Title: Pittsfield Cottages from CA $286 | Expedia.ca [Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d3000447085.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d3000447085.Travel-Guide-VacationRentals)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d3000447085.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.ca/Pittsfield.d3000447085.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Pittsfield Cottage Rentals from CA $286 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=3000447085&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=3000447085&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=3000447085&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000447085&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Pittsfield Cottages ![Exterior](https://images.trvl-media.com/lodging/89000000/88660000/88656300/88656238/e8ade1ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88660000/88656300/88656238/66ab8ed4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/89000000/88660000/88656300/88656238/0e804321.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, memory foam beds, desk, iron/ironing board](https://images.trvl-media.com/lodging/89000000/88660000/88656300/88656238/85d61a9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rustic Rose Cottage of Historic West Lebanon Lebanon 10/10 Exceptional (23) "Beautiful, easy access, well appointed" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey J. CA $180 CA $352 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Lebanon-Hotels-Rustic-Rose-Cottage-Of-Historic-West-Lebanon.h88656238.Hotel-Information) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121240000/121233000/121232998/0522720b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121240000/121233000/121232998/58443375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121240000/121233000/121232998/9b4a1a49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121240000/121233000/121232998/92ecff2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### On Baxter Lake: Wooded Retreat Near Trails Farmington [](https://www.expedia.ca/Farmington-Hotels-On-Baxter-Lake-Wooded-Retreat-Near-Trails.h121232998.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001306/1e15d00e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001306/7d170157.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001306/a476f6fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001306/c1131a3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Renovated Cottage 6 Alton 10/10 Exceptional (2) "Great location, and amenities, including the game room, pool and bikes. Hosts were very responsive and accomodating. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vanessa CA $158 CA $326 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/Alton-Hotels-Newly-Renovated-Cottage-6.h118001306.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/119000000/118010000/118001300/118001292/cb2eddca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118010000/118001300/118001292/c0327754.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/119000000/118010000/118001300/118001292/1015507f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118010000/118001300/118001292/35cd68ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Renovated Cottage 4 in Alton Bay, NH Alton 9.0/10 Wonderful (4) "Game room fun for all ages. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $159 CA $503 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Alton-Bay-Hotels-Newly-Renovated-Cottage-4-In-Alton-Bay.h118001292.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78560000/78557100/78557029/0209a276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Towels](https://images.trvl-media.com/lodging/79000000/78560000/78557100/78557029/0b7cfe3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78560000/78557100/78557029/a1981967.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Internet, bed sheets](https://images.trvl-media.com/lodging/79000000/78560000/78557100/78557029/e027707e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette Alton 8.6/10 Excellent (18) "Nice location on the lake." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary L. CA $210 CA $435 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Alton-Bay-Hotels-Picturesque-Studio-In-Bay-Front-Locale-Just-Steps-To-Water-WWiFi-Kitchenette.h78557029.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/74000000/73640000/73635000/73634950/25c5d3fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73640000/73635000/73634950/4599c31e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73640000/73635000/73634950/5181889b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/74000000/73640000/73635000/73634950/e2822ee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage 10 - 1 Bedroom w/ Loft / 1 Bath Wolfeboro 10/10 Exceptional (4) "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](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica G. CA $312 CA $382 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Wolfeboro-Hotels-Cottage-10-1-Bedroom-W-Loft-1-Bath.h73634950.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/74000000/73640000/73634800/73634717/2990226c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/74000000/73640000/73634800/73634717/b06df502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73640000/73634800/73634717/ecd42a73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/74000000/73640000/73634800/73634717/9be24eaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard Wolfeboro 9.6/10 Exceptional (10) "Great property. Loved our stay and the owners were great! Definitely will book again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marcus CA $283 CA $348 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Wolfeboro-Hotels-Cottage-4-1-Bed-W-Loft-1-Bath-Courtyard.h73634717.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001301/e2ba1d00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001301/b0bb680d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001301/3aa3d4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001301/4bd7acf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Renovated Cottage on Main Street Alton Bay #5 Alton 10/10 Exceptional (1) "Great places. Quiet and quaint and close to the lake and restaurants. Will rent again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian B. CA $159 CA $334 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Alton-Hotels-Newly-Renovated-Cottage-On-Main-Street-Alton-Bay-5.h118001301.