Pittsfield Holiday Rentals

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Holiday Rentals in Pittsfield

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is NZ$1,816
includes taxes & fees
8 July - 9 July
Hancock Village Inn at Jiminy Peak

Tranquil Retreat 6-BR Total in the Berkshires

Tranquil Retreat 6-BR Total in the Berkshires

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 "
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 NZ$607
includes taxes & fees
9 July - 10 July
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

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 NZ$256
includes taxes & fees
2 July - 3 July
Deluxe Queen Room with 2 Queen Beds

Spacious 5-bedroom house in charming Lee with WiFi

The price is NZ$1,422
includes taxes & fees
16 July - 17 July
Spacious 5-bedroom house in charming Lee with WiFi

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 NZ$735
includes taxes & fees
30 June - 1 July
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 NZ$2,073
includes taxes & fees
30 June - 1 July
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 NZ$662
includes taxes & fees
30 June - 1 July
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 NZ$1,107
includes taxes & fees
29 June - 30 June
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 NZ$891
includes taxes & fees
29 June - 30 June
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 NZ$789
includes taxes & fees
29 June - 30 June
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)"
Near Tanglewood: Historic Summer Retreat

Enchanting Cottage, Come Enjoy Nature!

10.0 out of 10, Exceptional, (1)
"If you want TV, this isnt for you, but if you want a quiet place to check away and relax it fits the bill wonderfully"
The price is NZ$1,630
includes taxes & fees
5 July - 6 July
Enchanting Cottage, Come Enjoy Nature!

NEW RENO Historic Creamery in Berkshires w/hot tub

The price is NZ$775
includes taxes & fees
30 June - 1 July
NEW RENO Historic Creamery in Berkshires w/hot tub

Perfect House In Hillsdale, Brings Friends & Fam

8.6 out of 10, Excellent, (4)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
The price is NZ$938
includes taxes & fees
6 July - 7 July
Perfect House In Hillsdale, Brings Friends & Fam

Majestic views Hot tub Firepit Games Sleeps 14

The price is NZ$2,960
includes taxes & fees
18 July - 19 July
Majestic views Hot tub Firepit Games Sleeps 14

Wolf Hill Acres: A Charming & Modern Country Home

10.0 out of 10, Exceptional, (1)
"7 of us, 60 year old friends plus young adult had a fabulous time over 4 days including NY’s eve, cooking together, playing pool,ping pong, watching movies, taking walks from house, a little time in Great Barrington, Hudson and Kingston! Great beds! We’re eager to come back iin summer!!"
The price is NZ$2,339
includes taxes & fees
13 July - 14 July
Wolf Hill Acres: A Charming & Modern Country Home

Glass Lake Cottage

The price is NZ$1,108
includes taxes & fees
9 July - 10 July
Glass Lake Cottage

The Lakeshore House

The price is NZ$1,264
includes taxes & fees
7 July - 8 July
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 holiday rentals in Pittsfield?

Yes, there are holiday rentals in Pittsfield close to Berkshire Museum, or you can select a more secluded option if you're looking for a relaxing stay. Travellers 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 are some of the best holiday rentals that Pittsfield has to offer?

Lake Front Home in Heart of the Berkshires Near Jiminy Peak: This highly rated holiday home rental in Pittsfield is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Some other top choices in Pittsfield are Hancock Village Inn at Jiminy Peak and Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table.

How many holiday rentals are there in Pittsfield?

With 37 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Pittsfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pittsfield. Holiday rentals feature amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips or small group gatherings.