Title: Book the Best PET FRIENDLY Hotels in Chatham, NY from CA $107 - Chatham Dog-Friendly Hotels | 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) ![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__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 availability on Chatham Pet-friendly Hotels Tonight [Mar 21 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-03-21&endDate=2026-03-22&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 22 - Mar 23](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-03-22&endDate=2026-03-23&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-03-27&endDate=2026-03-29&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-04-03&endDate=2026-04-05&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chatham pet-friendly hotels ![View from property](https://images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/d4631129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/d71945c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/e46ce1bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/eb59c690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy [](https://www.expedia.ca/Catskill-Hotels-Postcard-Cabins-Eastern-Catskills.h109129528.Hotel-Information) Catskill 9.6/10 Exceptional (178 reviews) "I just love this place, this was my second time and ofc I will be back" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JANYRA CA $163 CA $236 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Catskill-Hotels-Postcard-Cabins-Eastern-Catskills.h109129528.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/4a1ad790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Untold [](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) Lenox 9.0/10 Wonderful (879 reviews) "Beautiful little quaint hotel. I will definitely be returning" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin CA $96 CA $107 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/8e50ee57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, Private Bathroom (Garden - Pets Allowed) | Miscellaneous](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/c68ae4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, Private Bathroom (Clark - Pets Allowed)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/04b1723e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, Private Bathroom (Honeymoon - Pets Allowed)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/7ac0f2b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shaker Mill Inn [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) West Stockbridge 9.6/10 Exceptional (446 reviews) "Had everything we needed. Very thoughtful touches. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark CA $144 CA $159 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) ![Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/5740b713.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/83c805e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Berkshire Hills Inn & Suites [](https://www.expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) Pittsfield 8.6/10 Excellent (1,000 reviews) "It was a solid experience at the Best western, staff was super nice, the room was spacious and clean, the breakfast was delicious and the location is superb. Overall it was a great experience and will definitely stay there again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristina CA $146 CA $163 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/251da7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/754813dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b38994ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/06dae0ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Element Lenox Berkshires [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) Lenox 9.8/10 Exceptional (23 reviews) "Friendly staff, beautiful interiors." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Izabela CA $191 CA $213 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/00c971b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/e459ce18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/6a32b13e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) Lee 9.2/10 Wonderful (1,001 reviews) "Room was spotless, staff was very kind!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ilia CA $130 CA $146 total includes taxes & fees Apr 6 - Apr 7 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7c78ca51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/e351f473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms, Non Smoking](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/723a5f12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Non Smoking](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/a393dfb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Great Barrington Berkshires [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) Great Barrington 7.6/10 Good (574 reviews) "Excellent location!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abdul Samad CA $103 CA $115 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) ![Double Room](https://images.trvl-media.com/lodging/126000000/125350000/125340300/125340225/b3935f27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125350000/125340300/125340225/9a417e14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125350000/125340300/125340225/1a233317.