Title: Hampshire County Cottages from CA $431 | Expedia.ca [Hampshire County Hotels](https://expedia.ca/Destinations-In-Hampshire-County.d3000443223.Hotel-Destinations)[Vacation Rentals in Hampshire County](https://expedia.ca/Destinations-In-Hampshire-County.d3000443223.Vacation-Rental-Destinations)[Hampshire County Car Rentals](https://expedia.ca/Destinations-In-Hampshire-County.d3000443223.Car-Rental-Destinations)[Hampshire County Vacations](https://expedia.ca/Hampshire-County.d3000443223.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/3f77d70c290336829a47f1f8f4f81078.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Hampshire County Cottage Rentals from CA $431 ## Compare and save ![](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 [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=3000443223&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=3000443223&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=3000443223&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=3000443223&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cities in Hampshire County ![](https://mediaim.expedia.com/destination/2/8b79416c267c66a0fe7820cb30d71155.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Amherst [](https://expedia.ca/Amherst-Cottages.d5948-aaCottages.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/62e8fd70ba8b07a5665a19f5becce243.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Northampton [](https://expedia.ca/Northampton-Cottages.d9187-aaCottages.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/429e802d31ae1701bd60611bd011435a.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### South Hadley [](https://expedia.ca/South-Hadley-Cottages.d6747-aaCottages.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/1c480d69ccad89b23bddcbee4c3f5644.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Hadley [](https://expedia.ca/Hadley-Cottages.d11961-aaCottages.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/100852cbeef726e642c42abfdd67fa60.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Belchertown [](https://expedia.ca/Belchertown-Cottages.d3000440953-aaCottages.Travel-Guide-Accommodation) ## Featured Cottages in Hampshire County ![Property grounds](https://images.trvl-media.com/lodging/100000000/99890000/99884200/99884118/e39ce86b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99890000/99884200/99884118/202e2fb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99890000/99884200/99884118/4aaa52e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/100000000/99890000/99884200/99884118/cb267221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake Stafford 9.8/10 Exceptional (26) "This prperty was GREAT! Clean, and very accomadating. Had everything you would need staying there. Didn't get to use the lake but sitting on the deck was relaxing. Will book again. 10 Stars!! Thank You!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) WILLIAM CA $163 CA $431 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Stafford-Hotels-Serene-2-Bedroom.h99884118.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/28000000/27120000/27116600/27116560/33b071c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/28000000/27120000/27116600/27116560/bdfcc84a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27120000/27116600/27116560/f51a799a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27120000/27116600/27116560/8f804994.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Clearing - Quiet - Close To Nature Cummington 10/10 Exceptional (207) "The property was beautiful and well maintained.The home where we stayed was perfect and cozy." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) colleen M. [](https://www.expedia.ca/Cummington-Hotels-The-Clearing-Quiet-Close-To-Nature.h27116560.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102020000/102016300/102016229/w507h683x259y0-2f359260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, stereo](https://images.trvl-media.com/lodging/103000000/102020000/102016300/102016229/w507h683x259y0-84851697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102020000/102016300/102016229/604c75fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/103000000/102020000/102016300/102016229/w506h683x259y0-693460cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brimfield Waterfront cottage Brimfield 10/10 Exceptional (13) "Property is in excellent condition, just the right amount of space for us. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) earl p. [](https://www.expedia.ca/Brimfield-Hotels-Brimfield-Waterfront-Cottage.h102016229.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117460000/117455700/117455678/96eb52a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117460000/117455700/117455678/a9bca719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117460000/117455700/117455678/7c5e7e23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117460000/117455700/117455678/dc84912b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village! Charlton 10/10 Exceptional (6) [](https://www.expedia.ca/Charlton-Hotels-Charming-2-Bedroom-Lakefront-Cottage-Near-Treehouse-Brewery.h117455678.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/68000000/67260000/67255100/67255071/c8b755bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, free WiFi](https://images.trvl-media.com/lodging/68000000/67260000/67255100/67255071/eb0a776d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67260000/67255100/67255071/4b89dca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/68000000/67260000/67255100/67255071/61b3f659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Island - Largest Fresh Water Reservoir in Mass Otis 8.6/10 Excellent (9) "We had a great time. The owner Bill was a great host." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Drew D. [](https://www.expedia.ca/Otis-Hotels-Private-Island-On-Largest-Fresh-Water-Reservoir-In-Mass-Ski-Boat-Included.h67255071.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103820000/103819100/103819022/a44d1ae1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103820000/103819100/103819022/813e5d41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103820000/103819100/103819022/b99e8c9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103820000/103819100/103819022/3ff94f68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Cottage 10 Min From Great Barrington New Marlborough 10/10 Exceptional (99) "very comfortable, great location on the lake, and near good hiking and nice towns" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John M. [](https://www.expedia.ca/Great-Barrington-Hotels-Waterfront-Cottage-10-Min-From-Great-Barrington.h103819022.