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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

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, (5)
Hot Tub & Boat Dock: Waterfront Maine Retreat!
The Modern Maine Retreat
Outdoor dining

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)
"Everything was good. Would stay there again."
Cozy House in the heart of Waterville Maine.
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
Dining

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

10.0 out of 10, Exceptional, (6)
"Beautiful property. Private. Would definitely stay again."
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
Rustic Lakeside Camp with an Amazing View

Rustic Lakeside Camp with an Amazing View

10.0 out of 10, Exceptional, (41)
"Could not have been happier with our stay! The house was beautiful, clean and had all the amenities one needs! Cant wait to stay there again next year!"
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
Lake

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)
"This place was perfect for our 3-night stay. Inside, it hits the sweet spot between well-equipped but uncluttered. The bird-watching overlooking the water was fantastic - from huge bald eagles to petite hummingbirds. "
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Waterfront Lakehouse
Sun loungers

Waterfront Lakehouse

9.8 out of 10, Exceptional, (51)
"Wonderful place to stay! Our family loves coming here."
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)
"Beautiful home right on a lake!"
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, (16)
"Located in a quiet area & was a great location to see the area sites."
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!
Terrace/patio

Waterville Home Rental w/ Private Yard + Deck!

9.4 out of 10, Exceptional, (3)
"We traveled from Alaska to ME with a large group. This home was large and had just about all the amenities we needed at an affordable price. The property was beautiful and the process was easy."
Waterville Home Rental w/ Private Yard + Deck!
Winnecook Lake House
Property grounds

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 AEDĀ 364
AEDĀ 989 total
includes taxes & fees
11 May - 12 May
Discover Oakland charm near Colby College 10 min
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, (41)
"Clean, comfortable and incredibly close to campus for a college visit."
Classy AF Home Steps from Colby and Trails
Maplewood Lakehouse in Newport
Miscellaneous

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
Sugarmaple Lakehouse; Cozy 2.6 Acre Lakefront Retreat
Pool

Sugarmaple Lakehouse; Cozy 2.6 Acre Lakefront Retreat

10.0 out of 10, Exceptional, (23)
"Wonderful property and great stay! Beautiful location!"
Sugarmaple Lakehouse; Cozy 2.6 Acre Lakefront Retreat
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.
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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 AEDĀ 459
AEDĀ 1,412 total
includes taxes & fees
7 May - 8 May
Family, Friends and Fun for all
Sister A-Frame in Woods B
Exterior

Sister A-Frame in Woods B

The price is AEDĀ 492
AEDĀ 785 total
includes taxes & fees
7 May - 8 May
Sister A-Frame in Woods B
Cabin in scenic woods with hiking trails, firepit, horseback riding nearby
Property grounds

Cabin in scenic woods with hiking trails, firepit, horseback riding nearby

9.8 out of 10, Exceptional, (120)
"The chalet cabin was beautiful and a wonderful place to stay. Debbie was a great host and made sure we had everything we needed for our stay."
Cabin in scenic woods with hiking trails, firepit, horseback riding nearby
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.