Title: Chatham Vacation Home Rentals from CA $179: Search Top Private Vacation Homes for Rent | 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) # Chatham Vacation Rentals - ![](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 [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chatham vacation homes ![Exterior](https://images.trvl-media.com/lodging/120000000/119910000/119905200/119905138/2f42a027.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119910000/119905200/119905138/6da6ca4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119910000/119905200/119905138/61fbb7ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/120000000/119910000/119905200/119905138/0312db51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tiny Home w/ Hot Tub and Sunset View! [](https://www.expedia.ca/Rural-Tiny-Home-Hot-Tub.h119905138.Hotel-Information) Selkirk 10/10 Exceptional (2) "Very nice place. Was in a quiet area and hosts were great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian H. CA $124 CA $179 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Rural-Tiny-Home-Hot-Tub.h119905138.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/52bc41a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/dcb799f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/c50e9e6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/6137aab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home in Great Barrington [](https://www.expedia.ca/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information) Great Barrington 9.8/10 Exceptional (26) "Enjoyed our stay!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fred W. CA $232 CA $384 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/4b325a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/90-950a0f87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/90-00a818b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/90-b25e9082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### All the comforts of home [](https://www.expedia.ca/Hudson-Hotels-All-The-Comforts-Of-Home.h59995220.Hotel-Information) Hudson 9.2/10 Wonderful (28) "Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marisa P. CA $146 CA $195 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Hudson-Hotels-All-The-Comforts-Of-Home.h59995220.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/f0ba5959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/6d1211ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/fbef3554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/23a17279.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Berkshires Home Near Tanglewood, Trails & Wineries [](https://www.expedia.ca/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information) Lebanon Springs 8.8/10 Excellent (20) "It was great - just what we were looking for. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kaye S. CA $207 CA $536 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/104000000/103820000/103820000/103819908/d16bb4cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/104000000/103820000/103820000/103819908/0afecb87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103820000/103820000/103819908/c945b9f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/104000000/103820000/103820000/103819908/fee8af1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Luxurious Cabin, Catskills - The Tiny Nook [](https://www.expedia.ca/Catskill-Hotels-The-Tiny-Nook-Escape-The-City-Life-Relaxing-Getaway-Tucked-In-Catskills.h103819908.Hotel-Information) Catskill 10/10 Exceptional (7) "Great place. Exactly like the pictures. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) robert a. CA $221 CA $465 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Catskill-Hotels-The-Tiny-Nook-Escape-The-City-Life-Relaxing-Getaway-Tucked-In-Catskills.h103819908.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/124000000/123270000/123260700/123260649/28a8e29c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123270000/123260700/123260649/f8964f30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123270000/123260700/123260649/d21a557f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123270000/123260700/123260649/34815278.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1 Bedroom | Cozy Lounge | Spacious [](https://www.expedia.ca/Catskill-Hotels-1-Bedroom-Cozy-Lounge-Spacious.h123260649.Hotel-Information) Catskill [](https://www.expedia.ca/Catskill-Hotels-1-Bedroom-Cozy-Lounge-Spacious.h123260649.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/665b8282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/8f9296e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/3e6e58ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, computer monitors](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/ab946d75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheerful 3-bedroom cottage with woodstove [](https://www.expedia.ca/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information) Sheffield 10/10 Exceptional (41) "The property was centrally located for skiing, and was a comfortable stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly R. CA $327 CA $694 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/94000000/93410000/93402500/93402422/61c037e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/94000000/93410000/93402500/93402422/60c87a00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93410000/93402500/93402422/fe54d0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93410000/93402500/93402422/809aa3f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Treat yourself at the stunning June Farms Wellness Huts! [](https://www.expedia.ca/Treat-Yourself-At-The-Stunning-June-Farms-Wellness-Huts.h93402422.Hotel-Information) West Sand Lake 10/10 Exceptional (8) "The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) SteveS CA $379 CA $773 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Treat-Yourself-At-The-Stunning-June-Farms-Wellness-Huts.h93402422.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/8de4c71d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/00cc85e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/06261f5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/43b40eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Near Tanglewood: Historic Summer Retreat [](https://www.expedia.ca/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information) New Lebanon 9.4/10 Exceptional (23) "Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul S. CA $385 CA $764 total includes taxes & fees Dec 27 - Dec 28 [](https://www.expedia.ca/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/862ec0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/055ed8a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/cc4451e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/9af2b9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Ski Getaway in the Berkshires [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) Great Barrington 9.4/10 Exceptional (6) CA $279 CA $410 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122120000/122118500/122118449/2158de3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/123000000/122120000/122118500/122118449/78c36899.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122120000/122118500/122118449/69de4eaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122120000/122118500/122118449/240ab0c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking [](https://www.expedia.ca/Albany-Hotels-3-Bedroom-House-In-Beautiful-Albany-With-AC.h122118449.Hotel-Information) Albany 8.0/10 Very good (1) "Overall nice stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $288 CA $430 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Albany-Hotels-3-Bedroom-House-In-Beautiful-Albany-With-AC.h122118449.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/bdc7550f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/811d3663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/a38bbe4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/44aa4835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions! [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information) Pittsfield 7.8/10 Good (6) "Very clean and spacious! We enjoyed our stay with our small pup!