Title: Pittsfield Vacation Rentals from $192: Search Short-Term Rentals | Expedia.com [Pittsfield Travel Guide](https://expedia.com/Pittsfield.dx184066)[Hotels in Pittsfield](https://expedia.com/Pittsfield-Hotels.d184066.Travel-Guide-Hotels)[Flights to Pittsfield](https://expedia.com/Cheap-Flights-To-Pittsfield.d184066.Travel-Guide-Flights)[Car Rentals in Pittsfield](https://expedia.com/Car-Rentals-In-Pittsfield.d184066.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.com/Pittsfield.d184066.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?impolicy=fcrop&w=1200&h=500&q=medium) ## Check prices for these dates In two weeks [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pittsfield vacation rentals ![Condo, 2 Bedrooms | Exterior](https://images.trvl-media.com/lodging/91000000/90030000/90027700/90027667/71b245e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 2 Bedrooms | Dining](https://images.trvl-media.com/lodging/91000000/90030000/90027700/90027667/4a5f95c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90030000/90027700/90027667/eb1b9bb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/91000000/90030000/90027700/90027667/6607861d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Killington [](https://www.expedia.com/Killington-Hotels-Fall-Line-Condos-By-Killington-VR-2-Bedrooms.h90027667.Hotel-Information) [](https://www.expedia.com/Killington-Hotels-Fall-Line-Condos-By-Killington-VR-2-Bedrooms.h90027667.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/101000000/101000000/100996900/100996829/2925807e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 3 Bedrooms | View from room](https://images.trvl-media.com/lodging/101000000/101000000/100996900/100996829/cf0bfccb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/101000000/101000000/100996900/100996829/dca1ec05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/101000000/101000000/100996900/100996829/a2bbfdb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo resort in Killington [](https://www.expedia.com/Killington-Hotels-Mountain-Green.h100996829.Hotel-Information) 7.4/10 Good (21 reviews) "Great !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raul $227 nightly $250 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Killington-Hotels-Mountain-Green.h100996829.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/17000000/16350000/16341300/16341282/bf24c523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/17000000/16350000/16341300/16341282/27dce88b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/17000000/16350000/16341300/16341282/96663a9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin 5 (Pet Friendly) - Owl's Branch | Exterior](https://images.trvl-media.com/lodging/17000000/16350000/16341300/16341282/4ce94b9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in Ripton [](https://www.expedia.com/Ripton-Hotels-Robert-Frost-Mountain-Cabins.h16341282.Hotel-Information) 10/10 Exceptional (40 reviews) "Ammazing,would go again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph $254 nightly $277 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Ripton-Hotels-Robert-Frost-Mountain-Cabins.h16341282.Hotel-Information) ![House, 6 Bedrooms | Living area](https://images.trvl-media.com/lodging/91000000/90030000/90027900/90027835/1f9e32bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 6 Bedrooms | Living area](https://images.trvl-media.com/lodging/91000000/90030000/90027900/90027835/8c4c5576.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/91000000/90030000/90027900/90027835/d9eeb9b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 3 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/91000000/90030000/90027900/90027835/8921270b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Killington [](https://www.expedia.com/Killington-Hotels-Breakaway-House-By-Killington-Vacation-Rentals.h90027835.Hotel-Information) [](https://www.expedia.com/Killington-Hotels-Breakaway-House-By-Killington-Vacation-Rentals.h90027835.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/91000000/90020000/90018700/90018667/bc4ee60b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 1 Bedroom | Interior](https://images.trvl-media.com/lodging/91000000/90020000/90018700/90018667/506781aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 1 Bedroom | Dining](https://images.trvl-media.com/lodging/91000000/90020000/90018700/90018667/79d090a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 1 Bedroom | Interior](https://images.trvl-media.com/lodging/91000000/90020000/90018700/90018667/432da712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Killington [](https://www.expedia.com/Killington-Hotels-Fall-Line-Condos-By-Killington-VR-1-Bedrooms.h90018667.Hotel-Information) [](https://www.expedia.com/Killington-Hotels-Fall-Line-Condos-By-Killington-VR-1-Bedrooms.h90018667.Hotel-Information) ![House, 2 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/118000000/117900000/117893100/117893016/e0869d09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 