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/28000000/27120000/27118900/27118877/20175c8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/28000000/27120000/27118900/27118877/8270895c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27120000/27118900/27118877/9d0b4955.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/28000000/27120000/27118900/27118877/270-0f39aab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming historic cottage on scenic road to Mt. Greylock Lanesboro 10/10 Exceptional (117) "What a lovely property! And Rich was just terrific!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](https://www.expedia.ca/Lanesborough-Hotels-Charming-Historic-Cottage-On-Scenic-Road-To-Mt-Greylock.h27118877.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/95000000/94460000/94458700/94458679/779b53f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/95000000/94460000/94458700/94458679/2edf975c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94460000/94458700/94458679/f8e45cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms)](https://images.trvl-media.com/lodging/95000000/94460000/94458700/94458679/83556d4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Massachusetts Vacation Rental w/ Deck Easthampton [](https://www.expedia.ca/Easthampton-Hotels-Massachusetts-Vacation-Rental-W-Deck.h94458679.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/108770000/108763000/108762972/62e20cf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/108770000/108763000/108762972/44ae956c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/108770000/108763000/108762972/ecc7a466.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/108770000/108763000/108762972/1bf3dbbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hawley Home w/ Deck & Mtn Views: Swim, Ski & More! Charlemont 10/10 Exceptional (1) "Loved this old home! Record player and records were fun to listen to. Pickle ball across the street was excellent! Well stocked kitchen great for cooking in. I had a tough time with water pressure and temperature but it could have been user error. Beds were comfortable except for the twin, which was a bit too firm! Would definitely rent here again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy [](https://www.expedia.ca/Charlemont-Hotels-Hawley-Home-W-Deck-Mtn-Views-Swim.h108762972.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/75000000/74450000/74444800/74444701/65dc1ab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74450000/74444800/74444701/3240d16c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, internet, bed sheets](https://images.trvl-media.com/lodging/75000000/74450000/74444800/74444701/7ebdc850.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74450000/74444800/74444701/c684f3a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Trainmaster's Inn - Caboose Palmer 9.6/10 Exceptional (8) "A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward L. CA $209 CA $457 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Palmer-Hotels-Trainmasters-Inn-Caboose.h74444701.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/106000000/105900000/105898600/105898516/34ab57f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/106000000/105900000/105898600/105898516/5749ede8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/106000000/105900000/105898600/105898516/6647b1ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/106000000/105900000/105898600/105898516/1e2b93a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Westfield Vacation Rental w/ Porch, Pets Welcome! Westfield [](https://www.expedia.ca/Westfield-Hotels-Westfield-Vacation-Rental-W-Porch.h105898516.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/24000000/23370000/23361200/23361174/c3a3670e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/24000000/23370000/23361200/23361174/2cf54d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/24000000/23370000/23361200/23361174/e16930a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/24000000/23370000/23361200/23361174/19940ced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Little Dipper Retreat Lakefront Cottage, Sunsets & Kayaks! Holland 10/10 Exceptional (86) "The home was cozy and comfortable. Very peaceful, tranquil location. Felt like we were the only ones on the lake. I highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bobbi B. [](https://www.expedia.ca/Holland-Hotels-Lakefront-Cottage-Sandy-Beach.h23361174.Hotel-Information) ![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/95000000/94370000/94361700/94361677/e5284c84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94370000/94361700/94361677/93530843.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94370000/94361700/94361677/4840c6ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94370000/94361700/94361677/2c894462.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Huntington Home - Walk to Westfield River Huntington 10/10 Exceptional (1) "Beautiful historical house in a rural setting. We were attending performances at Jacob’s Pillow. This house is approximately 20 minutes away, so very convenient." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas [](https://www.expedia.ca/Huntington-Hotels-Historic-Huntington-Home-Walk-To-Westfield-River.h94361677.Hotel-Information) ![House (2 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/95000000/94320000/94314200/94314154/d521de12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94320000/94314200/94314154/88240f1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94320000/94314200/94314154/044af5c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94320000/94314200/94314154/78b5321a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sun-dappled Retreat - Walk to Wickaboag Lake! West Brookfield [](https://www.expedia.ca/West-Brookfield-Hotels-Sun-Dappled-Retreat-Walk-To-Wickaboag-Lake.h94314154.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/95000000/94910000/94905400/94905364/w1024h681x0y0-35b585d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/95000000/94910000/94905400/94905364/85bd5591.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/95000000/94910000/94905400/94905364/c212bf26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/95000000/94910000/94905400/94905364/05ea63ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly! New Marlborough 9.6/10 Exceptional (17) "Smooth check-in and wonderful house in quiet location. The only thing I would add is some more draws in the bedrooms. Highly recommend for a nice getaway." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel B. [](https://www.expedia.ca/Great-Barrington-Hotels-Pine-View-Cottage.h94905364.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94480000/94478900/94478890/575b648c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94480000/94478900/94478890/1898baea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94480000/94478900/94478890/4c9e9db3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94480000/94478900/94478890/8e41f5a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Home w/ Modern Updates on < 4 Acres Royalston 10/10 Exceptional (2) "Great place. Enjoyed our stay. Wish it wasn’t raining so we could’ve enjoyed more of the outdoors." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa [](https://www.expedia.ca/Royalston-Hotels-Historic-Home-W-Modern-Updates-On-35-Acres.h94478890.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98550000/98546200/98546138/8ec53073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98550000/98546200/98546138/40a90154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98550000/98546200/98546138/a4a19ce7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98550000/98546200/98546138/4c263b16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Springfield Vacation Rental Near Downtown Forest Park [](https://www.expedia.ca/Springfield-Hotels-Cozy-Springfield-Vacation-Rental-Near-Downtown.h98546138.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94330000/94329400/94329371/00875219.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94330000/94329400/94329371/dccdd841.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94330000/94329400/94329371/5b3158c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94330000/94329400/94329371/edd95b7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charlemont Retreat on Chickley River w/ EV Charger Charlemont 10/10 Exceptional (1) "Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stacy [](https://www.expedia.ca/Charlemont-Hotels-Charlemont-Outdoor-Retreat-On-The-Chickley-River.h94329371.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94340000/94335700/94335615/2af9ab6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94340000/94335700/94335615/f8eca448.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94340000/94335700/94335615/b423bf77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94340000/94335700/94335615/f079d1b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakefront Berkshires Retreat w/ Deck, Dock & Boat! Great Barrington [](https://www.expedia.ca/Great-Barrington-Hotels-Lakefront-Berkshires-Retreat-W-Deck.h94335615.Hotel-Information) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/106000000/105220000/105211800/105211754/fbd33027.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/106000000/105220000/105211800/105211754/f8f9ccc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/106000000/105220000/105211800/105211754/b495eb82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/106000000/105220000/105211800/105211754/e38119ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quaint Massachusetts Home w/ Yard & Grill! Gill [](https://www.expedia.ca/Gill-Hotels-Quaint-Massachusetts-Home-W-Yard-Grill.h105211754.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=2025-11-12&endDate=2025-11-13®ionId=3000443223&adults=2&lodging=COTTAGE&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%2FHampshire-County-Cottages.d3000443223-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FHampshire-County-Cottages.d3000443223-aaCottages.Travel-Guide-Accommodation) ## Top Hampshire County Hotel Reviews ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Excellent all the way around" [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![The Ellery](//images.trvl-media.com/lodging/1000000/900000/892700/892654/0b76727c_y.jpg) ### The Ellery 10/10 Excellent "Great housekeeping. " [](https://expedia.ca/Springfield-Hotels-The-Ellery.h892654.Hotel-Information) ![Publick House Historic Inn and Country Motor Lodge](//images.trvl-media.com/lodging/1000000/180000/179700/179650/4c5a0c9e_y.jpg) ### Publick House Historic Inn and Country Motor Lodge 10/10 Excellent "We had a good time " [](https://expedia.ca/Sturbridge-Hotels-Publick-House-Historic-Inn-And-Country-Motor-Lodge.h179650.Hotel-Information) ![Vacation Village in the Berkshires](//images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Good location; reasonable price; very clean and quiet - would definitely return" [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](//images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Everything is clean " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Candlewood Suites Windsor Locks Bradley Arpt by IHG](//images.trvl-media.com/lodging/2000000/1620000/1619200/1619197/f7719b06_y.jpg) ### Candlewood Suites Windsor Locks Bradley Arpt by IHG 10/10 Excellent "Could use the walls updated but wa in good repair over all" [](https://expedia.ca/Hartford-Hotels-Candlewood-Suites-Windsor-Locks-Bradley-Arpt.h1619197.Hotel-Information) ![MGM Springfield](//images.trvl-media.com/lodging/28000000/27670000/27664900/27664860/c76c1f43_y.jpg) ### MGM Springfield 10/10 Excellent "Good" [](https://expedia.ca/Springfield-Hotels-MGM-Springfield.h27664860.Hotel-Information) ![Hotel UMass](//images.trvl-media.com/lodging/1000000/490000/480800/480785/4e423f91_y.jpg) ### Hotel UMass 10/10 Excellent "Very pleased with accommodations!" [](https://expedia.ca/Springfield-Hotels-Hotel-UMass.h480785.Hotel-Information) ![Motel 6 Windsor Locks, CT - Hartford](//images.trvl-media.com/lodging/1000000/1000000/996400/996399/6063d228_y.jpg) ### Motel 6 Windsor Locks, CT - Hartford 10/10 Excellent "clean room" [](https://expedia.ca/Hartford-Hotels-Motel-6-Windsor-Locks.h996399.Hotel-Information) ## Find out more about Hampshire County ## Hampshire County Cottages information | Number of reviews | 533 | | --- | --- | | Accommodation | 120 Cottages | | Lowest Price | CA $431 | | Highest Price | CA $457 | ## Frequently asked questions ### Why book your cottage in Hampshire County with Expedia? > Expedia has some great cottages in Hampshire County, so get ready for an unforgettable stay on nature's doorstep. If you're sticking to a budget, select how much you want to spend and your preferred property star rating. Or, make use of our filters to search for cottages with a hot tub or free WiFi. We'll help you find the perfect fit whatever your getaway looks like. ### How can I find cheap cottages in Hampshire County? > With Expedia's helpful filter tool, locating cheap cottages in Hampshire County has never been simpler. 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