Pittsfield Holiday Rentals

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Holiday Rentals in Pittsfield

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
The price is NZ$1,811
includes taxes & fees
28 Mar - 29 Mar
Hancock Village Inn at Jiminy Peak

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

9.8 out of 10, Exceptional, (139)
"We have stayed at this property twice before and have been very pleased with the amount of bedrooms and sleeping available. The property is always very clean and is equipped with everything you need for cooking and dining.the property is a half way point for family members in several directions. "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1792)
"Very nice accomodations, more like a mini apartment than a motel room. "
The price is NZ$266
includes taxes & fees
1 Apr - 2 Apr
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (925)
"Staff was exceptionally helpful and friendly."
The price is NZ$257
includes taxes & fees
2 Apr - 3 Apr
Jiminy Peak Mountain Resort

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (240)
"Great experience....very clean facility in excellent condition......except for driveway & sidewalk. Sheet of ice....yes there were unusual conditions this winter, but I would be concerned for any elderly or uncoordinated guests."
The price is NZ$396
includes taxes & fees
31 Mar - 1 Apr
Berkshire Village Carriage House - Super Private!!

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

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

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

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!

Peace and quiet on the lake

9.6 out of 10, Exceptional, (211)
"Property was very nice. Quite area. Host was fantastic. "
Peace and quiet on the lake

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (14)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods

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

9.4 out of 10, Exceptional, (8)
"The location was great and just a short walk to downtown. We thought the pictures on the site were a bit misleading. The house looked a little more open than it actually was, especially in the kitchen. The outside fire pit area was a little run down. A chair was broken and the string lights were down on the ground, water filled and no outlet to plug into. Plenty of bed space for everyone to sleep and beds were comfortable. Plenty of extra sheets and towels and the kitchen was well equipped. We...
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (19)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is NZ$591
includes taxes & fees
30 Mar - 31 Mar
Near Tanglewood: Historic Summer Retreat

Private Estate, Heated Yearround Outdoor Pool

9.8 out of 10, Exceptional, (17)
"The home was beautiful and it was a gorgeous property too. It had all the right amenities in the kitchen. "
Private Estate, Heated Yearround Outdoor Pool

Lakeside Retreat Just You, The Lake & The View!

9.8 out of 10, Exceptional, (69)
"We had a lovely stay. Views are amazing. Property owner was very responsive and helpful. Would love to go back in the fall."
Lakeside Retreat Just You, The Lake & The View!

Comfortable Berkshires retreat on mtn resort, SISO

The price is NZ$846
includes taxes & fees
2 Apr - 3 Apr
Comfortable Berkshires retreat on mtn resort, SISO

Private Access To Laurel Lake, Enjoy Lake Life

10.0 out of 10, Exceptional, (14)
"The property was better than advertised. Everything anyone could need was provided and we could not have hoped for a better experience. Very large home and could easily accomodate 8 people or more. The Berkshires are magical and this home was great for out time there."
Private Access To Laurel Lake, Enjoy Lake Life

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (212)
"The house was small, cozy and even had a small stream that ran through the backyard and under the deck. It had everything we needed. A bigger TV in the living room but definitely be a big upgrade but that isn't the end of the world. Would stay here again. "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

5 STAR ESTATE w/ POOL, POND, ARCADE, GYM, TRAILS! ASK ABOUT FANTASTIC DISCOUNT!

9.6 out of 10, Exceptional, (85)
"We had fun! Game room great! Spacious and comfortable. Never got to enjoy outdoors, so maybe another trip in the future!"
5 STAR ESTATE w/ POOL, POND, ARCADE, GYM, TRAILS! ASK ABOUT FANTASTIC DISCOUNT!

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for us. Spacious, clean, comfortable. Beds comfortable. Bathrooms really nice. The road in the development is dirt, a 4wd is needed as stated. It was muddy and rutty on arrival, then snow and ice , but do-able. Great house. Would recommend "
Quintessential 6-BR Berkshires Lodge

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

9.8 out of 10, Exceptional, (28)
"perfect size for group of 7 adults...Good location especially for snow shoeing....cross country sking...enjoyed being in berkshires..."
The Meadows House @ Otis Ridge w/ 7-person hot tub
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, (696)
"Nice stay at the property, the rooms are huge… the wooden floors do creek a bit so you can hear people walking around but if you don’t mind that, it’s a pretty cool hotel, nicely decorated. "
The price is NZ$213
includes taxes & fees
2 Apr - 3 Apr
Hotel On North

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (762)
"Easy check in, nice staff. Rug in the room was kind of musty. They were accommodating to me requesting to have a slightly later check out. Would return if in the area. "
The price is NZ$203
includes taxes & fees
4 Apr - 5 Apr
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (443)
"We had a great time at the hotel. My sons and I loved spending time in the pool and the hot tub. The bedroom was spacious, the kitchen had everything we needed, and the bathroom was ample and clean."
The price is NZ$251
includes taxes & fees
30 Mar - 31 Mar
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?

Hancock Village Inn at Jiminy Peak: This highly rated holiday home rental in Pittsfield is located on a river, and has a fireplace, a private garden and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a library and 1 hot tub. Our travellers also rate Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table 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.