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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 27 Cottages in Pittsfield with updated reviews, rates, and availability.

Springvale Farm: Freedom Home With Hiking Trail!
Property grounds

Springvale Farm: Freedom Home With Hiking Trail!

3.0 star property
Springvale Farm: Freedom Home With Hiking Trail!
Summer Getaway on North Pond - Hidden Harlow Lane Retreat
Loon Lodge

Summer 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. "
Summer Getaway on North Pond - Hidden Harlow Lane Retreat
Lakefront Getaway with Kayak, Canoe and dock
Mainstream Pond in the Fall

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
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Exterior

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
Cozy cabin with 200’ of waterfront on Whites Pond
Exterior

Cozy cabin with 200’ of waterfront on Whites Pond

9.6 out of 10, Exceptional, (35)
"We had a quiet chilly weekend to relax post Thanksgiving and loved it! Hope to get to go back again. "
Cozy cabin with 200’ of waterfront on Whites Pond
10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug
Maine Cottage of a Quilt Maker

10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug

10.0 out of 10, Exceptional, (111)
"We totally loved our stay. We are talking about our next stay. "
10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug
The Cabbage on Olive Street, overlooking Hayden Brook
Exterior

The Cabbage on Olive Street, overlooking Hayden Brook

9.0 out of 10, Wonderful, (11)
"If you, dear reader, and I have anything in common, then you're reading this at 1am after a long work day and you've reached this listing by googling "places to stay in Maine under $100." You're also probably saying to yourself "What a quaint little cabin in the heart of Stephen King country! I wonder if anything Stephen King-related would happen to me if I stayed there?" Dear reader, let me put your fears to rest: book the dang cabin!!! I went here on my first solo vacation and could not have...
The Cabbage on Olive Street, overlooking Hayden Brook
Lakefront Cabin on beautiful Unity Pond in Burnham, Maine
Loon Lodge

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
Palmyra Cottage w/ Deck on Whites Pond!
Palmyra Vacation Rental | 3BR | 1BA | 928 Sq Ft | 1 Step Required

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!
Timeless Lakefront Cottage with private dock- East Pond Belgrade Lakes Region

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
Lavender Haze Cottage in the Woods
Property grounds

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
Lakefront cabin on North Pond with private beach & 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
Family-friendly Troy Getaway With Furnished Deck!
Living area

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!
Lakefront Maine House ~ 4 Mi to Colby College
Living area

Lakefront Maine House ~ 4 Mi to Colby College

3.0 star property
Lakefront Maine House ~ 4 Mi to Colby College
Near Waterville: Cozy Midcoast Vacation Rental!
Living area

Near Waterville: Cozy Midcoast Vacation Rental!

3.0 star property
Near Waterville: Cozy Midcoast Vacation Rental!
Modern Lakefront Camp on East Pond - cozy fire pit, 3 kayaks, canoe
View from the parking area.

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
Quaint Oakland Getaway on East Pond Lake!
Living area

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!
Charming 3-bedroom cottage in peaceful Solon with WiFi
Exterior

Charming 3-bedroom cottage in peaceful Solon with WiFi

10.0 out of 10, Exceptional, (1)
"Beautiful area a little off the beaten path. Great for outdoor activities"
Charming 3-bedroom cottage in peaceful Solon with WiFi
Seasonal - Waterfront Cottage - Beautiful panoramic view
Interior

Seasonal - Waterfront Cottage - Beautiful panoramic view

Seasonal - Waterfront Cottage - Beautiful panoramic view
Unique Maine Log Cabin w/ Trout Ponds & Sauna!
Interior

Unique Maine Log Cabin w/ Trout Ponds & Sauna!

3.0 star property
Unique Maine Log Cabin w/ Trout Ponds & Sauna!
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

Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment

10.0 out of 10, Exceptional, (8)
"Very nice "
The price is AED 516
AED 1,135 total
includes taxes & fees
25 Feb - 26 Feb
Angel Mist Retreat Garage Apartment
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
Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding

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

9.8 out of 10, Exceptional, (151)
"We used two side chairs and an end table to have all our meals by the fire! Very relaxing reading in the big chair with a hassock.Beautiful sloping field in front, pristine snow. We had an equipment failure with cross country skis, but moved on to snowshoes for a lovely walk. Did one trail in boots alone, but wished we had gone back out with the snowshoes. Interesting ridge walk. We'd definitely go back at other seasons as well, but it was just what we wanted for February!snowshoes. "
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.

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