Title: Chatham Holiday Homes from £109: Search Holiday Homes in Chatham | Expedia.co.uk [Hotels in Chatham](https://expedia.co.uk/Chatham-Hotels.d6046736.Travel-Guide-Hotels)[Holiday Rentals in Chatham](https://expedia.co.uk/Chatham-Holiday-Rentals.d6046736.Travel-Guide-HolidayRentals)[Chatham Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chatham.d6046736.Car-Hire-Guide)[Chatham Holidays](https://expedia.co.uk/Chatham.d6046736.Holidays-City-Breaks) ![Tracy Memorial Village Hall, Chatham, New York](https://images.trvl-media.com/place/6046736/7198abd1-0904-483a-a024-c143d8de9574.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6046736/7198abd1-0904-483a-a024-c143d8de9574.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 [10 Apr - 12 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=6046736&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [22 May - 24 May](https://www.expedia.co.uk/Hotel-Search?regionId=6046736&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [19 Jun - 21 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=6046736&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [17 Jul - 19 Jul](https://www.expedia.co.uk/Hotel-Search?regionId=6046736&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chatham holiday homes ![Property grounds](https://images.trvl-media.com/lodging/125000000/124470000/124466500/124466418/dc6494b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/125000000/124470000/124466500/124466418/47a45e10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/125000000/124470000/124466500/124466418/b7d8032f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/125000000/124470000/124466500/124466418/7be72235.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renovated house. Built in 1890s. No neighbors in sight. [](https://www.expedia.co.uk/Chatham-Hotels-Renovated-House-Built-In-1890s-No-Neighbors-In-Sight.h124466418.Hotel-Information) Chatham 8.0/10 Very good (1 review) "Mark was very communicative and helpful, answering all questions quickly and accurately" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jim S. £230 includes taxes & fees 30 Mar - 31 Mar [](https://www.expedia.co.uk/Chatham-Hotels-Renovated-House-Built-In-1890s-No-Neighbors-In-Sight.h124466418.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.co.uk/Hudson-Hotels-All-The-Comforts-Of-Home.h59995220.Hotel-Information) Hudson 9.2/10 Wonderful (31 reviews) "The location was just what we were looking for, the cabin was cozy and clean, and the host was so helpful and welcoming!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Olivia C. £109 includes taxes & fees 30 Mar - 31 Mar [](https://www.expedia.co.uk/Hudson-Hotels-All-The-Comforts-Of-Home.h59995220.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/caf5dd09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home in Great Barrington [](https://www.expedia.co.uk/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information) Great Barrington 9.8/10 Exceptional (28 reviews) "The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) maureen k. £222 includes taxes & fees 30 Mar - 31 Mar [](https://www.expedia.co.uk/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.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) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/6b5af50f.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.co.uk/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information) New Lebanon 9.4/10 Exceptional (26 reviews) "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. £304 includes taxes & fees 29 Mar - 30 Mar [](https://www.expedia.co.uk/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.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) ![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) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/104000000/103820000/103820000/103819908/c363e795.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Luxurious Cabin, Catskills - The Tiny Nook [](https://www.expedia.co.uk/Catskill-Hotels-The-Tiny-Nook-Escape-The-City-Life-Relaxing-Getaway-Tucked-In-Catskills.h103819908.Hotel-Information) Catskill 10/10 Exceptional (10 reviews) "Great place. Exactly like the pictures. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) robert a. £255 includes taxes & fees 30 Mar - 31 Mar [](https://www.expedia.co.uk/Catskill-Hotels-The-Tiny-Nook-Escape-The-City-Life-Relaxing-Getaway-Tucked-In-Catskills.h103819908.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) ![Games room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/cc4451e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, electric kettle](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/52345b94.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) ### Cozy Riverside Berkshires Retreat [](https://www.expedia.co.uk/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) Great Barrington 9.0/10 Wonderful (12 reviews) "Close to a great bakery and near to a farm market and shopping mall. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cristine C. £232 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/101000000/100750000/100744600/100744543/17eb3346.