
Holiday rentals with a fireplace in Pittsfield
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Top-rated Accommodation with Fireplace in Pittsfield
Guests agree: these holiday homes with a fireplace are highly rated for location, cleanliness and more.
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Holiday House Rentals with a fireplace

Spring Hiking Pet Retreat I Game RM l ChimneyHill
Shannon’s place was perfect for our Christmas visit with our son. Clean, spacious, great location, fully stocked, and made the perfect place to host our son and his Copper Mountain colleagues for Christmas!

Rhinebeck Home with an amazing outdoor space+H/tub
Enrique's place was conveniently located near Rhinebeck, but alao far enough away that it was peaceful and quiet. Worth having a drink in the tavern at Beekman Arms and breakfast sandwiches at Rhinebeck Bagels. We especially enjoyed the hot tub. Enrique was a wonderful, informative host, and available if we needed (we didn't). Overall, we had a nice, relaxing weekend.

Cheerful, quiet 3 bedroom home
Our hosts were very easy to work with. I felt they cared about our visit and wanted to accommodate us in any way that would make her stay even more pleasurable. The house offered every convenience, including kitchen items for make-at-home meals. Thanks so much, Brandon and Brian!

Berkshire Lake- Modern and Updated-close to skiing
Home was beautiful, clean and close to Jiminy Peak, 16 minute drive! Great kitchen and living area to hang out

Cozy farmhouse @ the gateway to Mt Greylock/Jiminy
We had a great time staying here for a quick family ski weekend. The house was perfect for the 4 of us and only 10 minutes from Jiminy Peak.

Beautiful Period Home in the Berkshires
Really cozy and nicely decorated cabin in the Berkshires and only 5 min from Catamount Mountain. Loved the fireplace. Hosts were friendly and communicative. Would definitely stay here again.

The Gatehouse at Raspberry Ridge
If your looking for a great quiet stay while visiting Hudson or other local places this home is it. Very clean, super dog friendly. Close to the highways and hidden enough to really be apart of nature.

MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts
Place was great! Less than 10 minutes to Mount Snow. We had fun playing ping-pong, air hokey, pool, and darts! Relaxed by the wood burning stove. Lots of rooms and beds.
Apartment rentals with a fireplace

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
We loved staying at Patrick’s place. We are in the process of booking another stay with him. There were a lot of things to do in the area that we didn’t get to do. The room was perfect for us. It was comfortable and very cozy. It was just as described. The place was clean and inviting. Patrick suggested a perfect place for my husband to work out in nature. Can’t wait to see the flowers in bloom at his farm.

Steps to MoCA: 2bd + SAUNA!
This was our second stay at this getaway in North Adams, and it was every bit as enjoyable as our first. A very convenient walk into town, a unique property with a very spacious yard, and lovely trees and grounds. Definitely a favorite home base to explore western Mass.

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.

Modern Copake Falls Getaway - 8 Mins to Catamount
Our stay at Michael’s AirBnB was everything we needed! The property was easy to get to, secluded, and conveniently located to nearby stores. We brought our 3 dogs and the big yard was perfect for them. Highly recommend for anyone looking to unwind.

Sunny Duplex at the old boarding house
The place was wonderful. Very charming and homey, spotless with all the amenities and conveniences you could need. The information included in Joe’s binder gave great recommendations for meals and attractions within easy driving distance. We had never traveled to that area before and found the local scenery beautiful. Thanks for a lovely experience!

Newly renovated cutie
This was the perfect place for me to stay after a long day of travel and before the next day’s early site meeting. I felt so cozy after a wonderfully hot shower that I fell asleep early. And the bed was so comfortable I overslept, but Lisa saved the day by leaving a muffin and drinks so I was able to have a rushed breakfast. The accommodation was exactly what I needed.

The Shepherd's Retreat
i felt safe, in spacious surroundings! Loved the birds who visited the flowery swing-patio in the early am !! thank u !
Villas with a fireplace

Dancing Bear Lodge The Charm of Chimney Hill
We had a great stay at Marlene’s guest house. 15 min drive to Mount Snow and 5 min drive to the grocery store. We had plenty of space for two families with bunk beds for the 4 kids on the lower level. The air hockey table and access to the clubhouse swimming pool was a big hit. There were two tvs and board games to keep the group occupied after a long day of skiing. Host was also very responsive to any questions we had. Place was very clean and well stocked. Would highly recommend this place.

5-BR Villa with Pool and Dog Friendly!
The villa is exactly as promised. It’s on a hill overlooking the Hudson with great views and outdoor space. It’s dog friendly with a fenced in yard, a wonderful feature for dogs and people. We were there for a family wedding so did not make full use of the outdoor spaces, but the pool and fire pit are very inviting. The bedrooms were comfortable and we enjoyed lounging in the living room with tv football games. The location is a short walk from downtown Coxsackie for coffee and treats. You should know that access to front door is up about 12 or so steps but there was a railing if anyone has mobility issues. We would return if we were to come back to the area. Lakpa is super responsive.

Vermont Vacation Villa—Grapevine Getaway
lovely stay for my group’s annual ski trip! beautiful home - would love to stay here again :)

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
Sourove’s place is great. It is a spacious and well apportioned home that is perfect for a family. The view of the mountains from the front window is beautiful and provides a relaxing sunset view. We absolutely recommend this house for anyone looking for a modern, well equipped place to stay in Hudson. Thanks again!
Quick stats about holiday rentals with a fireplace in Pittsfield
Total rentals
50 properties
Nightly prices starting at
$110 AUD before taxes and fees
Total number of reviews
2.9K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Stratton Mountain
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Six Flags New England
- Albany Center Gallery
- Berkshire East Mountain Resort
- Taconic State Park
- Mount Snow Ski Resort
- Zoom Flume
- John Boyd Thacher State Park
- Mount Greylock Ski Club
- Mohawk Mountain Ski Area
- Mount Sugarloaf State Reservation
- Opus 40
- Bash Bish Falls State Park
- Norman Rockwell Museum
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Beartown State Forest
- Naumkeag
- Otis Ridge
- Ekwanok Country Club
- Talcott Mountain State Park