Pittsfield Holiday Rentals

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Holiday Rentals in Pittsfield

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (139)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Very kinda hosts, and wonderful house."
The price is NZ$1,734
includes taxes & fees
23 Apr - 24 Apr
Hancock Village Inn at Jiminy Peak

Dancing Horse Lodge

9.4 out of 10, Exceptional, (40)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (56)
"Perfect lake front home to get away for a quick weekend trip with the family over the holidays!! Location, location location, close proximity to downtown Pittsfield, 15 from Jiminy peak & Bousquet Mt. Andrey was extremely helpful throughout the process with suggestions for food and activities for the kids. The house was a perfect fit for our family and friends. Everyone enjoyed their time there and would definitely book again"
Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1798)
"Always a great place to stay!!"
The price is NZ$214
includes taxes & fees
28 Apr - 29 Apr
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (928)
"Staff was exceptionally helpful and friendly."
The price is NZ$251
includes taxes & fees
23 Apr - 24 Apr
Jiminy Peak Mountain Resort

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (187)
"Wonderful getaway, lovely hosts, great location, overall a fabulous place to relax and recharge. "
The Clearing - Quiet - Close To Nature

Deluxe Queen Room with 2 Queen Beds

2.0 star property
The price is NZ$241
includes taxes & fees
21 Apr - 22 Apr
Deluxe Queen Room with 2 Queen Beds

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (61)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Lakeside Oasis Just You, The Lake & The View!

9.8 out of 10, Exceptional, (70)
"Perfect location for a peaceful, scenic vacation."
Lakeside Oasis Just You, The Lake & The View!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (43)
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (40)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

The Meadows House @ Otis Ridge w/ 7-person hot tub

9.8 out of 10, Exceptional, (28)
"We had a great time staying at Lars place. The hot tub was very relaxing and the location was just what we were looking for to get away for a few days."
The Meadows House @ Otis Ridge w/ 7-person hot tub

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (14)
"Near Jacob's Pillow!"
Pristine Home In Becket Woods

Private Access To Laurel Lake, Enjoy Lake Life

10.0 out of 10, Exceptional, (14)
"Enjoyed the property."
Private Access To Laurel Lake, Enjoy Lake Life

Near Tanglewood: Historic Summer Retreat

9.4 out of 10, Exceptional, (20)
"Beautiful house in a quiet location. Perfect for our trip to go see The Norman Rockwell museum , Stockbridge Christmas holiday lights only about 25 minutes away. "
The price is NZ$655
includes taxes & fees
22 Apr - 23 Apr
Near Tanglewood: Historic Summer Retreat

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (8)
"Lots of cozy relaxation by the fire and fun meals at the spacious dinning table. We had plenty of room to spread out and enjoy ourselves. "
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Comfortable Berkshires retreat on mtn resort, SISO

10.0 out of 10, Exceptional, (3)
"Hosts were very responsiveHouse was clean and well maintainedExcellent locationOverall great stay"
The price is NZ$808
includes taxes & fees
20 Apr - 21 Apr
Comfortable Berkshires retreat on mtn resort, SISO

Exclusive Estate, Heated Yearround Outdoor Pool

9.6 out of 10, Exceptional, (19)
"Beautiful property, well-appointed, and comfortable for extended family of 12."
Exclusive Estate, Heated Yearround Outdoor Pool
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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Other types of properties in Pittsfield you may be interested in

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (705)
" Lovely hotel"
The price is NZ$208
includes taxes & fees
27 Apr - 28 Apr
Hotel On North

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (774)
"Great place."
The price is NZ$204
includes taxes & fees
21 Apr - 22 Apr
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (455)
"Pool and hot tub wonderful. "
The price is NZ$225
includes taxes & fees
29 Apr - 30 Apr
Berkshire Mountain Lodge
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.

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. Our travellers also rate Hancock Village Inn at Jiminy Peak as a favourite home for rent in Pittsfield.

How many holiday rentals are there in Pittsfield?

With 36 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.