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001312/d83cab16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001312/69bfa62e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001312/99b4b8d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001312/7158700d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Renovated Cottage 7 in Alton Bay Alton 10/10 Exceptional (1) "endroit magnifique,emplacement agréable avec commodité sur place et près du lac et restaurant." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Alexandra R. CA $168 CA $349 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Alton-Hotels-Newly-Renovated-Cottage-7-In-Alton-Bay.h118001312.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001316/a6a777cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001316/3b9dff3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001316/f71b0678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001316/e8a1d880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Renovated Cottage 3 on Main Street Alton Bay! Alton 10/10 Exceptional (1) "Great little spot right next to the bay. Team was super responsive prior, during and after check in. Would highly recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andy S. CA $158 CA $328 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Alton-Hotels-Newly-Renovated-Cottage-3-On-Main-Street-Alton-Bay.h118001316.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001320/3a1c44d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001320/b4831b37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001320/be5c1620.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001320/a265ead9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Renovated Cottage 8 Main Street Alton Bay! Alton 7.0/10 Good (2) " 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Pedram S. CA $175 CA $391 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Alton-Hotels-Newly-Renovated-Cottage-8-Main-Street-Alton-Bay.h118001320.Hotel-Information) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114350000/114340400/114340373/ef7d27ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114350000/114340400/114340373/d394793c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114350000/114340400/114340373/70c78a91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114350000/114340400/114340373/1c63870c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hiking & Snowmobile Trails On-site: Alton Retreat! Alton CA $129 CA $286 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Alton-Hotels-Hiking-Snowmobile-Trails-On-Site-Alton-Retreat.h114340373.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001326/9e35be04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001326/47fcdeef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001326/ceb10bc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/119000000/118010000/118001400/118001326/562de23e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Alton Bay Getaway – 1BR Cottage, Pool Access & Walk to Lake Alton CA $175 CA $344 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/Alton-Hotels-Charming-Alton-Bay-Getaway-1BR-Cottage.h118001326.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/74000000/73640000/73634900/73634833/02bd108f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/74000000/73640000/73634900/73634833/05d080a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/74000000/73640000/73634900/73634833/w3179h1510x0y0-ae033c71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73640000/73634900/73634833/51720dea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath Wolfeboro 10/10 Exceptional (4) "Great location & comfortable! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeanine L. CA $255 CA $315 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Wolfeboro-Hotels-Cottage-7-Stand-Alone-1-Bedroom-1-Bath.h73634833.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73640000/73633700/73633671/35521981.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73640000/73633700/73633671/d02e513b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/74000000/73640000/73633700/73633671/78e7855d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/74000000/73640000/73633700/73633671/4c593ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath Wolfeboro 10/10 Exceptional (4) "It was very cute and clean, loved the outside area and would def be back again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anais & Zach CA $283 CA $348 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Wolfeboro-Hotels-Cottage-3-Pet-Friendly-1-Bedroom-1-Bath.h73633671.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73640000/73635100/73635099/a3863e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/74000000/73640000/73635100/73635099/w1037h687x0y0-102e19a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73640000/73635100/73635099/920d885b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73640000/73635100/73635099/76513f48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard Wolfeboro 10/10 Exceptional (16) "I love and have had a couple decades of Lake Winnepesaukee summers. With my boys now grown and raising their own families in other parts of the country, I drove up for a couple days, by myself, for a Lake Winni fix. The on site cottage was perfect in terms of location, privacy, cleanliness and the unspoken presence of security that was important to me a line traveler. I highly recommend this Inn for a special week on the lake, couples, small families. Accommodations are beautifully updated and... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa B. CA $312 CA $384 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Wolfeboro-Hotels-Cottage-12-1-King-Bed-1-Bath-Courtyard.h73635099.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/74000000/73640000/73635100/73635040/c4307c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73640000/73635100/73635040/c8558033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73640000/73635100/73635040/ecf79e58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/74000000/73640000/73635100/73635040/w1920h1861x0y96-5d731ae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage 11 - Year Round - Pet Friendly - 1 Bed / 1 Bath w/ Private Courtyard Wolfeboro 10/10 Exceptional (5) "Booked a last minute trip with the family and it was perfect. Right near downtown and a cozy place to rest with the kids." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sean P. CA $304 CA $374 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Wolfeboro-Hotels-Cottage-11-1-Bed-1-Bath-W-Private-Courtyard.h73635040.