Title: Pittsfield Vacation Home Rentals from CA $208: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d553248635975875351.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d553248635975875351.Travel-Guide-VacationRentals)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d553248635975875351.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.ca/Pittsfield.d553248635975875351.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 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635975875351&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635975875351&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635975875351&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635975875351&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Pittsfield Vacation Homes ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/115000000/114410000/114406700/114406622/ea27a7fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114410000/114406700/114406622/2dfb667f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/115000000/114410000/114406700/114406622/8551f51e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/115000000/114410000/114406700/114406622/4d2028c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Refined Retreat Celoron 10/10 Exceptional (10) "In beautiful/excellent condition for us. Communication owner easy and helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alan S. CA $153 CA $419 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Celoron-Hotels-The-Refined-Retreat.h114406622.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111750000/111747400/111747321/97aa0d60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/112000000/111750000/111747400/111747321/82c140d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111750000/111747400/111747321/2928f149.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111750000/111747400/111747321/6e98ab2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eagle's Peak Cottage Pleasantville 8.8/10 Excellent (19) "We had a great time and will be back again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samantha H. CA $63 CA $208 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/West-Hickory-Hotels-Eagles-Peak-Cottage.h111747321.Hotel-Information) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/79000000/78430000/78425800/78425800/3003a703.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78430000/78425800/78425800/2cba032b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78430000/78425800/78425800/fa5d7b33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/79000000/78430000/78425800/78425800/90844d39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River view getaway Warren 9.8/10 Exceptional (45) "Comfortable, great location Everything we could ask for." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason A. CA $203 CA $378 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Warren-Hotels-River-View-Getaway.h78425800.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/49000000/48630000/48627000/48626943/6bd0fe23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/49000000/48630000/48627000/48626943/0d62ce2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/49000000/48630000/48627000/48626943/eba5ee9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/49000000/48630000/48627000/48626943/44b34d55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Resort in the Heart of Bemus Village on CHQ Lake Bemus Point 10/10 Exceptional (195) "This property was amazing! Plenty of space, very clean, and within walking distance of shops and restaurants in Bemus Point and also very close to the lake. The property has an excellent layout, wonderful side and front porches, and is kid friendly. I would highly recommend and we will be staying there again in the future!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zackary F. CA $302 CA $702 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Jamestown-Hotels-Resort-On-Main-In-The-Heart-Of-Bemus-Point-On-Lake-Chautauqua.h48626943.Hotel-Information) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119110000/119100300/119100227/1e9574e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119110000/119100300/119100227/a1276cf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119110000/119100300/119100227/299c982a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/120000000/119110000/119100300/119100227/63a56818.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 20 Park-Walk to Everything CHQ-Pets OK-Free Bikes Chautauqua 10/10 Exceptional (1) "It was a very clean house with spacious areas including a full apartment upstairs. It was one of the better places we have ever stayed at as far as accommodations go. Highly recommended! Thank you." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Bill T. CA $261 CA $608 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Mayville-Hotels-20-Park-Walk-To-Everything-CHQ-Pets-OK-Free-Bikes.h119100227.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/98000000/97080000/97078800/97078739/4648ceff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/98000000/97080000/97078800/97078739/b59dbb3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/98000000/97080000/97078800/97078739/763869e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/98000000/97080000/97078800/97078739/83d1566d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quaint historic home in the heart of Bemus Point Village- a stroll to the water! Bemus Point 10/10 Exceptional (27) "Loved our stay in this quaint home! Great location, very clean, plenty of room for our family of six, and included everything we needed for our visit to Bemus Point. Highly recommend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Colleen G. CA $258 CA $651 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Bemus-Point-Hotels-Quaint-Historic-Home-In-The-Heart-Of-Bemus-Point-Village-A-Stroll-To-The-Water.h97078739.