Pittsfield Vacation Rentals

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Browse Select Pittsfield Vacation Homes

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (5)
Contemporary Berkshire Home with Views of Taconic Golf Course

Peace and quiet on the lake

9.6 out of 10, Exceptional, (217)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake

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

10.0 out of 10, Exceptional, (127)
"Fantastic home! Clean, well stocked and very comfortable. We had a great time and will be back. The owner was kind, considerate and appreciative of our stay. Thanks again! "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (14)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (3)
"Pool is caving in with pool cover partly pulled away. Gate to access pool area was unlocked. Hazard for children. Staff is not onsite. Room was clean, but sheets had stains. Used bar of soap left on bathroom sink. "
The price is CA $136
CA $183 total
includes taxes & fees
Sep 1 - Sep 2
Deluxe Queen Room with 2 Queen Beds

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (4)
"We had a wonderful stay in Great Barrington for the long holiday weekend. The house is very comfortable, super clean, and the property is lovely. We were able to cool off in the pool and enjoy time with family. 10/10!"
Spectacular views and close to Great Barrington.

Poolside Luxe at Long Pond

Poolside Luxe at Long Pond

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (129)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (22)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
Near Tanglewood: Historic Summer Retreat

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (54)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Quiet Cabin On Over 12 Acres Of Woods!

10.0 out of 10, Exceptional, (12)
"The property was perfect for our weekend in Becket. The house was very comfortable and the grounds quite beautiful. We enjoyed our visit."
Quiet Cabin On Over 12 Acres Of Woods!

Spacious 7 bedroom house, Near jiminy Peak in Hancock ma , In the Berkshires

2.0 star property
10.0 out of 10, Exceptional, (5)
"A very good place to stay. Best of all, each bedroom has its own bathroom. There's plenty of hot water, even if multiple people are showering at the same time. The only downside to me is that the washer is broken when we checked in. We want to come again!"
Spacious 7 bedroom house, Near jiminy Peak in Hancock ma , In the Berkshires

Art House! Spacious Getaway By Mass Moca

10.0 out of 10, Exceptional, (11)
"We had a great girls weekend e joying local trails, MassMOCA, local restaurants and this very clean, spacious house! Location is walkable to the museum and down town and we enjoyed a soak in the tub after a day of hiking in local conservation areas! "
Art House! Spacious Getaway By Mass Moca

8 Mi to Tanglewood & Butternut Ski: Spacious Home!

10.0 out of 10, Exceptional, (1)
"This place truly has everything you could want in a vacation rental. It was exceptionally clean, spacious, and accommodating. From the moment we arrived, it felt like a home away from home. The host clearly puts a lot of care into maintaining the property and ensuring guests are comfortable. We had everything we needed for an enjoyable stay. Highly recommend and would definitely book again!"
8 Mi to Tanglewood & Butternut Ski: Spacious Home!

Star Gazer Farm

10.0 out of 10, Exceptional, (15)
"Thank you for the lovely get away! The property was lovely. "
Star Gazer Farm

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (45)
"The home is very nice and cozy. It really felt like a comfy home."
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

StrautmanHaus - All-Season Chalet at Berkshire East

9.8 out of 10, Exceptional, (13)
"The house was definitely nice and we enjoyed our stay. I didn’t give it 5 stars because the two downstairs bedrooms had a strong musty smell."
StrautmanHaus - All-Season Chalet at Berkshire East

Cabin Retreat in the Berkshire Woods

Cabin Retreat in the Berkshire Woods

Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!

10.0 out of 10, Exceptional, (94)
"Exactly what you want in a ski house!"
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!

Secluded Family Home in Serene Stockbridge Woods

10.0 out of 10, Exceptional, (21)
"We spent a short weekend here in Stockbridge to attend the Naumkeag Pumpkin Show. The kids (2 + 4) were in amazement the entire time. The house was a fantastically creative environment with books, games, toys, and a massive yard with swings. A+ would stay again."
Secluded Family Home in Serene Stockbridge Woods
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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Top Pittsfield Hotel Reviews