Guest house holiday rentals in Hudson Valley

We were in Lenox to attend a reunion for the Lenox School for Boys ( Grad “66” ). The cabin was perfect for our needs especially because we could have our dog with us. Most of our time was spent with activities scheduled for the reunion so we didn’t really get to enjoy the peaceful atmosphere surrounding the cabin. There will be another reunion in 2026 so we will be looking forward to another stay at the Luv Shack. Thanks for sharing your abode. Pete & Becky Davis Mechanicsburg PA

A massive thank you to Julian and Karen! I brought my girlfriend here for our 5 year anniversary and it did not disappoint. The cabin was so cozy and our hosts were so kind. Woodstock was a really cool area and it is only 20 minutes away from the cabin. We would love to come back in the future :)

We absolutely loved Maple Hill Farms. It's a wonderful place and a perfect choice for a trip to the Berkshires if you're an animal lover. The best part of our weekend was bonding with Philip's sweet and friendly donkeys! The studio is well laid out with everything you need, the farm is beautiful and peaceful (except for the roosters, haha!), and the location is great for visiting local sights like Mass MoCA and The Mount. We hope to be back!

We were stunned by how magical this place was with all it's uniqueness of historic house. Spotless clean, spacious, very friendly owners. Our kids loved running around the back yard and playing board games that were provided. We would definitely come back, the only thing we regret is that we couldn't stay for longer, the area is very picturesque. many thanks!

This is I believe our 4th year staying at Sheena’s place in Saugerties the same weekend in May for a hockey tournament. The space is walking distance to town and the rink so we can enjoy the nightlife. The place is always immaculate, with fresh lilacs on table, water tea and coffee available for the morning. Bonus washer and dryer especially helpful during the hockey tournament. Sheen is always super responsive and flexible during our stays. Highly recommend Sheena’s place.

Great place to stay. Quiet and secluded. Has everything you need. Great host.

By far the best Airbnb experience I've ever had! Joni was an amazing host, and I also had the pleasure of meeting her husband Rob/seeing their unique, beautiful home. She was responsive and very helpful throughout my stay, and even taught this "non tech savvy" person how to operate the TV! The location is perfect- and in my case even more so, as I attended a family wedding at the Colony just a block away! Its a 5 minute walk to town, and at the same time very peaceful/private- a perfect combination. I fell in love with Woodstock and wish I could have stayed longer. I'll definitely be back, as there is much more to explore in the area- will definitely stay at Logstock when I return!

Jeff’s place was a hidden gem. It was private, close to the beach and town and the home was safe, clean and well designed. Jeff was kind and super responsive. There is a reason this place is always booked. I highly recommend staying here and can’t wait to return!

This stay offers a lovely home and view. Photos in the advertisement are accurate & communication was easy with the airbnb app. Upon our arrival we looked out back to see a young male deer in the adjacent field nibbling on his meal. Welcoming scene. Everything in the home is very clean; bed is a comfy king; there is one television in the livingroom with you tube available, but no live tv, so bring your Hulu/Netflix info or Firestick if you're a tv enthusiast. We we're in the area for a family wedding so that wasn't impt to us. We felt very comfortable & would recommend this home for any single or couple looking for a stay in the area.

We had a great time staying for a week at the Sherwood Barn ❤️ Thank you!

Quiet and and clean Pocono cottage within 30 minutes of places like Bushkill Falls, Pocono Outlets, Casino, water parks, and much more! The cottage is in the middle of everything.

Great experience! 2 wineries within 1 mile. Close to great hiking. William, was very accommodating with check in & check out time. Would highly recommend staying here. Very cute , clean and comfortable with get amenities.

I chose The Little Bliss Pond House as my proposal site. The location was absolutely breathtaking and exactly what I imagined. Cara was extremely responsive and helpful during the entire process. I would highly recommend The Little Bliss Pond House to anyone looking for a quaint and peaceful location surrounded by the best nature has to offer. About a 10 minute drive to some great restaurants and shops in Saugerties, The Little Bliss Pond House is the perfect escape for a weekend. 10/10. Thanks Cara!

Loved our stay and hope to come back in the future! Denise's place is beautifully designed and has lots of thoughtful touches. The house is less than a 10 min drive from Accord and 15 min from New Paltz, so there was a nice balance of nature/privacy with easy access to restaurants and things to see. Denise was very helpful and friendly, and check in was smooth and easy.

Very much enjoyed our stay. The place was clean and easy to check into. The best part was how close it is to Saratoga race track. We were in Saratoga for the Belmont Stakes and were able to walk to the track. Would definitely come back again.

Lovely aesthetics, close to many GB treasures. Wonderful kitchen space, with stocked pantry. Would recommend!

We had a really good time staying at this place, everything was better than in the pictures, wonderful view, very clean apartment, I would rent it again!

We had a nice, albeit quick, stay at Jane and Fred's place. Easy access, check-in, and living! Clean, quiet, and lovely location. The bonus for us was having morning coffee on the deck, watching the morning antics of birds, and having horses come graze right in front of us. Will visit again in the future!

I hope John will rename the place “The Cow House”. We enjoyed watching the cows every morning over coffee as they work their way across the property. While I love the windows to see the magnificent scenery (including cows) I wish there was a curtain option upstairs - 05:00 sunrise can be rough. The hot tub was fantastic and we got a chance to be in with the evening mist at dusk. We really enjoyed our time.

The location is very peaceful and serene and the hosts are very thoughtful. It was a wonderful stay, thank you so much for having us!

The Barn is very cozy and has a well appointed kitchen - we enjoyed cooking most of our meals here and enjoying the views out the large windows facing the field! Ilana was super accommodating and communicative before & during our stay. The location is excellent, within minutes of most major Berkshires attractions.

This was our second stay at Jen's place, and we hope to stay here again. Everything is exactly as pictured and described. Jen is a fantastic host. I highly recommend staying here!

The Eco Cottage was a perfect, tiny gem tucked away in the middle of the beautiful green woods. It was so private, peaceful, and serene. It truly felt like my own little retreat and since I was there to go on a retreat, this was the perfect place to lay my head at night. I loved walking the trails and wow, the pool, which looked so inviting (even if it was a bit too chilly to use this time!). Everything was clean, and the instructions were clear and easy to follow. Hosts checked in regularly but gave me my privacy. I really enjoyed my stay SO MUCH and will absolutely be booking here again the next time I’m in the area. Highly recommend!

I can't imagine staying anywhere else, Jeff and Dawn set an extremely high bar. The home is beautiful, clean, and as described. Jeff is responsive, warm, and wonderful to talk to. We will absolutely be staying again, I can't thank you enough! See you again soon!