Pittsfield Vacation Rentals

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Vacation Rentals in Pittsfield

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

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is CA $409
CA $730 total
includes taxes & fees
Aug 5 - Aug 6
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is CA $817
CA $1,503 total
includes taxes & fees
Jul 21 - Jul 22
Hancock Village Inn at Jiminy Peak

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

10.0 out of 10, Exceptional, (5)
"My wife, two kids, and chocolate lab spent a few days at the cottage to enjoy the snow and hot tub. Everything was set up exactly as described and Nicole was very friendly and proactive. We had a great time and would do it again "
The price is CA $294
CA $627 total
includes taxes & fees
Jul 23 - Jul 24
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

The price is CA $232
CA $556 total
includes taxes & fees
Jul 28 - Jul 29
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

Tranquil 3-BR Waterfront Retreat

10.0 out of 10, Exceptional, (14)
"A well maintained and clean property with a peaceful lake out your back door. As described and had everything needed for a pleasant stay. "
Tranquil 3-BR Waterfront Retreat

Hummingbird Haven is a Berkshires retreat surrounded by nature and local charm.

10.0 out of 10, Exceptional, (3)
"This property was amazing! Very clean and spacious, perfect location for a nice peaceful getaway. Kendra was very communicative and made sure our stay was comfortable. 10/10 highly recommend you to stay here. "
The price is CA $390
CA $754 total
includes taxes & fees
Jul 16 - Jul 17
Hummingbird Haven is a Berkshires retreat surrounded by nature and local charm.

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
The price is CA $149
CA $197 total
includes taxes & fees
Aug 10 - Aug 11
Deluxe Queen Room with 2 Queen Beds

Spacious 5-bedroom house in charming Lee with WiFi

The price is CA $649
CA $1,177 total
includes taxes & fees
Jul 17 - Jul 18
Spacious 5-bedroom house in charming Lee with WiFi

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (252)
"One of the best properties i've ever stayed at "
The price is CA $273
CA $400 total
includes taxes & fees
Jul 31 - Aug 1
Berkshire Village Carriage House - Super Private!!

North Getaway Cottage

9.6 out of 10, Exceptional, (20)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is CA $277
CA $613 total
includes taxes & fees
Jul 14 - Jul 15
North Getaway Cottage

New Home - Heart of Williamstown 183

10.0 out of 10, Exceptional, (1)
"Great place to stay. House is brand new with plenty of room. Has 3 bedrooms plus a finished room in basement which is equivalent of a 4th room. Hiking and restaurants are close to the property. Plenty of parking. Highly recommend. Absolutely no complaints."
The price is CA $1,074
CA $1,716 total
includes taxes & fees
Jul 17 - Jul 18
New Home - Heart of Williamstown 183

Home in Great Barrington

9.8 out of 10, Exceptional, (21)
"Our family had a wonderful experience and stay. "
The price is CA $379
CA $570 total
includes taxes & fees
Aug 6 - Aug 7
Home in Great Barrington

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"Nice, cozy, clean house with character. Great location as we could walk to town. Would stay again for sure."
The price is CA $615
CA $1,003 total
includes taxes & fees
Jul 13 - Jul 14
Great Barrington Get Away

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

9.8 out of 10, Exceptional, (70)
"We had a wonderful stay, thank you! "
The price is CA $359
CA $752 total
includes taxes & fees
Jul 14 - Jul 15
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Comfortable Berkshires retreat on mtn resort, SISO

9.6 out of 10, Exceptional, (4)
"Hosts were very responsiveHouse was clean and well maintainedExcellent locationOverall great stay"
The price is CA $220
CA $662 total
includes taxes & fees
Jul 11 - Jul 12
Comfortable Berkshires retreat on mtn resort, SISO

Near Tanglewood: Historic Summer Retreat

9.4 out of 10, Exceptional, (20)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is CA $234
CA $551 total
includes taxes & fees
Jul 13 - Jul 14
Near Tanglewood: Historic Summer Retreat

NEW RENO Historic Creamery in Berkshires w/hot tub

The price is CA $279
CA $648 total
includes taxes & fees
Jul 11 - Jul 12
NEW RENO Historic Creamery in Berkshires w/hot tub

Majestic views Hot tub Firepit Games Sleeps 14

The price is CA $1,286
CA $2,226 total
includes taxes & fees
Aug 4 - Aug 5
Majestic views Hot tub Firepit Games Sleeps 14

Glass Lake Cottage

The price is CA $584
CA $1,088 total
includes taxes & fees
Jul 13 - Jul 14
Glass Lake Cottage

The Lakeshore House

The price is CA $741
CA $1,151 total
includes taxes & fees
Jul 15 - Jul 16
The Lakeshore House
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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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 at Jiminy Peak as a favorite home for rent in Pittsfield.

How many vacation rentals are there in Pittsfield?

With 38 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 Barrington Stage Company.

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.