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
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Compare 36 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

Cozy House in the heart of Waterville Maine.
Living area

Cozy House in the heart of Waterville Maine.

9.6 out of 10, Exceptional, (37)
"A lovely cozy house, well situated close to downtown and easy access to stores. The house was very clean and tidy. Cozy and felt like home, and worked out well for our Thanksgiving break with our college students. Would use againnif dates worked out."
Cozy House in the heart of Waterville Maine.
Peaceful, Spacious Lodge with Golf & Sunset Views
Living area

Peaceful, Spacious Lodge with Golf & Sunset Views

10.0 out of 10, Exceptional, (13)
"This July we had a family reunion in Newport with 66 people attending. My large-ish family wanted to stay together and the accommodations in the lodge at Fogg Brook Resort could not have been more perfect. The space was large enough for 10 of us to be together without being on top of each other and the deck space added even more room for us to enjoy. We've recommended Fogg Brook's VRBO space to everyone at our event and will definitely stay there again!"
Peaceful, Spacious Lodge with Golf & Sunset Views
Lake Front with Amazing Sunsets on McGrath Pond
Enjoy beautiful sunsets every night.

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
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, (5)
"Clean, private, modern, reasonable "
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
Charming 2-bedroom house with AC, WiFi in enchanting Skowhegan
Living area

Charming 2-bedroom house with AC, WiFi in enchanting Skowhegan

2.0 star property
10.0 out of 10, Exceptional, (2)
"This house was perfect for our stay. We could host our family for meals and meetings. We could enjoy quiet evenings by ourselves and Walmart and grocery were close enough to walk to. "
Charming 2-bedroom house with AC, WiFi in enchanting Skowhegan
Waterfront Lakehouse
Kayaks, canoe and paddleboat

Waterfront Lakehouse

9.8 out of 10, Exceptional, (51)
"This camp is fabulous! Happy to come back whenever we can!"
Waterfront Lakehouse
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Exterior

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
The Maine Lake House with an Amazing Sand Beach!

The Maine Lake House with an Amazing Sand Beach!

8.8 out of 10, Excellent, (6)
"The house was nice, newer updates and a step up from the typical lake rentals in Maine. The main floor has a nice kitchen, living room, dining, master bedroom and full bath. Wish the upstairs had more than a loveseat for gathering and watching tv. The downstairs is big, has a bedroom, living area, and half bath. The, property was nice except the construction in front of the house that we weren't told about till the day we arrived. It was understandable that it needed to be done but wish we were...
The Maine Lake House with an Amazing Sand Beach!
Quiet setting 1 minute drive to China lake boat launch and ATV trail
Interior

Quiet setting 1 minute drive to China lake boat launch and ATV trail

10.0 out of 10, Exceptional, (32)
"Enjoyed the large kitchen and living room. Has a small dog that enjoyed the fenced front yard"
Quiet setting 1 minute drive to China lake boat launch and ATV trail
the Corner cottage: Overlooking Hayden Brook, Steps to Lakewood Summer Theater
Interior

the Corner cottage: Overlooking Hayden Brook, Steps to Lakewood Summer Theater

9.0 out of 10, Wonderful, (12)
"My brother and I were traveling for our Uncle's funeral. We were thrilled to find the Perkins House was available. The house reminded us of our grandparents house in Harrison, ME. It brought us back in time to days of our childhood. I definitely want to return with my family to enjoy the Lakewood Theatre and the lake."
the Corner cottage: Overlooking Hayden Brook, Steps to Lakewood Summer Theater
Classy AF Home Steps from Colby and Trails
Exterior

Classy AF Home Steps from Colby and Trails

10.0 out of 10, Exceptional, (39)
"Lovely house. Only thing was just one bathroom bit otherwise recommend. "
Classy AF Home Steps from Colby and Trails
Near Waterville: Cozy Midcoast Vacation Rental!
Albion Vacation Rental | 3BR | 2BA | 1,508 Sq Ft | Stairs Required

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!
Directly across the street from China Lake and boat launch
Backyard - you can see the lake

Directly across the street from China Lake and boat launch

Directly across the street from China Lake and boat launch
The Modern Maine Retreat
Room

The Modern Maine Retreat

10.0 out of 10, Exceptional, (2)
"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
Lakeside Cabin Retreat: Waterfront, Near Colby College, Waterville & Augusta
Unwind & relax in our open concept, spacious cabin! Lake view from deck!

