Vacation rentals in Pittsfield

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Popular amenities for Pittsfield vacation rentals

Other great vacation rentals in Pittsfield

Guest favorite
Guesthouse in Gilmanton
5 out of 5 average rating, 8 reviews

Little red guest house

BenjaminRating, 5 stars3 weeks ago
This place was great for what I needed For the weekend. It is avery quaint, rustic guest house. Thomas is very welcoming and kind and was great at giving specific instructions for arriving in the rain after dark.
Superhost
Apartment in Alton Bay
5 out of 5 average rating, 3 reviews

Upper Views of Alton Bay

ChristopherRating, 5 stars7 months ago
Great location
Guest favorite
Apartment in Alton
4.91 out of 5 average rating, 80 reviews

Downtown, Super Private & Cozy Loft Style Apt.

KlaudiaRating, 5 stars4 months ago
We spent almost a month in this place and felt at home the entire time. The place was very well equipped and we lacked nothing. It was clean and the hosts even took care of snacks and bath products. Contact with Parvaneh was easy and we always got a quick response. We would definitely come back to this place.
Cabin in Dunbarton
5 out of 5 average rating, 4 reviews

Waterfront-2/1- Cozy Cottage -Adventure & Romance

MarinaRating, 5 stars6 days ago
Our stay at the lakefront cottage was fantastic! The place was clean and welcoming. We enjoyed the fully stocked kitchen and the sitting areas. But most of all we loved the outdoors. The lake was perfect for paddle-boarding, and there were wonderful trails nearby in the walking distance. Watching beautiful sunsets over the lake made our trip magical. Nico is a gracious host, responsive, genuine, and welcoming. He went out of his way to make sure the kids and I had everything we needed.
Top guest favorite
Apartment in Henniker
5 out of 5 average rating, 10 reviews

Luxe Henniker Hideaway

EmmaRating, 5 stars3 weeks ago
We had a lovely stay here. It smelled like fresh eucalyptus inside. Mike gifted us homemade banana bread and the most delicious honey fresh from his backyard. The place was spacious, cozy, well decorated with a wide assortment of games. Would stay again in a heartbeat. We walked into Henniker and had a yummy lunch at Daniel’s pub. If trying to get into Manchester via uber, schedule it in advance to ensure you can get a ride.
Superhost
Apartment in Canterbury
4.85 out of 5 average rating, 13 reviews

Harmony lane retreat

BryanRating, 5 stars9 months ago
Very nice, peaceful place. Was a good weekend get away will definitely go back when I get the chance!!
Top guest favorite
Tiny home in Loudon
5 out of 5 average rating, 19 reviews

Cozy Retreat with Private Yard, Grill & Fire Pit

CarlaRating, 5 stars4 weeks ago
My husband and I absolutely loved our stay at this tiny house! It was surprisingly spacious, incredibly comfortable, and had everything we could possibly need. The place is thoughtfully stocked—from plenty of towels and a toothbrush to an air fryer, cooking supplies, coffee, and even games. The outdoor area is private, roomy, and perfect for relaxing, with a great grill and a cozy fire pit. Honestly, one of the cutest and most complete places we've ever stayed. Amber is an awesome host! We didn’t want to leave. Highly recommend!
Top guest favorite
Apartment in Canterbury
4.92 out of 5 average rating, 65 reviews

1000sf Private Suite- 1 Mile off Exit 17, i93

ShauntiRating, 5 stars2 weeks ago
Robbyn helped us get settled in and was very responsive and proactive from the beginning, and was sure we had everything we needed. We had an unexpected scenario arise in which Robbyn accommodated, showing that she is a very diligent and dedicated host!

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