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100750000/100744600/100744543/f35e406e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100750000/100744600/100744543/86ccc561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100750000/100744600/100744543/e34520e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Catskill Cottage Walk to Downtown & River Views [](https://www.expedia.co.uk/Catskill-Hotels-Catskill-Cottage-Walk-To-Downtown-River-Views.h100744543.Hotel-Information) Catskill 10/10 Exceptional (19 reviews) "Great little place to stay at right in downtown!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryan S. £160 includes taxes & fees 10 Apr - 11 Apr [](https://www.expedia.co.uk/Catskill-Hotels-Catskill-Cottage-Walk-To-Downtown-River-Views.h100744543.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) ![Interior](https://images.trvl-media.com/lodging/94000000/93410000/93402500/93402422/fe54d0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/94000000/93410000/93402500/93402422/w1723h1192x9y0-d5fc0e07.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.co.uk/Treat-Yourself-At-The-Stunning-June-Farms-Wellness-Huts.h93402422.Hotel-Information) West Sand Lake 10/10 Exceptional (8 reviews) "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 £335 includes taxes & fees 1 Apr - 2 Apr [](https://www.expedia.co.uk/Treat-Yourself-At-The-Stunning-June-Farms-Wellness-Huts.h93402422.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) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/1df26d5d.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) ![Terrace/patio](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/fbef3554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Berkshires Home Near Tanglewood, Trails & Wineries [](https://www.expedia.co.uk/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information) Lebanon Springs 9.0/10 Wonderful (21 reviews) "Comfy beds, clean, great big deck with a view. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Corinne T. £362 includes taxes & fees 30 Mar - 31 Mar [](https://www.expedia.co.uk/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/w1419h960x21y0-4ecf9f4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/68e2333c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/4fb2bcba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/768d59cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Artists’ Hideaway in Old Chatham [](https://www.expedia.co.uk/Old-Chatham-Hotels-Artists-Hideaway-In-Old-Chatham.h121082559.Hotel-Information) Old Chatham £380 includes taxes & fees 28 Mar - 29 Mar [](https://www.expedia.co.uk/Old-Chatham-Hotels-Artists-Hideaway-In-Old-Chatham.h121082559.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) ![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) ![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) ### Cheerful 3-bedroom cottage with woodstove [](https://www.expedia.co.uk/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information) Sheffield 10/10 Exceptional (42 reviews) "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. £368 includes taxes & fees 30 Mar - 31 Mar [](https://www.expedia.co.uk/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/3fc8dc3b.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 Bedroom home w/ lake and mountain views near skiing, and cultural attractions! [](https://www.expedia.co.uk/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information) Pittsfield 7.8/10 Good (7 reviews) "The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Liz V. £371 includes taxes & fees 28 Mar - 29 Mar [](https://www.expedia.co.uk/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/2802a7bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/58aa3713.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/f0716890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/20ff0e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Barn Retreat — All-Season Escape Awaits! [](https://www.expedia.co.uk/East-Chatham-Hotels-Spectacular-Barn-With-1-Bedroom-1-Loft.h108908975.Hotel-Information) East Chatham 10/10 Exceptional (2 reviews) "Accommodations were even better than we expected. The rooms were very clean, and there are unique (and sometimes whimsical, other times thought-provoking) decorations/pictures throughout the barn. The kitchen was basically a chef’s kitchen- all appliances were top notch. The backyard was spacious, and even contained a (non-working) pay phone booth! My wife loved the swinging two-seat chair on the porch! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy S. £463 includes taxes & fees 30 Mar - 31 Mar [](https://www.expedia.co.uk/East-Chatham-Hotels-Spectacular-Barn-With-1-Bedroom-1-Loft.h108908975.Hotel-Information) ![TV, offices](https://images.trvl-media.com/lodging/116000000/115500000/115491000/115490904/fbe651db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115500000/115491000/115490904/1d777bf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/116000000/115500000/115491000/115490904/d106f31a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115500000/115491000/115490904/cff06c8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Catskill Stay w/ Deck & Fire Pit [](https://www.expedia.co.uk/Catskill-Hotels-Catskill-Stay-W-Deck-Fire-Pit.h115490904.Hotel-Information) Catskill 8.8/10 Excellent (3 reviews) "we had a great stay at this house with a group of friends - rooms were comfortable and kitchen had a lot of things we needed for meals. