A lake surrounded by autumn-colored trees and a rocky shoreline.

Search Cottages in Pittsfield

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
25 Sep - 27 Sep
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Pittsfield cottages

Exterior

1. Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Leicester
10.0 out of 10, Exceptional, (89 reviews)
"Definitely super SUPER clean all throughout! The ambiance is perfect, just a beautiful cottage with all the amenities you might need. Perfect place to stay."
United States
Julian V.
The price is AED 436
AED 694 total
includes taxes & fees
10 Sep - 11 Sep
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Property grounds

2. Cozy Cabin Retreat

Cozy Cabin Retreat
Roxbury
10.0 out of 10, Exceptional, (40 reviews)
"Host was very friendly and accommodating "
United States
Alexandria
The price is AED 433
AED 781 total
includes taxes & fees
9 Sep - 10 Sep
Cozy Cabin Retreat
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

Mountain Meadows Lodge

Mountain Meadows Lodge

10/10 Excellent
"Learning about the family running the place made us feel more at home. Snacks always available was a plus."
Nancy 4-night trip
Posted 6 hours ago
Mountain Meadows Lodge

Frequently asked questions

Why book your cottage in Pittsfield with Expedia?
We think that a vacation should be a breeze, so if you're chasing cottages in Pittsfield at an affordable price, Expedia is here to help. Keep the budget in check and stay in an economical option surrounded by nature, or splurge on a luxury cottage to treat your loved ones.
How can I find cheap cottages in Pittsfield?
With Expedia's filter tool, comparing cheap cottages in Pittsfield has never been easier. To discover properties that are very pocket friendly, refine your search by amenities, star rating and budget.