Search Cottages 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
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Cottages in Pittsfield and around

10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug
9.8 out of 10, Exceptional, (109)
"Great space and location. Very clean cabin with all the amenities you need. The enclosed back porch facing the lake and the master bedroom with a wall of windows facing the lake were our favorite features!"
10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
9.6 out of 10, Exceptional, (49)
"It was OK."
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
The Cabbage on Olive Street, overlooking Hayden Brook
8.8 out of 10, Excellent, (10)
"I absolutely loved spending time here! It brought me right back to my childhood growing up near Embden Lake, spending summers in the lakeside cabins. The amenities were all great, exactly as advertised. I will say it's a little tricky finding it in the dark! I'm looking forward to my next trip to Maine so that I can stay here again! "
The Cabbage on Olive Street, overlooking Hayden Brook
Springvale Farm: Freedom Home With Hiking Trail!
3.0 star property
Springvale Farm: Freedom Home With Hiking Trail!
Cozy Winter Getaway on North Pond - Hidden Harlow Lane Retreat
9.6 out of 10, Exceptional, (25)
"The view of the lake is beautiful and the loon was perfect, but we did not have drinkable water and for the price of cleaning and using only the Loon it was overpriced for the stay. "
Cozy Winter Getaway on North Pond - Hidden Harlow Lane Retreat
Cozy cabin with 200’ of waterfront on Whites Pond
9.6 out of 10, Exceptional, (30)
"Had a very pleasant stay. Great fishing and pond is very quiet only saw a couple other canoes had 2 labs with us and they enjoyed the pond too, just be aware that the neighbors are very close, wasn’t an issue for us but if you have dogs that are bothered by strangers it might be "
Cozy cabin with 200’ of waterfront on Whites Pond
Lakefront Getaway with Kayak, Canoe and dock
10.0 out of 10, Exceptional, (3)
"Great weekend. Beautiful spot!"
Lakefront Getaway with Kayak, Canoe and dock
Lakefront cabin on North Pond with private beach & dock
9.4 out of 10, Exceptional, (6)
"The location was very peaceful. The inside of the cottage was great. Thanks for sharing your place with us. "
Lakefront cabin on North Pond with private beach & dock
Lakefront Cabin on beautiful Unity Pond in Burnham, Maine
9.0 out of 10, Wonderful, (6)
"We had a fantastic time at this property! The cottage was cozy and had everything we needed, even coffee. Vince gave us a tour and let us know everything we needed to know when we arrived. The kayaking was amazing. We got so close to bald eagles it was breathtaking, we were simply awed. We saw eagles, osprey, herons and so much wildlife. Vince and Sandy were absolutely wonderful hosts, so friendly, accessible and helpful. They even took us out on the boat one evening for a tour of the lake and...
Lakefront Cabin on beautiful Unity Pond in Burnham, Maine
Lavender Haze Cottage in the Woods
9.2 out of 10, Wonderful, (5)
"Honestly, we were not expecting much based on the VRBO posting, but we were pleasantly surprised. The space was adorable, and much roomier than we expected. Waking up to baby deer at our front door, this place was a great get-away for a night."
Lavender Haze Cottage in the Woods
Timeless Lakefront Cottage with private dock- East Pond Belgrade Lakes Region
10.0 out of 10, Exceptional, (31)
"Great spot right on quiet East Pond. Cottage is perfect and had everything and more than we needed. Owner was easy to communicate with and very pleasant. Highly recommended rental. "
Timeless Lakefront Cottage with private dock- East Pond Belgrade Lakes Region
Family-friendly Troy Getaway With Furnished Deck!
3.0 star property
10.0 out of 10, Exceptional, (1)
"Great property and the owner was very welcoming and accommodating. Would recommend!!"
Family-friendly Troy Getaway With Furnished Deck!
Modern Lakefront Camp on East Pond - cozy fire pit, 3 kayaks, canoe
10.0 out of 10, Exceptional, (2)
"We had a wonderful Tim staying at the little cottage"
Modern Lakefront Camp on East Pond - cozy fire pit, 3 kayaks, canoe
Near Waterville: Cozy Midcoast Vacation Rental!
3.0 star property
Near Waterville: Cozy Midcoast Vacation Rental!
Quaint Oakland Getaway on East Pond Lake!
2.0 star property
9.0 out of 10, Wonderful, (2)
"Lovely little cabin on a lake. No frills just quiet! Bed very comfortable. Hot water in shower. Dishes and accessories all provided. Only additions could be a coffee maker. French press was there but I was looking for a regular drip pot. Some better assortment of games might be nice too. Playing Clue with only 2 people is a little pointless!! 😂😂😂 Country Deli on the corner was great for coffee and sandwiches. Less than a mile up the road. "
Quaint Oakland Getaway on East Pond Lake!
Palmyra Cottage w/ Deck on Whites Pond!
10.0 out of 10, Exceptional, (4)
"Smaller then expected, but overall we enjoyed it. Was a nice quiet place. We were here for a family reunion in newport,so the location was perfect."
Palmyra Cottage w/ Deck on Whites Pond!
Lakefront Maine House ~ 4 Mi to Colby College
3.0 star property
Lakefront Maine House ~ 4 Mi to Colby College
Unique Maine Log Cabin w/ Trout Ponds & Sauna!
3.0 star property
Unique Maine Log Cabin w/ Trout Ponds & Sauna!
NEW LISTING ♥ Lake-House on Water, East Lake, Belgrade Lakes
9.6 out of 10, Exceptional, (10)
"The lake setting was gorgeous and mark was very welcoming."
NEW LISTING ♥ Lake-House on Water, East Lake, Belgrade Lakes
Waterville Home Rental w/ Private Yard + Deck!
3.0 star property
Waterville Home Rental w/ Private Yard + Deck!
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

