Title: Book the Best PET FRIENDLY Hotels in Sheffield, MA from CA $328 - 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) ![](https://mediaim.expedia.com/destination/1/0c91d6ccb27784bad8a181efd70e605a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Pet-friendly Hotels in Sheffield, MA from CA $328 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Sep 15 - Sep 16](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-09-15&endDate=2025-09-16&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 16 - Sep 17](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-09-16&endDate=2025-09-17&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 19 - Sep 21](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-09-19&endDate=2025-09-21&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-09-26&endDate=2025-09-28&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Sheffield Pet-friendly Hotels ![Dining](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/9fa6f837.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) ![Exterior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/edf60411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/13f82703.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Guesthouse Cabin vacation rentals in Berkshire County Sheffield 10/10 Exceptional (9) "Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. " CA $511 CA $962 total includes taxes & fees Sep 16 - Sep 17 [](https://www.expedia.ca/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/109000000/108970000/108962900/108962866/b98061a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining tables](https://images.trvl-media.com/lodging/109000000/108970000/108962900/108962866/e296f608_edited_2926.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/109000000/108970000/108962900/108962866/5ee60839.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108970000/108962900/108962866/fe732a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Race Mountain House Sheffield 9.2/10 Wonderful (5) "I spent my 60th birthday with a few friends at Mountain House and it was even better than I dreamed. The comfort and simplicity of the decor along with the mountain views. A must for those who like simple elegance." [](https://www.expedia.ca/Sheffield-Hotels-The-Race-Mountain-House.h108962866.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/28000000/27130000/27129600/27129515/46c8a41a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27130000/27129600/27129515/1e626f4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/28000000/27130000/27129600/27129515/7d583158.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27130000/27129600/27129515/751b9826.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Antique Farmhouse Totally Restored Sheffield 10/10 Exceptional (91) "Enjoyed the property, location and charming house that was well stocked with everything we needed." [](https://www.expedia.ca/Sheffield-Hotels-Antique-Farmhouse-Totally-Restored.h27129515.Hotel-Information) ![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) ![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) ![Dining](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/8f9296e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheerful 3-bedroom cottage with woodstove Sheffield 10/10 Exceptional (39) "The property was centrally located for skiing, and was a comfortable stay." CA $328 CA $685 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/89000000/88340000/88338100/88338003/dc374c2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/89000000/88340000/88338100/88338003/53147420.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88340000/88338100/88338003/97afaec9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball](https://images.trvl-media.com/lodging/89000000/88340000/88338100/88338003/3950c197.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Whitney by AvantStay | Private Berkshires Estate Sheffield 8.4/10 Very good (12) "Great old house with charming details and well equipped with modern conveniences. The views outside of the mountains and meadow next door were a nice bonus. Communication and attentiveness to any questions or issues were quickly taken care of. Overall a great trip!" [](https://www.expedia.ca/Sheffield-Hotels-Whitney-By-AvantStay-Private-Berkshires-Estate.h88338003.