Title: Book the Best Pittsfield Hotels with FREE WIFI in 2025 | 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/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Wifi in Pittsfield, VT from CA $137 ![](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 Hotels with Wifi Tonight [Oct 27 - Oct 28](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-10-27&endDate=2025-10-28&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 28 - Oct 29](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-10-28&endDate=2025-10-29&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Pittsfield Hotels with Wifi ![Front of property](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/7b3b252e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/783dc891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/75edb3bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, free cribs/infant beds](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/816d0aac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Sports Inn The Woods 8.8/10 Excellent (969) "This is a great place to stay. Attentive staff, easy parking, lots of options on the continental breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lana CA $124 CA $137 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Killington-Hotels-Mountain-Sports-Inn.h1339833.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1530000/1523000/1522922/f4f05fc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![32-inch LCD TV with cable channels, TV, pay movies](https://images.trvl-media.com/lodging/2000000/1530000/1523000/1522922/14edbde8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1530000/1523000/1522922/d77eacdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1530000/1523000/1522922/075005f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Rutland Rutland 9.0/10 Wonderful (954) "Friendly staff, comfortable bed, very clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas CA $182 CA $201 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Rutland-Hotels-Hampton-Inn-Rutland.h1522922.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/9000000/8280000/8270200/8270194/8c210e59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Queen Room with Spring](https://images.trvl-media.com/lodging/9000000/8280000/8270200/8270194/23d8da75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/9000000/8280000/8270200/8270194/98d3a06f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Queen Room with View](https://images.trvl-media.com/lodging/9000000/8280000/8270200/8270194/dc02869f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Valley Retreat Killington 9.6/10 Exceptional (189) "Absolutely lovely stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $154 CA $174 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Killington-Hotels-Mountain-Valley-Retreat.h8270194.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) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/18beef69.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) ### The Mountain Inn at Killington Killington 9.2/10 Wonderful (928) "Nice accommodations, very inviting and friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott CA $185 CA $214 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/5b9c435c.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) ![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 (1005) "Nice, quiet and clean hotel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CARLOS CA $153 CA $169 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Rutland-Hotels-Comfort-Inn-Trolley-Square.h4621.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/ec2b6d3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/5aae86a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/869870f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/0a464c94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brandon Inn Brandon 8.6/10 Excellent (550) "Great charming stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tessa CA $156 CA $172 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Brandon-Hotels-Brandon-Inn.h25184647.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) ![Deluxe Suite](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/4dec58ad.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) ### Sleep Woodstock Motel Woodstock 9.6/10 Exceptional (539) "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 $182 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Woodstock-Hotels-Sleep-Woodstock-Motel.h9658860.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/12000000/11490000/11480100/11480085/03ebd066.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 (382) "Friendly staff, clean, comfortable and convenient to downtown. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa CA $137 CA $151 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Middlebury-Hotels-Middlebury-Sweets-Motel.h11480085.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/05237c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee and/or coffee maker](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/302c3d84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/a73c2787.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Shire Woodstock Woodstock 8.8/10 Excellent (865) "great location and the staff were great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheryl CA $162 CA $189 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.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) ![Game room](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/0dbf9fa1.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) ![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 (1003) "Great stay!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $182 CA $201 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.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=184066&adults=2&amenities=WIFI&sort=RECOMMENDED&openPlayBack=true) ## Top Pittsfield Hotel Reviews ![Woodstock Inn & Resort](//images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg) ### Woodstock Inn & Resort 10/10 Excellent "This was our ideal hotel! Charmingly decorated, functional, and a walking distance to the town. We appreciated the complimentary champagne on our arrival, it was a wonderful place to spend our honeymoon." [](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.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) ![The Shire Woodstock](//images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Beautiful view from the waterside " [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.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 "Beds were ok, fine for 1 night stay. Kids enjoyed pool and I enjoyed hot tub. Breakfast was really good as well." [](https://expedia.ca/Rutland-Hotels-Comfort-Inn-Trolley-Square.h4621.Hotel-Information) ![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 "very nice place " [](https://expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information) ![Mountain Sports Inn](//images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/7b3b252e_y.jpg) ### Mountain Sports Inn 10/10 Excellent "Piaf parking is my only complaint. Seems excessive " [](https://expedia.ca/Killington-Hotels-Mountain-Sports-Inn.h1339833.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 "Everything was great. I will definitely go back. Just next time I would pick a higher room it felt like a basement. But loved it other then that " [](https://expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information) ![Greenbrier Inn](//images.trvl-media.com/lodging/2000000/1180000/1176800/1176792/e5569f51_y.jpg) ### Greenbrier Inn 10/10 Excellent "Didn't have breakfast so I can't comment. I got a sizable room and the setting was central to Killington activities and very quiet." [](https://expedia.ca/Killington-Hotels-Greenbrier-Inn.h1176792.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 room and setting were both relaxing. 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[North Sherburne Hotels](https://www.expedia.ca/North-Sherburne-Killington-Hotels.0-n553248635975848264-0.Travel-Guide-Filter-Hotels) - [Farmstay in Rochester](https://www.expedia.ca/Rochester-Agritourism.d152205-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Rochester](https://www.expedia.ca/Rochester-Apart-Hotels.d152205-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Rochester](https://www.expedia.ca/Rochester-Bed-And-Breakfast.d152205-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Rochester](https://www.expedia.ca/Rochester-Chalets.d152205-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Rochester](https://www.expedia.ca/Rochester-Guest-Houses.d152205-aaGuestHouses.Travel-Guide-Accommodation) - [Hostels in Rochester](https://www.expedia.ca/Rochester-Hostels.d152205-aaHostels.Travel-Guide-Accommodation) - [Rochester Hotels](https://www.expedia.ca/Rochester-Hotels.d152205.Travel-Guide-Hotels) - [Resorts in Rochester](https://www.expedia.ca/Rochester-Resort-Hotels.d152205-aaResortHotels.Travel-Guide-Accommodation) - [Treehouses in Rochester](https://www.expedia.ca/Rochester-Treehouses.d152205-aaTreehouses.Travel-Guide-Accommodation) - [B&B in Stockbridge](https://www.expedia.ca/Stockbridge-Bed-And-Breakfast.d6357893-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cheap Hotels in Stockbridge](https://www.expedia.ca/Stockbridge-Hotels-Cheap-Hotels.0-0-d6357893-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Stockbridge](https://www.expedia.ca/Stockbridge-Hotels-Hotels-With-Balconies.0-0-d6357893-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Stockbridge](https://www.expedia.ca/Stockbridge-Hotels-Pet-Friendly-Hotel.0-0-d6357893-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Stockbridge Hotels](https://www.expedia.ca/Stockbridge-Hotels.d6357893.Travel-Guide-Hotels) - [Vacation Homes in Stockbridge](https://www.expedia.ca/Stockbridge-Private-Vacation-Homes.d6357893-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Flights to Killington](https://www.expedia.ca/Cheap-Flights-To-Killington.d10780.Travel-Guide-Flights) - 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