Pittsfield Holiday Rentals

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Holiday Rentals in Pittsfield

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
2.0 star property
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is AU$753
includes taxes & fees
20 Oct - 21 Oct
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, (15)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is AU$1,630
includes taxes & fees
21 Oct - 22 Oct
Hancock Village Inn at Jiminy Peak
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
2.0 star property
2.0 out of 10, (1)
"THIS. PLACE. IS. A. DUMP. Do NOT STAY HERE under any circumstances."
United States
Michael
The price is AU$316
includes taxes & fees
31 Oct - 1 Nov
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Sugar Shack - 300 square feet of pure sweetness.
2.0 star property
10.0 out of 10, Exceptional, (3)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is AU$561
includes taxes & fees
20 Oct - 21 Oct
Sugar Shack - 300 square feet of pure sweetness.
Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (5)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
Huttopia Berkshires
HunnyHAUS: Deluxe TINY*private spa*walk to town
10.0 out of 10, Exceptional, (9)
"No stone left unturned. The hot tub was clean and perfectly situated. the house was clean, with very sweet finishing touches. Within walking distance to shops. Hosts were very responsive. I highly recommend."
United States
Jamie F.
The price is AU$631
includes taxes & fees
20 Oct - 21 Oct
HunnyHAUS: Deluxe TINY*private spa*walk to town
Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2081)
"Clean and great pool and hot tub facilities "
United States
Alyce
The price is AU$175
includes taxes & fees
2 Nov - 3 Nov
Vacation Village in the Berkshires
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
2.0 star property
The price is AU$443
includes taxes & fees
20 Oct - 21 Oct
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
Florida Mountain Log Cabin!
2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is AU$620
includes taxes & fees
23 Oct - 24 Oct
Florida Mountain Log Cabin!
Park Street Penthouse Apartment
9.6 out of 10, Exceptional, (12)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
The price is AU$303
includes taxes & fees
27 Oct - 28 Oct
Park Street Penthouse Apartment
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (982)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
The price is AU$231
includes taxes & fees
3 Nov - 4 Nov
Jiminy Peak Mountain Resort
Charming 3-bedroom Cabin for nature lovers
8.0 out of 10, Very good, (1)
"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...
United States
John O.
The price is AU$457
includes taxes & fees
20 Oct - 21 Oct
Charming 3-bedroom Cabin for nature lovers
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
10.0 out of 10, Exceptional, (8)
"Great location. Howie is very communicative. Wish we could have stayed longer. "
United States
Una D.
The price is AU$374
includes taxes & fees
20 Oct - 21 Oct
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
10.0 out of 10, Exceptional, (3)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
The price is AU$374
includes taxes & fees
20 Oct - 21 Oct
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Taborton Harvest Boulder Pines Cabin in the woods
10.0 out of 10, Exceptional, (12)
"Such a sweet spot in the woods! Can’t wait to come back."
United States
Mariel
The price is AU$285
includes taxes & fees
20 Oct - 21 Oct
Taborton Harvest Boulder Pines Cabin in the woods
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
9.6 out of 10, Exceptional, (8)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is AU$612
includes taxes & fees
27 Oct - 28 Oct
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
2-Bdr Apt In Town, By the Water
9.6 out of 10, Exceptional, (8)
"Lovely property, in good shape. Close to many Williamstown attractions."
United States
Scott M.
The price is AU$420
includes taxes & fees
20 Oct - 21 Oct
2-Bdr Apt In Town, By the Water
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$621
includes taxes & fees
28 Oct - 29 Oct
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
9.8 out of 10, Exceptional, (18)
"We had a great time with our 2 kids during our stay at the Disney Magic Suite. The kids loved all of the Disney decor and surprise touches (and their stuffed animals thank you!). Location was amazing, walk to the lifts, and the ski school was one of the best we've been to. Thanks for a great stay, we'll be back!"
United States
Debbie H.
The price is AU$363
includes taxes & fees
20 Oct - 21 Oct
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Downtown | Waterfront | Walk to Shops
10.0 out of 10, Exceptional, (6)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is AU$429
includes taxes & fees
23 Oct - 24 Oct
Downtown | Waterfront | Walk to Shops
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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Top Pittsfield Hotel Reviews

Find out more about Pittsfield

Everything you need to know about Pittsfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsfield holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Pittsfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pittsfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsfield holiday rentals we have selected for you start as low as AU$175 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pittsfield rentals

At Expedia, we put the best Pittsfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pittsfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pittsfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 6 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 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.