Bed and breakfast holiday rentals in Lenox

Staying at Tim's was a fantastic experience for our family. We felt at home, part of a community made up of kind and welcoming people. Tim is much more than a host: he is a friend who makes his best to make his guests feel at ease and he is one of the most generous people I have ever met. The house is lovely and is in a pleasant place. We would like to return in the future.

From start to finish, we so enjoyed the Gables Inn. It is quaint and cozy with impeccable furnishings, a comfortable bed and lovely room, great coffee and pastry for breakfast and an excellent location in Rhinebeck.

Very beautiful and quiet house in the nature. The room is large and the bed very comfortable. Thank you Susan for the warm welcome, great breakfast and nice conversation! Recommendation for diner for future guests : Bimi’s canteen and bar in Chatham !

As the other reviews have mentioned, John is a beyond excellent host!!! And very responsive! He is also very knowledgeable and helpful regarding shops and restaurants in Troy. Nigel and Margaret (John’s greyhounds) are also very good companions at this Inn! The decor in the rooms and in the shared rooms and hallways is just beautiful and very interesting! And he serves delicious homemade breakfast! With alfresco dining as an option in the warmer weather.

This house was the perfect place for our family get together. We were able to use both dwelling and socially isolate while indoors. The grounds are extensive and nicely cared for. There were plenty of gathering spots outdoors where family could gather comfortably while maintaining distance. These are cray times, but this property was well suited for our family needs. The garden is gorgeous and there was plenty of room to spread out for a softball game or badminton, but intimate enough to find a nice corner to read or just relax. The location was very good as well. It was a short distance to the walkway over the Hudson (30 min) and to Lake Minnewaska State Park (40 min). This was our first trip to Hudson Valley but will not be our last.

Great spot for our son’s graduation. We had the upstairs which gave us privacy and flexibility in case our other son and a cousin could join us. Cozy, clean and comfortable. Charmaine was a warm and gracious hostess. Good coffee in the morning.

I loved my stay. Yulia was very responsive to my messages as I arrived later than expected. The space is very private with a lovely garden outside the window. The bed was super-comfy with plenty of storage space in the room. And the shower water pressure was a dream! Both hosts were very friendly and made me feel welcome right away. I would definitely stay here again. Thank you both! Nancy

Ilja was wonderful, friendly, and helpful. He was able to accommodate an early check-in so we could prepare for a wedding we needed to attend. Every amenity that you could think of was offered, down to the lint roller and flashlight, and he even asked if we needed anything else. Ilja had fresh coffee available at all times and space offered in kitchen with glasses, water, tea, etc. He was very respectful and helpful. We enjoyed the peaceful areas outside the home, and would have enjoyed sitting by the pond if it had not been raining during our entire stay. We liked the historic character and charm of both the inside and outside of the home. I would highly recommend and will return if in the area again.

The Inn at Pine Plains hosted by Patricia was great for our long weekend stay (couple with son & dog), the room was cosy and exceptionally clean and tidy. The location is close to walking trails, a beautiful drive to the Catskills and nearby to restaurants. It had a lovely dining space and had everything we needed should we have stayed longer. There is a large lawn backyard that our son and dog loved running around in each morning.

It was an absolute delight staying at The Granville House. The hosts were friendly and responsive, the space was beautifully curated and well appointed, and the location could not have been better. The breakfast provided was super tasty (muffin masters!), and the dining room vibes were excellent — music, decor, & the overall aesthetics of this place blew my mind. You can tell Terry and Terri have worked in hospitality for a long time and put a great deal of care into making the guest experience superb. I booked our long weekend on a whim and am so lucky there was availability; I have already recommended The Granville House to several of my friends.

Fantastic stay! Jill is truly the best host we’ve ever had in all our Airbnb experiences. She made us feel so welcome, and we truly appreciated her hospitality. The place was perfect, comfortable, and had everything we needed. We would absolutely love to come back and highly recommend this place to others!

