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Our top choices for Pittsfield cottages
$347 nightly
The price is $374
Dec 30 - Dec 31
Total with taxes and fees
Rustic Rose Cottage of Historic West Lebanon
Rustic Rose Cottage of Historic West LebanonLebanon
10.0 out of 10, Exceptional, (24)
"Everything about our stay was lovely! Check-in was smooth, the property was gorgeous, and the cottage was full of charm. "
Daniel S.
$231 nightly
The price is $252
Dec 23 - Dec 24
Total with taxes and fees
Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
Cottage 10 - 1 Bedroom w/ Loft / 1 BathWolfeboro
10.0 out of 10, Exceptional, (4)
"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."
Jessica G.
$171 nightly
The price is $185
Dec 23 - Dec 24
Total with taxes and fees
Cozy Cottage on a Lake, near Gunstock Mountain
Cozy Cottage on a Lake, near Gunstock MountainGilmanton
9.0 out of 10, Wonderful, (2)
"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 "
kim M.
$354 nightly
The price is $384
Jan 7 - Jan 8, 2026
Total with taxes and fees
Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath
Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 BathWolfeboro
10.0 out of 10, Exceptional, (4)
"Great location & comfortable! "
Jeanine L.
$173 nightly
The price is $188
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & CourtyardWolfeboro
10.0 out of 10, Exceptional, (17)
"Very nice spot nice get away would stay there again"
Alan T.
$185 nightly
The price is $200
Dec 23 - Dec 24
Total with taxes and fees
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 CourtyardWolfeboro
10.0 out of 10, Exceptional, (5)
"Booked a last minute trip with the family and it was perfect. Right near downtown and a cozy place to rest with the kids."
Sean P.
$171 nightly
The price is $185
Dec 23 - Dec 24
Total with taxes and fees
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 BathWolfeboro
10.0 out of 10, Exceptional, (4)
"Everything was great!"
Leah F.
$283 nightly
The price is $307
Dec 23 - Dec 24
Total with taxes and fees
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
Best Western Plus Landmark Inn
10/10 Excellent
Find out more about Pittsfield
Pittsfield Cottages information
Number of reviews | 47 |
|---|---|
Accommodation | 150 Cottages |
Lowest Price | $185 |
Highest Price | $384 |
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