Holiday Rentals in Pittsfield

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Pittsfield

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (9)
"Annual mother/son ski and food fest!Lots of fun with family and friends. Plenty of space for everyone.. Kitchen wascwell"
The price is €1,038
includes taxes & fees
12 Feb - 13 Feb
Hancock Village Inn at Jiminy Peak

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (55)
"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

Chic Pittsfield Home With A View!

8.6 out of 10, Excellent, (10)
"This property was just as shown in the listing and met our needs very well. It was well appointed and had many inviting areas to gather and relax in. The kitchen was well equipped and easy to use. Some very nice touches with closets and bathroom storage areas that made staying there user friendly. "
Chic Pittsfield Home With A View!

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

2.0 star property
10.0 out of 10, Exceptional, (3)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is €527
includes taxes & fees
14 Feb - 15 Feb
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

10.0 out of 10, Exceptional, (2)
"The house was fantastic. It had more rooms than we needed, everything was clean, the dining/living area had a lot of lighting, and there was a large fenced in backyard which our dogs loved running around in. It was a great getaway for us as we were coming from Brooklyn. Grocery stores were only 15 min away. Would highly recommend booking! When there was a minor issue, our host Lindsey was very communicative and had it solved right away!"
6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1759)
"Great place "
The price is €121
includes taxes & fees
9 Feb - 10 Feb
Vacation Village in the Berkshires

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is €257
includes taxes & fees
14 Feb - 15 Feb
The Ponds at Foxhollow by Capital Vacations

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 €200
includes taxes & fees
23 Feb - 24 Feb
Jiminy Peak Mountain Resort

Private Estate, Heated Yearround Outdoor Pool

10.0 out of 10, Exceptional, (16)
"The home was beautiful and it was a gorgeous property too. It had all the right amenities in the kitchen. "
The price is €2,869
includes taxes & fees
19 Feb - 20 Feb
Private Estate, Heated Yearround Outdoor Pool

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

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"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

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is €225
includes taxes & fees
11 Feb - 12 Feb
Berkshire Village Carriage House - Super Private!!

Amore Estate - beautiful room with many places to explore and relax in.

9.4 out of 10, Exceptional, (21)
"Fantastic, large house with tons of places to explore in the house and on the property. We came for a long weekend with 3 families and both the adults and kids felt quickly at home and really enjoyed our stay. We cannot wait to some back!"
Amore Estate - beautiful room with many places to explore and relax in.

Peace and quiet on the lake

9.6 out of 10, Exceptional, (204)
"Such a cozy cabin for a perfect weekend stay with friends. Located close to multiple ski spots around the area, coming back to the cabin after to relax with hot cocoa and a fire going on. Right down the street is a shop that sells delicious sandwiches too. Owners of the property were super nice and quick to respond with any questions we had. Hoping to come back soon and check this place out during the summer time to enjoy the lake life!"
Peace and quiet on the lake

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (210)
"The cabin is quiet, tidy, and comfortable. It is within driving distance of several hiking trails and was a great place to spend a long weekend. The host was friendly and communicative, and made sure that we had everything we needed for a nice stay. "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Amazing Estate w/pool, gym, pond, trails, arcade! Chef dinner w/week long stay!

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!"
Amazing Estate w/pool, gym, pond, trails, arcade! Chef dinner w/week long stay!

Peaceful Retreat Compound 10 Minutes to Great Barrington!

10.0 out of 10, Exceptional, (21)
"This home is located in a beautiful area with plenty of nature surrounding. The amenities included are incredible. A large group of us visited and had so much fun on the pickle ball courts, hanging around the bonfire, and relaxing with the sauna and hot tub. This place can’t be beat!!"
Peaceful Retreat Compound 10 Minutes to Great Barrington!

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

10.0 out of 10, Exceptional, (5)
"Condo was conveniently located at the base of the mountain. Had everything you would need for a quick weekend getaway. Owner was available for any questions."
The price is €290
includes taxes & fees
12 Feb - 13 Feb
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

10.0 out of 10, Exceptional, (23)
"We stayed at the house with extended family for a ski trip weekend at Catamount. The drive was 30mins away and the house a wonderful place to relax together after a long day on the mountain. The house is spacious, bright, clean and tastefully decorated. The layout is comfortable and practical. The lovely, open-kitchen was well-equipped and allowed us all to gather and chat pre and post dinner. The sauna is a great perk with gorgeous views! Highly recommend! Would love to come back in the summer...
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
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.
Don't see what you're looking for?
See all available properties in Pittsfield
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Pittsfield you may be interested in

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (731)
"We stay here often because it is close to our daughter’s school in New York. We love staying here and choose this hotel every time. "
The price is €115
includes taxes & fees
19 Feb - 20 Feb
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (681)
"The staff was fantastic "
The price is €117
includes taxes & fees
10 Feb - 11 Feb
Hotel On North

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (429)
"Great place for a family vacation"
The price is €137
includes taxes & fees
9 Feb - 10 Feb
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?

Spacious Luxury Berkshire's Estate on 21 acres : This highly rated holiday home rental in Pittsfield offers a fireplace, 1 hot tub and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave. 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 Pittsfield State Forest 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.