Search Vacation Homes in Pittsfield
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 43 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

Hot Tub & Boat Dock: Waterfront Maine Retreat!
Hot Tub & Boat Dock: Waterfront Maine Retreat!
10.0 out of 10, Exceptional, (1)

Beautiful lakeside 4 bedroom retreat with private dock and walkout basement
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

The Modern Maine Retreat
The Modern Maine Retreat
10.0 out of 10, Exceptional, (3)

Cozy House in the heart of Waterville Maine.
Cozy House in the heart of Waterville Maine.
9.6 out of 10, Exceptional, (38)

Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
10.0 out of 10, Exceptional, (5)

Rustic Lakeside Camp with an Amazing View
Rustic Lakeside Camp with an Amazing View
10.0 out of 10, Exceptional, (41)

Modern Cornville Ranch
Modern Cornville Ranch
10.0 out of 10, Exceptional, (5)

Lake Front with Amazing Sunsets on McGrath Pond
Lake Front with Amazing Sunsets on McGrath Pond
10.0 out of 10, Exceptional, (17)
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Pittsfield

Angel Mist Retreat Garage Apartment
Angel Mist Retreat Garage Apartment
10.0 out of 10, Exceptional, (8)
The price is AED 516
AED 1,127 total
includes taxes & fees
27 Apr - 28 Apr

Cabin in scenic woods with hiking trails, firepit, horseback riding nearby
Cabin in scenic woods with hiking trails, firepit, horseback riding nearby
9.8 out of 10, Exceptional, (119)

Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding
Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding
9.8 out of 10, Exceptional, (152)
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.
Recent reviews of Pittsfield hotels
Recent reviews of Pittsfield hotels

Holiday Inn Express & Suites Waterville - North by IHG
5/5 Excellent
"Great service "
A verified traveler stayed at Holiday Inn Express & Suites Waterville - North by IHG
Posted 2 days ago