Title: Pittsfield Vacation Home Rentals from CA $213: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d6053891.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d6053891.Travel-Guide-VacationRentals)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d6053891.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.ca/Pittsfield.d6053891.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) # Pittsfield Vacation Rentals - ![](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 [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6053891&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6053891&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6053891&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6053891&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Pittsfield Vacation Homes ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120700000/120691000/120690958/f312f5a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120700000/120691000/120690958/b11f313d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/121000000/120700000/120691000/120690958/b385ea09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120700000/120691000/120690958/bf91d158.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming In-Town New Build – Comfortable, Convenient, Efficient Pittsfield CA $157 CA $325 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Pittsfield-Hotels-Charming-In-Town-New-Build-Stylish.h120690958.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/122000000/121710000/121709900/121709874/8b35343e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/122000000/121710000/121709900/121709874/d8edb774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121710000/121709900/121709874/579b86fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/122000000/121710000/121709900/121709874/257fce69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pine Tree Trail Lodge Pittsfield CA $211 CA $405 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Pittsfield-Hotels-Pine-Tree-Trail-Lodge.h121709874.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113530000/113522100/113522019/4b703bf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113530000/113522100/113522019/aed9cb99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113530000/113522100/113522019/e447dc65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113530000/113522100/113522019/31ceecc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Guest House on Farm - Pets Welcome Oakland 10/10 Exceptional (7) "The farmhouse was clean and charming. The kitchen was well-stocked. Kathleen was an excellent communicator. She went out of her way to make sure we were comfortable— including making a bonfire for smores! We loved getting to be with her sweet kitties and amazing donkeys, mule, and horse." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) amy C. CA $247 CA $375 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Oakland-Hotels-Cozy-Farm-Stay-Pet-Friendly-Peaceful.h113522019.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/116000000/115930000/115923400/115923334/e0ffec4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115930000/115923400/115923334/2dd0dee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115930000/115923400/115923334/14681d34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/116000000/115930000/115923400/115923334/27f2044c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine Madison 9.0/10 Wonderful (4) "Excellent service and perfect for our stay. Would book again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott CA $167 CA $213 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Madison-Hotels-Charming-1-Bedroom-Building-With-WiFi.h115923334.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107420000/107414500/107414470/5d63eee3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107420000/107414500/107414470/24687d8e_edited_120b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/108000000/107420000/107414500/107414470/2be335e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/108000000/107420000/107414500/107414470/9219ab3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Discover Oakland charm near Colby College 10 min Oakland 10/10 Exceptional (6) "I would highly recommend this beautiful rental to anyone. Brand new, super clean , all necessities ( down to complimentary shampoo/ conditioner)A lot of bang for your buck! Host was absolutely amazing to work with . " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary G. CA $140 CA $380 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Oakland-Hotels-Oakland-Condo-Furnished-2-Bdrm-1-Bath-Newly-Built.h107414470.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121270000/121269300/121269271/262abcab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/122000000/121270000/121269300/121269271/354636c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/122000000/121270000/121269300/121269271/79d4c0b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/122000000/121270000/121269300/121269271/143036a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### My Valhalla Farm Oakland CA $342 CA $514 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/Oakland-Hotels-My-Valhalla-Farm.h121269271.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107860000/107856700/107856647/89280a44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107860000/107856700/107856647/ffd77f17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107860000/107856700/107856647/f94dbcde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107860000/107856700/107856647/912753b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pretty old house in Newport with WiFi Newport CA $169 CA $380 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Newport-Hotels-Pretty-Old-House-In-Newport-With-WiFi.h107856647.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/79000000/78500000/78497800/78497731/w1424h960x15y0-c93bc618.