
Holiday rentals with a fireplace in Stockbridge
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Top-rated rentals with a fireplace in Stockbridge
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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!

Fenced yard, playroom & the Berkshires - $0 fees
The house was clean and nice! Beds were huge and comfortable and the area is beautiful. The hosts were very responsive. It was the perfect trip.

Berkshires Forest Retreat with Hot Tub
The house was a great place to spend a weekend with family and friends. Very comfortable with a baby. We loved the outdoor space and Annie was very responsive when we needed help.

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!

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi
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!

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.

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

Suite 23 - Spacious Sunny 2-BR with Mountain view
We had another wonderful weekend at Barbara & Chad's suite. We've stayed there multiple times and love it for our family of four. The hosts are always responsive and so very helpful. We also love the nearby Berkshire East Mountain resort and nearby local towns. Looking forward to our next visit!

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 🙂↕️

Steps to MoCA: 2bd + SAUNA!
Matti was a friendly and thoughtful host who made us feel welcome from the start. He reached out ahead of time with helpful info and made check-in easy. The place matched the listing perfectly—if anything, it was a bit nicer than expected—and was a great value for the area. Both bedrooms were comfortable and had blackout shades. The shower had great water pressure and was a nice way to start the day. Everything was clean and functional, and we enjoyed the custom furniture pieces. The location was another plus- it was easy to get around on foot. We walked to dinner, grabbed coffee in the morning, and picked up a few things from the grocery store—all without needing to drive. Overall, this was a great place to stay with everything we needed. I’d definitely recommend it for anyone looking for a well-priced, comfortable option in the area.

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.

Modern Copake Falls Getaway - 8 Mins to Catamount
My wife, dog, and I had a wonderful and peaceful stay at Michael's place. The land is beautiful, the place itself is actually even nicer than the pictures, and there is plenty to do in the area. We will definitely be coming back!
Villa rentals with a fireplace

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

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

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!

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.
Quick stats about holiday rentals with a fireplace in Stockbridge
Total rentals
60 properties
Nightly prices starting at
$103 SGD 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
- Albany Center Gallery
- Bushnell Park
- Jiminy Peak Mountain Resort
- Taconic State Park
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Zoom Flume
- Windham Mountain
- Kent Falls State Park
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Beartown State Forest
- Hartford Golf Club
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Hunter Mountain Resort
- Opus 40
- Naumkeag