Other property types in Pittsfield

Cabin in scenic woods with hiking trails, firepit, horseback riding nearby
9.8 out of 10, Exceptional, (117)
"It was an absolutely beautiful cabin hard to get to so the directions should be changed because it takes through the back side in order to get into the location and then you end up having to turn around because you end up in a corn field in the middle of the night and that's a little rugged no TVs in any of the rooms. Other than that our stay was amazing. Very clean everything equipped inside. You just had to get your own food and stuff. Other than that we enjoyed our stay and hope to be back"
Cabin in scenic woods with hiking trails, firepit, horseback riding nearby
10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug
9.8 out of 10, Exceptional, (109)
"Great space and location. Very clean cabin with all the amenities you need. The enclosed back porch facing the lake and the master bedroom with a wall of windows facing the lake were our favorite features!"
10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug
Cozy Winter Getaway on North Pond - Hidden Harlow Lane Retreat
9.6 out of 10, Exceptional, (25)
"The view of the lake is beautiful and the loon was perfect, but we did not have drinkable water and for the price of cleaning and using only the Loon it was overpriced for the stay. "
Cozy Winter Getaway on North Pond - Hidden Harlow Lane 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.

Frequently asked questions

Why book your cottage in Pittsfield with Expedia?
Booking a cottage in Pittsfield is as simple as deciding on your travel dates and choosing an ideal place for outdoor fun and relaxation. From upmarket retreats to low-cost stays and cottages that offer perks like free WiFi, Expedia has something for all styles and tastes. As for epic deals? We’ve got them as well!
How can I find cheap cottages in Pittsfield?
Expedia is here to help you track down cheap cottages in Pittsfield. To book a superb stay in just a few clicks, use the filter tool to tailor your search results by amenities, star rating and budget.
What is there to do in Pittsfield near my cottage?
Once you’ve unpacked your bags and settled in, set out and explore the cool things Pittsfield has for you to experience. JW Parks Golf Course is a top attraction to add to your must-see list.