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78500000/78497800/78497731/89eb3d15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78500000/78497800/78497731/17c726b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78500000/78497800/78497731/c1a539bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Maine Lake House with an Amazing Sand Beach! Burnham 8.8/10 Excellent (6) "Great stay, property was a great fit for a few day stay to visit family." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy M. CA $279 CA $705 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Burnham-Hotels-The-Maine-Lake-House-With-An-Amazing-Sand-Beach.h78497731.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/114000000/113970000/113961400/113961345/b6073572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113970000/113961400/113961345/f5af7b97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113970000/113961400/113961345/97c016b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113970000/113961400/113961345/d65eda33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ice fishing, king size beds, dog friendly Canaan 10/10 Exceptional (3) "This is the PERFECT place to truly disconnect and relax! The house is clean, spacious, and has everything you need! Being steps away from the lake was very convenient and having the kayaks available for use was awesome. Being able to wake up to a sunrise, and hang in the porch watching the sunset was amazing. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brianna P. CA $192 CA $503 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Canaan-Hotels-3-Bedroom-Lakefront-Home-With-Beach-Front.h113961345.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=2025-11-19&endDate=2025-11-20®ionId=6053891&adults=2&lodging=VACATION_HOME&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-Private-Vacation-Homes.d6053891-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Private-Vacation-Homes.d6053891-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![Best Western Plus Waterville Grand Hotel](//images.trvl-media.com/lodging/1000000/30000/22100/22003/c76e225a_y.jpg) ### Best Western Plus Waterville Grand Hotel 10/10 Excellent "Room was fabulous, clean, well accommodated. Staff is friendly." [](https://expedia.ca/Augusta-Hotels-Best-Western-Plus-Waterville-Grand-Hotel.h22003.Hotel-Information) ![Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore](//images.trvl-media.com/lodging/108000000/107350000/107340300/107340207/20d8d18f_y.jpg) ### Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore 10/10 Excellent "Great spot!" [](https://expedia.ca/Oakland-Hotels-Lakefront-3-Bedroom-Pet-Friendly-On-Messalonski.h107340207.Hotel-Information) ![Fireside Inn & Suites Waterville](//images.trvl-media.com/lodging/1000000/20000/19700/19607/0fbc096a_y.jpg) ### Fireside Inn & Suites Waterville 10/10 Excellent "Great hotel in Waterville " [](https://expedia.ca/Augusta-Hotels-Fireside-Inn-Suites-Waterville.h19607.Hotel-Information) ![The Elmwood](//images.trvl-media.com/lodging/72000000/71560000/71556000/71555928/6685e6ca_y.jpg) ### The Elmwood 10/10 Excellent "This is a former motel that has been renovated to resemble more of today’s boutique style. Room was very nice and clean. Good value. We had a pizze delivered from a place in Watertown, I believe? Really good pizza, I think the front desk recommended. " [](https://expedia.ca/Waterville-Hotels-The-Elmwood.h71555928.Hotel-Information) ![Holiday Inn Express & Suites Waterville - North by IHG](//images.trvl-media.com/lodging/1000000/810000/802200/802109/d5d283f3_y.jpg) ### Holiday Inn Express & Suites Waterville - North by IHG 10/10 Excellent "Nice staff, good location" [](https://expedia.ca/Augusta-Hotels-Holiday-Inn-Express-Suites-Waterville-North.h802109.Hotel-Information) ![The Skowhegan By Kasa](//images.trvl-media.com/lodging/115000000/114720000/114717300/114717254/f4aad0c9_y.jpg) ### The Skowhegan By Kasa 10/10 Excellent "Easy and perfect " [](https://expedia.ca/Skowhegan-Hotels-The-Skowhegan-By-Kasa.h114717254.Hotel-Information) ![The Towne Motel](//images.trvl-media.com/lodging/6000000/5500000/5490200/5490125/82b2c35d_y.jpg) ### The Towne Motel 10/10 Excellent "Our room was neat and clean. The entire staff was very friendly and courteous. We would stay here again. " [](https://expedia.ca/Skowhegan-Hotels-The-Towne-Motel.h5490125.Hotel-Information) ![Hampton Inn Waterville](//images.trvl-media.com/lodging/1000000/730000/721100/721075/3c11b972_y.jpg) ### Hampton Inn Waterville 10/10 Excellent "Great room. Close to good food." [](https://expedia.ca/Augusta-Hotels-Hampton-Inn-Waterville.h721075.Hotel-Information) ![Cabin in scenic woods with hiking trails, firepit, horseback riding nearby](//images.trvl-media.com/lodging/32000000/31190000/31189900/31189874/0def602e_y.jpg) ### Cabin in scenic woods with hiking trails, firepit, horseback riding nearby 10/10 Excellent "We enjoyed our visit and it felt just like home to us. We hope we can come back and visit again " [](https://expedia.ca/Exeter-Hotels-Cabin-In-Scenic-Woods-With-Hiking-Trails.h31189874.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Vacation Homes information | Number of reviews | 18 | | --- | --- | | Accommodation | 41 Vacation Homes | | Lowest Price | CA $213 | | Highest Price | CA $514 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [4 Star Hotels in Dixmont](https://www.expedia.ca/4Star-Dixmont-Hotels.s40-0-d553248635975849550.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Detroit](https://www.expedia.ca/5Star-Detroit-Hotels.s50-0-d6333765.Travel-Guide-Filter-Hotels) - [Bangor Hotels](https://www.expedia.ca/Bangor-Hotels.d6050918.Travel-Guide-Hotels) - [Capsule Hotels in Bar Harbor](https://www.expedia.ca/Bar-Harbor-Capsule-Hotels.d561-aaCapsuleHotels.Travel-Guide-Accommodation) - [Condo Rentals in Burnham](https://www.expedia.ca/Burnham-Condos.d553248635975876553-aaCondos.Travel-Guide-Accommodation) - 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