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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Pittsfield cottages

A residential property with a wooden deck, a small garden, and a blue house with a chimney.

1. 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 CA $154
CA $331 total
includes taxes & fees
Sep 29 - Sep 30
Newly Renovated Cottage on Main Street Alton Bay #5
A rustic wooden cabin with a red roof, a covered picnic table, and a small shed.

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

Hiking & Snowmobile Trails On-site: Alton Retreat!
3.0 star property
Alton
The price is CA $219
CA $426 total
includes taxes & fees
Oct 12 - Oct 13
Hiking & Snowmobile Trails On-site: Alton Retreat!
A small, single-story cabin with a porch, outdoor seating, and a hot tub.

3. 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, (44 reviews)
"Lovely stay in a quiet area. The hot tub was great to unwind in after hiking in the area!"
United States
Cristofer V.
The price is CA $215
CA $482 total
includes taxes & fees
Sep 28 - Sep 29
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
A small cabin with a porch, a bench, and a staircase leading to the entrance.

4. 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 CA $177
CA $528 total
includes taxes & fees
Oct 5 - Oct 6
Newly Renovated Cottage 4 in Alton Bay, NH
A white cabin with a green roof, surrounded by dense green trees.

5. Cozy Cottage on a Lake, near Gunstock Mountain

Cozy Cottage on a Lake, near Gunstock Mountain
Gilmanton
9.0 out of 10, Wonderful, (7 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 CA $242
CA $559 total
includes taxes & fees
Sep 28 - Sep 29
Cozy Cottage on a Lake, near Gunstock Mountain
An aerial view of a residential area with a swimming pool, multiple houses, and a road.

6. 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 CA $171
CA $341 total
includes taxes & fees
Sep 27 - Sep 28
Charming Alton Bay Getaway – 1BR Cottage, Pool Access & Walk to Lake
A red wooden building with a balcony and a staircase leading to a deck.

7. Rustic Rose Cottage of Historic West Lebanon

Rustic Rose Cottage of Historic West Lebanon
Lebanon
9.6 out of 10, Exceptional, (29 reviews)
"Everything was great. Very clean and comfortable! Thank you for a great place to stay. "
United States
Heather K.
The price is CA $147
CA $327 total
includes taxes & fees
Oct 27 - Oct 28
Rustic Rose Cottage of Historic West Lebanon
A small cabin with a deck, a front door, and a window.

8. 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 CA $198
CA $424 total
includes taxes & fees
Sep 29 - Sep 30
Newly Renovated Cottage 8 Main Street Alton Bay!
An aerial view of a residential area with a swimming pool, multiple houses, and a road.

9. 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 CA $163
CA $333 total
includes taxes & fees
Oct 6 - Oct 7
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
A spacious kitchen with a large island, white cabinetry, and a view of a playground through large windows.

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

Newly Renovated Cottage 3 on Main Street Alton Bay!
Alton
9.4 out of 10, Exceptional, (6 reviews)
"Staff was very freindly"
United States
David
The price is CA $182
CA $359 total
includes taxes & fees
Oct 6 - Oct 7
Newly Renovated Cottage 3 on Main Street Alton Bay!
A two-story house with a white picket fence, a gravel driveway, and autumn foliage in the background.

11. Cottage 5-6 - Year Round Pet Friendly $50 Fee- 2 Bedroom / 1 Bath End Unit

Cottage 5-6 - Year Round Pet Friendly $50 Fee- 2 Bedroom / 1 Bath End Unit
Wolfeboro
9.4 out of 10, Exceptional, (3 reviews)
"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.
Cottage 5-6 - Year Round Pet Friendly $50 Fee- 2 Bedroom / 1 Bath End Unit
A lakeside seating area with Adirondack chairs, a stone fire pit, and an American flag.

12. 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 CA $351
CA $803 total
includes taxes & fees
Sep 27 - Sep 28
7 Mi to Hiking: Waterfront Long Pond Gem!
An outdoor deck with a table and chairs, a grill, and a yellow shade sail.

13. Serene Pondside Retreat Surrounded by Nature

Serene Pondside Retreat Surrounded by Nature
Deerfield
The price is CA $239
CA $941 total
includes taxes & fees
Oct 26 - Oct 27
Serene Pondside Retreat Surrounded by Nature

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

Cozy, Pet-Friendly Escape Near Lake & Mountains
Gilford
10.0 out of 10, Exceptional, (48 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 CA $271
CA $687 total
includes taxes & fees
Oct 4 - Oct 5
Cozy, Pet-Friendly Escape Near Lake & Mountains
A small cabin with a porch, outdoor seating, and a bird sculpture on the roof.

15. 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 CA $260
CA $447 total
includes taxes & fees
Oct 6 - Oct 7
Newly Renovated Cottage 6
A two-story cabin with a wooden deck and a staircase leading to the upper level.

16. 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 CA $392
CA $629 total
includes taxes & fees
Oct 5 - Oct 6
Newly Renovated Cottage 7 in Alton Bay
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
9.4 out of 10, Exceptional, (13 reviews)
"Great place "
United States
Anonymous traveller
The price is CA $215
CA $264 total
includes taxes & fees
Oct 26 - Oct 27
Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
A two-story house with a white picket fence, a gravel driveway, and autumn foliage in the background.

18. 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 CA $232
CA $285 total
includes taxes & fees
Oct 5 - Oct 6
Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath
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
10.0 out of 10, Exceptional, (21 reviews)
"This is a great place to stay with a dog"
United States
David M.
The price is CA $233
CA $286 total
includes taxes & fees
Sep 27 - Sep 28
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, (7 reviews)
"Great location & comfortable! "
United States
Jeanine L.
The price is CA $211
CA $260 total
includes taxes & fees
Sep 27 - Sep 28
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 Governor's Inn

The Governor's Inn

8/10 Good
"Adorable decor except the room choice undesirable. Big industrial fan noise right outside our window which kept us awake all night & bathroom fan nonfunctional. The restaurant was quaint and the food very good. Worth the price with continental breakfast a plus. Staff very pleasant"
Carol 1-night trip
Posted 4 hours ago
The Governor's Inn

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
196
Accommodation
161 Cottages
Lowest Price
CA $260
Highest Price
CA $941

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