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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for Pittsfield cottages

Exterior

Rustic Rose Cottage of Historic West Lebanon

Rustic Rose Cottage of Historic West Lebanon
Lebanon
10.0 out of 10, Exceptional, (24 reviews)
"Everything about our stay was lovely! Check-in was smooth, the property was gorgeous, and the cottage was full of charm. "
United States
Daniel S.
The price is €217
includes taxes & fees
21 Feb - 22 Feb
Rustic Rose Cottage of Historic West Lebanon
Terrace/patio

Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard

Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
Wolfeboro
9.6 out of 10, Exceptional, (11 reviews)
"Great property. Loved our stay and the owners were great! Definitely will book again "
United States
Marcus
The price is €159
includes taxes & fees
19 Feb - 20 Feb
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
Property grounds

Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath

Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (4 reviews)
"Great location & comfortable! "
United States
Jeanine L.
The price is €159
includes taxes & fees
19 Feb - 20 Feb
Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath
Marina

Cottage 10 - 1 Bedroom w/ Loft / 1 Bath

Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (4 reviews)
"We had a perfect stay. Super cute cabin, clean and very comfortable.We thoroughly enjoyed or time there. Very easy process and would absolutely recommend and book again."
United States
Jessica G.
The price is €171
includes taxes & fees
3 Mar - 4 Mar
Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
Exterior

Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard

Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Wolfeboro
10.0 out of 10, Exceptional, (17 reviews)
"This is a great place to stay with a dog"
United States
David M.
The price is €171
includes taxes & fees
17 Mar - 18 Mar
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Golf

Cottage 11 - Year Round - Pet Friendly - 1 Bed / 1 Bath w/ Private Courtyard

Cottage 11 - Year Round - Pet Friendly - 1 Bed / 1 Bath w/ Private Courtyard
Wolfeboro
9.8 out of 10, Exceptional, (6 reviews)
"These cottages are very well maintained and very clean. The little compound was beautifully decorated and easy to navigate. This is a great place for families and groups traveling together."
United States
David M.
The price is €171
includes taxes & fees
22 Feb - 23 Feb
Cottage 11 - Year Round - Pet Friendly - 1 Bed / 1 Bath w/ Private Courtyard
Exterior

Cottage 5-6 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit

Cottage 5-6 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit
Wolfeboro
9.4 out of 10, Exceptional, (3 reviews)
"The two connected Cottages were Perfect for myself husband & teenage daughter. Loved the private outdoor space & firepit! Onsite manager was super accessible and really helpful! Will definitely be back!!"
United States
Dorenda W.
The price is €317
includes taxes & fees
19 Feb - 20 Feb
Cottage 5-6 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit
Terrace/patio

Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath

Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath
Wolfeboro
10.0 out of 10, Exceptional, (4 reviews)
"Everything was great!"
United States
Leah F.
The price is €299
includes taxes & fees
3 Mar - 4 Mar
Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath
Exterior

Cozy Cottage on a Lake, near Gunstock Mountain

Cozy Cottage on a Lake, near Gunstock Mountain
Gilmanton
9.0 out of 10, Wonderful, (2 reviews)
"We had a great time. Loved the cabin super cute. Neighborhood & neighbors very nice. The lake & private beaches were great. We enjoyed the hot tub & fire pit. I brought a few games, but you had a nice selection as well. Kitchen was very nice with everything we needed for some nice big breakfasts to start our day. We did run into a bit of a problem with the water running out. During showers, but we worked through it. Over all it was a great place. Thank you. Kim, Steve,Brianna,Cam & Brody "
United States
kim M.
The price is €332
includes taxes & fees
2 Mar - 3 Mar
Cozy Cottage on a Lake, near Gunstock Mountain
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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Top Pittsfield Hotel Reviews

The Centennial

The Centennial

10/10 Excellent
"The breakfast was very bad, only cold items and staled bread. "
Daniel 3-night trip
Posted 2 days ago
The Centennial

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
71
Accommodation
150 Cottages
Lowest Price
€159
Highest Price
€332

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