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Compare 336 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is SAR 548
SAR 843 total
includes taxes & fees
2 Dec - 3 Dec
Berkshire Village Carriage House - Super Private!!
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Comfortable New Decor in Living Room Equipped w Smart TV and Deck

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

10.0 out of 10, Exceptional, (63)
"It was an amazing stay. The host was very proactive and helpful. "
The price is SAR 984
SAR 2,013 total
includes taxes & fees
26 Nov - 27 Nov
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Spectacular views and close to Great Barrington.
Private kitchen

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
Peace and quiet on the lake
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Breakfast Nook - wake up to the best sunshine ever!

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.
Christmas at Lakeview Retreat

Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.

10.0 out of 10, Exceptional, (20)
"clean, wonderful views of the lake. "
Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.
Berkshire Ski House on Lake Garfield w/HT By Great Barrington
Our house location

Berkshire Ski House on Lake Garfield w/HT By Great Barrington

10.0 out of 10, Exceptional, (3)
"We had a lovely stay! The space was perfect for our group of 4 moms looking for a peaceful getaway. The host was very responsive. Only note for those visiting, rideshares (Uber and otherwise) are few and far between. Schedule ahead! We'd definitely stay again :)"
Berkshire Ski House on Lake Garfield w/HT By Great Barrington
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
the house

Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond

10.0 out of 10, Exceptional, (33)
"We had a wonderful time at this property! It was perfect for what we wanted- a place to ourselves in nature with beautiful views. Host was great! Would definitely recommend! "
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
Beautiful Berkshire Farm House on 160+ Acres
Exterior

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (34)
"The house was spacious and comfortable for our large group (13 people). The basketball court in the barn was a lot of fun."
Beautiful Berkshire Farm House on 160+ Acres
Quintessential 6-BR Berkshires Lodge

Quintessential 6-BR Berkshires Lodge

9.8 out of 10, Exceptional, (8)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Great Room with lake view

Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

10.0 out of 10, Exceptional, (90)
"Very clean, spacious, and comfortable. Property manager’s information was helpful."
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Hearts Desire is a furnished whole house in a small, colorful garden center.
Exterior

Hearts Desire is a furnished whole house in a small, colorful garden center.

10.0 out of 10, Exceptional, (82)
"My mom and I did a mother/daughter trip to the Berkshires in October. Everything about this property is perfect! Location was 5/10 min from groceries/restaurants but felt like we were in the middle of nowhere. The house itself was very clean and so comfortable (the bed felt like a dream)! We spent our days exploring the surrounding towns and our evenings relaxing at he house. We saw deer in the mornings and 2 bald eagles! Thank you for the incredible stay!! "
Hearts Desire is a furnished whole house in a small, colorful garden center.
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Exterior

Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

10.0 out of 10, Exceptional, (112)
"A very nice place in a very nice part of the state. Perfect for groups and families. "
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Marina

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (10)
"As advertised "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Hudson Valley and The Berkshires getaway
Kitchen and dining room

Hudson Valley and The Berkshires getaway

10.0 out of 10, Exceptional, (3)
"We very much enjoyed our stay at this lovely home. The hosts were wonderful communicators!"
Hudson Valley and The Berkshires getaway
Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!
Lush woodland setting is private, yet five minutes to Spring Street.

Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!

9.8 out of 10, Exceptional, (19)
"Such a gorgeous house! We loved walking the nearby trails and how close it was to Williams. Venetia was the best!"
Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!
Plainfield House in a 10,000 acre state forest and private pond
Front lawn for sledding

Plainfield House in a 10,000 acre state forest and private pond

9.6 out of 10, Exceptional, (82)
"Great property in beautiful surroundings. House was sparkling clean with lots of space for everyone. "
Plainfield House in a 10,000 acre state forest and private pond
Woodland Zen by AvantStay | Modern Design + Patio
Welcome to Woodland Zen!

Woodland Zen by AvantStay | Modern Design + Patio

10.0 out of 10, Exceptional, (5)
"This home is large, full of light and has modern decor. Mostly bare floors so bring slippers/socks for cold nights. Fully appointed kitchen that has everything, including plenty of trash bags, dish soap, pots, pans, dishes, etc. We cooked several meals there and it was easy to do. Bedroom windows have blinds, bathroom windows do not! The house is surrounded by trees but showering in a room with bare windows took some getting used to. There are many light switches that some labeling might be...
Woodland Zen by AvantStay | Modern Design + Patio
Pristine Home In Becket Woods

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods
Near Tanglewood: Historic Summer Retreat
Living area

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (15)
"This was a beautiful, spacious, and peaceful place for us in our friends to get together. It was centrally located to everything we wanted to do. Amanda was wonderful in her communications and everything was clean and ready for us."
The price is SAR 526
SAR 1,304 total
includes taxes & fees
9 Dec - 10 Dec
Near Tanglewood: Historic Summer Retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Pittsfield

Chic Pittsfield Home With A View!

Chic Pittsfield Home With A View!

8.8 out of 10, Excellent, (8)
"Great view from the property, lovely house and yard. Coiuldn't have been a better stay. "
Chic Pittsfield Home With A View!
Hancock Village Inn at Jiminy Peak
The Hancock Village Inn

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (8)
"We loved this large, well-kept home. The house has tons of room, so even though we had a large group, everyone found space and we never felt crowded. The kitchen/dining area is a great space for gathering and sharing a meal. And, the younger members of our group loved the hot tub and large yard for playing in. The owner was extremely easy to communicate with. We hope to be back!"
The price is SAR 2,433
SAR 4,163 total
includes taxes & fees
3 Dec - 4 Dec
Hancock Village Inn at Jiminy Peak
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1746)
"Property was beautiful, great staff "
The price is SAR 634
SAR 733 total
includes taxes & fees
26 Nov - 27 Nov
Vacation Village in the Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.