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/91000000/90930000/90929700/90929611/4db3e78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90930000/90929700/90929611/344420b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms](https://images.trvl-media.com/lodging/91000000/90930000/90929700/90929611/2a5680c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90930000/90929700/90929611/4c779a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Whitney by Avantstay Private Berkshires Estate Sheffield [](https://www.expedia.ca/Sheffield-Hotels-Whitney-By-Avantstay-Private-Berkshires-Estate.h90929611.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35680000/35672200/35672127/e3f5175b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, offices](https://images.trvl-media.com/lodging/36000000/35680000/35672200/35672127/b9146e48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/36000000/35680000/35672200/35672127/c72a0644.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/36000000/35680000/35672200/35672127/5c38b0d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Little House in the Woods by Evergreen Home Sheffield 10/10 Exceptional (33) "This was a perfect quiet serene location on a beautiful property. Would love to visit again" [](https://www.expedia.ca/Sheffield-Hotels-Little-House-In-The-Woods.h35672127.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119160000/119155800/119155752/f222de62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119160000/119155800/119155752/4e19cbbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119160000/119155800/119155752/729642c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/120000000/119160000/119155800/119155752/4d24b65f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW Beautiful Berkshires Farmhouse Sheffield [](https://www.expedia.ca/Sheffield-Hotels-NEW-Beautiful-Berkshires-Farmhouse.h119155752.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/50000000/49010000/49000800/49000721/44994e8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/50000000/49010000/49000800/49000721/230e646f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/50000000/49010000/49000800/49000721/10cad851.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/50000000/49010000/49000800/49000721/651b2c43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music Sheffield 9.8/10 Exceptional (36) "We really enjoyed our stay here - location was great and being surrounded by the lake was amazing. The owner was super responsive and helped us out with a minor issue right away. Highly recommend!" [](https://www.expedia.ca/Sheffield-Hotels-PRIVATE-PENINSULA-2ac-Surrounded-By-Water-Min-From-Hiking-Skiing-Theater-Music.h49000721.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/80000000/79650000/79648900/79648835/136ad812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/80000000/79650000/79648900/79648835/12409178.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/80000000/79650000/79648900/79648835/a5b3ac5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/80000000/79650000/79648900/79648835/eb33d488.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Orchard Meadow Sheffield 8.0/10 Very good (1) "Comfortable and centrally located to beautiful surroundings and towns." [](https://www.expedia.ca/Sheffield-Hotels-River-Orchard-Meadow.h79648835.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=2025-09-29&endDate=2025-09-30®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](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "A-1 made you feel you were in 1800 " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ## Explore a world of travel with Expedia - Explore a world of travel with Expedia ### Find More Hotels near Sheffield - [Pet-friendly Hotels in Boston](https://expedia.ca/Boston-Hotels-Pet-Friendly-Hotel.0-0-d178239-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) ### More Hotel Options in Sheffield - [Historic Hotels in Sheffield](https://expedia.ca/Sheffield-Hotels-Historic-Hotel.0-0-d157238-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Sheffield](https://expedia.ca/Sheffield-Hotels-Hotels-With-Kitchenettes.0-0-d157238-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Sheffield](https://expedia.ca/Sheffield-Hotels-Hotel-With-Pool.0-0-d157238-tHotelwithPool.Travel-Guide-Filter-Hotels) ### More Accommodation Types in Sheffield - [Vacation Homes in Massachusetts](https://expedia.ca/Massachusetts-Private-Vacation-Homes.d223-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Apartments in Massachusetts](https://expedia.ca/Massachusetts-Apartments.d223-aaApartments.Travel-Guide-Accommodation) - [Cottages in Massachusetts](https://expedia.ca/Massachusetts-Cottages.d223-aaCottages.Travel-Guide-Accommodation) - [Condo Rentals in Massachusetts](https://expedia.ca/Massachusetts-Condos.d223-aaCondos.Travel-Guide-Accommodation) - [B&B in