of his way to ensure we had a great stay. It was a great place that accommodates many and the hot tub was relaxing after a long day of golf.

What a gorgeous stay. My partner and I celebrated our five year anniversary here and each detail was perfect. The home is wonderfully curated, with stunning art, decor, puzzles, plates, you name it! And by the window, the feeders attract all kinds of birds that I’ve never seen so up close. Woodpeckers, cardinals, chickadees. You hardly need the TV, it’s so entertaining. The place is spotless and serene. And Rosy is so responsive while giving you complete privacy! You can tell she really cares about the experience she provides. If you’re looking to stay in an artfully cozy home, this is the place.

This is our second time staying in The Farmhouse, and our 5th or 6th time booking with Ginny. This property is very relaxing, we brought our three dogs and they loved the backyard. The house was clean and organized. We enjoyed breakfast on the farmers porch. The hot tub was nice. It’s a quick drive to downtown NoHo, Florence and EastHampton. So much to do in this area. We highly recommend.

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.***

Porter & Sara run an amazing cabin. Their container cabins are well equipped for a fun, romantic stay. The layout of the cabin lends itself to a warm welcome and the positioning of the couch, bed, and table make perfect use of the landscape - all facing the beautiful pristine meadow that hosts a ton of wonderful sights including deer, flowers and interesting insects! One thing that stood out was the lack of mosquitoes. Given the clearing and the amount of other wildlife, we were pleasantly surprised how comfortable it was to stay outside and not worry about being eaten alive. There are plenty of lounging accommodations, from nicely kept hammocks, to comfortable lounging chairs to a lovely hot tub . The low lights outside make the hot tub and patio a fun place to hang all night. When getting into bed, you’re greeted by the beautiful stary night. It was amazing to lay down and feel like we were all alone in the woods. We will absolutely be coming back for another romantic adventure.

Really nothing negative to say. We appreciate all extra personal touch the hosts left for us. I wish all ABNB locations had the same care and attention to detail for their guests.

We loved staying at Anat’s gorgeous home. We’ve been in many spots in the HRV and even Columbia County, but this stood out for being so tranquil and for having such lovely grounds. We enjoyed the Copake Hillsdale Farmers Market and a great meals at Local 111 and Zinneas. Cooking at the house was a breeze and there were more than enough beds and living spaces for our two families to feel so comfortable. Hot tub was lovely! We can’t wait to return.

I stayed for a month, and this space is something rare. A masterclass in design; farmhouse aesthetics reinterpreted through a modern, editorial lens. Every detail is intentional, embodying the essence of Hudson: a precise blend of historic rural charm and upstate sophistication. The kitchen practically insists you visit the local market and cook. The clawfoot tub and heated floors reframe the idea of routine. The beds make it hard to get up, but you wake deeply rested. The home is immersive. It doesn’t borrow from Hudson—it distills it. Thoughtful, intuitive, and exquisitely executed. I left inspired. Anthony and the This Old Hudson team were exceptional. We can’t wait to return.

This was so charming & cozy, while also being conveniently close to nature nails & downtown Woodstock. We thoroughly enjoyed our stay & would recommend!

The guesthouse was so dreamy! We had a wonderful stay, the hosts were super friendly, and we loved meeting their sweet dogs. The house was close to great restaurants and shops in Hudson, Kinderhook, and Ghent, as well as hiking trails. The lovely trail on the property was a great bonus, one we took advantage of 4 times throughout the weekend :). Would definitely visit again!

so beautiful and cozy! private and in just the right location.

Staying at Will and Aenne's barn house was fun and wholesome. I enjoyed saying hello to the animals and the jungle shower most of all. The barn has everything one needs. Though, I must say I was very intimidated by having to light the chef's stove. We walked from the barn to the waterfall down town which was beautiful--great place to hang out and swim in the warmer months. The village of Kinderhook is adorable with quaint little shops. Hudson city had some of the best food I've had in a long time; I strongly recommend eating at Cafe Mutton. Overall, Will and Aenne were very hands-off hosts--as in, they gave us our space and privacy--while still being responsive and attentive. Thank you for the stay! I hope to come back again!