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ann C. CA $371 CA $682 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/f9227a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/54590b16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/079bb1c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/411deb16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3-bedroom house in beautiful Berkshires, close to amenities! [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-House-In-Beautiful-Berkshires.h119322276.Hotel-Information) Pittsfield CA $290 CA $470 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-House-In-Beautiful-Berkshires.h119322276.Hotel-Information) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99770000/99761000/99760997/223b97ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/100000000/99770000/99761000/99760997/b0fcb999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99770000/99761000/99760997/fc7a38f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99770000/99761000/99760997/6ae561f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tranquil Victorian on Charming Street [](https://www.expedia.ca/Hudson-Hotels-Tranquil-Victorian-On-Charming-Street.h99760997.Hotel-Information) Hudson 8.0/10 Very good (2) "What a darling house! We stayed with my mother and my adult kids for Thanksgiving and it was the perfect spot! The host was most attentive to all of our questions and request ex! It’s the perfect location for visiting the Hudson Valley and the house was so comfortable and accommodating for all of us! We loved everything about it!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary R. CA $343 CA $792 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Hudson-Hotels-Tranquil-Victorian-On-Charming-Street.h99760997.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/094a3cc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/e3e0e9fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/168d77f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/d9fe6b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!! [](https://www.expedia.ca/Albany-Hotels-Escape-To-Lakefront-Leisurehudson.h32807378.Hotel-Information) Valatie 10/10 Exceptional (60) "Great spot on the lake. Super quiet and relaxing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) vincent m. CA $373 CA $739 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Albany-Hotels-Escape-To-Lakefront-Leisurehudson.h32807378.Hotel-Information) ![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/8d87241a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/64f95c5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/87b97def.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/d712468a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Great Barrington Get Away [](https://www.expedia.ca/Great-Barrington-Hotels-Great-Barrington-Get-Away.h29615546.Hotel-Information) Great Barrington 9.4/10 Exceptional (25) "We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth G. CA $427 CA $763 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Great-Barrington-Hotels-Great-Barrington-Get-Away.h29615546.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/dac46480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/97c48259.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/c0195267.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/18a5d5ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hudson Hot Tub & Pet Escape [](https://www.expedia.ca/Hudson-Hotels-Hudson-Hot-Tub-Pet-Escape.h120658957.Hotel-Information) Stottville CA $311 CA $545 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Hudson-Hotels-Hudson-Hot-Tub-Pet-Escape.h120658957.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/79000000/78090000/78084300/78084253/b3db0757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/79000000/78090000/78084300/78084253/4faff5bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78090000/78084300/78084253/w1440h1897x0y5-29f33d7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78090000/78084300/78084253/3fbdaaad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tao Estate in Catskills : Close to Hiking & Nature & Pet Friendly [](https://www.expedia.ca/Catskill-Hotels-Tao-Estate.h78084253.Hotel-Information) CATSKILL 9.4/10 Exceptional (3) "Lovely short weekend in the countryside. Calm zen retreat surrounded by nature and animals." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sarah j. CA $496 CA $1,028 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Catskill-Hotels-Tao-Estate.h78084253.Hotel-Information) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/4f2c31bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/b9e06e08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/w1424h960x16y0-bffb2a3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/6873f6f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy. Clean. Free bagel shop. 3 Fireplaces. [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop-3-Fireplaces.h120045407.Hotel-Information) Great Barrington 10/10 Exceptional (1) "The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary R. CA $469 CA $808 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop-3-Fireplaces.h120045407.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110090000/110084500/110084444/ac902314.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/111000000/110090000/110084500/110084444/f6050e1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/111000000/110090000/110084500/110084444/c757aa29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110090000/110084500/110084444/w1024h680x0y0-d212e81c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room [](https://www.expedia.ca/Hillsdale-Hotels-Majestic-Views-Hot-Tub-Firepit-Games-Sleeps-14.h110084444.Hotel-Information) Hillsdale 10/10 Exceptional (1) "Beautiful house! It was a big house and we loved all the rooms and how they were decorated! When we first arrived the heat wasn’t working and the host had someone there with the half hour fixing the problem. Beautiful quite area as well " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gabrielle T. CA $689 CA $1,739 total includes taxes & fees Jan 19 - Jan 20, 2026 [](https://www.expedia.ca/Hillsdale-Hotels-Majestic-Views-Hot-Tub-Firepit-Games-Sleeps-14.h110084444.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=2026-01-03&endDate=2026-01-04®ionId=6046736&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-Private-Vacation-Homes.d6046736-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChatham-Private-Vacation-Homes.d6046736-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Chatham Hotel Reviews ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Spacious room and loved pool and hot tub!" [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "Everything was awesome" [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Very good" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "Old time charm and hot tub under the stars" [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "From check in to the room itself to parking and breakfast everything was wonderful!!" [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Four Points by Sheraton Albany](https://images.trvl-media.com/lodging/55000000/54080000/54077800/54077744/55bb8198_y.jpg) ### Four Points by Sheraton Albany 10/10 Excellent "Clean " [](https://expedia.ca/Albany-Hotels-Four-Points-By-Sheraton-Albany.h54077744.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 "This is a wonderful place to stay. The breakfast is delicious. The pool and hot tub are delightful. The staff are like family. " [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ### Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy 10/10 Excellent "Everything has exceeded expectations!!!" [](https://expedia.ca/Catskill-Hotels-Postcard-Cabins-Eastern-Catskills.h109129528.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Awesome for ski" [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ## Find out more about Chatham ## Chatham Vacation Homes information | Number of reviews | 238 | | ----------------- | ------------------ | | Accommodation | 490 Vacation Homes | | Lowest Price | CA $179 | | Highest Price | CA $1,739 | ## 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) - 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