Title: Chatham Condo Rentals from CA $177 | Expedia.ca [Hotels in Chatham](https://expedia.ca/Chatham-Hotels.d6046736.Travel-Guide-Hotels)[Vacation Rentals in Chatham](https://expedia.ca/Chatham-Vacation-Rentals.d6046736.Travel-Guide-VacationRentals)[Chatham Car Rentals](https://expedia.ca/Car-Rentals-In-Chatham.d6046736.Car-Rental-Guide)[Chatham Vacation Packages](https://expedia.ca/Chatham.d6046736.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Condos Rentals in Chatham from CA $177 ![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=6046736&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chatham Condo Rentals ## Our top choices for Chatham condo rentals ![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/18127ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/03675fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining room](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/16150550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Village in the Berkshires Williamstown 8.6/10 Excellent (2020) "All around loved everything about the place! " CA $144 CA $177 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/34492d26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/d1c43c74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/a111c8ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/7e1d3e97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7 Hancock 8.0/10 Very good (8) "Cozy little condo, good for a group of four or five. We stayed there with my two kids 8 &10 and wife. It’s a nice place overall we had a great time. It is a short drive to the slopes, which is fine as long as you have a car but you still need to park at the inn" CA $203 CA $472 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Hancock-Hotels-2-BR-Condo-Mountain-Views-At-Jiminy-Peak-Sleeps-7.h111663271.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/d5e215b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/b5c16e1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/cdf98da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/b6c32865.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous Hancock 8.0/10 Very good (1) "very nice and roomy! really enjoyed." CA $188 CA $416 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Hancock-Hotels-2-BR-Jiminy-Peak-W-Mountain-View-Sleeps-7-Gorgeous.h118080540.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1080h783x0y5-9ee375ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/a814c17c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1075h808x0y2-de6afae7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/c54967a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### UNIQUE - 1BR Country Condo @ Jiminy Peak Hancock 10/10 Exceptional (13) "Clean and quiet, nicely decorated! " CA $138 CA $435 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Hancock-Hotels-UNIQUE-Gnome-Themed-1BR-Condo.h74312811.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89990000/89988500/89988465/2a7da31c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/90000000/89990000/89988500/89988465/72689c3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89990000/89988500/89988465/f644198b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/90000000/89990000/89988500/89988465/23c030ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski-In/Ski-Out at Jiminy Peak in the Country Inn Hancock 9.0/10 Wonderful (27) "We had a great experience with this rental. Nice location for skiing on and off the mountain and close to the heart of the ski facility. " [](https://www.expedia.ca/Hancock-Hotels-Ski-InSki-Out-At-Jiminy-Peak-In-The-Country-Inn.h89988465.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66550000/66542300/66542211/b6a3217f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66550000/66542300/66542211/f2860ac4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/67000000/66550000/66542300/66542211/9ca3e72b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/67000000/66550000/66542300/66542211/w2916h2186x0y0-1cc358cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1 Hancock 10/10 Exceptional (40) "3rd time staying here. The host is great, the place is clean, and the location couldn't be better!" [](https://www.expedia.ca/Hancock-Hotels-Ski-In.h66542211.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112880000/112874000/112873953/8e8a723a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/113000000/112880000/112874000/112873953/6d6a9392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112880000/112874000/112873953/884f571c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games, DVD player, table tennis](https://images.trvl-media.com/lodging/113000000/112880000/112874000/112873953/7b4cff83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Wyndham Bentley Brook Resort - 2 Bedroom Hancock [](https://www.expedia.ca/Hancock-Hotels-Club-Wyndham-Bentley-Brook-Resort-2-Bedroom.h112873953.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112880000/112874000/112873966/7f4d0925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games, DVD player, table tennis](https://images.trvl-media.com/lodging/113000000/112880000/112874000/112873966/9d8fe636.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112880000/112874000/112873966/7ca9c813.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/113000000/112880000/112874000/112873966/b637468e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Wyndham Bentley Brook Resort - 2 Bedroom Hancock [](https://www.expedia.ca/Hancock-Hotels-Club-Wyndham-Bentley-Brook-Resort-2-Bedroom.h112873966.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/71000000/70580000/70570900/70570807/ee219097.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70580000/70570900/70570807/afedea82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70580000/70570900/70570807/4de3fdd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/71000000/70580000/70570900/70570807/b0766675.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook Hancock 10/10 Exceptional (13) "Great location, all the amenities were available to us. Right on the base of the mountain. Thx for the stay! " [](https://www.expedia.ca/Hancock-Hotels-The-Berkshires-Jiminy-Mountains-Club-Wyndham-Bentley-Brook.h70570807.