A calm lake reflecting colorful autumn trees and misty mountains in the distance.

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Pittsfield cottages

A spacious kitchen with a large island, white cabinetry, and a view of a playground through large windows.

1. Newly Renovated Cottage 3 on Main Street Alton Bay!

Newly Renovated Cottage 3 on Main Street Alton Bay!
Alton
9.6 out of 10, Exceptional, (8 reviews)
"Staff was very freindly"
United States
David
The price is €237
includes taxes & fees
1 Nov - 2 Nov
Newly Renovated Cottage 3 on Main Street Alton Bay!
A white cabin with a green roof, surrounded by dense green trees.

2. Cozy Cottage on a Lake, near Gunstock Mountain

Cozy Cottage on a Lake, near Gunstock Mountain
Gilmanton
9.0 out of 10, Wonderful, (8 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.
The price is €357
includes taxes & fees
25 Oct - 26 Oct
Cozy Cottage on a Lake, near Gunstock Mountain
A lakeside seating area with Adirondack chairs, a stone fire pit, and an American flag.

3. 7 Mi to Hiking: Waterfront Long Pond Gem!

7 Mi to Hiking: Waterfront Long Pond Gem!
3.0 star property
Barrington
10.0 out of 10, Exceptional, (1 review)
"Well designed and maintained property. We enjoyed the little touches like the automatic nightlights and heater in bathroom. Wish we could have spent more time here but we attended the Deerfield fair. Highly recommended. "
United States
Ronald
The price is €506
includes taxes & fees
24 Oct - 25 Oct
7 Mi to Hiking: Waterfront Long Pond Gem!
A pool area with a vending machine, a poolside view, and a sign indicating 'POOL AREA'.

4. Newly Renovated Cottage 8 Main Street Alton Bay!

Newly Renovated Cottage 8 Main Street Alton Bay!
Alton
7.4 out of 10, Good, (6 reviews)
"My bed was broken to the point where I was sleeping at an angle & The couch bed was nasty it had stains and dirt all over it , The bunk beds were like taking a trip to bar heaven it was truly a painful stay"
United States
Eric
The price is €342
includes taxes & fees
29 Oct - 30 Oct
Newly Renovated Cottage 8 Main Street Alton Bay!
A cabin surrounded by dense forest, a pond with green algae, and a clear sky.

5. Serene Pondside Retreat Surrounded by Nature

Serene Pondside Retreat Surrounded by Nature
Deerfield
10.0 out of 10, Exceptional, (1 review)
"Wonderful property - we stayed here to visit our nearby family and attend opening day of the Deerfield fair. The property is immaculately maintained and the host responsive. We’ll be back!"
United States
Bobbi S.
Serene Pondside Retreat Surrounded by Nature
A red wooden building with a balcony and a staircase leading to a deck.

6. Rustic Rose Cottage of Historic West Lebanon

Rustic Rose Cottage of Historic West Lebanon
Lebanon
9.8 out of 10, Exceptional, (31 reviews)
"Everything was great. Very clean and comfortable! Thank you for a great place to stay. "
United States
Heather K.
The price is €215
includes taxes & fees
8 Nov - 9 Nov
Rustic Rose Cottage of Historic West Lebanon
A storefront with a blue awning and American flags, named "Paper Store Blacks Gift Shop."

7. Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard

Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard
Wolfeboro
9.8 out of 10, Exceptional, (22 reviews)
"This is a great place to stay with a dog"
United States
David M.
The price is €171
includes taxes & fees
25 Oct - 26 Oct
Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard
A garden with a white pergola, red chairs, and pink flowers.

8. Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard

Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
Wolfeboro
9.6 out of 10, Exceptional, (14 reviews)
"Great place "
United States
Anonymous traveller
The price is €161
includes taxes & fees
25 Oct - 26 Oct
Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
Outdoor dining

9. Cozy, Pet-Friendly Escape Near Lake & Mountains

Cozy, Pet-Friendly Escape Near Lake & Mountains
Gilford
10.0 out of 10, Exceptional, (49 reviews)
"Cute and comfortable. The host communicated well and had all the essentials available. We enjoyed our stay."
United States
Julie W.
The price is €424
includes taxes & fees
26 Oct - 27 Oct
Cozy, Pet-Friendly Escape Near Lake & Mountains
A two-story house with a white picket fence, a gravel driveway, and autumn foliage in the background.

10. Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath

Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (6 reviews)
"It was very cute and clean, loved the outside area and would def be back again."
United States
Anais & Zach
The price is €161
includes taxes & fees
22 Nov - 23 Nov
Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath
A golf course with a pond, surrounded by trees with autumn foliage.

11. Cottage 11 - Year Round - Pet Friendly $50 Fee- 1 Bed / 1 Bath w/ Courtyard

Cottage 11 - Year Round - Pet Friendly $50 Fee- 1 Bed / 1 Bath w/ Courtyard
Wolfeboro
9.8 out of 10, Exceptional, (9 reviews)
"Had a great time at the cottages at Wolfeboro. Nice and relaxing stay for 2 nights"
United States
Connie S.
The price is €173
includes taxes & fees
25 Oct - 26 Oct
Cottage 11 - Year Round - Pet Friendly $50 Fee- 1 Bed / 1 Bath w/ Courtyard
A house with a porch, surrounded by a garden with pink and yellow flowers.

12. Cottage 7 - Year Round - Pet Friendly $50 Fee - Stand Alone 1 Bedroom / 1 Bath

Cottage 7 - Year Round - Pet Friendly $50 Fee - Stand Alone 1 Bedroom / 1 Bath
Wolfeboro
9.0 out of 10, Wonderful, (8 reviews)
"Great location & comfortable! "
United States
Jeanine L.
The price is €159
includes taxes & fees
25 Oct - 26 Oct
Cottage 7 - Year Round - Pet Friendly $50 Fee - Stand Alone 1 Bedroom / 1 Bath
A waterfront area with a large white building, a dock with boats, and a clock tower in the background.

13. Cottage 10-Pet Friendly-1 Bedroom w/ Loft / 1 Bath

Cottage 10-Pet Friendly-1 Bedroom w/ Loft / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (5 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 €181
includes taxes & fees
26 Oct - 27 Oct
Cottage 10-Pet Friendly-1 Bedroom w/ Loft / 1 Bath
A garden with a white pergola, red chairs, and pink flowers.

14. Cottage 8-9 - Year Round - Pet Friendly $50 Fee- Stand Alone 2 Bedroom / 2 Bath

Cottage 8-9 - Year Round - Pet Friendly $50 Fee- 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 €248
includes taxes & fees
25 Oct - 26 Oct
Cottage 8-9 - Year Round - Pet Friendly $50 Fee- Stand Alone 2 Bedroom / 2 Bath
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

Hampton Inn by Hilton Concord/Bow

Hampton Inn by Hilton Concord/Bow

10/10 Excellent
"Great location. Close to interstates. Very nice inside. They had a freezer with Ben&Jerry ice cream!!! Would come back here anytime."
Jeff 1-night trip
Posted 13 hours ago
Hampton Inn by Hilton Concord/Bow

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
168
Accommodation
164 Cottages
Lowest Price
€159
Highest Price
€506

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