Pittsfield Holiday Rentals

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Pittsfield holiday rentals

Exterior detail

Holiday Home in Pittsfield

3-bedroom house in beautiful Berkshires, close to amenities!
The price is HK$1,408
HK$2,403 total
includes taxes & fees
3 Mar - 4 Mar
3-bedroom house in beautiful Berkshires, close to amenities!
Outdoor dining

Holiday Home in Pittsfield

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is HK$2,105
HK$3,872 total
includes taxes & fees
3 Mar - 4 Mar
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Outdoor dining

Holiday Home in Hancock

Hancock Village Inn Near Jiminy Peak
10.0 out of 10, Exceptional, (18 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is HK$4,510
HK$8,469 total
includes taxes & fees
3 Mar - 4 Mar
Hancock Village Inn Near Jiminy Peak
Exterior

Camping in Williamstown

Huttopia Berkshires
1.0 star property
9.4 out of 10, Exceptional, (9 reviews)
"Healthy food too!"
United States
GEORGINA
The price is HK$1,317
HK$1,471 total
includes taxes & fees
16 Mar - 17 Mar
Huttopia Berkshires
Dining

Mobile Home in Chatham

Sugar Shack - 300 square feet of pure sweetness.
10.0 out of 10, Exceptional, (3 reviews)
"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 HK$1,478
HK$2,558 total
includes taxes & fees
5 Mar - 6 Mar
Sugar Shack - 300 square feet of pure sweetness.
Terrace/patio

Mobile Home in Chatham

BLUSH: Boutique TINY home*private spa*walk to town
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is HK$1,479
HK$2,515 total
includes taxes & fees
10 Mar - 11 Mar
BLUSH: Boutique TINY home*private spa*walk to town
Exterior

Condo in Williamstown

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2,274 reviews)
"Excellent location and terrific space and amenities."
United States
Michelle
The price is HK$813
HK$994 total
includes taxes & fees
31 Mar - 1 Apr
Vacation Village in the Berkshires
Interior

Cottage in Stephentown

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
The price is HK$1,533
HK$4,331 total
includes taxes & fees
3 Mar - 4 Mar
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Daily to-go breakfast for a fee

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (989 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is HK$1,166
HK$1,302 total
includes taxes & fees
1 Apr - 2 Apr
Jiminy Peak Mountain Resort
Exterior

Cabin in Charlemont

Bear Creek Cabin
10.0 out of 10, Exceptional, (46 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
The price is HK$3,129
HK$4,684 total
includes taxes & fees
7 Mar - 8 Mar
Bear Creek Cabin
Exterior

Cabin in Sand Lake

Taborton Harvest Boulder Pines Cabin in the woods
10.0 out of 10, Exceptional, (13 reviews)
"Loved this cabin! The communal building is very clean & bathrooms are spotless. There is a farm stand near the entrance where you can buy firewood and fresh eggs. Trails are literally connected to the property for easy nature walks. We plan on coming back!"
United States
Abby L.
The price is HK$978
HK$1,433 total
includes taxes & fees
3 Mar - 4 Mar
Taborton Harvest Boulder Pines Cabin in the woods
Fridge, microwave, oven, stovetop

Holiday Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (27 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is HK$1,260
HK$2,107 total
includes taxes & fees
3 Mar - 4 Mar
Home in Great Barrington
Smart TV, books

Holiday Home in Sherwood Forest

Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is HK$1,253
HK$3,086 total
includes taxes & fees
12 Mar - 13 Mar
Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Property grounds

Cabin in Hinsdale

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is HK$2,065
HK$4,256 total
includes taxes & fees
31 Mar - 1 Apr
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Property grounds

Apartment in Hancock

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
10.0 out of 10, Exceptional, (5 reviews)
"It was great experience and we loved the ammenities."
United States
Carrie C.
The price is HK$876
HK$1,888 total
includes taxes & fees
3 Mar - 4 Mar
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Outdoor dining

Apartment in Williamstown

2-Bdr Apt In Town, By the Water
9.6 out of 10, Exceptional, (12 reviews)
"Clean, close to town, very convenient. On a busy road, so just be aware of that. But overall a good place to stay. "
United States
Brian L.
The price is HK$939
HK$2,209 total
includes taxes & fees
5 Mar - 6 Mar
2-Bdr Apt In Town, By the Water
TV

Holiday Home in Florida

Florida Mountain Log Cabin
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is HK$1,438
HK$2,669 total
includes taxes & fees
3 Mar - 4 Mar
Florida Mountain Log Cabin

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
7.0 out of 10, Good, (4 reviews)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
United States
John P.
The price is HK$1,244
HK$1,568 total
includes taxes & fees
3 Mar - 4 Mar
The Brooks Motel: Exceptional Suite
Exterior

Holiday Home in Stockbridge

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
10.0 out of 10, Exceptional, (34 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is HK$2,339
HK$5,086 total
includes taxes & fees
4 Mar - 5 Mar
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Property grounds

Holiday Home in Charlemont

Riverbend Berkshire East Basecamp - 3 bedrooms available
10.0 out of 10, Exceptional, (2 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is HK$1,369
HK$3,452 total
includes taxes & fees
3 Mar - 4 Mar
Riverbend Berkshire East Basecamp - 3 bedrooms available
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Love it here. We stay a few times a year and are actually local to the hotel. Just a relaxed experience. "
Anthony 2-night trip
Posted 17 hours ago
Berkshire Mountain Lodge

Find out more about Pittsfield

Search for holiday rentals in Pittsfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsfield using one of the methods below:

  • View our selection of featured holiday rentals in Pittsfield
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  • Enter your travel dates to view the best deals on holiday rentals in Pittsfield while they last

Look no further and take a look at our great range of rental properties in Pittsfield!

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 Near 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.

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 Hancock Shaker Village.

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.