Title: Book the Best Pittsfield FAMILY FRIENDLY Hotels from CA $168 - Kid-Friendly Hotels in Pittsfield, VT | Expedia.ca [Pittsfield Travel Guide](https://expedia.ca/Pittsfield.dx184066)[Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d184066.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d184066.Travel-Guide-VacationRentals)[Flights to Pittsfield](https://expedia.ca/Cheap-Flights-To-Pittsfield.d184066.Travel-Guide-Flights)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d184066.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.ca/Pittsfield.d184066.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/family_friendly.jpeg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Family Hotels in Pittsfield, VT from CA $168 - ![](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 availability on Pittsfield Family Hotels Tonight [Nov 8 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-11-08&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Nov 9 - Nov 10](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-11-09&endDate=2025-11-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Top Pittsfield Family Hotels ![House, 4 Bedrooms | Exterior](https://images.trvl-media.com/lodging/108000000/107560000/107550500/107550402/3b0a27aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 4 Bedrooms | Outdoor spa tub](https://images.trvl-media.com/lodging/108000000/107560000/107550500/107550402/504f7a89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 4 Bedrooms](https://images.trvl-media.com/lodging/108000000/107560000/107550500/107550402/0af54003.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 4 Bedrooms | Dining](https://images.trvl-media.com/lodging/108000000/107560000/107550500/107550402/c881e78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Getaway 4 Bedroom Home Pittsfield CA $590 CA $1,351 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Pittsfield-Hotels-The-Getaway-4-Bedroom-Home.h107550402.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107530000/107521000/107520989/5220a9fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107530000/107521000/107520989/7719248c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/108000000/107530000/107521000/107520989/be0c8839.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/108000000/107530000/107521000/107520989/1f0b9c8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes! Pittsfield CA $463 CA $1,144 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Pittsfield-Hotels-The-Getaway-Relax-With-Hot-Tub.h107520989.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/15d4fef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/325364db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/5b9c435c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/62720c61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Rutland - Killington Rutland 8.0/10 Very good (1003) "Clean, great steak house by the hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caridad CA $154 CA $169 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Rutland-Hotels-Comfort-Inn-Trolley-Square.h4621.Hotel-Information) ![Classic Room, 2 Queen Beds](https://images.trvl-media.com/lodging/12000000/11490000/11480100/11480085/5dc2814c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/12000000/11490000/11480100/11480085/03ebd066.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/12000000/11490000/11480100/11480085/42f23c30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11490000/11480100/11480085/05005b52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Middlebury Sweets Motel Middlebury 8.6/10 Excellent (384) "Friendly staff, clean, comfortable and convenient to downtown. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa CA $153 CA $168 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Middlebury-Hotels-Middlebury-Sweets-Motel.h11480085.Hotel-Information) ![Standard Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/0612ebf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/bed9fca9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/f6266999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/db156eb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Star Lodge and Resort Killington 8.6/10 Excellent (1002) "Was perfect for our one night stay " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Ian CA $183 CA $201 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information) ![Deluxe Suite](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/7b3a7c11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/32c31fca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Accessible, Dog-Friendly Double](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/53cc1cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/d5194d53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Woodstock Motel Woodstock 9.6/10 Exceptional (540) "Great motel with complete amenities.. beautiful surrounding especially in this fall" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Giana CA $145 CA $222 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Woodstock-Hotels-Sleep-Woodstock-Motel.h9658860.Hotel-Information) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/29356441.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/72849c1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/374f8e02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/3cca622a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Mountain Inn at Killington Killington 9.2/10 Wonderful (934) "Excellent hotel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristan CA $168 CA $194 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/403a8548.