Absolutely beautiful and relaxing setting. The house is so lovely, and well appointed with a wonderful array of antique furnishings and art. The front screened porch was our favorite spot- Anita is the epitome of the hostess extraordinaire. She is friendly and attentive to her guests, but not at all overbearing. Her pride in her family home and history is evident from the moment she greets you. We loved it and would definitely go back. Breakfast was delicious and she looks to everyone detail… down to the doilies on the delicate tea cups. I highly recommend this gem in New Markboriugh. The best of the Berkshires for sure.

Gorgeous home with an artist’s touch. Bill and Pamela are kind and thoughtful. Very much enjoyed my stay with them.

Oh....it was a great place to stay. I had my pup with me, and it worked out so well. Attended a concert down the street, and it was great to be back at the inn at a few minute's after the concert ended. Breakfast was wonderful, and the staff were so personable and accommodating . Look forward to my next visit!!

I can’t say enough good things about this place. From the moment we arrived, everything exceeded expectations. The inn was spotless, beautifully decorated, and had every amenity we could have needed—and then some. The bed was super comfortable, the view was stunning, and every little detail was clearly thought out with care. The host was incredibly warm, responsive, and welcoming. They went above and beyond to make our stay special, offering great local recommendations and making us feel truly at home. We’ve stayed at a number of places, but this one stands out as one of the best. If you’re considering booking—do it! You won’t regret it. We’re already planning our return trip.

Debbie was amazing! She was so kind and so sweet! She cooked us an amazing breakfast in the morning and made sure our rooms were clean and comfortable! We’ll definitely stay here again!

The Carriage House offers a stay that feels both luxuriously curated and effortlessly welcoming. Every detail is carefully considered—from the plush robes to the thoughtfully selected snacks in the common area, a small yet telling gesture of hospitality. The aesthetics are impeccable, blending historic charm with modern elegance. While communication can be slow and breakfast sometimes arrives later than expected, the beauty and coziness of the space make for a truly memorable stay.

Beautiful, relaxing getaway with friendly and helpful host. We truly enjoyed every moment in Diane's lovely home. The suite was spacious, comfortable, and full of amenities. We especially made time to enjoy the covered deck and pool, which were as wonderful as we hoped. The continental breakfast was incredibly helpful for getting our days started. Close to many restaurants, hikes, and lovely Hudson Valley towns. We would return in a heartbeat.

Kathleen was very kind and informative when we checked in. She has a wonderful bed and breakfast and the food she prepared is phenomenal. She made us feel very welcome. Would definitely recommend to anyone staying in Stillwater or surrounding areas

We totally loved our stay! The town of Norfolk is so quaint. But Airbnb bed-and-breakfast, we felt right at home really loved the breakfast in the morning when we all sat around the table and had conversations with all the guests that were staying. I would definitely stay there if we return to the area.

This is an idyllic setting for a beautiful home with super friendly and caring hosts. The large house, a retreat center with facilities for large groups, sits on a lake overlooked by a gorgeous modern treehouse. Tom and Ravi are excellent hosts and I enjoyed chatting and eating with them and learning about their vision for the property, communal and artistic, with nourishing food fresh from local farms, and a mix of interesting guests. This is the kind of place where you can truly unwind in natural green, wander the extensive grounds and connect socially if that suits you. The beds are comfortable, each room with its own bathroom, and the living rooms are spacious and with walls of books and artwork. Cannot recommend this place more highly. If you’re lucky enough to find availability, don’t hesitate!

Fantastic to spend some time at the Goldenrod with Aaron and Eric with our two kids and family this weekend. The hospitality was fantastic, location incredible, and we loved the restaurant, our beds, and the 3 goats to feed in the back. Thank guys for hosting us! Can’t wait to return on our next trip to the Berkshires

Sandra and Tom are amazing hosts. Everything is so cozy and they are incredibly warm and welcoming, it was home away from home! Sandra is an amazing cook and was so accommodating to our individual preferences. Highly recommend and definitely would stay here again!!

This inn was very nicely renovated and appointed. We loved the parking right out front, the front porch in the afternoons and the free snacks in the lounge ;-). We would stay again. A few restaurants on the block are nice and the waterfront area is great for walking and dining and it’s less than a 5 minute walk away.