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Compare 99 Cottages in Pittsfield with updated reviews, rates, and availability.

Rustic cottage in private location - Pet friendly!
9.8 out of 10, Exceptional, (89)
"My boyfriend & I stayed at the Pemi Shore Cottages for 2 nights and it was exactly what we was looking for. Privacy in a wooded area with a quick walk to a beach? What more can we ask for :). We brought our two dogs and even that was a great accommodation! Our host John was super friendly and just one call away! I would highly recommend this location if you want to disconnect and relax."
Rustic cottage in private location - Pet friendly!
Waterfront cottage on large, wooded lot with amazing swimming and fishing
10.0 out of 10, Exceptional, (19)
"Our son and granddaughter live in Dover so we always find a place to stay so we can visit. This was one of our favorites. Right on bear lake beautiful sunsets the water was warm enough to swim. There was kayaks there to use. The kitchen was well stocked with pots and pans, dishes,seasoning. We had a great time. Just be careful driving in the road is pretty rough."
Waterfront cottage on large, wooded lot with amazing swimming and fishing
LAKE FRONT!! SKI ALL WINTER!!!
9.2 out of 10, Wonderful, (97)
"My family and I had a very nice time at the cottage. The location is right across from a small beach, and the view of the lake is perfect."
LAKE FRONT!! SKI ALL WINTER!!!
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Winnipesaukee house w/ dock included.
8.0 out of 10, Very Good, (2)
"The house was very nice and comfortable for four of us. Even though it rained each day, there is plenty of nearby shopping. We always try to do short term rentals when we travel. A couple of suggestions - the house had no wash cloths, no can opener, no salt & pepper shakers. Towels racks in the bathrooms would be a huge help. The listing indicated a hot tub and 2+ bathrooms. There was no hot tub and two full baths. There was no welcome booklet with local restaurants, points of interest, wifi...
Winnipesaukee house w/ dock included.
Lakefront home with a deck, gas grill, WiFi, dock & golf nearby
9.0 out of 10, Wonderful, (2)
"Pleasant accommodations, modern updated amenities. Convenient to restaurants and businesses. The views of the lake were great."
Lakefront home with a deck, gas grill, WiFi, dock & golf nearby
Lakefront Winnisquam Cottage with dock & boat ramp
10.0 out of 10, Exceptional, (25)
"My wife and I recently returned from a 6 night stay at the property. Our visit exceeded our expectations. The cottage and grounds were exceptionally clean. The cottage had everything we need for a great stay ! The on-site boat launch with dock and pet friendly property were definitely a deciding factor when we booked our trip. Thanks to Karen and John for sharing their beautiful property. Looking forward to staying next year !!"
Lakefront Winnisquam Cottage with dock & boat ramp
Cozy Waterfront Cottage!!
Cozy Waterfront Cottage!!
Cottage 8-9 - Stand Alone 2 Bedroom / 2 Bath
10.0 out of 10, Exceptional, (2)
"Everything was great!"
The price is $209
$378 total
includes taxes & fees
Jun 6 - Jun 7
Cottage 8-9 - Stand Alone 2 Bedroom / 2 Bath
Dog-friendly cabin with beach/dock access, foosball, fireplace, deck, & W/D
10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay in Belmont. I really liked their wall of sports memorabilia. We enjoyed playing darts on their dart board. Also, the next-door neighbor was super friendly to us. It was really nice."
Dog-friendly cabin with beach/dock access, foosball, fireplace, deck, & W/D
Cozy Cottage 2 Bedroom With Amazing View <br>
10.0 out of 10, Exceptional, (22)
"My wife and I had a great week at the Cozy Cottage. Loved the location. Although it is described as cozy, it was plenty spacious for the two of us and our Corgi."
Cozy Cottage 2 Bedroom With Amazing View <br>
Waterfront Cottage, Quiet and Secluded, on Swains Lake
9.4 out of 10, Exceptional, (53)
"Loved the cottage, it was peaceful and relaxing. We will be back again"
Waterfront Cottage, Quiet and Secluded, on Swains Lake
Lake Winnipesaukee Waterfront Cottage with Boat Slip and Dogs Welcome!
Lake Winnipesaukee Waterfront Cottage with Boat Slip and Dogs Welcome!
Lakefront Cottage with private beach
10.0 out of 10, Exceptional, (2)
"this time of year is the start of a busy summer, especially since Bike Week was extended for it's 100th anniversary. Suprisingly, the entire week was very peaceful. The other visitors in the area were very friendly as well. The owners don't bother you on a daily basis. For the most part, they let you know they are there if you need anything, and they are easy to contact if necessary. I loved sitting on the newly built deck to have my morning coffee and do some work before the heat increased....
Lakefront Cottage with private beach
Welcome to the Lake
9.8 out of 10, Exceptional, (30)
"The view is lovely & yard well manicured. The gazebo & patio are very nice. The owners are super respectful, which is appreciated. Most everything was quite clean. The banana bread, waters, coffee & creamer were very nice touches. The decore was wonderfully eclectic. I did have a nice time hiking and going through the antique shops. Loved having a little face time with your corgies. The price point cannot be beat. Thank you for sharing your beautiful home."
Welcome to the Lake
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
9.6 out of 10, Exceptional, (16)
"4 stars all day long"
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
Charming dog-friendly lakefront cottage with private dock & community beach
6.0 out of 10, (1)
"we loved this place very much, and we can tell by the logbooks that I've been there for years that many people have enjoyed this house, aside from what I am about to say next about the rental company this place is awesome and beautiful water great fishing, and we absolutely just loved the classic New Hampshire cottage, that we we always have strive to rent for. 100% would recommend staying here. But.......it appears as though it is being rented through a new company called Vacasa. this company...
Charming dog-friendly lakefront cottage with private dock & community beach
Alton Bay 2 Bed Room Cottage with Dock
10.0 out of 10, Exceptional, (12)
"I stayed here with my spouse and two kids (6 and 3yo). We all really enjoyed our stay. The cabin is quant but beautiful. The 5th cabin is the closest to the pool and play area (there is a play set with swings and a “treehouse” as well as a smaller structure for little ones. The main bedroom has a full size bed and there are two twins in the other bedroom. The beds were comfy and the cabin functions beautifully. We thoroughly enjoyed our stay!"
Alton Bay 2 Bed Room Cottage with Dock
Rustic Rose Cottage of Historic West Lebanon
9.8 out of 10, Exceptional, (10)
"As a traveling single female who is also a remote worker, this place is a dream. It's a great small space that has everything you need, Rob and Kayleigh thought of all the details. Check in was easy, it was super clean and inviting, and I felt safe the entire time. I was there for about a month and Rob's communication through out the stay was great, always asking if I need supplies, clean linens, and offering suggestions if needed. Wifi was fast, lots of privacy, and friendly locals. The...
The price is $109
$241 total
includes taxes & fees
Jun 11 - Jun 12
Rustic Rose Cottage of Historic West Lebanon
Cozy lakefront rental for two with private beach
10.0 out of 10, Exceptional, (13)
"Very clean and well hept up. Appreciated the access to the lake."
Cozy lakefront rental for two with private beach
Charming waterfront cottage at Weirs Beach with shared dock and WifI
10.0 out of 10, Exceptional, (10)
"Very charming, well appointed home in an awesome spot. Gorgeous view, spectacular swimming right out front, excellent boating."
Charming waterfront cottage at Weirs Beach with shared dock and WifI
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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.