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) raquel p. £299 includes taxes & fees 30 Mar - 31 Mar [](https://www.expedia.co.uk/Catskill-Hotels-Catskill-Stay-W-Deck-Fire-Pit.h115490904.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) ![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) ![Games room](https://images.trvl-media.com/lodging/79000000/78090000/78084300/78084253/707c656a.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) ### Tao Estate in Catskills : Close to Hiking & Nature & Pet Friendly [](https://www.expedia.co.uk/Catskill-Hotels-Tao-Estate.h78084253.Hotel-Information) CATSKILL 9.4/10 Exceptional (3 reviews) "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. £557 includes taxes & fees 2 Apr - 3 Apr [](https://www.expedia.co.uk/Catskill-Hotels-Tao-Estate.h78084253.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/e3f04cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/129a2984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/dc4b2063.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/d96d2729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Treetop Hideaway in Tyringham [](https://www.expedia.co.uk/Lee-Hotels-Treetop-Hideaway-In-Tyringham.h92899508.Hotel-Information) Monterey 9.0/10 Wonderful (10 reviews) "This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah B. £407 includes taxes & fees 30 Mar - 31 Mar [](https://www.expedia.co.uk/Lee-Hotels-Treetop-Hideaway-In-Tyringham.h92899508.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/127000000/126400000/126398500/126398409/db1d8490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/127000000/126400000/126398500/126398409/82eca24d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/127000000/126400000/126398500/126398409/c79d5486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, Internet, bed sheets](https://images.trvl-media.com/lodging/127000000/126400000/126398500/126398409/9b4019a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet [](https://www.expedia.co.uk/New-Lebanon-Hotels-NEW-Spacious-4BR-Ski-Getaway-Minutes-To-Jiminy-Bousquet.h126398409.Hotel-Information) New Lebanon £242 includes taxes & fees 28 Mar - 29 Mar [](https://www.expedia.co.uk/New-Lebanon-Hotels-NEW-Spacious-4BR-Ski-Getaway-Minutes-To-Jiminy-Bousquet.h126398409.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/w2439h1242x124y0-c2be86b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/b7940a62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/d970b68c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/9046d578.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk into town, soak up sun on enclosed porch & steps away from nature trails! [](https://www.expedia.co.uk/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information) Stockbridge 10/10 Exceptional (35 reviews) "A very special, well equipped, and comfortable house with a great kitchen, bedrooms and bathrooms as well as a lovely enclosed porch and outdoor area in an amazing location. Wonderful home with all amenities and thoughtful details provided for guests. A short walk to charming town and across from a beautiful hiking area. Excellent stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan £537 includes taxes & fees 28 Mar - 29 Mar [](https://www.expedia.co.uk/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/cd1323be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/621adf1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/412632db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/d3c8327e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sun Filled Lenox Retreat - Minutes to Tanglewood! [](https://www.expedia.co.uk/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information) Lee 9.6/10 Exceptional (5 reviews) "Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paulo I. £335 includes taxes & fees 29 Mar - 30 Mar [](https://www.expedia.co.uk/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.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) ![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) ![TV, fireplace](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/97c48259.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.co.uk/Hudson-Hotels-Hudson-Hot-Tub-Pet-Escape.h120658957.Hotel-Information) Stottville 10/10 Exceptional (2 reviews) £212 includes taxes & fees 30 Mar - 31 Mar [](https://www.expedia.co.uk/Hudson-Hotels-Hudson-Hot-Tub-Pet-Escape.h120658957.