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/74000000/73640000/73634900/73634899/790de7f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/74000000/73640000/73634900/73634899/f915d58e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73640000/73634900/73634899/07b974e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/74000000/73640000/73634900/73634899/w3179h1510x0y0-e6be37a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath Wolfeboro 10/10 Exceptional (4) "Everything was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leah F. CA $436 CA $534 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Wolfeboro-Hotels-Cottage-8-9-Stand-Alone-2-Bedroom-2-Bath.h73634899.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73640000/73633400/73633399/8c23cd63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/74000000/73640000/73633400/73633399/w3179h1510x0y0-b5172781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73640000/73633400/73633399/88260456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/74000000/73640000/73633400/73633399/w1920h1275x0y0-99da1653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage 1-2 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit Wolfeboro 10/10 Exceptional (2) "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](https://a.travel-assets.com/egds/marks/flags/us.svg) Justin CA $376 CA $458 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Wolfeboro-Hotels-Cottage-1-2-2-Bedroom-1-Bath-End-Unit.h73633399.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/115000000/114280000/114277500/114277402/970c7839.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/115000000/114280000/114277500/114277402/94ba3bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/115000000/114280000/114277500/114277402/e04ed936.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114280000/114277500/114277402/c7c91372.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage on a Lake, near Gunstock Mountain Gilmanton 9.0/10 Wonderful (2) "We had a great time. Loved the cabin super cute. Neighborhood & neighbors very nice. The lake & private beaches were great. We enjoyed the hot tub & fire pit. I brought a few games, but you had a nice selection as well. Kitchen was very nice with everything we needed for some nice big breakfasts to start our day. We did run into a bit of a problem with the water running out. During showers, but we worked through it. Over all it was a great place. Thank you. Kim, Steve,Brianna,Cam & Brody " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) kim M. CA $239 CA $554 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Gilmanton-Hotels-Cozy-Cottage-On-A-Lake.h114277402.Hotel-Information) 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](https://expedia.ca/Hotel-Search?startDate=2025-11-06&endDate=2025-11-07®ionId=3000447085&adults=2&lodging=COTTAGE&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Cottages.d3000447085-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Cottages.d3000447085-aaCottages.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![Fireside Inn & Suites Gilford](//images.trvl-media.com/lodging/2000000/1540000/1536900/1536870/c9dd5729_y.jpg) ### Fireside Inn & Suites Gilford 10/10 Excellent "We had a great time , the staff was very pleasant made us feel very welcomed . The hrs and go breakfast was lots of diff options and a big room to eat . The rooms were very clean " [](https://expedia.ca/Laconia-Hotels-Fireside-Inn-Suites-Gilford.h1536870.Hotel-Information) ![TownePlace Suites by Marriott Gilford](//images.trvl-media.com/lodging/3000000/2700000/2699400/2699325/406a36b6_y.jpg) ### TownePlace Suites by Marriott Gilford 10/10 Excellent "😊" [](https://expedia.ca/Laconia-Hotels-TownePlace-Suites-By-Marriott-Gilford.h2699325.Hotel-Information) ![Hampton Inn & Suites Tilton](//images.trvl-media.com/lodging/3000000/2100000/2096400/2096324/367ce831_y.jpg) ### Hampton Inn & Suites Tilton 10/10 Excellent "Super clean room, delicious breakfast. The only thing was the loud noise the room doors make when closing (we were awake by other guests either arriving or leaving their rooms because of the doors closing too loud), and we can hear people talking in the next room (I’m sure they could hear us too). " [](https://expedia.ca/Laconia-Hotels-Hampton-Inn-Suites-Tilton.h2096324.Hotel-Information) ![The Naswa Resort](//images.trvl-media.com/lodging/6000000/5060000/5059100/5059005/ca1dd37a_y.jpg) ### The Naswa Resort 10/10 Excellent "Friendly vibe and great food and entertainment. " [](https://expedia.ca/Laconia-Hotels-The-Naswa-Resort.h5059005.Hotel-Information) ![Best Western Plus Landmark Inn](//images.trvl-media.com/lodging/3000000/2610000/2601700/2601613/ace38470_y.jpg) ### Best Western Plus Landmark Inn 10/10 Excellent "Nice clean modern hotel near the Laconia train station. " [](https://expedia.ca/Laconia-Hotels-Best-Western-Plus-Landmark-Inn.h2601613.Hotel-Information) ![Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy](//images.trvl-media.com/lodging/111000000/110280000/110270400/110270350/d77df0a7_y.jpg) ### Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy 10/10 Excellent "Clean. Cozy. Comfortable. Perfect for two. Loved the big window to the woods at the bedside. We will look for more Postcard Cabins in the future!" [](https://expedia.ca/Epsom-Hotels-Postcard-Cabins-Blake-Brook.h110270350.Hotel-Information) ![Holiday Inn Express Hotel & Suites Rochester by IHG](//images.trvl-media.com/lodging/2000000/1760000/1753900/1753823/430aade8_y.jpg) ### Holiday Inn Express Hotel & Suites Rochester by IHG 10/10 Excellent "Easy for travelers " [](https://expedia.ca/Portsmouth-Hotels-Holiday-Inn-Express-Hotel-Suites-Rochester.h1753823.Hotel-Information) ![The Centennial](//images.trvl-media.com/lodging/1000000/50000/42700/42642/e7221520_y.jpg) ### The Centennial 10/10 Excellent "Beautiful rooms, clean, out going friendly helpful staff " [](https://expedia.ca/Manchester-Hotels-The-Centennial.h42642.Hotel-Information) ![Hampton Inn by Hilton Concord/Bow](//images.trvl-media.com/lodging/1000000/20000/18900/18833/635b84bc_y.jpg) ### Hampton Inn by Hilton Concord/Bow 10/10 Excellent "The staff were efficient and helpful. The room was very comfortable and everything was extremely clean. We would stay here again!" [](https://expedia.ca/Manchester-Hotels-Hampton-Inn-By-Hilton-ConcordBow.h18833.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Cottages information | Number of reviews | 74 | | --- | --- | | Accommodation | 158 Cottages | | Lowest Price | CA $286 | | Highest Price | CA $554 | ## 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. 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