Bed and breakfast holiday rentals in The Berkshires

We had an absolutely amazing stay at this cozy cabin by the lake! The location is perfect, peaceful, scenic, and surrounded by nature. One of the highlights was waking up to deer grazing right in the backyard. It felt like a nature retreat, and we loved just sitting on the porch with chai, watching them wander by. The cabin itself was clean, comfortable, and well-equipped with everything we needed for a relaxing getaway. The kitchen had all the essentials, and the living space was super cozy, especially with the fireplace going in the evening. The cabin is perfectly nestled right by the lake, which is literally in the backyard, such a dream to wake up to that view every morning. The fire pit was another highlight, we spent our evenings roasting marshmallows, sharing stories, and stargazing. A huge shoutout to Meghan, the host, she was so helpful and kind! She shared a bunch of local spots to check out. We’re already talking about coming back again!

We recently enjoyed a lovely stay at The Carriage Barn in Guilford. Our host, Katherine, was very responsive to everything we might have needed during our visit: a very easy check in and out process, detailed instructions on how everything worked, items for our comfort (a gift of delicious chocolates, many fluffy towels, silky sheets, etc.), and was easily available via texting. The photos of her restored historic barn are very accurate - it's a beautifully designed renovation and is decorated with lovely art pieces, cozy furniture, and a huge library of books for your enjoyment. The tv works great and so does the WiFii. We traveled with our small dog and there is a baby gate available that easily snaps onto the staircase posts so I was not concerned about my dog's safety.. Best of all is the beautiful views of the gorgeous Vermont countryside. You'll see lovely sunsets here and spectacular sunrises. It's a great spot to truly relax.

My husband and 2 year old stayed at Ellen’s barn for the weekend. The space was very big, clean and the bed was very comfortable. The location is excellent for exploring the area, we didn’t spend much time in the barn as we spent much of our day exploring. Would highly recommend Ellen’s place!

5 of us stayed at David's place for our family ski vacation and all of us loved the location and the house. the house was as described and has so many linens and amenities. it's 30 minutes to Stratton Ski Report and 5 minutes to downtown Manchester where you can find anything, including Shaws supermarket. It's a great location and house and we are looking forward to come back to this place next year for our family vacation. Thanks

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.

The home was clean, spacious, and comfortable and Rosemary was a friendly and welcoming host. Highly recommend.

Leo and Michelle were very responsive with any questions we had, and even reached out to offer us an early check in. The location was close enough to our places of interest, while still being slightly rural. The place looked just like the pictures and we felt right at home. We will stay there again when we return!

Incredible house for a weekend trip with a group of friends! The house was charming and the grounds were stunning. We loved using the lake and visiting the town of Pine Plains. Thank you!

Best value! Very nicely uniquely decorated lovely house with many interesting antique Ray collected . Clean and comfortable. Host Ray is the nicely host I ever had. Not only he got up very early to prepare delicious breakfast for my family when I had to leave the place early to catch a skiing lesson at Okemo, he also prepared the pit fire for us after he saw my daughter trying to pick up items for s'more making when we ran into each other coincidentally at the nearby grocery store. I will highly recommend Ray's unit for anyone who visit the area. Thanks Ray for your top notch hospitality!!

Another amazing, restful, and rejuvenating stay at Benmarl! Will be sure to return again.

Jim and Michelle were such welcoming and accommodating hosts. Their home is the perfect location tucked away in the countryside. Enjoying coffee and breakfast with Michelle on Sunday and their super friendly dog, Darby, was such a pleasant treat. Would love to come back more and explore the area. One thing to note, if you have Verizon you'll be off the grid here because cell service is sparse - but that's probably the best way to fully immerse yourself in the property and truly enjoy it!

Renee was a very nice host. The room was clean and the bed comfortable!

Sue and her husband were very welcoming and made sure my son and I were comfortable. They were pleasant and hospitable. They even left us fresh pastries, chocolates, and wine. This was a perfect location for a show we came to see, and we were close to shops and restaurants. The neighborhood was quiet and charming. We had a great stay!

We had a wonderful experience staying here! Tina was incredibly welcoming and even provided us with a complimentary breakfast, which was a really thoughtful touch. We also really appreciated the great selection of books and board games—it made the stay feel even more like home. Everything was exactly as described, and the stay was quiet and relaxing. Would definitely recommend to anyone looking for a cozy and well-kept place to stay. Highly recommend and we’re looking forward to visiting again!

This is a very comfortable and pleasant B&B in a well-preserved and beautiful old house--they had a little guide to the history in each room. The beds are very comfortable to sleep in and the temperature in the rooms is nice and warm. Breakfast was delicious. The best thing about it was the hosts: they are very friendly and attentive. You get the impression they really like their guests and enjoy sharing their beautiful home. This place is an absolute gem.

My boyfriend and I loved staying at Borland House; it was comfortable, charming, and the folks who manage the B&B were very helpful and responsive. It's right in town near several restaurants and shops and the history of the home and period details made for a welcoming and enjoyable stay! Get brunch there on the weekends!

Kathleen was a pleasure to work with and spend time with. We were there in “off season” and we enjoyed having her spend time with us at breakfasts. They were doing some upgrades to the house but it did not affect our stay at all. It will be really nice when it is completed soon.

Our stay with Priscilla in the farmhouse was wonderful. The room we stayed in was very spacious with a big bed and several very comfy chairs. Priscilla greeted us in a very friendly manner and showed us all around and gave us recommendations for dinner. She was available to us for whatever we needed. We had two incredible breakfasts during our stay. Her avocado toast, which she was trying for the first time, was the best that I have had! On day number two we had delicious chicken sausage and blueberry pancakes, along with fresh fruit and orange juice and coffee. Once again, delicious. I grew up in a rural area so staying at this farmhouse on a rural road brought back many memories for me. The peace and the quiet was incredible….. And yet… You don’t have to go far to get to major roads or delicious food. On our last night, we went to Stacy‘s Scratch Kitchen in Broad Albin. Don’t miss this one! We gave it an 11 out of 10. 😊 Thank you, Priscilla, for everything!

The bed was nice and comfy! Appreciate the stay!

What a lovely and beautiful location amongst the woods... perfect living space, a wonderful kitchen with everything we could want or need. Sharon is the consummate host. We absolutely love being there and our 2 dogs do too! We can't wait for our next visit!!

Catalpa House is exactly what you want in a small town retreat; comfortable bedding, well chosen amenities, superb breakfast, accommodating but not intrusive hosts, lovely common areas with local literature and current periodicals. It doesn't get better.

We had a lovely stay at The Lacey Rose. The house itself is very impressive and beautiful inside. The beds were very comfy and breakfast was terrific. Denise was great and stayed up to welcome us on a bit of a late arrival. Will have no hesitation in staying there again.

lovely stay at the Warwick Inn. The loft is situated above a very nice restaurant and a very convenient location and is quite charming with its own world feel and expose being. The host was communicative the entire way and I would definitely stay here again, thank you!

In one word, cozy. Lauren and Blake's cabin was a quiet retreat, with a cozy wood burning stove, simple and elegant decor and the most comfortable beds our party of three has ever experienced. Only minutes to the quaint little village of West Stockbridge the cabin is a beautiful haven we didn't want to leave. We will stay here again.