
Holiday houses in Pittsfield
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Top-rated holiday rentals in Pittsfield
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Other great holiday rentals in Pittsfield
Guest favourite

Cabin in Knox
4.88 out of 5 average rating, 97 reviewsBlue Life Farm
JadeRating, 5 stars3 weeks ago
We had an amazing stay! Ben was very responsive and helpful when it came to instructions on navigations and recommendations on places in the area! Would definitely stay here again and would highly recommend it to others! :)
Top Guest favourite

Treehouse in Newport
4.95 out of 5 average rating, 65 reviewsNewport, Maine Lakeside Treehouse Near ATV Trail
NickRating, 5 stars9 months ago
My son and I truly enjoyed every moment we spent at the Treehouse. Whether it was using the kayaks in the cove, or enjoying the amazing views while sitting around the firepit (also enjoyed cooking hotdogs and s'mores on it), we felt right at home. The Treehouse is nicely furnished with amazing pieces that just add to the authentic feel of being in a treehouse. If only mine as a kid had all these features. I enjoyed listening to the loons out on the lake in the evenings and the ospreys fishing during the days. Definitely an experience that should not be passed up. Thank you to both Paul and Maureen for allowing us to share your little spot of heaven on earth.
Superhost

Cabin in Brooks
5 out of 5 average rating, 5 reviewsCozy Lakefront Cabin * CampChamp
BenRating, 5 stars4 days ago
Overall, we had a very peaceful and smooth stay at this beautiful cabin! We found it with no troubles, hosts were very responsive, and the boats and board games were nice touches. We had a few minor issues (coffee container was empty and firewood costs were a bit steep), but we’d recommend the cabin and would love to come back.
Top Guest favourite

Cabin in Madison
5 out of 5 average rating, 11 reviewsGrace Landing
KatieRating, 5 stars1 month ago
We loved our stay here! It is so quiet and peaceful. The house was comfortable and we loved that we could bring out dogs. Thank you so much, hope to be back!
Top Guest favourite

Cabin in Harmony
4.97 out of 5 average rating, 32 reviewsThe Great Escape!
KalebRating, 5 stars3 days ago
We had a last second event we had to go to and it was a perfect place just for the night. Super beautiful and super clean.
Top Guest favourite

Apartment in Unity
4.97 out of 5 average rating, 78 reviewsThe Heron's Nest Cozy apartment in the woods.
KristinRating, 5 stars1 week ago
Robin was very communicative and thoughtful during our stay. The place was exactly as described in the listing and was immaculate upon our arrival. The space was decorated tastefully and had everything we needed to be comfortable. Great location to be near the fair in the fall! Would recommend this location and host.
Guest favourite

Guest suite in Pittsfield
4.96 out of 5 average rating, 23 reviewsAngel Mist Retreat Garage Apartment
JenniferRating, 5 stars3 months ago
Angel was a kind, helpful host. Her property was beautiful…pics did not do it justice. We were accommodated last minute, and I was pleasantly surprised at how comfortable an apartment above a garage ended up being for us. It was well stocked, spotless, decorated beautifully, and so well thought out with lots of nice small touches everywhere (like plug ins for chargers by the beds). The view was pretty in the winter, and I imagine it would be way more so in the warmer months. Thank you for a great stay!
Top Guest favourite

Cabin in Bingham
4.91 out of 5 average rating, 22 reviewsWarden Camp on Kingsbury Pond, Couples retreat/ATV
AlexandraRating, 5 stars3 weeks ago
Lovely hosts with a lovelier cabin! Definitely a great getaway for those looking for a quiet spot. Would absolutely come again.
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- Samoset Resort
- Belgrade Lakes Golf Club
- Dragonfly Farm & Winery
- Hermon Mountain Ski Area
- Eaton Mountain Ski Resort
- Pinnacle Park
- Spragues Beach
- Rockland Breakwater Light
- Lighthouse Beach
- Pebble Beach
- Bear Island Beach
- Three Island Beach
- Redman Beach
- Orchard Beach
- Driftwood Beach
- North Point Beach
- Farnsworth Art Museum
- Sandy Point Beach
- Wadsworth Cove Beach
- Islesboro Town Beach
- Titcomb Mountain
- The Camden Snow Bowl
- Billys Shore