Pittsfield Holiday Rentals

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Holiday Rentals in Pittsfield

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (253)
"One of the best properties i've ever stayed at "
The price is AU$454
includes taxes & fees
31 July - 1 Aug
Berkshire Village Carriage House - Super Private!!

NEW RENO Historic Creamery in Berkshires w/hot tub

10.0 out of 10, Exceptional, (1)
"We used all amenities (besides hot tub) full kitchen and only brought food which worked well."
The price is AU$741
includes taxes & fees
21 July - 22 July
NEW RENO Historic Creamery in Berkshires w/hot tub

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 AU$1,027
includes taxes & fees
4 Aug - 5 Aug
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 AU$1,705
includes taxes & fees
4 Aug - 5 Aug
Hancock Village Inn at Jiminy Peak

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

The price is AU$648
includes taxes & fees
28 July - 29 July
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

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 AU$697
includes taxes & fees
21 July - 22 July
North Getaway Cottage

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 AU$802
includes taxes & fees
6 Aug - 7 Aug
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

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 AU$757
includes taxes & fees
19 July - 20 July
Comfortable Berkshires retreat on mtn resort, SISO

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 AU$952
includes taxes & fees
13 Aug - 14 Aug
Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm.

Home in Great Barrington

9.8 out of 10, Exceptional, (21)
"Our family had a wonderful experience and stay. "
The price is AU$642
includes taxes & fees
6 Aug - 7 Aug
Home in Great Barrington

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 AU$825
includes taxes & fees
18 July - 19 July
Near Tanglewood: Historic Summer Retreat

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 AU$1,137
includes taxes & fees
21 July - 22 July
Great Barrington Get Away

Treat yourself at the stunning June Farms Wellness Huts!

10.0 out of 10, Exceptional, (8)
"Most AMAZING!!!!Going back sooooon!!!"
The price is AU$578
includes taxes & fees
30 July - 31 July
Treat yourself at the stunning June Farms Wellness Huts!

Experience Timeless Elegance in The Edith Wharton Room!

The price is AU$608
includes taxes & fees
30 July - 31 July
Experience Timeless Elegance in The Edith Wharton Room!

Hillsdale Escape with Pool, Firepit, Hot Tub, Game Room

The price is AU$2,396
includes taxes & fees
4 Aug - 5 Aug
Hillsdale Escape with Pool, Firepit, Hot Tub, Game Room

Glass Lake Cottage

10.0 out of 10, Exceptional, (1)
"Glass lake cottage was the perfect relaxing retreat while I was visiting for a wedding at the Old Daley Inn! The place was clean, had a well stocked kitchen and everything I needed. We were lucky to catch a fantastic sunset and enjoyed the view from the large deck. Will definitely be back! "
The price is AU$1,217
includes taxes & fees
25 July - 26 July
Glass Lake Cottage

The Lakeshore House

The price is AU$1,319
includes taxes & fees
23 July - 24 July
The Lakeshore House

★Private Pool★ Spacious Historic 1850s "Bell House" @ Hillsdale, NY Town Center

The price is AU$1,201
includes taxes & fees
28 July - 29 July
★Private Pool★ Spacious Historic 1850s "Bell House" @ Hillsdale, NY Town Center

Spacious 5-bedroom house in charming Lee with WiFi

The price is AU$1,544
includes taxes & fees
12 Aug - 13 Aug
Spacious 5-bedroom house in charming Lee with WiFi

Treat yourself at the stunning June Farms Wellness Huts!

10.0 out of 10, Exceptional, (8)
"June Farms is a hidden gem. We stayed there on an overnight trip. The grounds are beautiful and well maintained. We took an ATV tour w Michelle who gave us the grand tour and showed us all the properties and animals. The Pony Barn was open for pizzas, drinks top notch! It was dog park night and drew a fun crowd. Would def visit again!!!"
The price is AU$661
includes taxes & fees
29 July - 30 July
Treat yourself at the stunning June Farms Wellness Huts!
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?

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table: 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 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Some other top choices in Pittsfield are Hancock Village Inn at Jiminy Peak and Lake Front Home in Heart of the Berkshires Near Jiminy Peak.

How many holiday rentals are there in Pittsfield?

With 38 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.