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.co.uk/Hotel-Search?startDate=2026-04-10&endDate=2026-04-11®ionId=6046736&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find holiday rentals that suit your style Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America®ionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=APART_HOTEL) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America®ionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=APARTMENT) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America®ionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=VACATION_HOME) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America®ionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=COTTAGE) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America®ionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=CONDO) Cabins [](https://www.expedia.co.uk/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America®ionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=CABIN) Houseboats [](https://www.expedia.co.uk/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America®ionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=HOUSE_BOAT) Chalets [](https://www.expedia.co.uk/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America®ionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=CHALET) ![](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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChatham-Private-Holiday-Homes.d6046736-aaPrivateHolidayHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChatham-Private-Holiday-Homes.d6046736-aaPrivateHolidayHomes.Travel-Guide-Accommodation) ## Top Chatham Hotel Reviews ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb_y.jpg) ### Berkshires Untold 10/10 Excellent "Berkshires Untold is an old roadside motel that has been very spiffed up. The rooms are small but clean, comfortable, and nicely decorated and updated. Our bed was comfy with high end linens and a nice updated bathroom. The major drawback to the room is the very noisy HVAC unit. There's a super cozy, attractive lounge area and a charming little restaurant and bar. The menu is small but the food is quite good and having an onsite restaurant is convenient. The price we paid for a very off season Saturday night was excellent, but the rates really jack up during the summer Tanglewood season, far beyond what one would expect for a small motel room. The staff is friendly and professional, and dogs are welcome for an $85 fee. All in all, this is a very nice and sometimes very affordable Berkshires option. " [](https://expedia.co.uk/Lenox-Hotels-Berkshires-Untold.h76297618.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 "Room was comfortable and quiet. Staff accommodated a request to change rooms after check-in as we discovered there was someone next door who was constantly on the phone speaking loudly in a voice that carried on something business related. Relocating us was very appreciated." [](https://expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Country Inn & Suites by Radisson, Downtown Albany New York](https://images.trvl-media.com/lodging/112000000/111490000/111484500/111484416/9956a2ad_y.jpg) ### Country Inn & Suites by Radisson, Downtown Albany New York 4/10 Poor "My room was 79 degrees. I called and someone was sent up promptly to fix. He came in the room, worked for about 10-15 mins and said it was set. The room did not cool down and it was a terrible nights sleep." [](https://expedia.co.uk/Albany-Hotels-Country-Inn-Suites-By-Radisson.h111484416.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 6/10 Okay "The Property is dated " [](https://expedia.co.uk/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Comfort Inn & Suites East Greenbush - Albany](https://images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/f6e88d04_y.jpg) ### Comfort Inn & Suites East Greenbush - Albany 6/10 Okay "Ok" [](https://expedia.co.uk/Albany-Hotels-Comfort-Inn-Suites-East-Greenbush-Albany.h1052319.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "very clean and friendly staff" [](https://expedia.co.uk/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/bca96d17_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "Great, neat, convoy my son. " [](https://expedia.co.uk/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy](https://images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/d4631129_y.jpg) ### Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy 10/10 Excellent "The plane is so beautiful and relaxing " [](https://expedia.co.uk/Catskill-Hotels-Postcard-Cabins-Eastern-Catskills.h109129528.Hotel-Information) ![voco James Newbury Hudson Valley by IHG](https://images.trvl-media.com/lodging/95000000/94300000/94292700/94292624/c531473a_y.jpg) ### voco James Newbury Hudson Valley by IHG 10/10 Excellent "Very nice common area and the room was well decorated, well appointed, and comfortable. Fun music bingo in the bar on Saturday night. Only drawback was service in the restaurant during breakfast - only two overworked servers, resulting in long waits between visits to the table." [](https://expedia.co.uk/Coxsackie-Hotels-James-Newbury-Hotel.h94292624.Hotel-Information) ## Find out more about Chatham ## Chatham Holiday Homes information | Number of reviews | 253 | | ----------------- | ----------------- | | Accommodation | 490 Holiday Homes | | Lowest Price | £109 | | Highest Price | £537 | ## Explore a world of travel with Expedia - More ways to book - [Book Holiday Homes in Chatham on Expedia.com ](https://www.expedia.com/Chatham-Private-Vacation-Homes.d6046736-aaPrivateVacationHomes.Travel-Guide-Accommodation)