Title: Sheffield Guest Houses from CA $425 | 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 prices for these dates Next weekend [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-04-24&endDate=2026-04-26&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-05-22&endDate=2026-05-24&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Sheffield guest houses ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/103000000/102470000/102462900/102462881/5ec352f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102470000/102462900/102462881/ca444bdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/103000000/102470000/102462900/102462881/761b9b0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/103000000/102470000/102462900/102462881/7c480e6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hudson valley and The Berkshires Cottage [](https://www.expedia.ca/Hillsdale-Hotels-Hudson-Valley-And-The-Berkshires-Cottage.h102462881.Hotel-Information) Hillsdale 10/10 Exceptional (18 reviews) "Very clean and great for a couples trip!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sean C. CA $114 CA $425 total includes taxes & fees Apr 15 - Apr 16 [](https://www.expedia.ca/Hillsdale-Hotels-Hudson-Valley-And-The-Berkshires-Cottage.h102462881.Hotel-Information) ![The Garden Suite](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/8d4ea02b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Parlor Suite | Living area](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/fe8573a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/0b5f32ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Loft Suite | Terrace/patio](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/892e10da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 9 Academy [](https://www.expedia.ca/Salisbury-Hotels-9-Academy.h102680999.Hotel-Information) Salisbury 9.2/10 Wonderful (11 reviews) "Extremely clean and the rooms are beautifully decorated with warm minimal decor. We will definitely be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gina CA $679 CA $781 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Salisbury-Hotels-9-Academy.h102680999.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=2026-04-06&endDate=2026-04-07®ionId=157238&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSheffield-Guest-Houses.d157238-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSheffield-Guest-Houses.d157238-aaGuestHouses.Travel-Guide-Accommodation) ## Top Sheffield Hotel Reviews ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "Staff was very friendly and helpful" [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "Great place to enjoy with the whole family!!!" [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![The Whitlock](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/f0d9797c_y.jpg) ### The Whitlock 10/10 Excellent "The facility is unfortunately only staffed 2-8pm daily. None of exterior doors lock at night. Front desk staff was very helpful. The place was very clean and convenient to shops and restaurants." [](https://expedia.ca/Lenox-Hotels-The-Whitlock.h66244754.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Great property to stay - clean comfortable and close to many attractions in the Berkshire area" [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb_y.jpg) ### Berkshires Untold 10/10 Excellent "Wonderful place, great toiletries and great friendly staff. We will be back" [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "This is our 3rd year staying here for my son’s birthday in March. Affordable and having the 2 rooms with a kitchen is so nice. My son’s favorite part is the pool which is always warm and clean, never smells too strong like some places. Hot tub feels amazing too. Will be back next year, or sooner :)" [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Interlaken Inn & Resort](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/dbbfdf3a_y.jpg) ### Interlaken Inn & Resort 10/10 Excellent "Overall great amenities and great price" [](https://expedia.ca/Torrington-Hotels-Interlaken-Inn-Resort.h19679605.