Other property types in Pittsfield

Cedar Lodge condo with mountain & lake Winnipesauke views!
10.0 out of 10, Exceptional, (23)
"Many of the aspects about this property were good, as expected. The location was perfect, near restaurants, and convenient to the venue at which we attended a concert. The unit was very clean, also, and quiet, which we were looking for. Because this was our first VRBO stay, we did not know entirely what to expect. We would have appreciated a little more communication regarding accessing the unit, and/or someone on site to welcome us and be available to answer questions. We also were not thrilled...
The price is $70
$156 total
includes taxes & fees
Jun 6 - Jun 7
Cedar Lodge condo with mountain & lake Winnipesauke views!
Reuben Dimond House, Renovated Historic Farmhouse in the Capital, Concord, NH.
10.0 out of 10, Exceptional, (29)
"Our family had a busy weekend scheduled for our daughter’s softball tournament in Concord, and wanted a quiet place to rest and recharge in between games. This place exceeded our expectations - I wish we’d had more time to spend at the property, it was beautiful and super quiet. We would definitely stay here again."
Reuben Dimond House, Renovated Historic Farmhouse in the Capital, Concord, NH.
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
10.0 out of 10, Exceptional, (148)
"Pool was certainly a hit with the children. Communication with owner was excellent as well as the response to issues raised. Owners should be very proud of this gem in Gilford!"
The price is $1,300
$2,538 total
includes taxes & fees
Jun 17 - Jun 18
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
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.

Pittsfield Cottages information

Number of reviews
395
Accommodation
99 Cottages
Lowest Price
$109
Highest Price
$209

Frequently asked questions

How much do cottages in Pittsfield cost?
Prepare to pay between $109 and $209 per night for cottages in Pittsfield. No matter your budget, an epic stay is only a click or two away on Expedia. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Pittsfield with Expedia?
We think a getaway should be a piece of cake, so if you’re after cottages in Pittsfield at the perfect price, Expedia has got your back. Save money and stay in an inexpensive option far from the hustle and bustle, or book an upmarket cottage to spoil your favorite people.
How can I find cheap cottages in Pittsfield?
With Expedia’s user-friendly filter tool, scoring cheap cottages in Pittsfield is easy. To find accommodations that are very pocket friendly, narrow down your search by star rating, amenities and budget.
What is there to do in Pittsfield near my cottage?
The most useful travel accessory is a well-planned itinerary. New Hampshire International Speedway is a good place to start your exploration of Pittsfield.

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