Title: 5 Stars Hotels in Woolford, Maryland from CA $280 - Find Cheap Woolford Hotels With 5 Stars | Expedia.ca [Woolford Travel Guide](https://expedia.ca/Woolford.dx553248635975865928)[Hotels in Woolford](https://expedia.ca/Woolford-Hotels.d553248635975865928.Travel-Guide-Hotels)[Vacation Rentals in Woolford](https://expedia.ca/Woolford-Vacation-Rentals.d553248635975865928.Travel-Guide-VacationRentals)[Flights to Woolford](https://expedia.ca/Cheap-Flights-To-Woolford.d553248635975865928.Travel-Guide-Flights)[Woolford Car Rentals](https://expedia.ca/Car-Rentals-In-Woolford.d553248635975865928.Car-Rental-Guide)[Woolford Vacation Packages](https://expedia.ca/Woolford.d553248635975865928.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Woolford, Maryland from CA $280 ![](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 Woolford 5 Star Hotels Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=553248635975865928&startDate=2025-10-13&endDate=2025-10-14&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=553248635975865928&startDate=2025-10-14&endDate=2025-10-15&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635975865928&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635975865928&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Woolford 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) ![Interior](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/6a6b34d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/2de6ebed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/3dd4d01f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Perry Cabin St. Michaels 9.6/10 Exceptional (365) "Beautiful place to stay." CA $566 CA $685 total includes taxes & fees Nov 12 - Nov 13 [](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) ![Exterior](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/w264h344x4y2-b20fcf10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/625fcac5.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 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." [](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-Woolford-Hotels.s50-0-d553248635975865928.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Woolford-Hotels.s50-0-d553248635975865928.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 Woolford. ![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 $268 CA $371 total Oct 15 - Oct 16 includes taxes & fees 8.6/10 Excellent! (1,004 reviews) [](https://expedia.ca/Cambridge-Hotels-Hyatt-Regency-Chesapeake-Bay.h890486.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, Royal Oak, Easton, MD CA $579 CA $636 total Oct 14 - Oct 15 includes taxes & fees 9.8/10 Exceptional! (38 reviews) [](https://expedia.ca/Easton-Hotels-The-Oaks-Waterfront-Inn.h1721586.Hotel-Information) ![Marvel's on the Creek](https://images.trvl-media.com/lodging/30000000/29320000/29313500/29313486/6c5e583a_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Marvel's on the Creek 6230 Beverly Rd, East New Market, MD CA $252 CA $280 total Oct 27 - Oct 28 includes taxes & fees 9.8/10 Exceptional! (159 reviews) [](https://expedia.ca/Secretary-Hotels-Marvels-On-The-Creek.h29313486.Hotel-Information) Still don't see what you're looking for? [See all properties in Woolford.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635975865928&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%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635975865928&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635975865928&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635975865928&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635975865928&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635975865928&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. ## Top Woolford Hotel Reviews ![Inn at Perry Cabin](//images.trvl-media.com/lodging/1000000/20000/14600/14576/38b8c334_y.jpg) ### Inn at Perry Cabin 10/10 Excellent "Nice place to stay. Thru can’t do enough for you to make your stay comfortable and enjoyable Rooms are beautiful and clean " [](https://expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) ## Find out more about Woolford Luxury is the name of the game at the best 5 Stars hotels in Woolford. 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 Woolford 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 Woolford 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 Woolford without giving up even an inch of quality. Everything your heart desires (and a few perks designed to make it skip a beat): That’s what’s on offer when you plan a trip to the hotels with 5 Stars in Woolford. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [2 Star Hotels in Berlin](https://www.expedia.ca/2Star-Berlin-Hotels.s20-0-d79155.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Cheltenham](https://www.expedia.ca/2Star-Cheltenham-Hotels.s20-0-d553248635975874284.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Washington](https://www.expedia.ca/3Star-Washington-Hotels.s30-0-d178318.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Algonquin](https://www.expedia.ca/4Star-Algonquin-Hotels.s40-0-d553248635975860123.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Anchorage](https://www.expedia.ca/4Star-Anchorage-Annapolis-Hotels.s40-n553248635976473602-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Annapolis](https://www.expedia.ca/4Star-Annapolis-Hotels.s40-0-d6034082.Travel-Guide-Filter-Hotels) - 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