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110690000/110688100/110688006/477b9b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110690000/110688100/110688006/63890e40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/111000000/110690000/110688100/110688006/f6e437f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/111000000/110690000/110688100/110688006/853af5e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Main St Bemus-HOT TUB-1 Block from Lake Ellery 10/10 Exceptional (5) "Enjoyed the property and our stay in Bemus Point. The home was clean and comfortable. Plenty of space for multiple families. We enjoyed the firepit several nights and the smores bar was a special treat. The home is walkable to Bemus Point restaurants and shops. We would highly recommend staying at this home and we hope to return in the near future. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bart C. CA $306 CA $720 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Bemus-Point-Hotels-Main-St-Bemus-1-Block-From-Lake.h110688006.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/95000000/95000000/94994100/94994040/92f04ce7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/95000000/95000000/94994100/94994040/50e15195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/95000000/95000000/94994100/94994040/d620216a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/95000000/95000000/94994100/94994040/w905h683x60y0-65faed99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LAKE VIEW. TWO MASTER BEDROOMS. PARKING. LOCATION! Chautauqua CA $280 CA $722 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Mayville-Hotels-LAKE-VIEW-TWO-MASTER-BEDROOMS-PARKING-LOCATION.h94994040.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=2025-11-11&endDate=2025-11-12®ionId=553248635975875351&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.d553248635975875351-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.d553248635975875351-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![Secluded Chautauqua Lake House, private dock & beach, short stroll to town!](//images.trvl-media.com/lodging/65000000/65000000/64995600/64995546/038ceb78_y.jpg) ### Secluded Chautauqua Lake House, private dock & beach, short stroll to town! 10/10 Excellent "Great stay, very clean house, decorated so cute, definitely a cottagy feel. Very well stocked kitchen, everything we needed. Great view of the lake. We had a wonderful time." [](https://expedia.ca/Jamestown-Hotels-100-Feet-Lakefront-Secluded-Resort-Property.h64995546.Hotel-Information) ![Peek'n Peak Resort Trademark Collection by Wyndham](//images.trvl-media.com/lodging/6000000/5270000/5261700/5261672/b2139787_y.jpg) ### Peek'n Peak Resort Trademark Collection by Wyndham 10/10 Excellent "We were in the area for a wedding,staff at front desk were great" [](https://expedia.ca/Jamestown-Hotels-Peekn-Peak-Resort-Trademark-Collection-By-Wyndham.h5261672.Hotel-Information) ![Hampton Inn & Suites Jamestown](//images.trvl-media.com/lodging/2000000/1470000/1460400/1460358/dc17262d_y.jpg) ### Hampton Inn & Suites Jamestown 10/10 Excellent "Beautiful setting. Friendly staff. Clean hotel and rooms. Convenient to town and dining. " [](https://expedia.ca/Jamestown-Hotels-Hampton-Inn-Suites-Jamestown.h1460358.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Jamestown](//images.trvl-media.com/lodging/1000000/980000/978100/978061/3af0ac86_y.jpg) ### La Quinta Inn & Suites by Wyndham Jamestown 10/10 Excellent "clean room, staff was helpful and knowledgeable about the area and things to do." [](https://expedia.ca/Jamestown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Jamestown.h978061.Hotel-Information) ![Chautauqua Harbor Hotel - Jamestown](//images.trvl-media.com/lodging/24000000/23840000/23832100/23832022/a14ac39d_y.jpg) ### Chautauqua Harbor Hotel - Jamestown 10/10 Excellent "." [](https://expedia.ca/Celoron-Hotels-Chautauqua-Harbor-Hotel-Jamestown.h23832022.Hotel-Information) ![Charming Resort in the Heart of Bemus Village on CHQ Lake](//images.trvl-media.com/lodging/49000000/48630000/48627000/48626943/6bd0fe23_y.jpg) ### Charming Resort in the Heart of Bemus Village on CHQ Lake 10/10 Excellent "Clean house and bedrooms. Spacious. Large lot. Located in quaint village setting. Nice large front and side porches. Host was responsive and listing was accurate. " [](https://expedia.ca/Jamestown-Hotels-Resort-On-Main-In-The-Heart-Of-Bemus-Point-On-Lake-Chautauqua.h48626943.Hotel-Information) ![Cobblestone Inn & Suites - Corry](//images.trvl-media.com/lodging/10000000/9020000/9013700/9013700/c9a7af98_y.jpg) ### Cobblestone Inn & Suites - Corry 10/10 Excellent "Easy parking , good food and coffee. Fast and easy check in. " [](https://expedia.ca/Corry-Hotels-Cobblestone-Inn-Suites-Corry.h9013700.Hotel-Information) ![Athenaeum Hotel](//images.trvl-media.com/lodging/38000000/37530000/37523600/37523548/44104d5d_y.jpg) ### Athenaeum Hotel 10/10 Excellent "This Grand Lady was a very impressive vintage hotel with charm and elegance. Room was much more updated than expected, staff couldn’t have been nicer and the grounds were spectacular! " [](https://expedia.ca/Jamestown-Hotels-Athenaeum-Hotel.h37523548.Hotel-Information) ![DoubleTree by Hilton Jamestown](//images.trvl-media.com/lodging/1000000/20000/11500/11426/8fd588ff_y.jpg) ### DoubleTree by Hilton Jamestown 10/10 Excellent "Excellent customer service. Very friendly and accommodating. Our room was clean and inviting. The location was great. We enjoyed ourselves very. Also, the cookies were awesome! Thank you!!" [](https://expedia.ca/Jamestown-Hotels-DoubleTree-By-Hilton-Jamestown.h11426.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Vacation Homes information | Number of reviews | 299 | | --- | --- | | Accommodation | 136 Vacation Homes | | Lowest Price | CA $208 | | Highest Price | CA $722 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in Centerville](https://www.expedia.ca/4Star-Centerville-Hotels.s40-0-d553248634998807404.Travel-Guide-Filter-Hotels) - [Allegheny National Forest Hotels](https://www.expedia.ca/Allegheny-National-Forest-Hotels.d6090475.Travel-Guide-Hotels) - [Hotels near Allegheny River](https://www.expedia.ca/Allegheny-River-Hotels.0-l553248621532660618-0.Travel-Guide-Filter-Hotels) - [Canadohta Lake Hotels](https://www.expedia.ca/Canadohta-Lake-Hotels.d553248634999200459.Travel-Guide-Hotels) - [Cheap Hotels in Centerville](https://www.expedia.ca/Centerville-Hotels-Cheap-Hotels.0-0-d553248634998807404-tCheapHotels.Travel-Guide-Filter-Hotels) - 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