Vacation rentals with a fireplace in Pittsfield

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Popular amenities for Pittsfield fireplace rentals

House rentals with a fireplace

Top guest favorite
A historic white house is surrounded by lush green grass and trees. The two-story structure features a covered porch on one side, with large windows reflecting the natural light. Scenic hills are visible in the background, adding to the serene countryside setting.
Home in Dalton
4.99 out of 5 average rating, 156 reviews

Cleveland House - renovated Berkshires' gem.

InessaRating, 5 stars3 days ago
We had a lovely stay at Elizabeth's place. The house was big enough for our large group, the kitchen was well stocked with anything we might need, and the area was peaceful and beautiful.
Superhost
The historic farmhouse features a white exterior with a covered front porch and red doors. Surrounding the house is a spacious lawn with a variety of greenery, including tall trees in the background. The setting is peaceful, ideal for outdoor relaxation.
Home in Lanesborough
4.9 out of 5 average rating, 110 reviews

Elmwood Farmhouse

HannahRating, 5 stars3 weeks ago
Our friend group really enjoyed staying here on a rainy weekend in May. Hanging out by the wood burning stove and doing puzzles at the table was a highlight, and our dog loved being able to be outside on the dog run. The location was fantastic - right in between Lenox and North Adams - so we were able to access museums and hikes easily. Would highly recommend!
Top guest favorite
Home in Canaan
5 out of 5 average rating, 66 reviews

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

MichelleRating, 5 stars1 week ago
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!
Superhost
A spacious living area is furnished with a light-colored sectional sofa, a cozy armchair, and a coffee table, all arranged around a stone fireplace. Natural light filters through the large windows, enhancing the warm wooden flooring and highlighted by subtle wooden beams.
Home in Hillsdale
4.89 out of 5 average rating, 146 reviews

Fenced yard, playroom & the Berkshires - $0 fees

SophiaRating, 5 stars2 weeks ago
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.
Guest favorite
A bright living space features a modern wood-burning fireplace with a distinctive red design. A spacious gray sectional sofa is positioned near a wooden coffee table adorned with decorative items. Large windows provide natural light and views of the surrounding nature.
Home in Hudson
4.96 out of 5 average rating, 156 reviews

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

ChristopherRating, 5 stars3 weeks ago
Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!
Guest favorite
A tranquil swimming pond is framed by lush greenery and surrounded by wooden decking. Two lounge chairs are positioned on the deck, providing a relaxing spot to enjoy the natural scenery. A shaded area with wooden slats offers a cool retreat beside the water.
Home in Ghent
4.88 out of 5 average rating, 318 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

JasonRating, 5 stars3 weeks ago
Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.
Guest favorite
An open living space features high wooden ceilings with exposed beams and a stylish pool table positioned at the center. A cozy couch sits nearby, with a staircase leading to a loft area visible in the background. Natural light fills the room through large windows.
Home in Dalton
4.93 out of 5 average rating, 195 reviews

Brooksong, the perfect Berkshires getaway

JoannaRating, 5 stars3 weeks ago
Thank you, Salome, for a wonderful stay. Our extended family felt very relaxed and comfortable in your lovely home. It was a rainy weekend, so it was especially nice that there was a pool table, a fuzeball table, and lots of places in the house to hang out together. The bedrooms and bathrooms were lovely and the shared space was large and inviting. We enjoyed making meals together in the open kitchen. And the neighbor was so picturesque! We loved staying next door to the horses and donkeys, and taking walks on your beautiful farm-filled road. Thanks so much for making our stay such a special weekend. We all hope to ba back again! Very best to you and yours, Joanna and family
Top guest favorite
A modern house is seen, constructed with a combination of stone and wood materials. Large picture windows are positioned throughout, allowing natural light to flow in. A landscaped rocky path leads to the entrance, surrounded by greenery and trees.
Home in Rhinebeck
5 out of 5 average rating, 213 reviews

Eagle Rock House

BeatrizRating, 5 stars1 week ago
Edina and Glen's house was beautiful, spacious, and pristine. It was the perfect setting for a "girls weekend". The grounds were stunning, and made for a great setting. Very close to town, shopping, and wonderful restaurants. We really appreciated that our hosts were very proactive in reaching out and making all instructions clear. They were communicative and flexible. Thank you for having us in your beautiful home! Very memorable weekend.

Apartment rentals with a fireplace

Top guest favorite
A vintage tractor is parked on a gravel driveway, surrounded by patches of greenery. In the background, a historic white house with a front porch is visible, framed by tall trees that are bare of leaves, typical of early spring.
Apartment in Pownal
4.94 out of 5 average rating, 120 reviews

"The Parlors"

RebeccaRating, 5 stars3 months ago
Doug and Amy's place is beautifully maintained and full of charm. I loved being in a 1880's home with all the original wood work and beautiful wall paper with fresh paint and modern comfort - we were warm and it was only 16 degrees outside. The place is very clean too (and I'm a clean freak)! Doug and Amy are very friendly, we enjoyed meeting them. I would definitely return to this beautiful home.
Top guest favorite
A modern kitchen features a central island with bar stools, stainless steel appliances, and white cabinetry. Natural light floods the space through a skylight and large windows, highlighting the open layout. A dining area with dark chairs sits adjacent to the kitchen.
Apartment in Charlemont
4.99 out of 5 average rating, 158 reviews

Suite 23 - Spacious Sunny 2-BR with Mountain view

MichelleRating, 5 stars3 months ago
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!
Guest favorite
The living area features warm wooden floors and a cozy seating arrangement, including a sofa and an armchair. Light pours through the window, illuminating a colorful area rug and a coffee table adorned with books. A pair of opened doors leads to the spacious bedroom, showcasing a bed with decorative bedding.
Apartment in North Adams
4.91 out of 5 average rating, 456 reviews

Private guest apartment. One block from downtown.

