Title: Book the Best Chatham LUXURY Hotels - Upscale Hotels in Chatham, MA | Expedia.ca [Chatham Travel Guide](https://expedia.ca/Chatham.dx10743)[Hotels in Chatham](https://expedia.ca/Chatham-Hotels.d10743.Travel-Guide-Hotels)[Vacation Rentals in Chatham](https://expedia.ca/Chatham-Vacation-Rentals.d10743.Travel-Guide-VacationRentals)[Flights to Chatham](https://expedia.ca/Cheap-Flights-To-Chatham.d10743.Travel-Guide-Flights)[Chatham Car Rentals](https://expedia.ca/Car-Rentals-In-Chatham.d10743.Car-Rental-Guide)[Chatham Vacation Packages](https://expedia.ca/Chatham.d10743.Destination-Travel-Guides) ![Chatham featuring a windmill, general coastal views and wild flowers](https://images.trvl-media.com/place/10743/d3f8b886-55a4-46b3-afab-39fd14b1b518.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find luxury hotels in Chatham, MA - ![](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 Luxury Hotels Tonight [Nov 23 - Nov 24](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-11-23&endDate=2025-11-24&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Nov 24 - Nov 25](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-11-24&endDate=2025-11-25&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-11-28&endDate=2025-11-30&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) In two weeks [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-12-05&endDate=2025-12-07&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Chatham Luxury Hotels ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/w5700h3895x0y5-016d240d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Ocean View (Cottage) | View from room](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/63585c06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/f7ed55d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/07d625ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chatham Bars Inn Chatham 9.2/10 Wonderful (795) "Great accommodation and staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $367 CA $441 total includes taxes & fees Nov 29 - Nov 30 [](https://www.expedia.ca/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information) ![Superior Room, 2 Double Beds, Kitchenette | Private kitchen](https://images.trvl-media.com/lodging/5000000/4620000/4616500/4616460/2260ae8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4620000/4616500/4616460/6225c6ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/5000000/4620000/4616500/4616460/f4f57159.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/5000000/4620000/4616500/4616460/084008b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Chatham Motel Chatham 9.2/10 Wonderful (631) "Good location, good calue" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William.Leo [](https://www.expedia.ca/Chatham-Hotels-The-Chatham-Motel.h4616460.Hotel-Information) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/7cf38365.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/e981387d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/94cdbe08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/550a87c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Greyfinch Chatham Inn Chatham 8.8/10 Excellent (254) "Wonderful place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John [](https://www.expedia.ca/Chatham-Hotels-Chatham-Highlander-Village-Inn.h7461681.Hotel-Information) ![Hiking](https://images.trvl-media.com/lodging/2000000/1510000/1502100/1502039/6cee3705.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury King](https://images.trvl-media.com/lodging/2000000/1510000/1502100/1502039/ac0b2bcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1510000/1502100/1502039/b104f6a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1502100/1502039/bce8afe8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Old Harbor Inn Chatham 9.6/10 Exceptional (162) "The innkeepers,Judy and Ray, make you feel welcome and at home. The breakfast was terrific. They have food and snacks and drinks available without additional charge all day and night. This is a wonderful and run by terrific people." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Howard [](https://www.expedia.ca/Chatham-Hotels-Old-Harbor-Inn.h1502039.