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/d8fde5b0_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 4/10 Poor "Hotel under construction/renovations. No hot water for morning shower." [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![The Cornell Inn, Lenox & The Berkshires](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/63812de9_y.jpg) ### The Cornell Inn, Lenox & The Berkshires 10/10 Excellent "Clean, quiet, and a great breakfast! The staff was friendly. We enjoyed a fire in our room and the free bottle of wine. " [](https://expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information) ## Find out more about Sheffield ## Sheffield Guest Houses information | Number of reviews | 29 | | ----------------- | -------------- | | Accommodation | 9 Guest Houses | | Lowest Price | CA $425 | | Highest Price | CA $781 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [3 Star Hotels in The Berkshires ](https://www.expedia.ca/3Star-The-Berkshires-Hotels.s30-0-d6047665.Travel-Guide-Filter-Hotels) - [5 Star Hotels in The Berkshires ](https://www.expedia.ca/5Star-The-Berkshires-Hotels.s50-0-d6047665.Travel-Guide-Filter-Hotels) - [Alford Hotels ](https://www.expedia.ca/Alford-Hotels.d3000421226.Travel-Guide-Hotels) - [Farmstay in Ashley Falls ](https://www.expedia.ca/Ashley-Falls-Agritourism.d901768766462177280-aaAgritourism.Travel-Guide-Accommodation) - [Boutique Hotels in Great Barrington ](https://www.expedia.ca/Great-Barrington-Hotels-Boutique-Hotel.0-0-d110336-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Great Barrington ](https://www.expedia.ca/Great-Barrington-Hotels-Cheap-Hotels.0-0-d110336-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Great Barrington ](https://www.expedia.ca/Great-Barrington-Hotels-Hotel-With-Pool.0-0-d110336-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Great Barrington ](https://www.expedia.ca/Great-Barrington-Hotels-Hotels-With-Hot-Tubs.0-0-d110336-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Great Barrington ](https://www.expedia.ca/Great-Barrington-Hotels-Hotels-With-Indoor-Pool.0-0-d110336-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Great Barrington ](https://www.expedia.ca/Great-Barrington-Hotels-Luxury-Hotel.0-0-d110336-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Great Barrington ](https://www.expedia.ca/Great-Barrington-Hotels-Pet-Friendly-Hotel.0-0-d110336-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Great Barrington ](https://www.expedia.ca/Great-Barrington-Hotels-Spa-Hotel.0-0-d110336-tSpaHotel.Travel-Guide-Filter-Hotels) - [Great Barrington Hotels ](https://www.expedia.ca/Great-Barrington-Hotels.d110336.Travel-Guide-Hotels) - [Housatonic Hotels ](https://www.expedia.ca/Housatonic-Hotels.d3000441135.Travel-Guide-Hotels) - [Hotels near Mahaiwe Performing Arts Center ](https://www.expedia.ca/Mahaiwe-Performing-Arts-Center-Hotels.0-l553248621532665242-0.Travel-Guide-Filter-Hotels) - [Farmstay in Mill River ](https://www.expedia.ca/Mill-River-Agritourism.d3000748895-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Mill River ](https://www.expedia.ca/Mill-River-Apart-Hotels.d3000748895-aaApartHotels.Travel-Guide-Accommodation) - [Cabin Rentals in Mill River ](https://www.expedia.ca/Mill-River-Cabins.d3000748895-aaCabins.Travel-Guide-Accommodation) - [Chalets in Mill River ](https://www.expedia.ca/Mill-River-Chalets.d3000748895-aaChalets.Travel-Guide-Accommodation) - [Cottages in Mill River ](https://www.expedia.ca/Mill-River-Cottages.d3000748895-aaCottages.Travel-Guide-Accommodation) - [Guest Houses in Mill River ](https://www.expedia.ca/Mill-River-Guest-Houses.d3000748895-aaGuestHouses.Travel-Guide-Accommodation) - [Mill River Hotels ](https://www.expedia.ca/Mill-River-Hotels.d3000748895.Travel-Guide-Hotels) - [Inns in Mill River ](https://www.expedia.ca/Mill-River-Inns.d3000748895-aaInns.Travel-Guide-Accommodation) - [Motels in Mill River ](https://www.expedia.ca/Mill-River-Motels.d3000748895-aaMotels.Travel-Guide-Accommodation) - [Resorts in Mill River ](https://www.expedia.ca/Mill-River-Resort-Hotels.d3000748895-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in Mill River ](https://www.expedia.ca/Mill-River-Townhomes.d3000748895-aaTownhomes.Travel-Guide-Accommodation) - [Family Hotels in Monterey ](https://www.expedia.ca/Monterey-Hotels-Family-Hotel.0-0-d6005411-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Monterey ](https://www.expedia.ca/Monterey-Hotels-Hotel-With-Pool.0-0-d6005411-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Monterey ](https://www.expedia.ca/Monterey-Hotels-Hotels-With-Balconies.0-0-d6005411-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Monterey ](https://www.expedia.ca/Monterey-Hotels-Luxury-Hotel.0-0-d6005411-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Monterey Hotels ](https://www.expedia.ca/Monterey-Hotels.d6005411.Travel-Guide-Hotels) - [Farmstay in Mount Washington ](https://www.expedia.ca/Mount-Washington-Agritourism.d553248634999242901-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Mount Washington ](https://www.expedia.ca/Mount-Washington-Apart-Hotels.d553248634999242901-aaApartHotels.Travel-Guide-Accommodation) - [Apartments in Mount Washington ](https://www.expedia.ca/Mount-Washington-Apartments.d553248634999242901-aaApartments.Travel-Guide-Accommodation) - [B&B in Mount Washington ](https://www.expedia.ca/Mount-Washington-Bed-And-Breakfast.d553248634999242901-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Mount Washington ](https://www.expedia.ca/Mount-Washington-Chalets.d553248634999242901-aaChalets.Travel-Guide-Accommodation) - [Condo Resorts in Mount Washington ](https://www.expedia.ca/Mount-Washington-Condominium-Resort.d553248634999242901-aaCondominiumResort.Travel-Guide-Accommodation) - [Guest Houses in Mount Washington ](https://www.expedia.ca/Mount-Washington-Guest-Houses.d553248634999242901-aaGuestHouses.Travel-Guide-Accommodation) - [Holiday Park Resorts in Mount Washington ](https://www.expedia.ca/Mount-Washington-Holiday-Parks.d553248634999242901-aaHolidayParks.Travel-Guide-Accommodation) - [Cheap Hotels in Mount Washington ](https://www.expedia.ca/Mount-Washington-Hotels-Cheap-Hotels.0-0-d553248634999242901-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Mount Washington ](https://www.expedia.ca/Mount-Washington-Hotels-Hotel-With-Pool.0-0-d553248634999242901-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Mount Washington ](https://www.expedia.ca/Mount-Washington-Hotels-Luxury-Hotel.0-0-d553248634999242901-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Mount Washington Hotels ](https://www.expedia.ca/Mount-Washington-Hotels.d553248634999242901.Travel-Guide-Hotels) - [Inns in Mount Washington ](https://www.expedia.ca/Mount-Washington-Inns.d553248634999242901-aaInns.Travel-Guide-Accommodation) - [Lodges in Mount Washington ](https://www.expedia.ca/Mount-Washington-Lodges.d553248634999242901-aaLodges.Travel-Guide-Accommodation) - [Motels in Mount Washington ](https://www.expedia.ca/Mount-Washington-Motels.d553248634999242901-aaMotels.Travel-Guide-Accommodation) - [Resorts in Mount Washington ](https://www.expedia.ca/Mount-Washington-Resort-Hotels.d553248634999242901-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in Mount Washington ](https://www.expedia.ca/Mount-Washington-Townhomes.d553248634999242901-aaTownhomes.Travel-Guide-Accommodation) - [B&B in New Marlborough ](https://www.expedia.ca/New-Marlborough-Bed-And-Breakfast.d137834-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in New Marlborough ](https://www.expedia.ca/New-Marlborough-Guest-Houses.d137834-aaGuestHouses.Travel-Guide-Accommodation) - [Boutique Hotels in New Marlborough ](https://www.expedia.ca/New-Marlborough-Hotels-Boutique-Hotel.0-0-d137834-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in New Marlborough ](https://www.expedia.ca/New-Marlborough-Hotels-Luxury-Hotel.0-0-d137834-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [New Marlborough Hotels ](https://www.expedia.ca/New-Marlborough-Hotels.d137834.Travel-Guide-Hotels) - [Resorts in New Marlborough ](https://www.expedia.ca/New-Marlborough-Resort-Hotels.d137834-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in New Marlborough ](https://www.expedia.ca/New-Marlborough-Townhomes.d137834-aaTownhomes.Travel-Guide-Accommodation) - [Sandisfield Hotels ](https://www.expedia.ca/Sandisfield-Hotels.d6005416.Travel-Guide-Hotels) - [Hotels near Ski Butternut ](https://www.expedia.ca/Ski-Butternut-Hotels.0-l6182072-0.Travel-Guide-Filter-Hotels) - [B&B in South Egremont ](https://www.expedia.ca/South-Egremont-Bed-And-Breakfast.d183341-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Pet-Friendly Hotels in South Egremont ](https://www.expedia.ca/South-Egremont-Hotels-Pet-Friendly-Hotel.0-0-d183341-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [South Egremont Hotels ](https://www.expedia.ca/South-Egremont-Hotels.d183341.Travel-Guide-Hotels) - [Inns in South Egremont ](https://www.expedia.ca/South-Egremont-Inns.d183341-aaInns.Travel-Guide-Accommodation) - [Luxury Hotels in Southfield ](https://www.expedia.ca/Southfield-Hotels-Luxury-Hotel.0-0-d6339785-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Southfield Hotels ](https://www.expedia.ca/Southfield-Hotels.d6339785.Travel-Guide-Hotels) - [Cheap Hotels in The Berkshires ](https://www.expedia.ca/The-Berkshires-Hotels-Cheap-Hotels.0-0-d6047665-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in The Berkshires ](https://www.expedia.ca/The-Berkshires-Hotels-Family-Hotel.0-0-d6047665-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in The Berkshires ](https://www.expedia.ca/The-Berkshires-Hotels-Golf-Hotel.0-0-d6047665-tGolfHotel.Travel-Guide-Filter-Hotels) - [Hilton Hotels in The Berkshires ](https://www.expedia.ca/The-Berkshires-Hotels-Hilton-Hotels.0-0-d6047665--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Hotels with Childcare in The Berkshires ](https://www.expedia.ca/The-Berkshires-Hotels-Hotels-With-Childcare.0-0-d6047665-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in The Berkshires ](https://www.expedia.ca/The-Berkshires-Hotels-Hotels-With-Free-Breakfast.0-0-d6047665-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Luxury Hotels in The Berkshires ](https://www.expedia.ca/The-Berkshires-Hotels-Luxury-Hotel.0-0-d6047665-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in The Berkshires ](https://www.expedia.ca/The-Berkshires-Hotels-Oceanfront-Hotels.0-0-d6047665-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Spa Hotels in The Berkshires ](https://www.expedia.ca/The-Berkshires-Hotels-Spa-Hotel.0-0-d6047665-tSpaHotel.Travel-Guide-Filter-Hotels) - [The Berkshires Hotels ](https://www.expedia.ca/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels) - [Flights to Great Barrington ](https://www.expedia.ca/Cheap-Flights-To-Great-Barrington.d110336.Travel-Guide-Flights) - [Flights to Monterey ](https://www.expedia.ca/Cheap-Flights-To-Monterey.d6005411.Travel-Guide-Flights) - [Flights to The Berkshires ](https://www.expedia.ca/Cheap-Flights-To-The-Berkshires.d6047665.Travel-Guide-Flights) - [Flights from New York to The Berkshires ](https://www.expedia.ca/lp/flights/178293/6047665/new-york-to-the-berkshires) - [Flights from Ottawa to The Berkshires ](https://www.expedia.ca/lp/flights/178296/6047665/ottawa-to-the-berkshires) - [Flights from Toronto to The Berkshires ](https://www.expedia.ca/lp/flights/178314/6047665/toronto-to-the-berkshires) - [Flights from Monterey ](https://www.expedia.ca/lp/flights/6005411/flights-from-monterey) - [Visit Ashley Falls ](https://www.expedia.ca/Ashley-Falls.dx901768766462177280) - [Great Barrington Vacations ](https://www.expedia.ca/Great-Barrington.d110336.Destination-Travel-Guides) - [Visit Great Barrington ](https://www.expedia.ca/Great-Barrington.dx110336) - [Lake Buel ](https://www.expedia.ca/Lake-Buel-Great-Barrington.d553248635976196476.Vacation-Attraction) - [Lake Mansfield Park ](https://www.expedia.ca/Lake-Mansfield-Park-Great-Barrington.d553248621560926695.Vacation-Attraction) - [Visit North Egremont ](https://www.expedia.ca/North-Egremont.dx553248635976384751) - [South Egremont Vacations ](https://www.expedia.ca/South-Egremont.d183341.Destination-Travel-Guides) - [Visit South Egremont ](https://www.expedia.ca/South-Egremont.dx183341) - [The Berkshires Vacations ](https://www.expedia.ca/The-Berkshires.d6047665.Destination-Travel-Guides) - [Visit The Berkshires ](https://www.expedia.ca/The-Berkshires.dx6047665) - [Budget Rental Cars in The Berkshires ](https://www.expedia.ca/Budget-Car-Rentals-In-The-Berkshires.d6047665-c39.Car-Rental-Guide-Suppliers) - [Car rental Great Barrington ](https://www.expedia.ca/Car-Rentals-In-Great-Barrington.d110336.Car-Rental-Guide) - [Car rentals near The Berkshires ](https://www.expedia.ca/Car-Rentals-In-The-Berkshires.d6047665.Car-Rental-Guide) - [Enterprise Rental Cars in Great Barrington ](https://www.expedia.ca/Enterprise-Car-Rentals-In-Great-Barrington.d110336-c15.Car-Rental-Guide-Suppliers) - [Enterprise Rental Cars in New Marlborough ](https://www.expedia.ca/Enterprise-Car-Rentals-In-New-Marlborough.d137834-c15.Car-Rental-Guide-Suppliers) - [Hertz Rental Cars in The Berkshires ](https://www.expedia.ca/Hertz-Car-Rentals-In-The-Berkshires.d6047665-c40.Car-Rental-Guide-Suppliers) - [Mex Rent A Car Rental Cars in Mount Washington ](https://www.expedia.ca/Mex-Rent-A-Car-Car-Rentals-In-Mount-Washington.d553248634999242901-c1084.Car-Rental-Guide-Suppliers) - [Great Barrington Vacation Rentals ](https://www.expedia.ca/Great-Barrington-Vacation-Rentals.d110336.Travel-Guide-VacationRentals) - [Mount Washington Vacation Rentals ](https://www.expedia.ca/Mount-Washington-Vacation-Rentals.d553248634999242901.Travel-Guide-VacationRentals) - [The Berkshires Vacation Rentals ](https://www.expedia.ca/The-Berkshires-Vacation-Rentals.d6047665.Travel-Guide-VacationRentals) - [Book Guest Houses in Sheffield on Expedia.com ](https://www.expedia.com/Sheffield-Guest-Houses.d157238-aaGuestHouses.Travel-Guide-Accommodation)