Search Vacation Homes in Pittsfield

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 43 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

Hot Tub & Boat Dock: Waterfront Maine Retreat!
Property grounds

Hot Tub & Boat Dock: Waterfront Maine Retreat!

10.0 out of 10, Exceptional, (4)
"The property was beautiful and just as advertised. The owners know how to rent a property and thought of everything! The hot tub was not working just prior to our stay and everyone involved worked extra hard to have it ready for our stay which we very much appreciated. Communication was good through the property manager, but what impressed us the most was the actual owner of the property was very invested and stayed connected throughout the prior weeks and during our stay! This is definitely a...
Hot Tub & Boat Dock: Waterfront Maine Retreat!
The Modern Maine Retreat
Property grounds

The Modern Maine Retreat

9.0 out of 10, Wonderful, (4)
"Worked out perfectly for our needs. Owner responded immediately to assist us with minor issue. We would, and most likely will, rent this home again. Location was great for our purpose. Plenty of room."
The Modern Maine Retreat
Cozy House in the heart of Waterville Maine.
TV

Cozy House in the heart of Waterville Maine.

9.6 out of 10, Exceptional, (39)
"Very clean nice home, close to restaurants and shops. The owner was easily accessible if needed. "
Cozy House in the heart of Waterville Maine.
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
Exterior

Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard

10.0 out of 10, Exceptional, (6)
"We come to Dexter often to visit family. Never stayed at this beautiful spot. Loved seeing the deer in the yard."
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
Rustic Lakeside Camp with an Amazing View
Property grounds

Rustic Lakeside Camp with an Amazing View

10.0 out of 10, Exceptional, (41)
"It has a graet view of the water. Very nice place. We got home from ice fishing there and already have talked about staying in the summer"
Rustic Lakeside Camp with an Amazing View
Modern Cornville Ranch
Fridge, microwave, oven, stovetop

Modern Cornville Ranch

10.0 out of 10, Exceptional, (5)
"House was awesome and clean definitely recommend "
Modern Cornville Ranch
Lake Front with Amazing Sunsets on McGrath Pond
4 bedrooms, iron/ironing board, travel crib, free WiFi

Lake Front with Amazing Sunsets on McGrath Pond

10.0 out of 10, Exceptional, (17)
"Very clean, cute lake house. Owner responsive, everything you need for a rental home. Lake and lake toys were so great! We really enjoyed our stay. Thank you!!! "
Lake Front with Amazing Sunsets on McGrath Pond
Lakefront Maine House ~ 4 Mi to Colby College
Microwave, stovetop, dishwasher, coffee/tea maker

Lakefront Maine House ~ 4 Mi to Colby College

8.0 out of 10, Very Good, (2)
"Convenient very clean but we were hardly there except to sleep. Thank you"
Lakefront Maine House ~ 4 Mi to Colby College
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Terrace/patio

Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

10.0 out of 10, Exceptional, (26)
"As described. Beautiful location. Clean and well stocked. Very cozy, comfortable and exactly what we were hoping for. Great host, thank you!"
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Waterfront Lakehouse
Fridge, microwave, oven, stovetop

Waterfront Lakehouse

9.8 out of 10, Exceptional, (51)
"This camp is fabulous! Happy to come back whenever we can!"
Waterfront Lakehouse
Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach
Exterior

Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach

9.6 out of 10, Exceptional, (64)
"There for project in the area .. accommodations were all as advertised .. old school camp feel with all the modern amenities .. well appointed with a local flair .. would recommend to all …"
Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach
Near Waterville: Cozy Midcoast Vacation Rental!
TV, fireplace, DVD player, books

Near Waterville: Cozy Midcoast Vacation Rental!

9.4 out of 10, Exceptional, (8)
"Nice comfortable home to stay in."
Near Waterville: Cozy Midcoast Vacation Rental!
Peaceful, Spacious Lodge with Golf & Sunset Views
Fridge, microwave, oven, stovetop

Peaceful, Spacious Lodge with Golf & Sunset Views

10.0 out of 10, Exceptional, (15)
"Had a great time, perfect accommodations. Plenty of room "
Peaceful, Spacious Lodge with Golf & Sunset Views
Directly across the street from China Lake and boat launch
Fridge, microwave, stovetop, cookware/dishes/utensils

Directly across the street from China Lake and boat launch

Directly across the street from China Lake and boat launch
Waterville Home Rental w/ Private Yard + Deck!
Exterior

Waterville Home Rental w/ Private Yard + Deck!

9.4 out of 10, Exceptional, (3)
"Everything was good. Had a little issue with weekly trash pick-ups but the property manager was very responsive and helpful in getting it resolved "
Waterville Home Rental w/ Private Yard + Deck!
Winnecook Lake House
Fridge, microwave, oven, stovetop

Winnecook Lake House

Winnecook Lake House
Discover Oakland charm near Colby College 10 min
Fridge, microwave, oven, stovetop

Discover Oakland charm near Colby College 10 min

2.0 star property
10.0 out of 10, Exceptional, (2)
"New, clean and had everything we needed. "
The price is AED 364
AED 989 total
includes taxes & fees
4 May - 5 May
Discover Oakland charm near Colby College 10 min
Lakeside Cabin Retreat: Waterfront, Near Colby College, Waterville & Augusta
Fridge, microwave, oven, stovetop

Lakeside Cabin Retreat: Waterfront, Near Colby College, Waterville & Augusta

10.0 out of 10, Exceptional, (6)
"Beautiful home and setting! Home was thoughtfully furnished and very clean. Comfortable beds and nice linens helped provide a great night’s sleep!"
Lakeside Cabin Retreat: Waterfront, Near Colby College, Waterville & Augusta
Classy AF Home Steps from Colby and Trails
Fridge, oven, stovetop, dishwasher

Classy AF Home Steps from Colby and Trails

10.0 out of 10, Exceptional, (40)
"So close to Colby College. Owners were incredible - so responsive & happy to answer any questions. House was clean, quiet & well-cared for."
Classy AF Home Steps from Colby and Trails
Maplewood Lakehouse in Newport
Exterior

Maplewood Lakehouse in Newport

10.0 out of 10, Exceptional, (1)
"The Maplewood Lakehouse is the PERFECT spot to gather with friends and family! The home itself is huge and inviting, but it's location to the town of Newport for gas, groceries, and take-out make it really stand out. This home has SO many bedrooms to accomodate our large group. We really appreciated having spaces to both be together (multiple living rooms, the game room/garage, and the kitchen/dining spaces) as well as the many bedrooms to have quiet space to recharge as well. And that's just...
Maplewood Lakehouse in Newport
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.
Don't see what you're looking for?
See all available properties in Pittsfield
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Pittsfield

Family, Friends and Fun for all
Fridge, microwave, oven, stovetop

Family, Friends and Fun for all

2.0 star property
The price is AED 459
AED 1,416 total
includes taxes & fees
28 Apr - 29 Apr
Family, Friends and Fun for all
The Cabin Skowhegan
Terrace/patio

The Cabin Skowhegan

9.8 out of 10, Exceptional, (39)
"This is a wonderful, cozy little cabin that is remote enough to be private and peaceful, but close enough to town to be convenient as well. Highly recommended!"
The price is AED 367
AED 681 total
includes taxes & fees
27 Apr - 28 Apr
The Cabin Skowhegan
Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding
Terrace/patio

Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding

9.8 out of 10, Exceptional, (152)
"Great place with nice hosts! They were very helpful "
Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding
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.