2 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/118000000/117900000/117893100/117893016/ff5bcf7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 2 Bedrooms | Terrace/patio](https://images.trvl-media.com/lodging/118000000/117900000/117893100/117893016/1ffa3f6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 2 Bedrooms | Interior](https://images.trvl-media.com/lodging/118000000/117900000/117893100/117893016/9c4fd6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in North Sherburne [](https://www.expedia.com/Killington-Hotels-Killington-A-Frame-2-Bedroom-Home.h117893016.Hotel-Information) $668 nightly $735 total Mar 16 - Mar 17 Total with taxes and fees [](https://www.expedia.com/Killington-Hotels-Killington-A-Frame-2-Bedroom-Home.h117893016.Hotel-Information) ![Condo, 2 Bedrooms | Pool | Indoor pool, a heated pool](https://images.trvl-media.com/lodging/124000000/123560000/123553200/123553104/c377788d_edited_9e69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 2 Bedrooms | Dining](https://images.trvl-media.com/lodging/124000000/123560000/123553200/123553104/0bc702ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/124000000/123560000/123553200/123553104/9404fb9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 2 Bedrooms | Exterior](https://images.trvl-media.com/lodging/124000000/123560000/123553200/123553104/7fc9a136.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Killington [](https://www.expedia.com/Killington-Hotels-Mountain-Green-Condo-2b4-2-Bedroom-Condo.h123553104.Hotel-Information) $749 nightly $824 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Killington-Hotels-Mountain-Green-Condo-2b4-2-Bedroom-Condo.h123553104.Hotel-Information) ![House, 3 Bedrooms | Living area | Smart TV](https://images.trvl-media.com/lodging/123000000/122050000/122041900/122041868/a1129868.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 3 Bedrooms | Living area | Smart TV](https://images.trvl-media.com/lodging/123000000/122050000/122041900/122041868/b809177b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 3 Bedrooms | Property grounds](https://images.trvl-media.com/lodging/123000000/122050000/122041900/122041868/d2d26b6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 3 Bedrooms | Living area | Smart TV](https://images.trvl-media.com/lodging/123000000/122050000/122041900/122041868/c7b27b75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Killington [](https://www.expedia.com/Killington-Hotels-Blue-Haven-3-Bedroom-Home.h122041868.Hotel-Information) $935 nightly $1,028 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Killington-Hotels-Blue-Haven-3-Bedroom-Home.h122041868.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.com/Hotel-Search?startDate=2026-03-26&endDate=2026-03-27®ionId=184066&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=VR_SPRING_PROMO_184066) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=CABIN) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=VACATION_HOME) Condos [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=CONDO) Apartments [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=APARTMENT) Cottages [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=COTTAGE) Chalets [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=CHALET) Villas [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=VILLA) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Vacation-Rentals.d184066.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Vacation-Rentals.d184066.Travel-Guide-VacationRentals) ## Top Pittsfield Hotel Reviews ![North Star Lodge and Resort](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/17fcad53_y.jpg) ### North Star Lodge and Resort 10/10 Excellent "Nice place to stay and room had a view of Superstar slope. " [](https://expedia.com/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information) ![Summit Lodge](https://images.trvl-media.com/lodging/2000000/1110000/1102600/1102506/bdef58fa_y.jpg) ### Summit Lodge 2/10 Terrible "We had a horrible stay and will not stay at this hotel again. This hotel has a lot of problems. The temperature in the room was so hot and the thermostat did not work. I ended up having to open the window and the door to cool the room down. The hot water took over 10 minutes to warm up. On our second and third nights, there was no water from about 6pm to 10pm. I saw one guest dip a small empty trash can in the hot tub to fill it with water so he could flush the toilet in his room. He was very upset. The beds are old, squeaky, and uncomfortable due to one side sunk lower than the other (likely due to guests sleeping in the same over a period of years). But the worst thing is that after we sat down for the breakfast buffet on our last day. My son found an approximately quarter inch silver hexagonal bolt on his plate (I have a photo), which appear to have been embedded in the home fries/potatoes. This was such a shock. I