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/2b1767e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/f9bd2dd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Billiards](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/b1730c3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Killington Mountain Lodge, Tapestry Collection by Hilton Killington 7.4/10 Good (1001) "Room was spotless and comfortable. Dog friendly, hassle free stay. Cleanliness was top tier, and staff was fantastic!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Desiree CA $184 CA $202 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information) ![Children's activities](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/baea9aeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/8d6bfa64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/125b9e2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### On The River Inn West Woodstock 9.4/10 Exceptional (1019) "The setting was beautiful, great amenities on site, complementary hot breakfast was delicious, lots of storage in the room. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah CA $212 CA $285 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16500/16411/9898f616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-fridge, microwave, coffee/tea maker](https://images.trvl-media.com/lodging/1000000/20000/16500/16411/e396a59f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16500/16411/b3171c2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds, Non Smoking, Kitchen (Third bed is a Sofabed)](https://images.trvl-media.com/lodging/1000000/20000/16500/16411/4b3b98ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Inn & Suites Rutland-Killington Rutland 8.8/10 Excellent (1000) "Fantastic place to stay. It was clean, comfortable and inviting. Staff were friendly and hospitable. Would stay here again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elexis CA $226 CA $249 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Rutland-Hotels-Best-Western-Inn-Suites-Rutland-Killington.h16411.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=2025-11-22&endDate=2025-11-23®ionId=184066&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Pittsfield Hotel Reviews ![Killington Mountain Lodge, Tapestry Collection by Hilton](//images.trvl-media.com/lodging/1000000/110000/103700/103640/403a8548_y.jpg) ### Killington Mountain Lodge, Tapestry Collection by Hilton 10/10 Excellent "Room was spotless and comfortable. Dog friendly, hassle free stay. Cleanliness was top tier, and staff was fantastic!" [](https://expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information) ![The Shire Woodstock](//images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Great place to stay" [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![The Mountain Inn at Killington](//images.trvl-media.com/lodging/1000000/980000/975400/975389/29356441_y.jpg) ### The Mountain Inn at Killington 10/10 Excellent "Excellent hotel. " [](https://expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information) ![Comfort Inn Rutland - Killington](//images.trvl-media.com/lodging/1000000/10000/4700/4621/15d4fef0_y.jpg) ### Comfort Inn Rutland - Killington 10/10 Excellent "Quiet and low key. " [](https://expedia.ca/Rutland-Hotels-Comfort-Inn-Trolley-Square.h4621.Hotel-Information) ![On The River Inn](//images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/528a7f5b_y.jpg) ### On The River Inn 10/10 Excellent "The restaurant was very nice. Great service. Delicious food." [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Woodstock Inn & Resort](//images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg) ### Woodstock Inn & Resort 10/10 Excellent "The staff were so welcoming and friendly! When we got engaged they all cheered for us and were so sweet!" [](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) ![Days Inn by Wyndham Rutland/Killington Area](//images.trvl-media.com/lodging/1000000/890000/889600/889570/2b102593_y.jpg) ### Days Inn by Wyndham Rutland/Killington Area 10/10 Excellent "The breakfast selection was good with eggs, sausage, toast, bagels, waffles, fresh fruit, cereal, yogurt. The room was clean however the bathroom could use updating but was adequate. " [](https://expedia.ca/Rutland-Hotels-Days-Inn-By-Wyndham-RutlandKillington-Area.h889570.Hotel-Information) ![North Star Lodge and Resort](//images.trvl-media.com/lodging/1000000/190000/185900/185873/0612ebf1_y.jpg) ### North Star Lodge and Resort 10/10 Excellent "The hotel is located up a hill in a nice town, and is very peaceful and quiet. The room was clean. I have no complaints. I would definitely stay here again." [](https://expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information) ![Greenbrier Inn](//images.trvl-media.com/lodging/2000000/1180000/1176800/1176792/e5569f51_y.jpg) ### Greenbrier Inn 10/10 Excellent "Hotel decor | Continental breakfast" [](https://expedia.ca/Killington-Hotels-Greenbrier-Inn.h1176792.Hotel-Information) ## Frequently asked questions ### What's Pittsfield like for family-friendly vacations? > You might want to consider the welcoming destination of Pittsfield if you've been thinking about a trip for the whole family. The restaurants here makes this an attractive vacation spot for families. Take to the air and fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is located 18.1 mi (29.2 km) from the city center. ### When's the best time to book a family-friendly vacation in Pittsfield? > The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 23°F. The snowiest months in Pittsfield are January, March, February, and December, with each month seeing an average of 10 inches of snowfall. ### What's there to see and do with your family in Pittsfield? > While you and your family are visiting Pittsfield, you might want to check out some kid-friendly attractions such as Roger Clark Memorial Central Library and Pico Mountain at Killington Ski Resort. 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