Title: Chesterfield Cottages | Expedia.ca [Hotels in Chesterfield](https://expedia.ca/Chesterfield-Hotels.d89029.Travel-Guide-Hotels)[Vacation Rentals in Chesterfield](https://expedia.ca/Chesterfield-Vacation-Rentals.d89029.Travel-Guide-VacationRentals)[Chesterfield Car Rentals](https://expedia.ca/Car-Rentals-In-Chesterfield.d89029.Car-Rental-Guide)[Chesterfield Vacation Packages](https://expedia.ca/Chesterfield.d89029.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Chesterfield Cottage Rentals ![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 prices for these dates In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chesterfield Cottages ![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) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27120000/27116600/27116560/7222c213.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Clearing - Quiet - Close To Nature Cummington 10/10 Exceptional (201) "The property was beautiful and well maintained.The home where we stayed was perfect and cozy." [](https://www.expedia.ca/Cummington-Hotels-The-Clearing-Quiet-Close-To-Nature.h27116560.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) ![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) ![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) ### Charming historic cottage on scenic road to Mt. Greylock Lanesboro 10/10 Exceptional (115) "What a lovely property! And Rich was just terrific!" [](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)](https://images.trvl-media.com/lodging/95000000/94460000/94458700/94458679/83556d4a.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) ### Massachusetts Vacation Rental w/ Deck Easthampton [](https://www.expedia.ca/Easthampton-Hotels-Massachusetts-Vacation-Rental-W-Deck.h94458679.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/68000000/67260000/67255100/67255071/w1024h683x0y1-30c5b99d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Island - Largest Fresh Water Reservoir in Mass Otis 8.8/10 Excellent (8) "We had a great time. The owner Bill was a great host." [](https://www.expedia.ca/Otis-Hotels-Private-Island-On-Largest-Fresh-Water-Reservoir-In-Mass-Ski-Boat-Included.h67255071.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/106000000/105900000/105898600/105898516/9e79992b.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) ### Westfield Vacation Rental w/ Porch, Pets Welcome! Westfield [](https://www.expedia.ca/Westfield-Hotels-Westfield-Vacation-Rental-W-Porch.h105898516.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/95000000/94370000/94361700/94361677/2c894462.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94370000/94361700/94361677/1d8fbef8.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." [](https://www.expedia.ca/Huntington-Hotels-Historic-Huntington-Home-Walk-To-Westfield-River.h94361677.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... [](https://www.expedia.ca/Charlemont-Hotels-Charlemont-Outdoor-Retreat-On-The-Chickley-River.h94329371.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/43000000/42440000/42436700/42436625/90-83af3588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Books, stereo](https://images.trvl-media.com/lodging/43000000/42440000/42436700/42436625/2dd57b46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/43000000/42440000/42436700/42436625/2070b1e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/43000000/42440000/42436700/42436625/ce6fb451.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Entire cottage in Berkshire Villiage Lanesborough 9.6/10 Exceptional (7) "The cottage was clean and as described. The street was very quiet." [](https://www.expedia.ca/Lanesborough-Hotels-Entire-Cottage-In-Berkshire-Villiage.h42436625.Hotel-Information) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/100000000/99250000/99248300/99248211/c6edc39c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/100000000/99250000/99248300/99248211/02262e40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/100000000/99250000/99248300/99248211/6e4e9c9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/100000000/99250000/99248300/99248211/dbea8017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A-frame Cabin w/ Furnished Deck in Becket! Becket [](https://www.expedia.ca/Becket-Hotels-A-Frame-Cabin-In-Becket-Deck-Private-Acreage.h99248211.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/19000000/18620000/18610500/18610415/dedaa3cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18620000/18610500/18610415/3391c48a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18620000/18610500/18610415/503a62e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![28-inch flat-screen TV with satellite channels, TV, DVD player](https://images.trvl-media.com/lodging/19000000/18620000/18610500/18610415/9658e53a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cavalier Cottage B&B Shelburne Falls 9.0/10 Wonderful (2) "Perfect for a quiet, weekend getaway. We went to celebrate our 5 year anniversary and brought our dog, Ollie. Ollie's a very timid and nervous guy, but he felt very comfortable here. We went during the winter, but would be interested in returning in the summer because there seems to be a lot of outdoor activities (white water rafting, fishing, hiking). " [](https://www.expedia.ca/Shelburne-Falls-Hotels-Cavalier-Cottage-BB.h18610415.