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

10.0 out of 10, Exceptional, (5)
"Such a comfortable stay! We felt very welcomed and the check in / check out process was easy. Great communication from the owners and the home came as advertised with thoughtful extras in case anyone forgot some basics needs. Beautiful views of the lake from the dock and easily accommodated 5 guys on a golf adventure to Belgrade Lakes Golf Club. It was quick drive to the course which is our favorite public course in Maine. Thanks for a great experience. Would definitely stay here...
Lakeside Cabin Retreat: Waterfront, Near Colby College, Waterville & Augusta
Sugarmaple Lakehouse; Cozy 2.6 Acre Lakefront Retreat
Terrace/patio

Sugarmaple Lakehouse; Cozy 2.6 Acre Lakefront Retreat

10.0 out of 10, Exceptional, (23)
"We came up for our daughter’s wedding and needed a spot to relax and reenergize between setting up, decorating, rehearsing and the big day. SugarMaple provided just that. We had my son and his girl and his best friend and his girlfriend with us and the accommodations were stellar. The view was beautiful! Thank you!! -DMB "
Sugarmaple Lakehouse; Cozy 2.6 Acre Lakefront Retreat
Waterville Home Rental w/ Private Yard + Deck!
Waterville Vacation Rental | 5BR | 2.5BA | 2,576 Sq Ft | Stairs Required

Waterville Home Rental w/ Private Yard + Deck!

9.0 out of 10, Wonderful, (2)
"The home worked great for my family of 10. Very clean"
Waterville Home Rental w/ Private Yard + Deck!
Springvale Farm: Freedom Home with Hiking Trail!
Freedom Vacation Rental | 4BR | 1.5BA | 1,500 Sq Ft | Stairs Required to Enter

Springvale Farm: Freedom Home with Hiking Trail!

10.0 out of 10, Exceptional, (3)
"It was truly the best place we’ve ever stayed in! Hubby and I loved all the woodwork throughout the house. The kitchen was fabulous! The bathroom was fun- a heated seat in the master bath! And the bedroom was extremely comfortable. Can’t wait to come back!"
Springvale Farm: Freedom Home with Hiking Trail!
Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach
Sunrise on the lake

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
Lakeside with Loons, Bald Eagles & Amazing Sunsets
Exterior

Lakeside with Loons, Bald Eagles & Amazing Sunsets

10.0 out of 10, Exceptional, (1)
"Very nice! Spacious, lots of rooms and very clean. The sunset was amazing. I just wish it wasn't so expensive. When I got the address a few days before our stay the address was listed 314.....unfortunately we drove to the very end of a long pitted, dirt road. Turned around. Luckily I had a photo of the house and we figured out the the number was 34, NOT 314. A bit of confusion."
Lakeside with Loons, Bald Eagles & Amazing Sunsets
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

Cozy House in the heart of Waterville Maine.
Living area

Cozy House in the heart of Waterville Maine.

9.6 out of 10, Exceptional, (37)
"A lovely cozy house, well situated close to downtown and easy access to stores. The house was very clean and tidy. Cozy and felt like home, and worked out well for our Thanksgiving break with our college students. Would use againnif dates worked out."
Cozy House in the heart of Waterville Maine.
Cabin in scenic woods with hiking trails, firepit, horseback riding nearby
Chalet Cabin

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

9.8 out of 10, Exceptional, (118)
"We had a lovely stay -- quite a cozy and well-appointed cabin, in an out-of-the-way spot that let us explore the area and just hunker down and enjoy the solitude, as the mood took us. Our host was very welcoming and considerate. A wonderful spot!"
Cabin in scenic woods with hiking trails, firepit, horseback riding nearby
The Cabin Skowhegan
Terrace/patio

The Cabin Skowhegan

9.8 out of 10, Exceptional, (38)
"In an age of "Live Laugh Love" vacation rentals -- every property a generic flip, done up in neutral tones and mass-manufactured message art -- it was so refreshing to enter the Cabin Skowhegan, where everything seemed like a real live person had put it there. The photos of local sites, sometimes captioned. The worn-in but sturdy and inviting furniture, arranged for comfort. The quirky mug collection, clearly someone's pride and joy, hanging around the dining area. Supplies and provisions...
The Cabin Skowhegan
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.