Massachusetts](https://expedia.ca/Massachusetts-Bed-And-Breakfast.d223-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Motels in Massachusetts](https://expedia.ca/Massachusetts-Motels.d223-aaMotels.Travel-Guide-Accommodation) - [Guest Houses in Massachusetts](https://expedia.ca/Massachusetts-Guest-Houses.d223-aaGuestHouses.Travel-Guide-Accommodation) - [Cabin Rentals in Massachusetts](https://expedia.ca/Massachusetts-Cabins.d223-aaCabins.Travel-Guide-Accommodation) - [Resorts in Massachusetts](https://expedia.ca/Massachusetts-Resort-Hotels.d223-aaResortHotels.Travel-Guide-Accommodation) - [Aparthotels in Massachusetts](https://expedia.ca/Massachusetts-Apart-Hotels.d223-aaApartHotels.Travel-Guide-Accommodation) - [Farmstay in Massachusetts](https://expedia.ca/Massachusetts-Agritourism.d223-aaAgritourism.Travel-Guide-Accommodation) - [Inns in Massachusetts](https://expedia.ca/Massachusetts-Inns.d223-aaInns.Travel-Guide-Accommodation) - [Houseboats in Massachusetts](https://expedia.ca/Massachusetts-Houseboats.d223-aaHouseboats.Travel-Guide-Accommodation) - [Villas in Massachusetts](https://expedia.ca/Massachusetts-Villas.d223-aaVillas.Travel-Guide-Accommodation) - [Hostels in Massachusetts](https://expedia.ca/Massachusetts-Hostels.d223-aaHostels.Travel-Guide-Accommodation) - [Lodges in Massachusetts](https://expedia.ca/Massachusetts-Lodges.d223-aaLodges.Travel-Guide-Accommodation) - [Chalets in Massachusetts](https://expedia.ca/Massachusetts-Chalets.d223-aaChalets.Travel-Guide-Accommodation) - [Condo Resorts in Massachusetts](https://expedia.ca/Massachusetts-Condominium-Resort.d223-aaCondominiumResort.Travel-Guide-Accommodation) - [RV Parks in Massachusetts](https://expedia.ca/Massachusetts-RV-Parks.d223-aaRVParks.Travel-Guide-Accommodation) - [Holiday Park Resorts in Massachusetts](https://expedia.ca/Massachusetts-Holiday-Parks.d223-aaHolidayParks.Travel-Guide-Accommodation) - [Castles in Massachusetts](https://expedia.ca/Massachusetts-Castles.d223-aaCastles.Travel-Guide-Accommodation) - [Country Houses in Massachusetts](https://expedia.ca/Massachusetts-Country-House.d223-aaCountryHouse.Travel-Guide-Accommodation) - [Residences in Massachusetts](https://expedia.ca/Massachusetts-Residences.d223-aaResidences.Travel-Guide-Accommodation) - [Townhomes in Massachusetts](https://expedia.ca/Massachusetts-Townhomes.d223-aaTownhomes.Travel-Guide-Accommodation) ### Hotels near popular Sheffield Attractions - [Hotels near Magnolia Bluffs Casino](https://expedia.ca/Magnolia-Bluffs-Casino-Hotels.0-l553248621532644877-0.Travel-Guide-Filter-Hotels) - [Hotels near Ashley House](https://expedia.ca/Ashley-House-Hotels.0-l553248621532664810-0.Travel-Guide-Filter-Hotels) - [Hotels near Tanglewood Music Center](https://expedia.ca/Tanglewood-Music-Center-Hotels.0-l503292-0.Travel-Guide-Filter-Hotels) - [Hotels near National Shrine of the Divine Mercy](https://expedia.ca/National-Shrine-Of-The-Divine-Mercy-Hotels.0-l553248621532665250-0.Travel-Guide-Filter-Hotels) - [Hotels near Catamount Ski Area](https://expedia.ca/Catamount-Ski-Area-Hotels.0-l6087211-0.Travel-Guide-Filter-Hotels) - [Hotels near Lime Rock Park](https://expedia.ca/Lime-Rock-Park-Hotels.0-l6127072-0.Travel-Guide-Filter-Hotels) - [Hotels near Mohawk Mountain Ski Area](https://expedia.ca/Mohawk-Mountain-Ski-Area-Hotels.0-l6182064-0.Travel-Guide-Filter-Hotels) - [Hotels near Norman Rockwell Museum](https://expedia.ca/Norman-Rockwell-Museum-Hotels.0-l6091839-0.Travel-Guide-Filter-Hotels) - [Hotels near Ski Butternut](https://expedia.ca/Ski-Butternut-Hotels.0-l6182072-0.Travel-Guide-Filter-Hotels) - [Hotels near Lee Premium Outlets](https://expedia.ca/Lee-Premium-Outlets-Hotels.0-l6127084-0.Travel-Guide-Filter-Hotels) ### Sheffield Hotels by Star Rating - [4 Star Hotels in Sheffield](https://expedia.ca/4Star-Sheffield-Hotels.s40-0-d157238.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Sheffield](https://expedia.ca/3Star-Sheffield-Hotels.s30-0-d157238.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Sheffield](https://expedia.ca/2Star-Sheffield-Hotels.s20-0-d157238.Travel-Guide-Filter-Hotels) ### Explore more hotels - [Holiday Inn Express & Suites Pittsfield - Berkshires by IHG](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) - [Hampton Inn & Suites Berkshires-Lenox](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) - [Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) - [The Ponds at Foxhollow](https://expedia.ca/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.Hotel-Information) - [The Constance by the Lenox Collection](https://expedia.ca/Lenox-Hotels-Rookwood-Inn.h4945461.Hotel-Information) - [Quality