Title: Book the Best PET FRIENDLY Hotels in Sheffield, MA from CA $115 - 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) ![](https://images.trvl-media.com/place/157238/14d96789-8e82-406f-8456-70392b70b95e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Jan 25 - Jan 26](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-01-25&endDate=2026-01-26&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 26 - Jan 27](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-01-26&endDate=2026-01-27&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-01-30&endDate=2026-02-01&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-02-06&endDate=2026-02-08&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Sheffield pet-friendly hotels ![Interior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/eca50f2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/a764aae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/51b9c734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/d00ad195.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 reviews) "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 $538 CA $950 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/251da7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/06dae0ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/754813dc.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) ### Element Lenox Berkshires [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) Lenox 9.8/10 Exceptional (17 reviews) "Spotless rooms and the friendliest service at the front desk! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $190 CA $213 total includes taxes & fees Feb 1 - Feb 2 [](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) ![Deluxe Suite, Private Bathroom (Garden - Pets Allowed) | Miscellaneous](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/c68ae4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, Private Bathroom (Honeymoon - Pets Allowed)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/7ac0f2b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, Private Bathroom (Clark - Pets Allowed)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/04b1723e.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 (444 reviews) "The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carin CA $145 CA $160 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/00c971b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/6a32b13e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/53f3f179.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 (1,001 reviews) "Room was clean and the staff was super friendly and helpful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ethan CA $139 CA $155 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb.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) ![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/6a569eff.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 (844 reviews) "So charming, clean, thoughtful touches and a really special place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Juliana CA $121 CA $135 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/f84b737e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/8dbc27a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Mobility Accessible](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/9c5d1ec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### The Little Lion [](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) Great Barrington 8.6/10 Excellent (550 reviews) "Perfect for pets " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $151 CA $168 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.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) ![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/e351f473.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/c5a54031.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 (567 reviews) "Excellent location!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abdul Samad CA $103 CA $115 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74120000/74111300/74111256/a75d4cd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Room, 1 King Bed](https://images.trvl-media.com/lodging/75000000/74120000/74111300/74111256/4b9b80d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 1 King Bed](https://images.trvl-media.com/lodging/75000000/74120000/74111300/74111256/0f83c46b.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 (197 reviews) "Nice room and reasonable prices! Will recommend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jianyang CA $163 CA $183 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Copake-Hotels-The-Alander.h74111256.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/d8fde5b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/320c2d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One King Studio Sofabed Non Smoking | View from room](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/w3837h2559x0y0-777976aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/601f8574.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Berkshires-Lenox [](https://www.expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) Lenox 9.2/10 Wonderful (1,002 reviews) "The room and amenities were amazing. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $152 CA $170 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/51000000/50880000/50873900/50873824/25fee020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/51000000/50880000/50873900/50873824/6d6ce66a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/51000000/50880000/50873900/50873824/2ff1c815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/51000000/50880000/50873900/50873824/835e48b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Granville House [](https://www.expedia.ca/Housatonic-Hotels-Granville-House.h50873824.Hotel-Information) Housatonic 10/10 Exceptional (92 reviews) "Absolutely magical at Christmas time! It was only for a quick overnight but felt like time stood still while we were there. The service was impeccable and Terry and Terri were a delight! I look forward to returning. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $238 CA $266 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Housatonic-Hotels-Granville-House.h50873824.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=2026-02-09&endDate=2026-02-10®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 "The room was large, clean and comfortable. The breakfast was good and the staff was great. The hotel is a little bit quaint which I enjoy and why I go there. The only issue was the shower took a while for the water to heat up." [](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 "Quiet and beautiful environment. Room is clean. Friendly and helpful front desk staff." [](https://expedia.ca/Torrington-Hotels-Interlaken-Inn-Resort.h19679605.Hotel-Information) ## Frequently asked questions ### How much does a pet-friendly hotel in Sheffield cost? ### Which area of Sheffield is best to stay in for pet-friendly hotels? > This area is convenient for travellers as it's the main route through Sheffield, offering easy access to various amenities. You'll find a selection of hotels here that welcome pets, often with dedicated facilities or policies to accommodate them. It's a practical choice for those travelling with animal companions. > > > Couples travelling with pets will find this area suitable due to the convenience of hotels located directly on US-7\. Many of these establishments are near walking paths and open spaces, superb for exercising pets. ### How do I ensure I have booked a pet-friendly room in Sheffield? ### What pet-friendly activities should we do in Sheffield? > For active travellers and their canine companions, a walk along the Appalachian Trail offers a rewarding experience. There are several access points in and around Sheffield, providing varying lengths and difficulties of trails. You'll find picturesque New England scenery, and it's a great way for both you and your pet to get some exercise in the fresh air. > > > Another excellent option is Bartholomew's Cobble, a nature preserve managed by The Trustees. This area is known for its unique geological formations and diverse plant life, and dogs are welcome on leads. It's a lovely spot for a leisurely hike, with well-maintained paths that wind through woodlands and along the Housatonic River. ### What amenities should I look for in a pet-friendly hotel in Sheffield? ### How can I save on a pet-friendly hotel in Sheffield with Expedia? ### Do any Sheffield hotels have restrictions on pet sizes or breeds? ### Is it cheaper to book flights and a pet-friendly hotel in Sheffield as a package? ### Can I cancel my pet-friendly hotel reservation on Expedia? ## 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) - 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