Title: Book the Best Dennis Port LUXURY Hotels - Upscale Hotels in Dennis Port, MA | Expedia.ca [Dennis Port Travel Guide](https://expedia.ca/Dennis-Port.dx6665)[Hotels in Dennis Port](https://expedia.ca/Dennis-Port-Hotels.d6665.Travel-Guide-Hotels)[Vacation Rentals in Dennis Port](https://expedia.ca/Dennis-Port-Vacation-Rentals.d6665.Travel-Guide-VacationRentals)[Flights to Dennis Port](https://expedia.ca/Cheap-Flights-To-Dennis-Port.d6665.Travel-Guide-Flights)[Dennis Port Car Rentals](https://expedia.ca/Car-Rentals-In-Dennis-Port.d6665.Car-Rental-Guide)[Dennis Port Vacation Packages](https://expedia.ca/Dennis-Port.d6665.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/484000/484400-dennis-port.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find luxury hotels in Dennis Port, MA ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Dennis Port Luxury Hotels Tonight [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=6665&startDate=2025-10-02&endDate=2025-10-03&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=6665&startDate=2025-10-03&endDate=2025-10-04&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6665&startDate=2025-10-03&endDate=2025-10-05&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6665&startDate=2025-10-10&endDate=2025-10-12&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Dennis Port Luxury Hotels ![Outdoor wedding area](https://images.trvl-media.com/lodging/10000000/9810000/9801600/9801551/5982af75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 1 Queen Bed with Sofa bed, Private Bathroom, Partial Ocean View (1 Bdrm. Suite) | View from room](https://images.trvl-media.com/lodging/10000000/9810000/9801600/9801551/5576d037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private Yellowtail House at By the Sea Bed & Breakfast | Private kitchen](https://images.trvl-media.com/lodging/10000000/9810000/9801600/9801551/0ae72b38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Quadruple Room, Private Bathroom, Ocean View (Room 202) | Beach/ocean view](https://images.trvl-media.com/lodging/10000000/9810000/9801600/9801551/7e4e0a0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### By the Sea Guests Bed & Breakfast & Suites Dennis Port 9.2/10 Wonderful (184) "Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year!" CA $229 CA $302 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Dennis-Port-Hotels-By-The-Sea-Guests-Bed-Breakfast-Suites.h9801551.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2850000/2840600/2840568/e928f229.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2850000/2840600/2840568/59aa54b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/3000000/2850000/2840600/2840568/b491533e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2850000/2840600/2840568/1329b22c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jonathan Edwards Motel Dennis Port 6.4/10 (43) "The customer service far outweighed any possible short comments. An excellent stay. We will be back. " CA $135 CA $155 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Dennis-Port-Hotels-Jonathan-Edwards-Motel.h2840568.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/970000/966500/966421/83ef5c9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/1000000/970000/966500/966421/6bbba73e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-golf](https://images.trvl-media.com/lodging/1000000/970000/966500/966421/48318c7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/970000/966500/966421/12b39c66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Hill Inn & Suites Dennis Port 8.4/10 Very good (950) "Clean, easy check in, stay here often" CA $159 CA $183 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Dennis-Port-Hotels-Holiday-Hill-Inn-Suites.h966421.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/9000000/8770000/8764800/8764759/1bd6a2f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/9000000/8770000/8764800/8764759/d2a6cd2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/9000000/8770000/8764800/8764759/1e657676.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/9000000/8770000/8764800/8764759/b48dfea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanside Motel Dennis Port 6.4/10 (598) "I liked every aspect of my stay." [](https://www.expedia.ca/Dennis-Port-Hotels-Oceanside-Motel.h8764759.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/6000000/5350000/5349300/5349280/9174ad8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Blackout drapes, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/6000000/5350000/5349300/5349280/ccae7cb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/6000000/5350000/5349300/5349280/daf156bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/6000000/5350000/5349300/5349280/39fa8ed1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cutty Sark Motor Lodge Dennis Port 9.0/10 Wonderful (192) "It was located very close to the beach, making it a fantastic spot." [](https://www.expedia.ca/Dennis-Port-Hotels-Cutty-Sark-Motor-Lodge.h5349280.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-16&endDate=2025-10-17®ionId=6665&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Top Dennis Port Hotel Reviews ![By the Sea Guests Bed & Breakfast & Suites](//images.trvl-media.com/lodging/10000000/9810000/9801600/9801551/5982af75_y.jpg) ### By the Sea Guests Bed & Breakfast & Suites 10/10 Excellent "Excellent con" [](https://expedia.ca/Dennis-Port-Hotels-By-The-Sea-Guests-Bed-Breakfast-Suites.h9801551.Hotel-Information) ![Holiday Hill Inn & Suites](//images.trvl-media.com/lodging/1000000/970000/966500/966421/83ef5c9f_y.jpg) ### Holiday Hill Inn & Suites 10/10 Excellent "Rooms are very well kept and clean. The pool is beautiful and the staff is friendly. Very good price" [](https://expedia.ca/Dennis-Port-Hotels-Holiday-Hill-Inn-Suites.h966421.Hotel-Information) ![Oceanside Motel](//images.trvl-media.com/lodging/9000000/8770000/8764800/8764759/1bd6a2f0_y.jpg) ### Oceanside Motel 10/10 Excellent "I liked every aspect of my stay." [](https://expedia.ca/Dennis-Port-Hotels-Oceanside-Motel.h8764759.Hotel-Information) ## Frequently asked questions ### Are you searching for the perfect hotel for your luxury getaway to Dennis Port? > Expedia can help you get a flight to Hyannis, MA (HYA-Barnstable Municipal) airport or Nantucket, MA (ACK-Nantucket Memorial) airport, and then you can select from a variety of places to stay that will deliver the luxury you seek. Amenities are important when you plan a trip, so we make it easy to find what you'd like to make your stay special. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Dennis Port offers. During your visit, you might want to enjoy the restaurants and seafood restaurants which Dennis Port is known for. ### When can I expect good weather in Dennis Port? > Planning for the weather is an important factor for making your trip to Dennis Port 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 Dennis Port is 48 inches. ### What's there to see and do in Dennis Port? > Enjoy all that Dennis Port has to offer when you visit Sea Street Beach, Cape Cod Theatre Company – Home of the Harwich Jr. Theatre, and Swan Pond River. 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