Holiday rentals with a fireplace in Pittsfield

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Popular amenities for Pittsfield Accommodation with Fireplace

Holiday House Rentals with a fireplace

Top Guest favourite
Home in Dalton
4.99 out of 5 average rating, 155 reviews

Cleveland House - renovated Berkshires' gem.

MasonRating, 5 stars2 weeks ago
We had a wonderful stay at this beautiful home. The beds were extremely comfortable, the house was clean and the kitchen was well stocked. The hosts were very responsive and kind and went above and beyond to make sure we had a great stay. The kids in our group were happy with the toys that were available for them. We would highly recommend staying here for group gatherings. We had a lovely cozy weekend and are so grateful to the hosts!
Top Guest favourite
Home in Canaan
5 out of 5 average rating, 65 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!
Guest favourite
Home in Ghent
4.95 out of 5 average rating, 247 reviews

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

JulieRating, 5 stars3 weeks ago
We loved staying at Erin’s place. Very private, yet so close to all the nearby towns and parks. The place was so comfortable, clean, great bed and linens, and easy to hang out and relax. For sure would love to come again!
Guest favourite
Home in Dalton
4.93 out of 5 average rating, 194 reviews

Brooksong, the perfect Berkshires getaway

JoannaRating, 5 stars2 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 favourite
Home in Craryville
4.92 out of 5 average rating, 119 reviews

The Gatehouse at Raspberry Ridge

HenryRating, 5 stars2 weeks ago
Lawrence and Ilze are great hosts! They actually just live next to the house and they own a farm. We took our kid to visit their farms with lots of beautiful chickens and roosters. My son even has a chance to feed the chickens. We will definitely come back!
Guest favourite
Home in Pittsfield
4.96 out of 5 average rating, 55 reviews

Charming lake home with amazing sunset views

EdRating, 5 stars3 months ago
My family and I had a great stay here. The property was well kept and matched the description. And the host was responsive and helpful. Would stay again if we're in the area.
Top Guest favourite
Home in Rhinebeck
5 out of 5 average rating, 212 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.
Guest favourite
Home in Lanesborough
4.96 out of 5 average rating, 101 reviews

Berkshire Bliss- 6BR/Minutes from Jiminy +38 acres

ElenaRating, 5 stars3 months ago
We stayed at Jonathan’s place with 3 families, 6 adults and 7 kids ranging in ages from 4-10. It couldn’t have fit our families more perfect. The room setup is amazing, especially when renting with kids. When having that many rooms it’s usually one in a basement which wasn’t the case! We skied all weekend at Jimny peak and it was a short 8 minute drive to the mountain. Very spacious with a cozy living space for the kids to play and a great bonus room downstairs. Kitchen had everything we needed to cook meals. They also supply lots of games, kids loved that. Thanks for a wonderful weekend will be renting again next ski season!

Apartment rentals with a fireplace

Top Guest favourite
Apartment in Northampton
4.98 out of 5 average rating, 363 reviews

Light filled three bedroom apartment DT Florence!

MandiRating, 5 stars3 days ago
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!
Top Guest favourite
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 favourite
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 favourite
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.
Superhost
Apartment in Ashfield
4.87 out of 5 average rating, 252 reviews

Zachariah House Main St. Ashfield

SophieRating, 5 stars2 weeks ago
Great location for exploring nearby towns like Northampton, Amherst, Shelburn falls. As Laura said, no cell service in this town but their WiFi worked great in the unit and it’s a quite peaceful area to stay. The home feels like a well maintained cabin. It’s rustic and cozy but you might find a spider in the shower. I did not find the beds very comfortable but otherwise had a very relaxing stay. Laura was a great host and very responsive
Guest favourite
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 favourite
Apartment in Troy
4.96 out of 5 average rating, 116 reviews

Retro Pinball Arcade/Board Game AirBnB

GraceRating, 5 stars3 weeks ago
The hosts are super helpful and the place has 10+ working pinball/other game machines! The apartment was very clean, and accurate to what is posted.
Guest favourite
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!

Villas with a fireplace

Guest favourite
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 favourite
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 favourite
Villa in Pownal
4.94 out of 5 average rating, 72 reviews

Vermont Vacation Villa—Grapevine Getaway

ChristopherRating, 5 stars3 weeks 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
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 favourite
Villa in Hudson
5 out of 5 average rating, 25 reviews

Mountain-View Retreat @ Hudson

JasminRating, 5 stars4 days ago
Beautiful home, great location and friendly host. Bed was comfortable, kitchen had everything needed, games room was an added bonus.

Quick stats about holiday rentals with a fireplace in Pittsfield

  • Total rentals

    50 properties

  • Nightly prices starting at

    $116 NZD 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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