Title: Pittsfield Vacation Home Rentals from CA $212: 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 In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6053891&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6053891&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6053891&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6053891&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Pittsfield Vacation Homes ![Exterior](https://images.trvl-media.com/lodging/114000000/113530000/113522100/113522019/a9427e87.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113530000/113522100/113522019/c8d60c8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming historic guest house on farm 3 bedrooms wood stove pet friendly Oakland 10/10 Exceptional (7) "Enjoyed a 2 night stay at this quiet country retreat. Our host was friendly and took time to visit. The kitchen was well stocked and it's a charming historic structure, equipped with modern conveniences. What more could you want! " CA $307 CA $504 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Oakland-Hotels-Cozy-Farm-Stay-Pet-Friendly-Peaceful.h113522019.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) ![Dining](https://images.trvl-media.com/lodging/108000000/107420000/107414500/107414470/9219ab3e.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) ![Exterior](https://images.trvl-media.com/lodging/108000000/107420000/107414500/107414470/1d81fc0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Discover Oakland charm near Colby College 10 min Oakland 10/10 Exceptional (4) "New, clean and had everything we needed. " CA $128 CA $367 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Oakland-Hotels-Oakland-Condo-Furnished-2-Bdrm-1-Bath-Newly-Built.h107414470.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) ![Smart TV, DVD player, books](https://images.trvl-media.com/lodging/116000000/115930000/115923400/115923334/a67fe484.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) ### Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine Madison 10/10 Exceptional (3) "Excellent service and perfect for our stay. Would book again!" CA $167 CA $212 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Madison-Hotels-Charming-1-Bedroom-Building-With-WiFi.h115923334.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) ![Interior](https://images.trvl-media.com/lodging/108000000/107860000/107856700/107856647/0e3db68c.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) ![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107860000/107856700/107856647/ffd77f17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pretty old house in Newport with WiFi Newport CA $168 CA $379 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Newport-Hotels-Pretty-Old-House-In-Newport-With-WiFi.h107856647.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) ![Smart TV, books](https://images.trvl-media.com/lodging/114000000/113970000/113961400/113961345/eeafa7fb.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) ### Zeus's Landing at Cottages of Maine Gradual beachfront, King Beds, Dog Friendly Canaan 10/10 Exceptional (3) "Great spot on the lake! The house was super clean, beds were very comfortable, kitchen was well stocked and had everything we needed while we were there. The neighbor's house is really close to the property along the shared beach, and while it was never an issue for us, you may hear the neighbors as they come and go from their house. Overall a fantastic stay." CA $235 CA $553 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Canaan-Hotels-3-Bedroom-Lakefront-Home-With-Beach-Front.h113961345.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/122000000/121270000/121269300/121269271/fb55cac2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Printers](https://images.trvl-media.com/lodging/122000000/121270000/121269300/121269271/4b6cacf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room dining](https://images.trvl-media.com/lodging/122000000/121270000/121269300/121269271/028ea602.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/122000000/121270000/121269300/121269271/587c3b76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### My Valhalla Farm Oakland CA $397 CA $573 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Oakland-Hotels-My-Valhalla-Farm.h121269271.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=2025-10-28&endDate=2025-10-29®ionId=6053891&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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 ![Fireside Inn & Suites Waterville](//images.trvl-media.com/lodging/1000000/20000/19700/19607/0fbc096a_y.jpg) ### Fireside Inn & Suites Waterville 10/10 Excellent "Staff " [](https://expedia.ca/Augusta-Hotels-Fireside-Inn-Suites-Waterville.h19607.Hotel-Information) ![Belmont Motel](//images.trvl-media.com/lodging/103000000/102340000/102332400/102332392/0ab312c7_y.jpg) ### Belmont Motel 10/10 Excellent "Very clean, the staff were friendly. We arrived before check in time but we're able to check in early. The room was comfortable and clean. It was very quiet even though all rooms were booked. The outdoor space was very nice. I would definitely go back here again." [](https://expedia.ca/Skowhegan-Hotels-Belmont-Motel.h102332392.Hotel-Information) ![The Elmwood](//images.trvl-media.com/lodging/72000000/71560000/71556000/71555928/6685e6ca_y.jpg) ### The Elmwood 10/10 Excellent "This was a charming little hotel that has been renovated. Rooms were very clean and smelled clean. Staff were very friendly had a simple but delicious breakfast available. " [](https://expedia.ca/Waterville-Hotels-The-Elmwood.h71555928.Hotel-Information) ![The Towne Motel](//images.trvl-media.com/lodging/6000000/5500000/5490200/5490125/82b2c35d_y.jpg) ### The Towne Motel 10/10 Excellent "Staff helpful " [](https://expedia.ca/Skowhegan-Hotels-The-Towne-Motel.h5490125.Hotel-Information) ![Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes](//images.trvl-media.com/lodging/62000000/61510000/61508300/61508289/569b4e0b_y.jpg) ### Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes 10/10 Excellent "An excellent location and very enjoyable setting on the pond. Great place to sit outside and enjoy coffee in the morning and a glass of wine in the evening." [](https://expedia.ca/Augusta-Hotels-Get-Away-From-It-All-At-This-Cottage-On-East-Pond-In-Oakland-Maine.h61508289.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 "Friendly and courteous staff. Very helpful with dining locations. Would recommend a lounge/pub setting to enjoy a drink after a long traveling day. Excellent hotel!!! " [](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 "Great room just needed a microwave" [](https://expedia.ca/Skowhegan-Hotels-The-Skowhegan-By-Kasa.h114717254.Hotel-Information) ![Lockwood Hotel](//images.trvl-media.com/lodging/79000000/78100000/78095000/78094968/d4c480e1_y.jpg) ### Lockwood Hotel 10/10 Excellent "Comfortable. New Hoel." [](https://expedia.ca/Waterville-Hotels-Lockwood-Hotel.h78094968.Hotel-Information) ![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 "Very helpful staff and a wonderful breakfast included." [](https://expedia.ca/Augusta-Hotels-Best-Western-Plus-Waterville-Grand-Hotel.h22003.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Vacation Homes information | Number of reviews | 16 | | --- | --- | | Accommodation | 41 Vacation Homes | | Lowest Price | CA $212 | | Highest Price | CA $553 | ## 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) - [Burnham Hotels](https://www.expedia.ca/Burnham-Hotels.d553248635975876553.Travel-Guide-Hotels) - 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