Title: 5 Stars Hotels in Madison, Maryland from CA $190 - Find Cheap Madison Hotels With 5 Stars | Expedia.ca [Madison Travel Guide](https://expedia.ca/Madison.dx553248635975869814)[Hotels in Madison](https://expedia.ca/Madison-Hotels.d553248635975869814.Travel-Guide-Hotels)[Vacation Rentals in Madison](https://expedia.ca/Madison-Vacation-Rentals.d553248635975869814.Travel-Guide-VacationRentals)[Flights to Madison](https://expedia.ca/Cheap-Flights-To-Madison.d553248635975869814.Travel-Guide-Flights)[Madison Car Rentals](https://expedia.ca/Car-Rentals-In-Madison.d553248635975869814.Car-Rental-Guide)[Madison Vacation Packages](https://expedia.ca/Madison.d553248635975869814.Destination-Travel-Guides) ![Harriet Tubman Underground Railroad National Historical Park showing signage, interior views and a statue or sculpture](https://images.trvl-media.com/place/553248633992438829/cea385ea-0b9b-4155-8f55-bd838e0ef0d8.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Madison, Maryland from CA $190 - ![](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 Madison 5 Star Hotels Tonight [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635975869814&startDate=2025-12-13&endDate=2025-12-14&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=553248635975869814&startDate=2025-12-14&endDate=2025-12-15&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635975869814&startDate=2025-12-19&endDate=2025-12-21&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635975869814&startDate=2025-12-26&endDate=2025-12-28&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Madison 5-star hotels ![Breakfast, lunch, dinner served; ocean views](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/38b8c334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Garden View | Garden view](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/b1a0ff2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/7a7c860e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/6a6b34d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Perry Cabin [](https://www.expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) Downtown St. Michaels 9.6/10 Exceptional (371) "Friendly and attentive staff, good cleaning services" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathan CA $646 CA $782 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) ![Dinner served](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/be8a1621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/0c9c2eb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/82384fab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/20605cd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at 202 Dover [](https://www.expedia.ca/Easton-Hotels-Inn-At-202-Dover.h5308723.Hotel-Information) Easton 10/10 Exceptional (14) "Celebrated our 33rd anniversary here and enjoyed it thoroughly. Felt pampered and welcomed. Best B&B ever! Everything from the room to the food was exceptional. Every need was anticipated and met. Looking forward to our next visit. The quintessential "living like a king" experience." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James [](https://www.expedia.ca/Easton-Hotels-Inn-At-202-Dover.h5308723.Hotel-Information) ![](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%2F5Star-Madison-Hotels.s50-0-d553248635975869814.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Madison-Hotels.s50-0-d553248635975869814.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Madison. ![Hyatt Regency Chesapeake Bay](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/6000a351_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hyatt Regency Chesapeake Bay 100 Heron Blvd Cambridge MD CA $208 CA $274 total Jan 1 - Jan 2, 2026 includes taxes & fees 8.6/10 Excellent! (1,002 reviews) [](https://expedia.ca/Cambridge-Hotels-Hyatt-Regency-Chesapeake-Bay.h890486.Hotel-Information) ![Rod 'N' Reel Resort](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4803b1f5_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Rod 'N' Reel Resort 4165 Mears Ave Chesapeake Beach MD CA $146 CA $190 total Jan 7 - Jan 8, 2026 includes taxes & fees 8.2/10 Very Good! (1,000 reviews) [](https://expedia.ca/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) ![The Oaks Waterfront](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/d0af41e9_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Oaks Waterfront 25876 Royal Oak Road Easton MD CA $569 CA $626 total Dec 15 - Dec 16 includes taxes & fees 10/10 Exceptional! (41 reviews) [](https://expedia.ca/Easton-Hotels-The-Oaks-Waterfront-Inn.h1721586.Hotel-Information) Still don't see what you're looking for? [See all properties in Madison.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025®ionId=553248635975869814&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025®ionId=553248635975869814&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025®ionId=553248635975869814&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025®ionId=553248635975869814&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025®ionId=553248635975869814&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025®ionId=553248635975869814&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Madison Head to sights like Harriet Tubman Underground Railroad National Historical Park and Blackwater National Wildlife Refuge as you discover Madison. [See all hotels in Madison](https://www.expedia.ca/Hotel-Search?startDate=2025-12-27&endDate=2025-12-28&adults=2®ionId=553248635975869814) ![Harriet Tubman Underground Railroad National Historical Park showing signage, interior views and a statue or sculpture](https://images.trvl-media.com/place/553248633992438829/cea385ea-0b9b-4155-8f55-bd838e0ef0d8.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) ## Top Madison Hotel Reviews ![Inn at Perry Cabin](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/38b8c334_y.jpg) ### Inn at Perry Cabin 10/10 Excellent "Fantastic resort; beautiful with lots of great history. Highly recommend the historic walking tour with Jay. " [](https://expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) ## Find out more about Madison Luxury is the name of the game at the best 5 Stars hotels in Madison. If you want to vacation like a true VIP, these are the places to go; from spacious resorts to boutique-inspired hot spots, the top Madison 5 Stars hotels are dedicated to immersing you in the ultimate experience. Want to relax with a serene treatment at a designer spa? These properties offer them. Interested in tasting delicious dishes from top chefs? The gourmet restaurants at the 5 Stars Madison hotels have you covered. You’ll even find first-class hotels near the city’s must-see attractions and most upscale entertainment districts. Plus, when you book your trip with Expedia.ca, you’ll get access to fantastic rates and seasonal discounts, so you can take advantage of a cheap deal on 5 Stars hotels Madison without giving up even an inch of quality. 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