Search 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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Top Holiday Rentals in Pittsfield

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1743)
"The suite was clean, comfortable, and ready when I arrived."
The price is 4.271.400 ₫
4.938.846 ₫ total
includes taxes & fees
6 Nov - 7 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (915)
"Nice fall view"
The price is 3.771.488 ₫
4.137.323 ₫ total
includes taxes & fees
6 Nov - 7 Nov
Jiminy Peak Mountain Resort
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
Sign in
Sign up, it's free

Other types of properties in Pittsfield you may be interested in

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Indoor pool
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3.0 star property
7.8 out of 10, Good, (670)
"My stay at the Holiday Inn was very pleasant!"
The price is 2.379.328 ₫
2.657.710 ₫ total
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express
2.5 star property
5.4 out of 10, (676)
"I don’t know so many complaints. Bed was good, clean. Plenty of park. Provided what we paid for and was expecting. "
The price is 1.999.648 ₫
2.233.531 ₫ total
includes taxes & fees
6 Nov - 7 Nov
FairBridge Inn Express
Berkshire Mountain Lodge
Fridge, microwave, stovetop, coffee/tea maker
Berkshire Mountain Lodge
3.0 star property
8.8 out of 10, Excellent, (406)
"My husband and I stayed here for 3 nights. It was a great location and the accommodations were exceptional. Loved having the separate bedroom and kitchen. It was quiet too. My husband watched football late into the evening and I went to bed... didn't hear his TV at all. Also we didn't hear any neighbors either... but I don't think the hotel was full. It was getting to be past peak on fall colors. Too bad they have only 1-bedroom rooms. Would have been fun to have more family members join in...
The price is 4.176.480 ₫
5.171.368 ₫ total
includes taxes & fees
6 Nov - 7 Nov
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.

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 Pittsfield State Forest and Housatonic River 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.