Search Pittsfield Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

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, (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.
$210 nightly
The price is $229
Apr 30 - May 1
Total with taxes and fees
Rustic Rose Cottage of Historic West Lebanon
Outdoor dining

Lakefront Salmon Cottage

Lakefront Salmon Cottage
Northwood
9.8 out of 10, Exceptional, (11 reviews)
"Awesome place for quite getaway."
United States
Jason L.
$156 nightly
The price is $169
Apr 30 - May 1
Total with taxes and fees
Lakefront Salmon Cottage
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)
"Excellent stay"
United States
Kara
$170 nightly
The price is $185
Apr 30 - May 1
Total with taxes and fees
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
Exterior

Newly Renovated Cottage on Main Street Alton Bay #5

Newly Renovated Cottage on Main Street Alton Bay #5
Alton
10.0 out of 10, Exceptional, (1 review)
"Great places. Quiet and quaint and close to the lake and restaurants. Will rent again "
United States
Brian B.
$211 nightly
The price is $230
Apr 30 - May 1
Total with taxes and fees
Newly Renovated Cottage on Main Street Alton Bay #5
Exterior

Lakefront Orange Cottage

Lakefront Orange Cottage
Northwood
8.8 out of 10, Excellent, (10 reviews)
"Location was nice right in front of the lake and we took advantage of the kayaks. Shower was very small and cottage a bit rustic but for the location and price was great. "
United States
Danna P.
$153 nightly
The price is $167
May 17 - May 18
Total with taxes and fees
Lakefront Orange Cottage
Dining

Lakefront Yellow Cottage

Lakefront Yellow Cottage
Northwood
10.0 out of 10, Exceptional, (5 reviews)
"Clean, friendly, a great place to stay. I kayaked in the lake and it was beautiful. Hope to stay again next summer!"
United States
Ravaioli N.
$156 nightly
The price is $169
Apr 30 - May 1
Total with taxes and fees
Lakefront Yellow Cottage
Exterior

Lakefront Purple Cottage

Lakefront Purple Cottage
Northwood
9.2 out of 10, Wonderful, (7 reviews)
"Quaint colorful just right ."
United States
Susan B.
$185 nightly
The price is $200
Apr 30 - May 1
Total with taxes and fees
Lakefront Purple Cottage
Outdoor dining

Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
Alton
8.6 out of 10, Excellent, (18 reviews)
"Nice location on the lake."
United States
Mary L.
$291 nightly
The price is $316
May 1 - May 2
Total with taxes and fees
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
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.
$172 nightly
The price is $186
Apr 30 - May 1
Total with taxes and fees
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Exterior

Newly Renovated Cottage 4 in Alton Bay, NH

Newly Renovated Cottage 4 in Alton Bay, NH
Alton
9.0 out of 10, Wonderful, (4 reviews)
"Communication was amazing, check in was a delightful, the house itself was perfect "
United States
Jennifer S.
$335 nightly
The price is $365
May 19 - May 20
Total with taxes and fees
Newly Renovated Cottage 4 in Alton Bay, NH
Dining

Lakefront Pink Cottage

Lakefront Pink Cottage
Northwood
10.0 out of 10, Exceptional, (1 review)
"Cozy cottage on the lake, beautiful view of the sunrise from bed! Plus kayak and paddle boats to use on the lake!"
United States
Caitlin H.
$185 nightly
The price is $200
Apr 30 - May 1
Total with taxes and fees
Lakefront Pink Cottage
Exterior

Cozy Cottage on a Lake, near Gunstock Mountain

Cozy Cottage on a Lake, near Gunstock Mountain
Gilmanton
9.6 out of 10, Exceptional, (4 reviews)
"We had a wonderful time during our stay. The cottage was in a great location, exactly as advertised, and spotlessly clean. The hot tub was great. Can’t think of a single thing we’d change. Would love to come back again during the summer months."
United States
Dawn P.
$362 nightly
The price is $393
May 3 - May 4
Total with taxes and fees
Cozy Cottage on a Lake, near Gunstock Mountain
Exterior

Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!

Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
Alton
10.0 out of 10, Exceptional, (1 review)
"This is a classic old-style cabin that reminded us of our childhood family trips in the 60’s. It’s not new, but a heck of a lot of fun if you’re in the right head space. Easily walked to town for dinner and to the shore. Clean and had everything we needed."
United States
Christine F.
$212 nightly
The price is $231
May 8 - May 9
Total with taxes and fees
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
Exterior

Newly Renovated Cottage 7 in Alton Bay

Newly Renovated Cottage 7 in Alton Bay
Alton
10.0 out of 10, Exceptional, (1 review)
"endroit magnifique,emplacement agréable avec commodité sur place et près du lac et restaurant."
Canada
Alexandra R.
$220 nightly
The price is $240
May 14 - May 15
Total with taxes and fees
Newly Renovated Cottage 7 in Alton Bay
Terrace/patio

Newly Renovated Cottage 6

Newly Renovated Cottage 6
Alton
10.0 out of 10, Exceptional, (3 reviews)
"Great location, and amenities, including the game room, pool and bikes. Hosts were very responsive and accomodating. "
United States
Vanessa
$207 nightly
The price is $226
May 10 - May 11
Total with taxes and fees
Newly Renovated Cottage 6
Outdoor dining

Newly Renovated Cottage 8 Main Street Alton Bay!

Newly Renovated Cottage 8 Main Street Alton Bay!
Alton
7.0 out of 10, Good, (2 reviews)
" Both bedroom doors don’t close properly, which affects privacy. There’s also no mirror in the bathroom and nowhere to hang clothes, either in the bathroom or closet. The space is really best suited for two adults — our third guest had trouble sleeping comfortably. Overall, we felt the value didn’t quite match the price and description."
United States
Pedram S.
$239 nightly
The price is $260
Apr 30 - May 1
Total with taxes and fees
Newly Renovated Cottage 8 Main Street Alton Bay!
Exterior

Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath

Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath
Wolfeboro
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
$165 nightly
The price is $179
Apr 30 - May 1
Total with taxes and fees
Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath
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
Wolfeboro
10.0 out of 10, Exceptional, (2 reviews)
"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
$260 nightly
The price is $282
May 4 - May 5
Total with taxes and fees
Cottage 1-2 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit
Exterior

Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit

Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
Gilmanton
9.6 out of 10, Exceptional, (35 reviews)
"Nice quiet visit. Lovely to be so close to the lake!"
United States
Phyllis S.
$599 nightly
The price is $650
May 30 - May 31
Total with taxes and fees
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
Exterior

Newly Renovated Cottage 3 on Main Street Alton Bay!

Newly Renovated Cottage 3 on Main Street Alton Bay!
Alton
10.0 out of 10, Exceptional, (1 review)
"Great little spot right next to the bay. Team was super responsive prior, during and after check in. Would highly recommend. "
United States
Andy S.
$211 nightly
The price is $230
Apr 30 - May 1
Total with taxes and fees
Newly Renovated Cottage 3 on Main Street Alton Bay!
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

Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

10/10 Excellent
"Warm room in pool area"
Susan 1-night trip
Posted 3 hours ago
Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
136
Accommodation
154 Cottages
Lowest Price
$167
Highest Price
$650

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