Search Cottages in Pittsfield

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

Cottages in Pittsfield

Property grounds
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Cottage in Leicester

10.0 out of 10, Exceptional, (66)
"Superb lodging. Enjoyed the cosmopolitan vibe in a rural setting. "
United States
Jason R.
The price is SAR 371
SAR 626 total
includes taxes & fees
15 Dec - 16 Dec
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Exterior
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

Cottage in Mendon

2.0 star property
9.8 out of 10, Exceptional, (11)
"Very clean, and just the perfect getaway. Private and quaint, but close enough to amenities. A very pleasant stay indeed."
United States
Linda B.
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
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

White Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now
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

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

10/10 Excellent
"The room was immaculate. It was clean and we appreciated the layout of the room, making it feel larger than most hotel rooms. We also loved the kitchenette in the room, even though we did t stay long enough to use it. We will most definitely be booking future stays at this hotel, especially given the proximity to Norwich University. "
Jennifer 1-night trip
Posted 2 days ago
My Place Hotel-Randolph VT

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.