Search Pittsfield Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Pittsfield cottages

1. The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Mendon
9.6 out of 10, Exceptional, (22 reviews)
"The communication with Host was awesome to a question we had; Dave's response was so helpful. Beautiful place, quiet. Get ‘get-away’."
United States
Diane
$383 nightly
The price is $433
Nov 8 - Nov 9
Total with taxes and fees
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

2. 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, (97 reviews)
"The cottage was just lovely. Very comfortable. And the host was really nice and helpful. A wonderful stay!"
United States
Laura Ann
$171 nightly
The price is $192
Nov 22 - Nov 23
Total with taxes and fees
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
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.

Learn more about Pittsfield

Nestled in Vermont's Green Mountains, Pittsfield offers excellent hiking on the Long Trail and thrilling mountain biking at Green Mountain Trails. Riverside picnics along the Tweed River provide peaceful breaks between seasonal activities at nearby Killington Resort.

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

Top reviews in Pittsfield

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.

Explore a world of travel with Expedia