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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Pittsfield cottages

A rustic wooden cabin with a red roof, a covered picnic table, and a small shed.

1. Hiking & Snowmobile Trails On-site: Alton Retreat!

Hiking & Snowmobile Trails On-site: Alton Retreat!
3.0 star property
Alton
The price is £227
includes taxes & fees
18 Oct - 19 Oct
Hiking & Snowmobile Trails On-site: Alton Retreat!
A spacious kitchen with a large island, white cabinetry, and a view of a playground through large windows.

2. 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, (7 reviews)
"Staff was very freindly"
United States
David
The price is £188
includes taxes & fees
26 Oct - 27 Oct
Newly Renovated Cottage 3 on Main Street Alton Bay!
A small cabin with a porch, a bench, and a staircase leading to the entrance.

3. 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.
The price is £271
includes taxes & fees
26 Oct - 27 Oct
Newly Renovated Cottage 4 in Alton Bay, NH
A white cabin with a green roof, surrounded by dense green trees.

4. 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 £296
includes taxes & fees
14 Oct - 15 Oct
Cozy Cottage on a Lake, near Gunstock Mountain
A small, single-story cabin with a porch, outdoor seating, and a hot tub.

5. 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
9.8 out of 10, Exceptional, (45 reviews)
"Lovely stay in a quiet area. The hot tub was great to unwind in after hiking in the area!"
United States
Cristofer V.
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
An aerial view of a residential area with a swimming pool, multiple houses, and a road.

6. 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.
The price is £179
includes taxes & fees
15 Oct - 16 Oct
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
An aerial view of a residential area with a swimming pool, multiple houses, and a road.

7. Charming Alton Bay Getaway – 1BR Cottage, Pool Access & Walk to Lake

Charming Alton Bay Getaway – 1BR Cottage, Pool Access & Walk to Lake
Alton
9.0 out of 10, Wonderful, (2 reviews)
The price is £190
includes taxes & fees
15 Oct - 16 Oct
Charming Alton Bay Getaway – 1BR Cottage, Pool Access & Walk to Lake
A residential property with a wooden deck, a small garden, and a blue house with a chimney.

8. Newly Renovated Cottage on Main Street Alton Bay #5

Newly Renovated Cottage on Main Street Alton Bay #5
Alton
8.4 out of 10, Very good, (6 reviews)
"Great places. Quiet and quaint and close to the lake and restaurants. Will rent again "
United States
Brian B.
The price is £202
includes taxes & fees
14 Oct - 15 Oct
Newly Renovated Cottage on Main Street Alton Bay #5
A small cabin with a porch, outdoor seating, and a bird sculpture on the roof.

9. Newly Renovated Cottage 6

Newly Renovated Cottage 6
Alton
8.0 out of 10, Very good, (5 reviews)
"Great location, and amenities, including the game room, pool and bikes. Hosts were very responsive and accomodating. "
United States
Vanessa
The price is £239
includes taxes & fees
29 Oct - 30 Oct
Newly Renovated Cottage 6
A beach resort sign with a weekly/monthly season rentals notice.

10. Cabin 45 at Historic Sandy Point Resort W/ Boat Slip and Onsite Boat Ramp

Cabin 45 at Historic Sandy Point Resort W/ Boat Slip and Onsite Boat Ramp
Alton
Cabin 45 at Historic Sandy Point Resort W/ Boat Slip and Onsite Boat Ramp
A lakeside seating area with Adirondack chairs, a stone fire pit, and an American flag.

11. 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 £429
includes taxes & fees
14 Oct - 15 Oct
7 Mi to Hiking: Waterfront Long Pond Gem!
A small cabin with a deck, a front door, and a window.

12. 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 £309
includes taxes & fees
20 Oct - 21 Oct
Newly Renovated Cottage 8 Main Street Alton Bay!
A two-story cabin with a wooden deck and a staircase leading to the upper level.

13. Newly Renovated Cottage 7 in Alton Bay

Newly Renovated Cottage 7 in Alton Bay
Alton
10.0 out of 10, Exceptional, (2 reviews)
"Host was responsive and the property was just close enough to enjoy laconia without a huge price premium. Its a simple cabin, but it did what we needed it to do. Gravel parking lot is not the best for motorcycles if i had to leave constructive feedback. Would rent again."
United States
fred j.
The price is £367
includes taxes & fees
27 Oct - 28 Oct
Newly Renovated Cottage 7 in Alton Bay
A red wooden building with a balcony and a staircase leading to a deck.

14. 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 £175
includes taxes & fees
4 Nov - 5 Nov
Rustic Rose Cottage of Historic West Lebanon
A two-story house with a white picket fence, a gravel driveway, and autumn foliage in the background.

15. 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 £136
includes taxes & fees
26 Oct - 27 Oct
Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath
A motel with a row of rooms, each with a front porch and a small table.

16. Cabin 41 at The Historic Sandy Point Resort w/ Boat Slip and Onsite Boat ramp

Cabin 41 at The Historic Sandy Point Resort w/ Boat Slip and Onsite Boat ramp
Alton
Cabin 41 at The Historic Sandy Point Resort w/ Boat Slip and Onsite Boat ramp
A garden with a white pergola, red chairs, and pink flowers.

17. 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 £135
includes taxes & fees
18 Oct - 19 Oct
Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
Outdoor dining

18. 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 £376
includes taxes & fees
15 Oct - 16 Oct
Cozy, Pet-Friendly Escape Near Lake & Mountains
A storefront with a blue awning and American flags, named "Paper Store Blacks Gift Shop."

19. 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 £145
includes taxes & fees
18 Oct - 19 Oct
Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard
A house with a porch, surrounded by a garden with pink and yellow flowers.

20. 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 £133
includes taxes & fees
22 Oct - 23 Oct
Cottage 7 - Year Round - Pet Friendly $50 Fee - Stand Alone 1 Bedroom / 1 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

The Centennial

The Centennial

10/10 Excellent
"Staff very friendly and room was awesome!"
Roger 1-night trip
Posted less than an hour ago
The Centennial

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
215
Accommodation
159 Cottages
Lowest Price
£133
Highest Price
£429

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