
Holiday rentals with a fireplace in Stockbridge
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Top-rated Accommodation with Fireplace in Stockbridge
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Holiday House Rentals with a fireplace

Stockbridge Cape Near Tanglewood!
One of the cleanest Airbnbs I've stayed in. Perfect for a group of 5 women. Space was great, all had our own bed, and the two bathrooms worked well for us. Minutes to all attractions and restaurants in the Stockbridge/Lenox area. Large, beautiful deck that we wished we had been able to use more but for all the rain. Only thing to note is that if you have mobility issues, the back stairs on the deck to get into the house might be challenging. Other than that, would definitely recommend to others and would stay here again!

Sunshine Cottage
We only stayed one evening but found the living space to be perfectly laid out and spotless. The kitchen is fully stocked with about every utensil and appliance you can think of. We especially enjoyed the fresh eggs, treats, and flowers that welcomed us! The living room was especially comfortable. The unit is attached to the rear of the main house but it’s kept totally private. There aren’t many places to eat in Richmond — after all, it is pretty rural— but Stockbridge and Lennox offer many dining options.

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove
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!

Classic Stockbridge Cottage
I had the best stay at Lucas’s beautifully decorated home. The house is warm and inviting, and I felt right at home. The location is quiet and peaceful, surrounded by woods, and located within a beautiful walkable neighborhood perfect for taking my dog on walks. Lucas was very responsive and helpful when I needed to extend my stay a couple extra nights. I can’t say enough good things about this place and host. I’d love to stay here again during warmer months and enjoy the porches and outdoor areas, but it was also very cozy during the cooler weather when I was there. It’s a perfect home away from home.

Modern and Stylish Country Lakeside Cottage
This was my second time staying at Maureen’s beautiful lakeside home and it surely won’t be my last. It’s the coziest, peaceful and inspiring place. Looking forward to future visits!

Stunning luxury home with pool
Beautiful home! Extremely clean upon arrival and excellent communication. Everything in the house was clearly labeled and directions for check-in and check-out were very clear. Sadly it rained our entire stay so we could not enjoy the pool or the beautiful backyard, but we still had a lovely stay. We hope to come back soon!

Cantabile life in the Berkshires
Jia place was great. Very spacious and plenty of things to do. It was very clean. The entire process was super simple. We enjoyed it quite a bit.

Beautiful Period Home in the Berkshires
We really enjoyed the our girls weekend in the Berkshires! The house had plenty of places to sit and hang out, which was especially useful because it was a rainy weekend. The house is in very private and in the woods, and was great for bird watching. It is also very close to Great Barrington with lots of restaurants. We would definitely stay again!!
Apartment rentals with a fireplace

Sunny, light filled loft in 1873 Colonial
Peter and the apartment were great! Peter was super responsive, friendly, and had nice touches like homemade granola with milk and coffee provided. After my original AirBNB fell through at check-in at 6pm, I was relieved (and saved) by Peter’s responsiveness.

Light filled three bedroom apartment DT Florence!
We are a family of 5, traveling with two young adults and a teen. Donna’s house was super comfortable and spacious for our family. Clean, uncluttered, and stocked with everything you could want! We loved walking through the beautiful neighborhood and grabbing breakfast at the Pie shop around the corner. Donna was a great host!

Romantic Warren St Penthouse w/Catskill Mtn Views
Great place in the heart of Hudson - very comfortable! Would definitely recommend.

Cozy Rustic Apt. in 18th c. Berkshire Farmhouse
Wonderful place to stay for an anniversary clean rustic apartment with a welcoming feeling, it felt like a cabin 10/10 would recommend 🙂↕️

Large Quirky Sunny Farmhouse Apartment
This private apartment is cute and quirky and cozy. It’s in a beautiful and quiet location with great amenities in Florence and a short drive to Northampton. The apartment is spacious and the bed was very comfortable. I would happily stay there again.

Steps to MoCA: 2bd + SAUNA!
David and Mátti’s place is truly special. I feel very lucky that we got to stay there for a few days! Thank you to our hosts for creating such a serene, comfortable space. They went out of their way to say hello and make us feel at home. We had a barbecue one night, and David even brought over extra strong bug spray! We also love supporting the incredible work that they are doing with artists. My friends and I would love to stay here again for another trip to the Berkshires.

Secluded but not isolated Berkshire Retreat
This was our 2nd weeklong stay. The space is clean and bright. Heating details were clearly explained. It was quiet and peaceful but only a 7 minute drive for milk I forgot to bring for coffee. We saw a small bobcat in the front yard on our last morning. Beds were very comfortable. Hosts were friendly and responsive. I’d recommend this place to friends/family and hope to stay again.

Warren St. Ensuites - Pets allowed
We spent a weekend at Roy's place and had a wonderful stay. The apartment was spotless and located right in the heart of Hudson. Our host Reta was very kind and always prompt in her communication and consideration. At one point there was a small leak to which we were quickly notified. It was repaired before we'd even noticed and we were additionally left with a thoughtful card and delicious muffins. We would happily stay here again and highly recommend to anyone looking for a large and perfectly situated stay in Hudson.
Villas with a fireplace

5-BR Villa with Pool and Dog Friendly!
cute house and wonderful weekend

Vermont Vacation Villa—Grapevine Getaway
Anthony's house was an excellent venue for the weekend of our son's wedding in Williamstown. It easily fit the eight family members staying there with plenty of privacy on three floors and great gathering spaces on the main floor, deck, and pool deck. We're grateful the pool was open; the kids loved it on a hot afternoon of our stay. If you are looking at this house, don't let the backroads approaching it look like a liability. They are well maintained and allow easy access to Williamstown and the southern Vermont towns along route 7, yet the quiet location will insure you sleep well.

Retreat to 56 Acres w/ Hot Tub, 2 Acre Pond, Pool
My daughters and I really enjoyed our stay at Jacks place. The house is beautiful, and the surrounding private property is stunning. Nicole was very helpful whenever I had any questions.

Mountain-View Retreat @ Hudson
Beautiful home, great location and friendly host. Bed was comfortable, kitchen had everything needed, games room was an added bonus.

Mediterranean Villa with Pool
Marco was a very accommodating host and his property is absolutely immaculate, my guests and I felt like we were in Europe or some tropical place. The kitchen was spacious enough to accommodate our large group and we had no issues with the property or any appliances the whole time. We enjoyed gorgeous sunsets off of the balcony and also hiked to a nearby waterfall. Absolute five out of five stars!
Quick stats about holiday rentals with a fireplace in Stockbridge
Total rentals
60 properties
Nightly prices starting at
$123 AUD before taxes and fees
Total number of reviews
2.3K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool
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- Hunter Mountain
- Six Flags New England
- John Boyd Thacher State Park
- Jiminy Peak Mountain Resort
- Windham Mountain
- Albany Center Gallery
- Bushnell Park
- Bash Bish Falls State Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Zoom Flume
- Kent Falls State Park
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Hunter Mountain Resort
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Bright Nights at Forest Park
- Hartford Golf Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Opus 40
- Naumkeag