Title: Book the Best PET FRIENDLY Hotels in Sheffield, MA from CA $116 - Sheffield Dog-Friendly Hotels | Expedia.ca [Hotels in Sheffield](https://expedia.ca/Sheffield-Hotels.d157238.Travel-Guide-Hotels)[Vacation Rentals in Sheffield](https://expedia.ca/Sheffield-Vacation-Rentals.d157238.Travel-Guide-VacationRentals)[Flights to Sheffield](https://expedia.ca/Cheap-Flights-To-Sheffield.d157238.Travel-Guide-Flights)[Sheffield Car Rentals](https://expedia.ca/Car-Rentals-In-Sheffield.d157238.Car-Rental-Guide)[Sheffield Vacation Packages](https://expedia.ca/Sheffield.d157238.Destination-Travel-Guides) ![FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA](https://images.trvl-media.com/place/157238/14d96789-8e82-406f-8456-70392b70b95e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Pet-friendly Hotels in Sheffield, MA from CA $116 - ![](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 Sheffield Pet-friendly Hotels Tonight [Dec 11 - Dec 12](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-12-11&endDate=2025-12-12&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-12-12&endDate=2025-12-13&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Sheffield pet-friendly hotels ![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/665b8282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/f26544ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/8f9296e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/99d3f85f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheerful 3-bedroom cottage with woodstove [](https://www.expedia.ca/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information) Sheffield 10/10 Exceptional (41) "The property was centrally located for skiing, and was a comfortable stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly R. CA $272 CA $613 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/9fa6f837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/edf60411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/565807cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/eca50f2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Guesthouse Cabin vacation rentals in Berkshire County [](https://www.expedia.ca/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.Hotel-Information) Sheffield 10/10 Exceptional (9) "Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) deborah d. CA $565 CA $960 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/c0933de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/f1aeba62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b38994ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker, dining tables](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/5fd0e723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Element Lenox Berkshires [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) Lenox 9.8/10 Exceptional (11) "New hotel very nice" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) joel CA $181 CA $202 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/8e50ee57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, Private Bathroom (Rockwell - No Pets)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/4d5a91f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Apartment, Private Bathroom (Greylock - No Pets)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/9aba043f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Suite, Private Bathroom (Catamount - Pets Allowed)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/13717808.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shaker Mill Inn [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) West Stockbridge 9.6/10 Exceptional (437) "Nice place, easy check in" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $143 CA $157 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) ![Dinner served, American cuisine](https://images.trvl-media.com/lodging/75000000/74120000/74111300/74111256/35e8d8d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Double Room](https://images.trvl-media.com/lodging/75000000/74120000/74111300/74111256/e6217d84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pet-friendly](https://images.trvl-media.com/lodging/75000000/74120000/74111300/74111256/ee2d524f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, American cuisine](https://images.trvl-media.com/lodging/75000000/74120000/74111300/74111256/22d5d509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### the Alander [](https://www.expedia.ca/Copake-Hotels-The-Alander.h74111256.Hotel-Information) Copake 9.0/10 Wonderful (188) "The Alander has such a fun story, and was a great stay. We were just passing through for the night and it had everything we could need! It reminded me of Rosebud Motel group from Schitts Creek ;) if you know you know! Will definitely be staying again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jenna CA $193 CA $216 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Copake-Hotels-The-Alander.h74111256.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Non Lakeside Superior Room, 2 Queen beds](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/d3eea453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ba9d3ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) Lee 9.0/10 Wonderful (1000) "The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elisabeth CA $140 CA $156 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/6fb451ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/c97f0de6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/aaa7fba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/36b54e77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Little Lion [](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) Great Barrington 8.6/10 Excellent (547) "The check-in was easy and the room was ready and clean. It was nice having our dogs with us. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $152 CA $169 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/9b4c64ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Untold [](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) Lenox 9.0/10 Wonderful (813) "Easiest check in and out. Great food in dining room. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $151 CA $169 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/20000000/19190000/19185500/19185424/c93a1f1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![36-inch flat-screen TV with digital channels, TV, DVD player](https://images.trvl-media.com/lodging/20000000/19190000/19185500/19185424/523420f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Ensuite (2nd Floor)](https://images.trvl-media.com/lodging/20000000/19190000/19185500/19185424/dc8b3c09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/20000000/19190000/19185500/19185424/26b177d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Changing Times Boutique Country Lodging [](https://www.expedia.ca/Craryville-Hotels-Changing-Times-Boutique-Country-BB.h19185424.Hotel-Information) Craryville 10/10 Exceptional (109) "Great experience, looking forward to staying again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Greg CA $207 CA $232 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Craryville-Hotels-Changing-Times-Boutique-Country-BB.h19185424.Hotel-Information) ![In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7c78ca51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/fd39ba7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms, Non Smoking](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/723a5f12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7f86e411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Great Barrington Berkshires [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) Great Barrington 7.6/10 Good (562) "The staff were very friendly and accommodating " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tom CA $103 CA $116 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.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=2025-12-25&endDate=2025-12-26®ionId=157238&adults=2&amenities=PETS&sort=RECOMMENDED&openPlayBack=true) ## Find out more about Sheffield ### Discover top Sheffield attractions with your pet In Sheffield, Massachusetts, pet owners can relish a range of activities that cater to their furry companions. Start your day with a stroll through the picturesque Bartholomew's Cobble, where scenic trails weave alongside the Housatonic River, allowing you and your pet to enjoy the serenity of nature. For a unique outing, the nearby Norman Rockwell Museum offers expansive grounds perfect for a picnic with your pet after exploring the exhibits. If you’re keen on some adventure, the Appalachian Trail runs close by, providing stunning views and ample opportunity for hiking with your four-legged friend. The quaint town centre boasts charming shops and cafes with outdoor seating, welcoming pets and creating a relaxed atmosphere for exploring the local culture. When it comes to accommodation, look for pet-friendly hotels in the heart of Sheffield, where you can unwind after a day of adventure. Many of these establishments offer amenities like dog-walking services and pet-friendly dining options, ensuring both you and your pet feel pampered during your stay. ## Top Sheffield Hotel Reviews ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "I love the ambience - historic and comfortable and excellent food. " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Interlaken Inn & Resort](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/dbbfdf3a_y.jpg) ### Interlaken Inn & Resort 10/10 Excellent "Super friendly and pet friendly. We are so grateful to have been able to check in early to finish getting ready for the wedding we attended! Thank you for the hospitality! " [](https://expedia.ca/Torrington-Hotels-Interlaken-Inn-Resort.h19679605.Hotel-Information) ## Frequently asked questions ### What's the best time of year to travel to Sheffield with my pet? ### What is there to see and do with your pet in Sheffield? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Farmstay in Ashley Falls ](https://www.expedia.ca/Ashley-Falls-Agritourism.d901768766462177280-aaAgritourism.Travel-Guide-Accommodation) - [Inns in Egremont ](https://www.expedia.ca/Egremont-Inns.d553248634998707560-aaInns.Travel-Guide-Accommodation) - [B&B in Great Barrington ](https://www.expedia.ca/Great-Barrington-Bed-And-Breakfast.d110336-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Castles in Great Barrington ](https://www.expedia.ca/Great-Barrington-Castles.d110336-aaCastles.Travel-Guide-Accommodation) - [Guest Houses in Great Barrington ](https://www.expedia.ca/Great-Barrington-Guest-Houses.d110336-aaGuestHouses.Travel-Guide-Accommodation) - 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