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125350000/125340300/125340225/65793401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Berkshire Mountain Inn [](https://www.expedia.ca/Great-Barrington-Hotels-The-Berkshire-Mountain-Inn.h125340225.Hotel-Information) Great Barrington 10/10 Exceptional (2 reviews) CA $206 CA $230 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Great-Barrington-Hotels-The-Berkshire-Mountain-Inn.h125340225.Hotel-Information) ![Deluxe Room, 1 King Bed, Ensuite (2nd Floor)](https://images.trvl-media.com/lodging/20000000/19190000/19185500/19185424/dc8b3c09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/20000000/19190000/19185500/19185424/83c74984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/20000000/19190000/19185500/19185424/b5703a1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![36-inch flat-screen TV with digital channels, TV, DVD player](https://images.trvl-media.com/lodging/20000000/19190000/19185500/19185424/523420f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Changing Times Boutique Country Lodging [](https://www.expedia.ca/Craryville-Hotels-Changing-Times-Boutique-Country-BB.h19185424.Hotel-Information) Craryville 10/10 Exceptional (113 reviews) "Great experience, looking forward to staying again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Greg CA $206 CA $231 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Craryville-Hotels-Changing-Times-Boutique-Country-BB.h19185424.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/279dc540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/ef9bad04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Mobility Accessible](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/9c5d1ec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/6fb451ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Little Lion [](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) Great Barrington 8.6/10 Excellent (555 reviews) "Clean … check in , good location for us .. we’ll be back in Maynn" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $149 CA $167 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.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=2026-04-04&endDate=2026-04-05®ionId=6046736&adults=2&amenities=PETS&sort=RECOMMENDED&openPlayBack=true) ## Find out more about Chatham ### Discover top Chatham attractions with your pet Chatham, New York, offers a quaint yet vibrant escape for travellers with pets, featuring several points of interest that both you and your furry companion can enjoy. Start your adventure at the scenic Chatham Fish and Game Club, where you can take leisurely strolls along the trails and even let your pet roam in designated areas. Next, head to the nearby Ooms Conservation Area, known for its picturesque walking paths and wildlife, making it a delightful spot for a leisurely hike with your dog. If you're in the mood for some local culture, visit the Chatham Arts Council, which often hosts events that welcome pets, allowing you to enjoy local arts while keeping your companion by your side. The charming Main Street, lined with pet-friendly cafes and shops, is perfect for a casual day out; many establishments have outdoor seating where your pet is welcome. For a relaxing stay, consider the pet-friendly accommodations near the town centre, where you can unwind after a day of exploring. Enjoy the convenience of being steps away from local attractions, while also having a welcoming place for your pet to rest. With attentive service and quality amenities, your stay in Chatham will be both comfortable and memorable. ## Top Chatham Hotel Reviews ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/ef3ce5c5_y.jpg) ### Hotel On North 10/10 Excellent "The hotel was even more beautiful in person! Rooms were incredibly spacious and lovely. The staff was incredibly friendly and helpful. Great stay would definitley return. " [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.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 "yes" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/6897a130_y.jpg) ### The Red Lion Inn 10/10 Excellent "great customer service" [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ## Frequently asked questions ### How much does a pet-friendly hotel in Chatham cost? ### Which area of Chatham is best to stay in for pet-friendly hotels? > The village centre of Chatham is the heart of the community, offering a selection of shops, eateries, and local services. Main Street runs through the middle, providing easy access to everything. It's a compact area, making it convenient to walk around with your pet. > > > Couples travelling with their pets will find the village centre particularly suitable. Many of the local businesses welcome well-behaved dogs, and there are several parks nearby for walks, such as the Chatham Village Park, which is a lovely spot for a stroll. ### How do I ensure I have booked a pet-friendly room in Chatham? ### What pet-friendly activities should we do in Chatham? > For active pets and their owners, the Old Chatham Sheepherding Company is an excellent choice. While the main buildings might have restrictions, the surrounding grounds offer lovely walking opportunities on lead, where you can enjoy the rural scenery and perhaps spot some sheep from a distance. It's a nice way to get some exercise together in a calm setting. > > > When you're in the village centre, many of the independent shops along Main Street and Park Row welcome well-behaved, leashed dogs. Look for water bowls outside establishments, which are a good sign of their pet-friendly policy. You can often browse with your dog by your side, making for a pleasant stroll through the town's charming boutiques and galleries. It's a great way for couples to enjoy the local flavour without leaving their pet behind. > > > For a more extended outdoor adventure, the Ooms Conservation Area at Sutherland Pond offers walking trails through woodlands and around a pond, superb for dogs who love to explore. ### What amenities should I look for in a pet-friendly hotel in Chatham? ### How can I save on a pet-friendly hotel in Chatham with Expedia? ### Do any Chatham hotels have restrictions on pet sizes or breeds? ### Is it cheaper to book flights and a pet-friendly hotel in Chatham as a package? ### Can I cancel my pet-friendly hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - More ways to book - [Business Hotels in Albany ](https://www.expedia.ca/Albany-Hotels-Business-Hotel.0-0-d603260-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Albany ](https://www.expedia.ca/Albany-Hotels-Couples-Resorts-Hotels.0-0-d603260-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - 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