Jason’s place was excellent! Exactly what we were looking for in a country getaway-cozy cabin in the woods, full of charm and close to farms, hiking and swimming. we loved listening to the records while cooking. Perfect spot, perfect vacation!

Bobby was the ultimate host in every way. I felt so relaxed and comfortable in his home that I extended my stay for another week and have already booked for a future stay. The home is beautiful, full of original art, cozy and perfectly suited for a quiet getaway yet close enough to Hudson, Kinderhook and Catskill. The house gets beautiful morning light and I found it very relaxing having my morning coffee on the sun porch. The flowers and trees were just starting to bloom in the garden - making it the perfect canopy for my guests and I to have an early evening cocktail before heading into town for dinner. Very much looking forward to returning in a few months!

We had an awesome trip - The location is charming, great views of the pond. During our stay, the wildflowers were blooming in the yard and across the water. Complete fresh air, could barely see only one cabin through the woods, and that's only if you squinted. It took us a minute to be sure we had the right cabin (some flowers had grown up over the street number, we missed it at first) but once up on the deck or inside, it was clear. And exactly the degree of 'rustic' and 'private' I was looking for - The inside is lovely, and I grilled out on the deck two of the nights. The grill worked like a charm, and I have to give the kitchen props for how well stocked it was relative to most cabins. - I landed myself on crutches two days before our visit, so did not hike the way I first planned. But we spent an evening at Tanglewood and the Lee town beach admits you with proof of rental in the town (airbnb counts). Small grassy park, sandy beach, plenty of picnic tables, v. family friendly

We had a magical weekend away and our stay was everything we hoped it would be, and more. Olia was incredibly responsive, friendly, and all around wonderful to connect with. The house was a magical time capsule holding the best of energy and a glimpse into the 70s - so fun. The pool and patio were awesome, with open and friendly spaces inside too, all made for the best of entertaining spaces. We could not have asked for a better weekend away, and we cannot wait to plan our next trip! Thank you!

Had a great time! Within 4 minutes of a stellar breakfast at Trail 87 and within 5 min of mount snow base.

Billy and Rhobin were so helpful and easy to communicate with. The house was so comfortable and peaceful. The property was lovely! 5 Stars all around! Thank you for a fantastic stay!

Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

Beautiful country home, SUPERB location, large grounds with a beautiful pool, and communicative and kind host. We had a wonderful stay.

We had a wonderful time at Tina’s place! Surrounded by woods, but somewhat close to the downtown area (super cute too!), the cabin had all we needed, and is also very cozy, neat, comfortable. Excellent bed and pillows, perfectly AC’d, with a fully stocked kitchen. We are happy, and our pups were THRILLED! Huge thanks to the host.

I got a great last minute deal on this place and am so so happy I stayed here! Fantastic location and truly such a lovely space. Felt right at home when I found our welcome gift of a bottle of wine, some cheese and crackers upon arrival! Thank you for having us Susan, we loved your home!

Diana and family were amazing super friendly, accommodating and checked in on use through out. We arrived later than expected but Diana waited for us and showed us around the property. We even got to see her dogs, meet her family, met the horse on the property behind and great conversations with Diana. She made us feel right at home. She prepped the pool for us, left us some good snacks and offered lots of recommendations. When you visit check out the theater set up, it’s pretty cool with insane sound system and clear video. Comfortable beds and all around beautiful property. If you visit in the summer it is a little warm on the second floor but we cooled off in the pool and just made sure to turn the fans on. It was the perfect birthday trip, relaxing, private and homey. My family and I are already looking forward to the next trip. Thank you to Diana for everything and hope we can meet again! 100% recommend.