have never seen or experienced anything like that. Why would a bolt be embedded in the food? I immediately reported the incident to the front desk clerk and she went and got the lady/server/attendant responsible for the breakfast buffet. She took a look and appeared surprised but simply said she had no idea how it got there, apologized, and asked me for my room number. Fortunately, my son saw it and luckily he did not scoop it into his mouth, which certainly would have broken his tooth. I request a full refund from this hotel. Horrible experience. Unforgivable." [](https://expedia.com/Killington-Hotels-Summit-Lodge.h1102506.Hotel-Information) ![Killington Mountain Lodge, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/f9bd2dd9_y.jpg) ### Killington Mountain Lodge, Tapestry Collection by Hilton 10/10 Excellent "Great place! Close to the mountain and restaurants on access road. " [](https://expedia.com/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information) ![The Mountain Inn at Killington](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/29356441_y.jpg) ### The Mountain Inn at Killington 10/10 Excellent "Love staying here. Staff is amazing! Super attentive. Great food at the restaurant. Cozy lodge feel. Basically on the mountain Without being ski in ski out. This is where I always stay when visiting killington. " [](https://expedia.com/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information) ![Mountain Sports Inn](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/fae277d0_y.jpg) ### Mountain Sports Inn 10/10 Excellent "The property is " [](https://expedia.com/Killington-Hotels-Mountain-Sports-Inn.h1339833.Hotel-Information) ![Killington Haus](https://images.trvl-media.com/lodging/124000000/123370000/123364300/123364293/84d48d73_y.jpg) ### Killington Haus 10/10 Excellent "Great location! Ramen restaurant awesome, kind housekeepers, nice board racks, game room, etc! See ya next time! Thanks!" [](https://expedia.com/Killington-Hotels-Killington-Haus.h123364293.Hotel-Information) ![My Place Hotel-Randolph VT](https://images.trvl-media.com/lodging/106000000/105670000/105665800/105665795/430b34b8_y.jpg) ### My Place Hotel-Randolph VT 10/10 Excellent "Rooms were very spacious and clean. Pillows were super fluffy as was the comforter. An amazing night sleep for sure." [](https://expedia.com/My-Place-Hotel-Randolph-VT.h105665795.Hotel-Information) ![Brandon Inn](https://images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/194828e3_y.jpg) ### Brandon Inn 10/10 Excellent "Slopes are close enough and it's worth it to get away from all the craziness! Brandon is a gem of a town and the Inn was a delight!" [](https://expedia.com/Brandon-Hotels-Brandon-Inn.h25184647.Hotel-Information) ![Days Inn by Wyndham Rutland/Killington Area](https://images.trvl-media.com/lodging/1000000/890000/889600/889570/4a1f2dfa_y.jpg) ### Days Inn by Wyndham Rutland/Killington Area 8/10 Good "The staff was very friendly, although I had some bathroom problems at first. Luckily, when I complained, they moved me to a better room. Otherwise, I liked it." [](https://expedia.com/Rutland-Hotels-Days-Inn-By-Wyndham-RutlandKillington-Area.h889570.Hotel-Information) ## Find out more about Pittsfield **Everything you need to know about Pittsfield vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on. There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **Pittsfield vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Pittsfield. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pittsfield in high season. Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $192 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals! **How to find incredible deals on Pittsfield rentals** At Expedia, we put the best Pittsfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. To find some top Pittsfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsfield vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pittsfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. ## Explore a world of travel with Expedia - Trending destinations on Expedia.com - All accommodation types in Pittsfield ### Trending destinations on Expedia.com - [Destin Vacation Rentals ](https://www.expedia.com/Destin-Vacation-Rentals.d6906.Travel-Guide-VacationRentals) - [Panama City Vacation Rentals ](https://www.expedia.com/Panama-City-Beach-Vacation-Rentals.d8021.Travel-Guide-VacationRentals) - [Hilton Head Vacation Rentals ](https://www.expedia.com/Hilton-Head-Island-Vacation-Rentals.d601684.Travel-Guide-VacationRentals) - [Gulf Shores Vacation Rentals ](https://www.expedia.com/Gulf-Shores-Vacation-Rentals.d603078.Travel-Guide-VacationRentals) - [Key West Vacation Rentals ](https://www.expedia.com/Key-West-Vacation-Rentals.d1187.Travel-Guide-VacationRentals) - [Gatlinburg Vacation Rentals ](https://www.expedia.com/Gatlinburg-Vacation-Rentals.d7474.Travel-Guide-VacationRentals) - 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