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593874/22f66f00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593874/589cb0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593874/ab36cb2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593874/f9dd0939.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tranquil Lakeside Escape in the Berkshires Lenox 10/10 Exceptional (1) "perfect location to go everywhere in the Berkshires" [](https://www.expedia.ca/Lenox-Hotels-Tranquil-Lakeside-Escape-In-The-Berkshires.h116593874.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593867/dba923f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593867/3996a0b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593867/25c39568.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593867/d1155757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful 1BR Condo with Pond View Lenox 8.0/10 Very good (2) "Beautiful grounds and views and so close to Tanglewood! We had a great time. Apartment was clean and very private. It was quiet and quaint.The only issue I should mention is the carpeting; seemed a bit dump and not very appealing." [](https://www.expedia.ca/Lenox-Hotels-Peaceful-1BR-Condo-With-Pond-View.h116593867.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/113000000/112060000/112056600/112056501/w1302h976x2y0-070db8a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112060000/112056600/112056501/w1302h978x0y0-88bd51f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112060000/112056600/112056501/e2d5b928.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/113000000/112060000/112056600/112056501/9d85af68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool Hancock 10/10 Exceptional (3) "Good base for Berkshires, responsive host, good rates, secure." [](https://www.expedia.ca/Hancock-Hotels-Family-Friendly-Mountain-Retreat-At-Jiminy-Peak.h112056501.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78360000/78357200/78357134/c6d14d4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78360000/78357200/78357134/w1656h1242x0y0-1afe4a3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78360000/78357200/78357134/d000d79a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78360000/78357200/78357134/w3836h2878x0y0-b2743c25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2 Hancock 10/10 Exceptional (33) "Everything was spot on. Will be back!!" [](https://www.expedia.ca/Hancock-Hotels-SKI-IN.h78357134.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74710000/74703700/74703683/9c584984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/75000000/74710000/74703700/74703683/w1170h870x0y0-ad76d082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74710000/74703700/74703683/w1170h846x0y0-b5c1c36e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74710000/74703700/74703683/b17375b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5 Hancock 10/10 Exceptional (6) "It was exactly as described, perfect for a family stay with easy ski on and off. I was pleasantly surprised with all the amenities of the property. Would stay again!" [](https://www.expedia.ca/Hancock-Hotels-Ski-In-Ski-Out-Deluxe-1-Bedroom-Condo.h74703683.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95480000/95472300/95472240/45301dba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95480000/95472300/95472240/b1af2160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/96000000/95480000/95472300/95472240/ae75dac8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/96000000/95480000/95472300/95472240/1332cd72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS! Hancock 10/10 Exceptional (12) "We'll be back!" [](https://www.expedia.ca/Hancock-Hotels-SKI-IN.h95472240.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112050000/112048700/112048690/e2552b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112050000/112048700/112048690/b9e96575.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/113000000/112050000/112048700/112048690/w1304h976x0y0-6793a9df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112050000/112048700/112048690/b5adc5ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths Hancock [](https://www.expedia.ca/Hancock-Hotels-Escape-To-The-Heart-Of-Jiminy-Peak-Ski-InSki-Out-Apartment-With-Stunning-Views.h112048690.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/111000000/110320000/110311200/110311175/1b5c2068.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/111000000/110320000/110311200/110311175/c7bbad58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games, DVD player, table tennis](https://images.trvl-media.com/lodging/111000000/110320000/110311200/110311175/54bf77ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/111000000/110320000/110311200/110311175/f57098a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Wyndham Bentley Brook Resort - 2 Bedroom Hancock 6.0/10 (2) "Great spot for family ski trip. Location was great. Condo and amenities were great. Overall super happy and would stay again. " [](https://www.expedia.ca/Hancock-Hotels-Club-Wyndham-Bentley-Brook-Resort-2-Bedroom.h110311175.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113400000/113390100/113390092/fa250819.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/114000000/113400000/113390100/113390092/d08fa1e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113400000/113390100/113390092/4cd0a1cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games, DVD player, table tennis](https://images.trvl-media.com/lodging/114000000/113400000/113390100/113390092/d8c6ad82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Wyndham Bentley Brook Resort - 2 Bedroom Hancock [](https://www.expedia.ca/Hancock-Hotels-Club-Wyndham-Bentley-Brook-Resort-2-Bedroom.h113390092.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113500000/113492900/113492900/e3c0b681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games, DVD player, table tennis](https://images.trvl-media.com/lodging/114000000/113500000/113492900/113492900/7193e718.