Search Pittsfield Cottages

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Next weekend
Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23
In one month
Dec 5 - Dec 7
In two months
Jan 2 - Jan 4

Cottages in Pittsfield

Exterior
Rustic Rose Cottage of Historic West Lebanon
Rustic Rose Cottage of Historic West Lebanon
10.0 out of 10, Exceptional, (23)
"Overall, we were very pleased, we will look into the availability of this listing on our next visit.It could use a room darkening shade next to the bed, the morning sun is quite bright and a non-skid shower mat."
United States
Richard H.
$231 nightly
The price is $252
Nov 12 - Nov 13
Total with taxes and fees
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
9.6 out of 10, Exceptional, (11)
"Excellent stay"
United States
Kara
$171 nightly
The price is $185
Nov 9 - Nov 10
Total with taxes and fees
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
Terrace/patio
Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath
Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath
10.0 out of 10, Exceptional, (4)
"Great location & comfortable! "
United States
Jeanine L.
$171 nightly
The price is $185
Nov 9 - Nov 10
Total with taxes and fees
Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath
Exterior
Cozy Cottage on a Lake, near Gunstock Mountain
Cozy Cottage on a Lake, near Gunstock Mountain
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 "
United States
kim M.
$365 nightly
The price is $396
Nov 17 - Nov 18
Total with taxes and fees
Cozy Cottage on a Lake, near Gunstock Mountain
Exterior
Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath
Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath
10.0 out of 10, Exceptional, (4)
"It was very cute and clean, loved the outside area and would def be back again."
United States
Anais & Zach
$193 nightly
The price is $209
Nov 9 - Nov 10
Total with taxes and fees
Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath
Terrace/patio
Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
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."
United States
Jessica G.
$248 nightly
The price is $270
Nov 7 - Nov 8
Total with taxes and fees
Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
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
10.0 out of 10, Exceptional, (4)
"Beautiful and clean"
United States
Dianne K.
$274 nightly
The price is $297
Nov 9 - Nov 10
Total with taxes and fees
Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 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
10.0 out of 10, Exceptional, (16)
"Very nice spot nice get away would stay there again"
United States
Alan T.
$250 nightly
The price is $271
Nov 7 - Nov 8
Total with taxes and fees
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Terrace/patio
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
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."
United States
Sean P.
$186 nightly
The price is $201
Nov 9 - Nov 10
Total with taxes and fees
Cottage 11 - Year Round - Pet Friendly - 1 Bed / 1 Bath w/ Private Courtyard
Exterior
Cottage 1-2 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit
Cottage 1-2 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit
10.0 out of 10, Exceptional, (2)
"In addition to everything this property offers we found there was a nearby 12mile bike trail that goes through the woods passing lakes on the the route, and bikes were available at the property."
United States
Justin
$287 nightly
The price is $311
Nov 9 - Nov 10
Total with taxes and fees
Cottage 1-2 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit
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
9.4 out of 10, Exceptional, (3)
"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.
$266 nightly
The price is $289
Nov 9 - Nov 10
Total with taxes and fees
Cottage 5-6 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"Very cozy! It had everything we needed. The staff was very attentive. "
Cruz 1-night trip
Posted 1 day ago
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
57
Accommodation
158 Cottages
Lowest Price
$185
Highest Price
$396

Frequently asked questions

Why book your cottage in Pittsfield with Expedia?
Reserving a cottage in Pittsfield is as easy as working out your travel dates and selecting your ideal place for a getaway in nature. From upmarket retreats to affordable properties and cottages that feature amenities like laundry facilities, Expedia has something for all tastes. As for awesome deals? We've got your back!
How can I find cheap cottages in Pittsfield?
Expedia can help you track down cheap cottages in Pittsfield. To discover a superb stay in just a few keystrokes, use our convenient filter tool to tailor your search results by star rating, budget and amenities.

Explore a world of travel with Expedia