House holiday rentals in The Berkshires

This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!

Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!

It was a fantastic house with a beautiful view. Plenty of space and we really enjoyed our stay. The property itself is absolutely gorgeous. Would definitely come back.

Truly one of a kind property. Relaxing, calm, extremely responsive and helpful host. If you are looking to get out of the city or just need some time away to think, look no further. 10/10.

The teahouse and surroundings were relaxing and peaceful. We saw groundhogs, deer, and chipmunks from the porch and our 2 dogs loved exploring the field and wandering in the nearby woods. The pool was amazing and warm despite the rain and the natural landscaping couldn’t have been more beautiful. We really enjoyed our stay!

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

We really enjoyed our time at Elizabeth Jane's place. The home is spacious and quaint, with nice furnishings, a tasteful colonial feel and easy access to downtown Litchfield and the Berkshires. The bucolic setting is lovely - scenic, relaxing and peaceful.

We had a great time during our stay! The indoor pool was the real highlight—clean, well-maintained, and the surround sound music made it extra fun. The entire property was spotless and clearly well cared for. We even enjoyed S’mores at the outdoor fire pit. Chantale and Toni were incredibly accommodating and ensured we had everything we needed for a comfortable visit. Highly recommend for a peaceful and enjoyable getaway!

Loved every part of our stay with Kristine. Perfect for a romantic weekend away - gorgeous cabin, well appointed, and great kitchen for cooking-in. Her recommendations for local spots were also so thoughtful. Thank you again!

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.

Very rustic, private, peaceful kind of like a camp but with air conditioning and excellent wifi. Bald eagle sat over the lake outside. Kayaks were fun. Tons of great hikes and historical things to see. Town of Great Barrington and Sheffield have great antiquing both high and low end. I would go back any time.

We enjoyed our stay at the house. Mitchell was very responsive and communication was easy. The house is near butternut and GB. Hopefully we will come back in the summer to enjoy the outdoors.

Erin’s place was absolutely lovely! We really enjoyed the location - so peaceful and conveniently close to Art Omi. The cabin was beautifully maintained, and we especially loved the interior design, which felt both stylish and cozy. We stayed for two nights but honestly wish we could have stayed longer. Highly recommend!

My husband and I were blown away by the beauty and thought that was put into this private destination. The moment you step on property, the freshness of the air and sounds of the creek are immediately calming. Diana was incredibly nice and very communicative before and during the entire stay. Activities: The sauna, creek, hot tub, pizza oven, grill, fire place/pits, hammocks- the amenities are amazing and unlike any other Airbnb I have ever been in before. So much that besides a quick dinner out one night (12 min away) and a nice walk around the Mountain Top Arboretum with our dog, we wanted to spend our time at the property. We called it our personal sanctuary spa!! The home: The home style is minimalistic but homey and every single item is top notch quality. There are no shortcuts- the entire place is a work of art. The bedroom and bathroom inspired me to reanalyze my own bedroom style. Thank you for upping the Airbnb game!! Can’t wait to come back to this magical spot! ✨

The charming house is in the most beautiful settings - tall trees with a creek running through. So peaceful! Secluded, but a short drive to cute shops and restaurants.

We highly recommend a stay with these seasoned hosts who know how to make a home away from home. This spacious, private location was perfect for our girls' weekend away. The house was clean and comfortable with loads of quirky mid-century modern touches making each room a visual delight. A handwritten note and bag of delicious shortbread cookies welcomed us when we arrived. We loved having the room to spread out and visit and then retreat to our own rooms for rest and relaxation. We did not use the kitchen to make meals, but it was well stocked with a big fridge and plenty of counterspace. The host was responsive and friendly. We hope to make a return trip in the future.

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.

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!

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.

We stayed here on our way to Stowe to break up our long drive with an 8 and 2 year old. It ended up being a wonderful mini trip that we didn't want to leave. The house exceeded our expectations in terms of quality, cleanliness, and amenities. And the location was excellent - about 10 to 12 min to the nearest grocery store and downtown with restaurants, Edith Wharton's estate about 20 min away, and Great Barrington/Stockbridge were easily accessible for day trips. We plan to come back for skiing, and to take advantage of the lake activities in the summer. The only downside was the busy road, as mentioned in the listing, but the traffic quieted down in the evening and it didn't affect our sleep at night with the bedrooms located in the back of the house (husband is a very light sleeper; we did bring and use sound machines just in case).

Perfect location for a few friends that came for a birthday party. Was perfect. I didn’t worry about them at all, and I knew they had a quality stay

Our stay at Hinterland Hall was a wonderful, unique experience. The property has been carefully restored and tastefully staged. The surrounding area includes some great hikes, like Mount Graylock to the north and Monument Mountain to the south.

Kellen and Samantha's home and property are very special--a wonderful location for a restful retreat in nature that is also a short drive to several charming towns in northwest Connecticut. The hilltop site offers breathtaking views of surrounding mountains, valleys, and forest. The residence sits atop a long driveway off a gravel road so is serenely quiet and private. Inside, the space was immaculate, thoughtfully designed, and very comfortably furnished. The shower, bed, towels, and linens were all particularly fantastic, as was the full kitchen which allowed us to cook nightly. The area is exceptional for hiking, culinary delights, and all sorts of shops. And our hosts were proactive, helpful, and clear in all of their communications. We really loved staying here, as did our dog, and we hope to return. Highly recommended!

I was planning on my proposal and wanted somewhere special. The window house was exactly that. Private, peaceful, super clean, amazing views and wildlife. Taylor and Marla were EXTREMELY good at communicating and getting back in a timely manner. If you and your significant other are looking to get away, this is the place. It’s sublime.