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113500000/113492900/113492900/af5a3eef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/114000000/113500000/113492900/113492900/433fe539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Wyndham Bentley Brook Resort - 2 Bedroom Hancock [](https://www.expedia.ca/Hancock-Hotels-Club-Wyndham-Bentley-Brook-Resort-2-Bedroom.h113492900.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112880000/112874000/112873975/34edfcd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/113000000/112880000/112874000/112873975/d5129adb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112880000/112874000/112873975/a98070fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/113000000/112880000/112874000/112873975/d3d15dc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Wyndham Bentley Brook Resort - 2 Bedroom Hancock [](https://www.expedia.ca/Hancock-Hotels-Club-Wyndham-Bentley-Brook-Resort-2-Bedroom.h112873975.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=2025-10-09&endDate=2025-10-10®ionId=6046736&adults=2&lodging=CONDO&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%2FChatham-Condos.d6046736-aaCondos.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChatham-Condos.d6046736-aaCondos.Travel-Guide-Accommodation) ## Top Chatham Hotel Reviews ![Comfort Inn & Suites East Greenbush - Albany](//images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/ea181a79_y.jpg) ### Comfort Inn & Suites East Greenbush - Albany 10/10 Excellent "The lobby was different and dramatic. Liked that the eating area was raised above it on the second floor and gave a view of the hotel and surrounding scenery. Breakfast was adequate - nothing special but good. We did have a bit of trouble with the toilet in our room which we were able to fix without calling the desk. Would definitely stay there again if we return to visit." [](https://expedia.ca/Albany-Hotels-Comfort-Inn-Suites-East-Greenbush-Albany.h1052319.Hotel-Information) ![Four Points by Sheraton Albany](//images.trvl-media.com/lodging/55000000/54080000/54077800/54077744/55bb8198_y.jpg) ### Four Points by Sheraton Albany 10/10 Excellent "Just a lovely place by the airport like 15 minutes. Comfy bed and very quiet. All the staff were exceptionally nice. In the bar I had Andrew as my bartender. He made me the most wonderful drink and wrote down for me how he made it!! He was very entertaining and nice! I will definitely stay there again. Ps- the guy at front desk- I didn’t catch his name. He too was so helpful to us so thank you!" [](https://expedia.ca/Albany-Hotels-Four-Points-By-Sheraton-Albany.h54077744.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 "Valerie at the front desk and who checked me in was above and beyond in customer service. She checked to see if I had a IGH account—which I did but had forgotten, and reminded me about the points and promotions. This Holiday Inn is a well managed property. Thank you" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](//images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "We stayed for 5 nights and really enjoyed the surroundings and the drive to the property. The area is peaceful and quiet, with plenty to do for kids, including a mountain hike that even our 2- and 6-year-olds managed well. The grounds are beautiful for photos, very well maintained, and we often saw the crew cleaning and painting the sidewalks. I booked 2 suites, which were a good size for a family of four and offered plenty of space. The only downsides were that check-in felt a bit tedious it took several tries to swipe my card and there was no housekeeping service or follow-up to check on amenities during our stay. A self check-in option would make things smoother. Overall, we loved the quietness, the family-friendly activities, and the clean, well-kept property. With a few improvements in guest service, this could easily be a 5-star experience." [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Jiminy Peak Mountain Resort](//images.trvl-media.com/lodging/1000000/920000/911400/911313/cf8c8830_y.jpg) ### Jiminy Peak Mountain Resort 10/10 Excellent "Absolutely beautiful " [](https://expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Excellent location. Friendly staff. " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](//images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 10/10 Excellent "Perfect for an overnight for the Tanglewood concert" [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "A great place if you appreciate and like history. The lobby is filled with antiques and the porch is great to rock in a chair and sip some wine. Parking is no issue and you can walk to local restaurants and shops. " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Postcard Cabins Eastern Catskills](//images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/fe54355c_y.jpg) ### Postcard Cabins Eastern Catskills 10/10 Excellent "The things I’ve loved about the experience were the cleanliness of the cabin, along with easy parking. There was nothing that I didn’t like about the experience, definitely would have to go there again." [](https://expedia.ca/Catskill-Hotels-Postcard-Cabins-Eastern-Catskills.h109129528.Hotel-Information) ## Find out more about Chatham ## Chatham Condo Rentals information | Number of reviews | 2,147 | | --- | --- | | Accommodation | 65 Condo Rentals | | Lowest Price | CA $177 | | Highest Price | CA $472 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Cheap Hotels in Austerlitz](https://www.expedia.ca/Austerlitz-Hotels-Cheap-Hotels.0-0-d500771-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Austerlitz](https://www.expedia.ca/Austerlitz-Hotels-Luxury-Hotel.0-0-d500771-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Austerlitz Hotels](https://www.expedia.ca/Austerlitz-Hotels.d500771.Travel-Guide-Hotels) - [Boutique Hotels in Canaan](https://www.expedia.ca/Canaan-Hotels-Boutique-Hotel.0-0-d55619-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Canaan](https://www.expedia.ca/Canaan-Hotels-Cheap-Hotels.0-0-d55619-tCheapHotels.Travel-Guide-Filter-Hotels) - 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