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=2025-12-07&endDate=2025-12-08®ionId=10743&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_10743) ## Find out more about Chatham ### Chathamand its attractions for luxury travelers For luxury travellers seeking an unforgettable experience in Chatham, Massachusetts, the stunning Chatham Lighthouse is a must-visit, standing tall at the entrance of the harbour, offering breathtaking coastal views and rich maritime history. Nearby, the charming Chatham Fish Pier is perfect for those who appreciate fresh seafood, where you can watch the day's catch being unloaded and even enjoy a meal at local eateries that pride themselves on their fresh offerings. Nature enthusiasts will delight in the Cape Cod National Seashore, where pristine beaches and scenic landscapes provide ample opportunities for leisurely walks or picnics with family. Don't miss the enchanting Monomoy National Wildlife Refuge, where guided boat tours allow for close encounters with seals and migratory birds, making for a truly unique experience. For a truly luxurious stay, consider the waterfront properties along the picturesque Main Street, where upscale hotels such as The Chatham Bars Inn offer exquisite amenities like private beaches, fine dining, and spa services, ensuring personalised attention and a pampered experience throughout your stay. ### Find the best luxury hotels and resorts in Chatham For those seeking an indulgent getaway in Chatham, Massachusetts, these luxurious hotels offer opulent amenities and exceptional service for an unforgettable experience. [Captain's House Inn](https://www.expedia.ca/Chatham-Hotels-Captains-House-Inn.h2824230.Hotel-Information) - **Why it's great for a luxury retreat:** Renowned for its exceptional service and luxury, Captain's House Inn boasts an impressive review rating of 9.8. Guests will appreciate the elegant touches such as fireplaces and premium bedding, alongside designer toiletries that enhance their stay. The inn’s intimate atmosphere makes it a perfect sanctuary for luxury-seeking travellers. - **Other amenities:** Guests can indulge in complimentary full breakfasts each morning and explore the nearby beach locations. The inn also features a terrace and patio for relaxation, with opportunities for kayaking and sailing just a stone's throw away. With express check-in and late check-out options, guests will enjoy a seamless and personalised experience throughout their stay. - **Nearby attractions:** Cape Cod Beaches - 0.7 km, Chatham Shark Center - 0.8 km, Chatham Fish Pier - 0.8 km [Old Harbor Inn](https://www.expedia.ca/Chatham-Hotels-Old-Harbor-Inn.h1502039.Hotel-Information) - **Why it's great for a luxury retreat:** Old Harbor Inn is a luxurious haven with a review rating of 9.6, perfect for those seeking a romantic getaway or a special retreat. Guests are treated to upscale comforts such as room service and in-room fireplaces, along with premium bedding and bathrobes for a touch of elegance. - **Other amenities:** The inn offers a complimentary breakfast each morning, alongside features like a terrace for outdoor relaxation. Guests can enjoy yoga classes on-site, and there are options for private picnics on the beach. The surrounding area provides opportunities for windsurfing and other water sports, while self-parking and express check-in add to the convenience of a luxurious stay. - **Nearby attractions:** Chatham Seaside Links - 0.9 km, Veterans Field - 0.4 km, Chatham Windmill - 1 km [Chatham Bars Inn](https://www.expedia.ca/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information) - **Why it's great for a luxury retreat:** Chatham Bars Inn is the epitome of luxury, a stellar review rating of 9.2. This stunning resort offers guests an array of upscale amenities including elegant in-room fireplaces, premium bedding, and designer toiletries, ensuring a lavish stay. Guests can also enjoy tennis on the outdoor courts and unwind at the private beach, making it the perfect retreat for discerning travellers. - **Other amenities:** The hotel features an extensive spa with treatment rooms and a variety of massage options to pamper guests, alongside a fitness centre and a heated pool for those looking to stay active. The concierge service is on hand to assist with bespoke arrangements, while the beach bar and on-site dining options provide delightful culinary experiences. Additional features include free beach shuttles, daily housekeeping, and luxurious bathrobes for ultimate comfort. - **Nearby attractions:** Cape Cod Beaches - 0.4 km, Chatham Seaside Links - 0.2 km, Chatham Fish Pier - 0.6 km [Chatham Wayside Inn](https://www.expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information) - **Why it's great for a luxury retreat:** With a review rating of 9.2, Chatham Wayside Inn delivers a blend of elegance and comfort. Guests are welcomed with premium bedding and bathrobes, complemented by thoughtful touches such as champagne service. The hotel’s restaurant offers beautiful garden views, making every meal a special occasion for luxury travellers. - **Other amenities:** This charming inn features a refreshing pool with sun loungers, along with a terrace that provides a serene place to relax. Guests can enjoy a complimentary breakfast, and the concierge service is available to help with local attractions or reservations. The inn is conveniently located near a vibrant shopping district and local beaches, enhancing the overall experience with easy access to leisure activities. - **Nearby attractions:** Cape Cod Beaches - 