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102370000/102361400/102361315/348b26d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/103000000/102370000/102361400/102361315/14fd9993.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, dishwasher, blender](https://images.trvl-media.com/lodging/103000000/102370000/102361400/102361315/825fede7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/103000000/102370000/102361400/102361315/f0cd3088.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Lake Cottage on 3 acres w/350 sq. ft. deck Becket 10/10 Exceptional (1) "We spent a lovely, relaxing weekend in this well kept and well situated property. Hoping to come back again." [](https://www.expedia.ca/Becket-Hotels-Private-Lake-Cottage-On-3-Acres-W350-Sq-Ft-Deck.h102361315.Hotel-Information) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94350000/94344900/94344810/639ee6af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94350000/94344900/94344810/95d39322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94350000/94344900/94344810/5e14af4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94350000/94344900/94344810/a6621c26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Historic Home in the Berkshires! Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-Historic-Home-1-Mi-To-Burbank-Park.h94344810.Hotel-Information) ![House (1 Bedroom) | Front of property](https://images.trvl-media.com/lodging/102000000/101700000/101698900/101698869/3c2975c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/102000000/101700000/101698900/101698869/a31aa1de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/102000000/101700000/101698900/101698869/20bb3371.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/102000000/101700000/101698900/101698869/a44d6923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hawley Home w/ Deck: 4 Mi to Berkshire East Resort Charlemont 6.0/10 (1) "I tried to reach out to the contact given regarding some checkout procedures and got zero response. " [](https://www.expedia.ca/Charlemont-Hotels-Hawley-Home-W-Deck-4-Mi-To-Berkshire-East-Resort.h101698869.Hotel-Information) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94480000/94479100/94479054/0bbae948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94480000/94479100/94479054/dcdab26d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94480000/94479100/94479054/f9059fff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94480000/94479100/94479054/562518eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck! Williamsburg [](https://www.expedia.ca/Williamsburg-Hotels-Pet-Friendly-Cabin-W-Fire-Pit.h94479054.Hotel-Information) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94460000/94458700/94458664/9722b793.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94460000/94458700/94458664/bc683188.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94460000/94458700/94458664/31aa8136.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94460000/94458700/94458664/110bca60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakefront Otis Home w/ Stunning Views & Boats! Otis [](https://www.expedia.ca/Otis-Hotels-Modern-Otis-Home-W-Hot-Tub.h94458664.Hotel-Information) ![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94340000/94335100/94335042/6111d668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94340000/94335100/94335042/1294fd0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94340000/94335100/94335042/e53c5653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94340000/94335100/94335042/ee95a4ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Picturesque Cottage With Sunroom on Ashmere Lake! Hinsdale [](https://www.expedia.ca/Hinsdale-Hotels-Picturesque-Cottage-With-Sunroom-On-Ashmere-Lake.h94335042.Hotel-Information) ![Cottage (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98552500/98552412/01863757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98552500/98552412/73042111.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98552500/98552412/b81105fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98552500/98552412/ad6f5845.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Becket Cottage Escape w/ Lake Access! Sherwood Forest [](https://www.expedia.ca/Becket-Hotels-Cozy-Becket-Cottage-Escape-W-Lake-Access.h98552412.