KelseyRating, 5 stars3 weeks ago
Jennifer’s place was lovely - extra touches like snacks and fresh flowers were very much appreciated! Great location easy to walk to town!
Top guest favorite
A quaint colonial home is surrounded by lush greenery, with a vibrant rainbow arcing across the sky in the background. The well-maintained garden features blooming daffodils, and the soft grass invites relaxation and exploration.
Apartment in Newfane
4.97 out of 5 average rating, 455 reviews

Rock River Retreat: VT Oasis Pet Friendly

Kate-LynnRating, 5 stars1 week ago
It was a wonderful stay. Whether you’re just looking to relax or for a little adventure this stay offers it all. Even though it was a rainy stay they offer plenty of movies, books and games.
Guest favorite
An outdoor patio area features a stone surface surrounded by colorful flower beds. A round table with chairs and a large umbrella provide seating, alongside a charcoal grill. The home's entrance is highlighted by a welcoming red door and large windows.
Apartment in Great Barrington
4.92 out of 5 average rating, 194 reviews

Secluded but not isolated Berkshire Retreat

GretchenRating, 5 stars5 months ago
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.
Guest favorite
A spacious living area is presented with exposed wooden beams and wide pine floors. A comfortable couch faces a welcoming dining area, where a large table is set for meals. Sunlight streams through a window adorned with sheer curtains, enhancing the cozy ambiance.
Apartment in Ashfield
4.87 out of 5 average rating, 253 reviews

Zachariah House Main St. Ashfield

MaryRating, 5 stars1 week ago
We Minnesotans felt like we had a true New England experience during our delightful stay at Zachariah House! The decor made us feel like we had dropped into another century, yet we had all the modern conveniences, including cozy beds and delicious coffee. It was perfect for grandparents, parents, and baby.
Guest favorite
A living area is visible, featuring a sleek gray couch and a modern chair positioned near a stylish fireplace. Artwork is displayed on the wall, and natural light illuminates the space. A neutral rug adds texture to the polished floor, with a bedroom area partially seen in the background.
Apartment in Copake Falls
4.91 out of 5 average rating, 331 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

TimRating, 5 stars3 weeks ago
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!
Guest favorite
The exterior of the vintage duplex is highlighted by blue siding and white trim, featuring a welcoming porch adorned with colorful decorations. A spacious lawn surrounds the property, complemented by shrubs and greenery, providing a peaceful outdoor setting.
Apartment in New Lebanon
4.95 out of 5 average rating, 131 reviews

Sunny Duplex at the old boarding house

ScottRating, 5 stars11 months ago
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!

Villa rentals with a fireplace

Guest favorite
The wooden lodge is set among lush green trees, with a gravel driveway leading to it. A two-car garage is visible to the left, and a spacious deck extends from the lodge. Large windows and skylights allow natural light to fill the space.
Villa in Wilmington
4.95 out of 5 average rating, 22 reviews

Dancing Bear Lodge The Charm of Chimney Hill

EmilyRating, 5 stars3 months ago
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.
Guest favorite
The outdoor heated swimming pool is framed by a stone patio, with a shaded pergola alongside. Sunlight reflects off the clear water, capturing the serenity of the surrounding landscape and distant hills at sunset.
Villa in Coxsackie
4.9 out of 5 average rating, 48 reviews

5-BR Villa with Pool and Dog Friendly!

ChenghaoRating, 5 stars8 months ago
cute house and wonderful weekend
Guest favorite
An aerial view captures the spacious villa surrounded by vibrant autumn foliage and rolling hills. The property features a pool nestled among trees, with expansive lawns and a gravel driveway leading up to the home, offering a serene retreat in nature.
Villa in Pownal
4.94 out of 5 average rating, 72 reviews

Vermont Vacation Villa—Grapevine Getaway

ChristopherRating, 5 stars1 month ago
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.
Superhost
The exterior of the spacious home is viewed from the lawn, showcasing a large stone chimney at the center. Two levels of balconies and decks are visible, bordered by lush greenery, creating a welcoming outdoor space. The structure features wooden siding and multiple entrances.
Villa in Taghkanic
5 out of 5 average rating, 3 reviews

Retreat to 56 Acres w/ Hot Tub, 2 Acre Pond, Pool

ThomasRating, 5 stars17 months ago
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.
Guest favorite
A bright living room features a comfortable seating area with a white sofa and chairs. A large artwork is mounted above a fireplace, while a decorative mirror is positioned nearby. Natural light enters through a large window, revealing expansive views outside.
Villa in Hudson
5 out of 5 average rating, 25 reviews

Mountain-View Retreat @ Hudson

JasminRating, 5 stars1 week ago
Beautiful home, great location and friendly host. Bed was comfortable, kitchen had everything needed, games room was an added bonus.
Superhost
The front of the property displays a spacious single-story structure with arched windows and a warm terracotta facade. A large lawn extends in front, bordered by well-maintained greenery, providing a serene setting against a backdrop of trees under a partly cloudy sky.
Villa in Catskill
4.75 out of 5 average rating, 478 reviews

Mediterranean Villa with Pool

NateRating, 5 stars2 weeks ago
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 vacation rentals with a fireplace in Pittsfield

  • Total rentals

    50 properties

  • Nightly prices starting at

    $70 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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