0.9 km, Veterans Field - 0.9 km, Chatham Windmill - 0.7 km [Chatham Seafarer Inn](https://www.expedia.ca/Chatham-Hotels-Chatham-Seafarer-Inn.h2034734.Hotel-Information) - **Why it's great for a luxury retreat:** Chatham Seafarer Inn provides a comfortable and stylish retreat with a solid review rating of 9.0. While it is more modest in luxury, it offers essential amenities for a pleasurable stay, including air-conditioned rooms that provide a refreshing escape during warmer months. - **Other amenities:** The inn features daily housekeeping to ensure cleanliness and comfort, alongside a kitchenette for added convenience. Guests can enjoy the inviting pool and lush garden, while nearby beach access allows for lovely seaside strolls. Free self-parking is available, making it easy for guests to explore the beautiful surroundings of Chatham. - **Nearby attractions:** Cape Cod Beaches - 1.3 km, Ridgevale Beach - 1.3 km, Cockle Cove Beach - 2.1 km ## Top Chatham Hotel Reviews ![Hyannis Travel Inn](https://images.trvl-media.com/lodging/2000000/1380000/1379200/1379109/fe11d49f_y.jpg) ### Hyannis Travel Inn 10/10 Excellent "Nice staff Clean room Comfortable bed Convenient location " [](https://expedia.ca/Hyannis-Hotels-Hyannis-Travel-Inn.h1379109.Hotel-Information) ![Bayside Resort Hotel](https://images.trvl-media.com/lodging/1000000/900000/896700/896697/85f07916_y.jpg) ### Bayside Resort Hotel 10/10 Excellent "Great place..Friday wonderful breakfast, clean as always. Have stayed here 6 timmes Never disappointed " [](https://expedia.ca/West-Yarmouth-Hotels-Bayside-Resort-Hotel.h896697.Hotel-Information) ![Cape Sands Inn](https://images.trvl-media.com/lodging/2000000/1340000/1330200/1330174/aa954682_y.jpg) ### Cape Sands Inn 10/10 Excellent "Clean room, great rate easy checkin and easy checkout. Will stay again. " [](https://expedia.ca/West-Yarmouth-Hotels-Cape-Sands-Inn.h1330174.Hotel-Information) ![Hyannis Plaza Hotel](https://images.trvl-media.com/lodging/2000000/1120000/1119300/1119277/f7fc1d07_y.jpg) ### Hyannis Plaza Hotel 10/10 Excellent "Staff was great and room was very clean " [](https://expedia.ca/Hyannis-Hotels-Hyannis-Plaza-Hotel.h1119277.Hotel-Information) ![Margaritaville Resort Cape Cod](https://images.trvl-media.com/lodging/1000000/20000/12900/12897/b57e0b1f_y.jpg) ### Margaritaville Resort Cape Cod 10/10 Excellent "The room were clean. The staff were all friendly! I will definitely go back!!! " [](https://expedia.ca/Hyannis-Hotels-Cape-Codder-Resort-And-Spa.h12897.Hotel-Information) ![Chatham Bars Inn](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/w5700h3895x0y5-016d240d_y.jpg) ### Chatham Bars Inn 10/10 Excellent "Great accommodation and staff." [](https://expedia.ca/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information) ![Red Jacket Beach Resort](https://images.trvl-media.com/lodging/1000000/60000/55000/54939/36198ab8_y.jpg) ### Red Jacket Beach Resort 10/10 Excellent "Great room, nice view, perfect location. Power did go out one night, coffee machine never worked and they had no fix, and the breakfast is obscenely expensive." [](https://expedia.ca/South-Yarmouth-Hotels-Red-Jacket-Beach-Resort.h54939.Hotel-Information) ![Greyfinch Chatham Inn](https://images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/7cf38365_y.jpg) ### Greyfinch Chatham Inn 10/10 Excellent "Lovely room, well kept and cozy " [](https://expedia.ca/Chatham-Hotels-Chatham-Highlander-Village-Inn.h7461681.Hotel-Information) ![Freebird Motor Lodge by Reverie Boutique Collection](https://images.trvl-media.com/lodging/7000000/6590000/6589400/6589307/82e2d962_y.jpg) ### Freebird Motor Lodge by Reverie Boutique Collection 10/10 Excellent "Very clean room. Staff was exceptionally nice." [](https://expedia.ca/West-Yarmouth-Hotels-Hunters-Green-Cape-Cod.h6589307.Hotel-Information) ## Frequently asked questions ### Are you looking for a luxury hotel for your stay in Chatham? > During your visit, you might want to enjoy the beaches which Chatham is known for. ### What's the best luxury accommodation in Chatham? > [Chatham Bars Inn](https://www.expedia.ca/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information) is a luxury resort with a private beach and a full-service spa, and it's a popular choice for Expedia travelers looking for an elegant place to stay. ### When can I expect good weather in Chatham? > Planning for the weather is an important factor for making your trip to Chatham a success, especially when you're splurging. The hottest months are usually August and July with an average temp of 67°F, while the coldest months are February and January with an average of 38°F. Average annual precipitation for Chatham is 54 inches. ### What's there to see and do in Chatham? > Enjoy Chatham with a stop at Chatham Fish Pier, Chatham Lighthouse, and Chatham Lighthouse Beach. 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