Search Vacation Homes in Pittsfield
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Pittsfield vacation homes
1. Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95Pittsfield
9.8 out of 10, Exceptional, (8 reviews)
"Great host great stay"
thomas v.
The price is AED 437
AED 845 total
includes taxes & fees
24 Aug - 25 Aug
2. Pine Tree Trail Lodge
Pine Tree Trail LodgePittsfield
10.0 out of 10, Exceptional, (1 review)
"Great place. The host so helpful. I would definitely stay here again. "
Amber G.
The price is AED 5,183
AED 6,407 total
includes taxes & fees
15 Sep - 16 Sep
The price is AED 477
AED 1,141 total
includes taxes & fees
8 Sep - 9 Sep
4. Peaceful, Spacious Lodge with Golf & Sunset Views
Peaceful, Spacious Lodge with Golf & Sunset ViewsPalmyra
10.0 out of 10, Exceptional, (24 reviews)
"Gorgeous property, very clean"
Aaliya J.
The price is AED 1,054
AED 2,230 total
includes taxes & fees
19 Aug - 20 Aug
5. 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 yardSangerville
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful place and location. Highly recommend and would stay here again."
Michelle W.
The price is AED 496
AED 1,169 total
includes taxes & fees
24 Aug - 25 Aug
6. Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Charming 1-bedroom building with WiFi, AC in brilliant Madison MaineMadison
9.4 out of 10, Exceptional, (8 reviews)
"Excellent service and perfect for our stay. Would book again!"
Scott
The price is AED 413
AED 530 total
includes taxes & fees
30 Aug - 31 Aug
7. Discover Oakland charm near Colby College 10 min
Discover Oakland charm near Colby College 10 minOakland
9.8 out of 10, Exceptional, (15 reviews)
"House very clean and convenient location for what we had going on. "
Tammy W.
The price is AED 511
AED 957 total
includes taxes & fees
17 Sep - 18 Sep
8. Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakesOakland
10.0 out of 10, Exceptional, (16 reviews)
"Kathleen was a wonderful host. My family and I found the property welcoming and relaxing. Great place to stay if you are looking for a laid back atmosphere and peaceful time in the country."
Jared
The price is AED 868
AED 1,709 total
includes taxes & fees
20 Aug - 21 Aug
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.
Find vacation rentals that suit your style
Apartments
Cabins
Save an average of 15% on thousands of hotels when you're signed in
Top Pittsfield Hotel Reviews
Fireside Inn & Suites Waterville
8/10 Good