Inn](https://expedia.ca/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) - [Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires](https://expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) - [the Alander](https://expedia.ca/Copake-Hotels-The-Alander.h74111256.Hotel-Information) - [Blackberry River Inn](https://expedia.ca/Norfolk-Hotels-Blackberry-River-Inn.h95991149.Hotel-Information) - [Berkshire Travel Lodge](https://expedia.ca/Albany-Hotels-Berkshire-Travel-Lodge.h1793522.Hotel-Information) - [Courtyard by Marriott Lenox Berkshires](https://expedia.ca/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.Hotel-Information) - [The Whitlock](https://expedia.ca/Lenox-Hotels-The-Whitlock.h66244754.Hotel-Information) - [Prospect Berkshires](https://expedia.ca/Great-Barrington-Hotels-Prospect-Berkshires.h116739795.Hotel-Information) - [The Little Lion](https://expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) - [Element Lenox Berkshires](https://expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) - [Hilton Garden Inn Lenox Pittsfield](https://expedia.ca/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information) - [Travelodge by Wyndham Great Barrington Berkshires](https://expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) - [Monument Mountain Motel](https://expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) - [The Cornell Inn, Lenox & The Berkshires](https://expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information) - [Chatham Travel Lodge](https://expedia.ca/Old-Chatham-Hotels-Chatham-Travel-Lodge.h12095246.Hotel-Information) [See a list of all hotels in Sheffield](https://expedia.ca/All-Sheffield-Hotels.d157238.Travel-Guide-City-All-Hotels) ### More ways to book - [Book Pet-friendly Hotels in Sheffield on Expedia.com](https://www.expedia.com/Sheffield-Hotels-Pet-Friendly-Hotel.0-0-d157238-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) ### Expedia's Latest Trends Hotels - [Best Hotels in Lowell](https://expedia.ca/Lowell-Hotels.d8422.Travel-Guide-Hotels) - [Best Hotels in Nantucket](https://expedia.ca/Nantucket-Hotels.d285.Travel-Guide-Hotels) - [Best Hotels in Plymouth](https://expedia.ca/Plymouth-Hotels.d9512.Travel-Guide-Hotels) - [Best Hotels in Andover](https://expedia.ca/Andover-Hotels.d5997.Travel-Guide-Hotels) - [Best Hotels in Worcester](https://expedia.ca/Worcester-Hotels.d6023336.Travel-Guide-Hotels) - [Best Hotels in Falmouth](https://expedia.ca/Falmouth-Hotels.d7287.Travel-Guide-Hotels) - [Best Hotels in Provincetown](https://expedia.ca/Provincetown-Hotels.d2909.Travel-Guide-Hotels) - [Best Hotels in Mansfield](https://expedia.ca/Mansfield-Hotels.d8456.Travel-Guide-Hotels) - [Best Hotels in Foxboro](https://expedia.ca/Foxboro-Hotels.d8136.Travel-Guide-Hotels) - [Best Hotels in Marlborough](https://expedia.ca/Marlborough-Hotels.d8869.Travel-Guide-Hotels) - [Best Hotels in Lenox](https://expedia.ca/Lenox-Hotels.d8587.Travel-Guide-Hotels) - [Best Hotels in Springfield](https://expedia.ca/Springfield-Hotels.d6047669.Travel-Guide-Hotels) - [Best Hotels in Amherst](https://expedia.ca/Amherst-Hotels.d5948.Travel-Guide-Hotels) - [Best Hotels in Hyannis](https://expedia.ca/Hyannis-Hotels.d1544.Travel-Guide-Hotels) - [Best Hotels in Fall River](https://expedia.ca/Fall-River-Hotels.d6057.Travel-Guide-Hotels) - [Best Hotels in Rockport](https://expedia.ca/Rockport-Hotels.d6350.Travel-Guide-Hotels) Flights - [Flights to HFD](https://expedia.ca/Cheap-Flights-To-Springfield.d6047669.Travel-Guide-Flights) - [Flights to PVD](https://expedia.ca/Cheap-Flights-To-Foxboro.d8136.Travel-Guide-Flights) - [Flights to ORH](https://expedia.ca/Cheap-Flights-To-Harvard.d3000441113.Travel-Guide-Flights) Activities - [Things to do in Gloucester](https://expedia.ca/Things-To-Do-In-Gloucester.d8008.Travel-Guide-Activities) - [Things to do in Provincetown](https://expedia.ca/Things-To-Do-In-Provincetown.d2909.Travel-Guide-Activities) Packages - [Halifax Vacation Packages](https://expedia.ca/Halifax.d6139204.Destination-Travel-Guides) - [Nantucket Vacation Packages](https://expedia.ca/Nantucket.d285.Destination-Travel-Guides) General - [Visit Great Barrington](https://expedia.ca/Great-Barrington.dx110336) - [Visit Worcester](https://expedia.ca/Worcester.dx6023336) - [Visit Shelburne Falls](https://expedia.ca/Shelburne-Falls.dx6294302) - [Visit Rockport](https://expedia.ca/Rockport.dx6350) - [Visit Centerville](https://expedia.ca/Centerville.dx88031) - [Visit West Yarmouth](https://expedia.ca/West-Yarmouth.dx10485) - [Visit Manchester-by-the-Sea](https://expedia.ca/Manchester-By-The-Sea.dx129363) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)