Pittsfield Holiday Rentals

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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Pittsfield holiday rentals

Outdoor dining
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
2.0 star property
Pittsfield
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$2,097
HK$3,839 total
includes taxes & fees
11 Jan - 12 Jan
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Outdoor dining
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (16 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is HK$4,901
HK$8,927 total
includes taxes & fees
13 Jan - 14 Jan
Hancock Village Inn Near Jiminy Peak
Smart TV
Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Chic corporate apartment in wonderful Pittsfield with AC, WiFi
2.0 star property
Pittsfield
2.0 out of 10, (1 review)
"THIS. PLACE. IS. A. DUMP. Do NOT STAY HERE under any circumstances."
United States
Michael
The price is HK$1,052
HK$1,593 total
includes taxes & fees
10 Jan - 11 Jan
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Dining
Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
2.0 star property
Chatham
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$1,675
HK$2,812 total
includes taxes & fees
12 Jan - 13 Jan
Sugar Shack - 300 square feet of pure sweetness.
Exterior
Huttopia Berkshires

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7 reviews)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is HK$1,489
HK$1,663 total
includes taxes & fees
11 Jan - 12 Jan
Huttopia Berkshires
Fridge, microwave, oven, stovetop
HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (9 reviews)
"Huny House was the most artistically created space we stayed in on our entire trip! We were sooo impressed and appreciated the attention to detail!"
Canada
Patti S.
The price is HK$1,753
HK$3,216 total
includes taxes & fees
13 Jan - 14 Jan
HunnyHAUS: Deluxe TINY*private spa*walk to town
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,204 reviews)
"I great place to stay!!"
United Kingdom
Maricel
The price is HK$810
HK$990 total
includes taxes & fees
21 Jan - 22 Jan
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very good, (988 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is HK$1,705
HK$1,905 total
includes taxes & fees
21 Jan - 22 Jan
Jiminy Peak Mountain Resort
Outdoor dining
Little Longbow Lakefront Chalet

Little Longbow Lakefront Chalet

Little Longbow Lakefront Chalet
Becket
9.8 out of 10, Exceptional, (21 reviews)
"Absolutely perfect quiet get away to relax and recharge will be back! "
United States
Dana V.
The price is HK$2,279
HK$3,964 total
includes taxes & fees
16 Jan - 17 Jan
Little Longbow Lakefront Chalet
TV
Florida Mountain Log Cabin

Florida Mountain Log Cabin

Florida Mountain Log Cabin
2.0 star property
Florida
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$1,431
HK$2,639 total
includes taxes & fees
19 Jan - 20 Jan
Florida Mountain Log Cabin
Pool
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
2.0 star property
Hancock
10.0 out of 10, Exceptional, (1 review)
"The host communicated everything and ensured we had all the necessary information for our arrival. The room was super clean and everything was new. Really enjoyed our stay and had plenty of room and closets for storage. Would definitely stay again and truly a premiere host!! Angelica "
United States
Jeffrey R.
The price is HK$1,068
HK$2,141 total
includes taxes & fees
11 Jan - 12 Jan
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Exterior
The Allen House historic North Adams Home in the Berkshire Mountains

The Allen House historic North Adams Home in the Berkshire Mountains

The Allen House historic North Adams Home in the Berkshire Mountains
2.0 star property
North Adams
10.0 out of 10, Exceptional, (1 review)
"The Allen House was a wonderful stay for my family and we cannot wait to go back! The view was incredible; the host was very approachable for questions; and there were lots of nice touches like ample dishes and silverware.Very spacious, clean and cared for location. "
United States
Annemarie M.
The price is HK$1,870
HK$3,133 total
includes taxes & fees
15 Jan - 16 Jan
The Allen House historic North Adams Home in the Berkshire Mountains
Exterior
Bear Creek Cabin

Bear Creek Cabin

Bear Creek Cabin
Charlemont
10.0 out of 10, Exceptional, (43 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
The price is HK$3,114
HK$4,583 total
includes taxes & fees
9 Feb - 10 Feb
Bear Creek Cabin
TV, fireplace, DVD player, books
Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
2.0 star property
New Lebanon
10.0 out of 10, Exceptional, (1 review)
The price is HK$6,405
HK$12,781 total
includes taxes & fees
12 Jan - 13 Jan
Berkshires farm, 30+ guests, 50 acres
Exterior
Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (28 reviews)
"Nice property for a quick and simple check-in. Near MassMOCA, the Clark Art Institute and much more."
United States
Mario R.
The price is HK$526
HK$1,113 total
includes taxes & fees
10 Jan - 11 Jan
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Interior
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is HK$1,527
HK$4,314 total
includes taxes & fees
10 Jan - 11 Jan
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
TV, fireplace
A stunning, modern Lodge with rustic charm at June Farms!

A stunning, modern Lodge with rustic charm at June Farms!

A stunning, modern Lodge with rustic charm at June Farms!
West Sand Lake
10.0 out of 10, Exceptional, (4 reviews)
"2nd time staying at The Lodge , had a wonderful relaxing few days ! Enjoyed long walks , and the animals . The weather was perfect , couldn't have asked for anything more! Thank you !"
United States
LisaL
The price is HK$3,450
HK$7,091 total
includes taxes & fees
14 Jan - 15 Jan
A stunning, modern Lodge with rustic charm at June Farms!
Living area
Penthouse Apartment on Park Street

Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
2.0 star property
Adams
9.6 out of 10, Exceptional, (13 reviews)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
The price is HK$904
HK$1,906 total
includes taxes & fees
10 Jan - 11 Jan
Penthouse Apartment on Park Street
TV, fireplace, books
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike
2.0 star property
Charlemont
The price is HK$1,752
HK$5,090 total
includes taxes & fees
11 Jan - 12 Jan
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike
Exterior
Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (13 reviews)
"Loved the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven "
United States
Joanna R.
The price is HK$973
HK$1,426 total
includes taxes & fees
9 Feb - 10 Feb
Taborton Harvest Boulder Pines Cabin in the woods
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

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"The kids loved it!"
Deana 1-night trip
Posted 2 days ago
Comfort Inn & Suites East Greenbush - Albany

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
  • Use the map to find apartments and other holiday homes in the Pittsfield neighbourhood you prefer
  • 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 39 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.