Search Pittsfield Cottage Rentals from CA $240

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Pittsfield cottages

Exterior

Cottage in Lebanon

Rustic Rose Cottage of Historic West Lebanon
10.0 out of 10, Exceptional, (25 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 CA $134
CA $308 total
includes taxes & fees
Mar 12 - Mar 13
Rustic Rose Cottage of Historic West Lebanon
House (1 Bedroom) | Interior

Cottage in Alton

Hiking & Snowmobile Trails On-site: Alton Retreat!
3.0 star property
The price is CA $159
CA $345 total
includes taxes & fees
Mar 15 - Mar 16
Hiking & Snowmobile Trails On-site: Alton Retreat!
Terrace/patio

Cottage in Wolfeboro

Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
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 CA $200
CA $246 total
includes taxes & fees
Mar 12 - Mar 13
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
Marina

Cottage in Wolfeboro

Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
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 CA $203
CA $250 total
includes taxes & fees
Mar 12 - Mar 13
Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
Property grounds

Cottage in Wolfeboro

Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath
10.0 out of 10, Exceptional, (4 reviews)
"Great location & comfortable! "
United States
Jeanine L.
The price is CA $194
CA $240 total
includes taxes & fees
Mar 16 - Mar 17
Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath
Exterior

Cottage in Wolfeboro

Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath
10.0 out of 10, Exceptional, (5 reviews)
"It was very cute and clean, loved the outside area and would def be back again."
United States
Anais & Zach
The price is CA $194
CA $240 total
includes taxes & fees
Mar 16 - Mar 17
Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath
Exterior

Cottage in Wolfeboro

Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
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 CA $212
CA $261 total
includes taxes & fees
Mar 19 - Mar 20
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Golf

Cottage in Wolfeboro

Cottage 11 - Year Round - Pet Friendly - 1 Bed / 1 Bath w/ Private Courtyard
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 CA $221
CA $272 total
includes taxes & fees
Mar 24 - Mar 25
Cottage 11 - Year Round - Pet Friendly - 1 Bed / 1 Bath w/ Private Courtyard
Terrace/patio

Cottage in Wolfeboro

Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath
10.0 out of 10, Exceptional, (4 reviews)
"Everything was great!"
United States
Leah F.
The price is CA $351
CA $431 total
includes taxes & fees
Mar 16 - Mar 17
Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath
Exterior

Cottage in Gilmanton

Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
9.6 out of 10, Exceptional, (34 reviews)
"Nice quiet visit. Lovely to be so close to the lake!"
United States
Phyllis S.
The price is CA $207
CA $467 total
includes taxes & fees
Mar 12 - Mar 13
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
Exterior

Cottage in Gilmanton

Cozy Cottage on a Lake, near Gunstock Mountain
9.4 out of 10, Exceptional, (3 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 CA $232
CA $535 total
includes taxes & fees
Mar 16 - Mar 17
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.
View all properties

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now
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

Best Western Concord Inn & Suites

Best Western Concord Inn & Suites

2/10 Terrible
"hotel definitely is a little out of date. there was an odd smell in the room, our curtains were also covered in stairs and there was a small spot of mold forming above our shower. however the staff working the front desk was amazing! from the moment we walked in they were helping and very welcoming. "
alex 1-night trip
Posted 8 hours ago
Best Western Concord Inn & Suites

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
109
Accommodation
150 Cottages
Lowest Price
CA $240
Highest Price
CA $535

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