Pittsfield Vacation Rentals

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Our top choices for Pittsfield vacation rentals

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is ¥42,703
¥76,415 total
includes taxes & fees
Mar 27 - Mar 28
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (19 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is ¥99,808
¥182,332 total
includes taxes & fees
Mar 31 - Apr 1
Hancock Village Inn Near Jiminy Peak

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (10 reviews)
"Healthy food too!"
United States
GEORGINA
The price is ¥26,708
¥29,832 total
includes taxes & fees
Mar 29 - Mar 30
Huttopia Berkshires

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Sand Lake
The price is ¥19,995
¥29,240 total
includes taxes & fees
Mar 27 - Mar 28
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (29 reviews)
"We enjoyed our stay "
United States
Lydia T.
The price is ¥10,712
¥22,663 total
includes taxes & fees
Mar 29 - Mar 30
Getaway Near Mass MoCA, Great Hiking, Scenic Views

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,317 reviews)
"Clean rooms, and very friendly staff"
United States
Amr
The price is ¥16,499
¥20,170 total
includes taxes & fees
Apr 7 - Apr 8
Vacation Village in the Berkshires

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is ¥31,103
¥87,855 total
includes taxes & fees
Mar 26 - Mar 27
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
The price is ¥16,504
¥52,431 total
includes taxes & fees
Mar 26 - Mar 27
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (1 review)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is ¥16,377
¥29,896 total
includes taxes & fees
Mar 26 - Mar 27
Cozy Home in Pownal VT

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Hancock
9.6 out of 10, Exceptional, (33 reviews)
"Was in town for my HS reunion and loved my stay! Great location and amenities and the condo itself is super cute."
United States
Maura S.
The price is ¥23,169
¥45,554 total
includes taxes & fees
Mar 29 - Mar 30
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very Good, (989 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is ¥23,645
¥26,412 total
includes taxes & fees
Apr 1 - Apr 2
Jiminy Peak Mountain Resort

Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (14 reviews)
"My whole experience was just what I needed! Im in love with this place inspired me and my dog was in heaven 💛 "
United States
Lea
The price is ¥19,836
¥29,064 total
includes taxes & fees
Mar 26 - Mar 27
Taborton Harvest Boulder Pines Cabin in the woods

New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (10 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is ¥19,043
¥42,643 total
includes taxes & fees
Apr 12 - Apr 13
New Studio In Town, By the Water

2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.6 out of 10, Exceptional, (12 reviews)
"wonderful apartment right in town."
United States
Stuart S.
The price is ¥19,043
¥44,976 total
includes taxes & fees
Mar 26 - Mar 27
2-Bdr Apt In Town, By the Water

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Hancock
8.8 out of 10, Excellent, (8 reviews)
"Everything was wonderful…"
United States
Alyne K.
The price is ¥17,773
¥37,754 total
includes taxes & fees
Mar 30 - Mar 31
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is ¥25,422
¥62,606 total
includes taxes & fees
Mar 26 - Mar 27
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

12-acre Vacation Rental in the Berkshires!

12-acre Vacation Rental in the Berkshires!
3.0 star property
Charlemont
The price is ¥38,562
¥86,415 total
includes taxes & fees
Mar 26 - Mar 27
12-acre Vacation Rental in the Berkshires!

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is ¥20,566
¥57,868 total
includes taxes & fees
Mar 27 - Mar 28
Near Tanglewood: Historic Summer Retreat

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Hancock
9.8 out of 10, Exceptional, (21 reviews)
"We enjoyed our stay in this adorable Disney Themed condo. The attention to detail in the theming was fantastic and the condo was perfect for our February Vacation ski trip."
United States
Allison V.
The price is ¥17,932
¥38,109 total
includes taxes & fees
Mar 30 - Mar 31
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain 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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Top Pittsfield Hotel Reviews

Find out more about Pittsfield

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Frequently asked questions

Can I find vacation rentals in Pittsfield?

Yes, we give you a choice of vacation rentals in Pittsfield near Berkshire Museum, or you can choose a more secluded option if you want a relaxing stay. Travelers who like culture and the arts say Pittsfield is known for its entertainment venues. Make sure you have time to check out the baseball games and museums during your trip.

What's the top vacation rental that Pittsfield has to offer?

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table: Visitors give good reviews to this Pittsfield vacation home rental, which is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. Our travelers also rate Hancock Village Inn Near Jiminy Peak as a favorite home for rent in Pittsfield.

How many vacation rentals are there in Pittsfield?

With 37 Expedia vacation rentals, you're sure to find just the right place for your Pittsfield stay.

What can I see and do in Pittsfield?

Family-friendly attractions include Berkshire Museum and Bousquet Ski Area, whereas Housatonic River and Canoe Meadows Wildlife Sanctuary are a couple of great spots to enjoy the outdoors. Other places in town to visit include Colonial Theater and Hancock Shaker Village.

What are vacation rentals like in Pittsfield?

Vacation rentals are privately owned properties you can reserve for several days or more in Pittsfield. Vacation rentals feature amenities such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.