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94370000/94361700/94361683/35d3ba8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/95000000/94370000/94361700/94361683/22a55c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94370000/94361700/94361683/0b84415f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94370000/94361700/94361683/64f73562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Granby Home w/ Deck < 1/2 Mi to Aldrich Lake! Granby [](https://www.expedia.ca/Granby-Hotels-Granby-Home-W-Deck-12-Mi-To-Aldrich-Lake.h94361683.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98550000/98549900/98549865/4e2d4b07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98550000/98549900/98549865/fbecfc15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98550000/98549900/98549865/4749a175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98550000/98549900/98549865/23f4a916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakefront Westhampton Cabin w/ Beach + Kayaks! Westhampton [](https://www.expedia.ca/Westhampton-Hotels-Lakefront-Westhampton-Cabin-W-Beach-Kayaks.h98549865.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/108000000/107430000/107424500/107424451/a5fa3eb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/108000000/107430000/107424500/107424451/a4349d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/108000000/107430000/107424500/107424451/5aa2fb85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/108000000/107430000/107424500/107424451/9ecd41cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Farmhouse Near Mountains & Colleges! Westfield [](https://www.expedia.ca/Westfield-Hotels-Historic-Farmhouse-Near-Mountains-Colleges.h107424451.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=2025-10-11&endDate=2025-10-12®ionId=89029&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%2FChesterfield-Cottages.d89029-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChesterfield-Cottages.d89029-aaCottages.Travel-Guide-Accommodation) ## Top Chesterfield Hotel Reviews ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Clean and spacious one bedroom suite with well stocked kitchen. Large indoor pool and outdoor year round Jacuzzi are wonderful. Also very affordable. Second time staying here and will stay here again. " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Comfort Inn & Suites](//images.trvl-media.com/lodging/1000000/560000/558100/558078/d1319a54_y.jpg) ### Comfort Inn & Suites 10/10 Excellent "Very clean, very quiet, very close to UMass " [](https://expedia.ca/Springfield-Hotels-Comfort-Inn-Suites.h558078.Hotel-Information) ![Courtyard by Marriott West Springfield](//images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/90293a2b_y.jpg) ### Courtyard by Marriott West Springfield 10/10 Excellent "Exceptionally clean and updated hotel with wonderful, large rooms and clean and comfortable bedding. Everything was thoughtfully appointed in the room with lots of extra touches. This is close to the Big E and within walking distance of restaurants." [](https://expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-West-Springfield.h33298677.Hotel-Information) ![Tru by Hilton Chicopee Springfield](//images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/2bcbba21_y.jpg) ### Tru by Hilton Chicopee Springfield 10/10 Excellent "Hard to get in the parking lot but was great. " [](https://expedia.ca/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.Hotel-Information) ![Quality Inn West Springfield](//images.trvl-media.com/lodging/1000000/10000/7500/7486/7f7ace74_y.jpg) ### Quality Inn West Springfield 10/10 Excellent "Convenient nice cozy hotel with breakfast included and spacious rooms. " [](https://expedia.ca/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.Hotel-Information) ![D. Hotel Suites & Spa](//images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg) ### D. Hotel Suites & Spa 10/10 Excellent "The restaurant was very good" [](https://expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Quality Inn Chicopee - Springfield](//images.trvl-media.com/lodging/1000000/860000/856300/856259/4454c273_y.jpg) ### Quality Inn Chicopee - Springfield 8/10 Good "Love it " [](https://expedia.ca/Springfield-Hotels-Quality-Inn-Chicopee-Springfield.h856259.Hotel-Information) ![Quality Inn Westfield - Springfield](//images.trvl-media.com/lodging/2000000/1120000/1118900/1118896/532eb0dc_y.jpg) ### Quality Inn Westfield - Springfield 10/10 Excellent "Clean" [](https://expedia.ca/Springfield-Hotels-Quality-Inn-Westfield-Springfield.h1118896.Hotel-Information) ![Motel 6 Chicopee, MA - Springfield](//images.trvl-media.com/lodging/1000000/1000000/996200/996151/f5fa8fea_y.jpg) ### Motel 6 Chicopee, MA - Springfield 10/10 Excellent "Clean, easy check in" [](https://expedia.ca/Springfield-Hotels-Motel-6-Chicopee.h996151.Hotel-Information) ## Find out more about Chesterfield ## Chesterfield Cottages information | Number of reviews | 307 | | --- | --- | | Accommodation | 55 Cottages | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - 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