United States Maryland Maryland Guide Things To Do Essentials Getaways All Maryland The 7 Best Chesapeake Bay Hotels The Tides Inn is the best stay within the Chesapeake region Written by Chris Abell Updated 04/27/21 Fact-Checked by Reviewed on 10/25/20 Patrice J. Williams Patrice J. Williams is a travel and style content creator and fact checker and author of thrift shopping book "Looking Fly on a Dime." About TripSavvy Fact-Checking Patrice J. Williams Share Pin Email FrozenShutter/GettyImages Our editors independently research, test, and recommend the best products and services; you can learn more about our review process here. We may receive commissions on purchases made from our chosen links. The Rundown Best Overall: Tides Inn Best Luxury: Inn at Perry Cabin Best for Families: Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina Best for Foodies: The Hope and Glory Inn Best for History Buffs: Robert Morris Inn Best Boutique Hotel: Kent Manor Inn Best Budget Hotel: Anchored Inn at Hidden Harbor Best B&B: Brampton Inn A stay in the areas surrounding the Chesapeake Bay offers travelers the epitome of relaxation. An underrated, slow-paced region of waterfront living in the mid-Atlantic, the Chesapeake itself is the largest estuary in the United States and boasts over 11,000 miles of gorgeous coastline along the eastern borders of Maryland and Virginia. Locals and visitors love the region for its landscape (think dramatic shoreline and deep blue waters), outdoor activities (like sailing and golfing), and seafood (there's no shortage of blue crabs and fresh oysters). It also has something for every travel budget, whether that allows for a luxurious escape or a modest, comfortable hotel that goes easy on the wallet. Whether you’re looking for a quaint weekend in a charming coastal town, a family trip with a resort feel, or something in between, this expert-curated list of Chesapeake Bay hotels and inns can help you find the perfect place to get away by the water. 01 of 07 Best Overall: Tides Inn Tides Inn See Rates on Tripadvisor.com Why We Chose It This hotel, set on a striking waterfront property, offers all the Chesapeake Bay area outdoor activities travelers (and locals) could ever want—and the rooms are exquisite, to boot. Pros Exceptional golf Fresh, local seafood Children’s program Close proximity to dozens of local attractions Cons Resort fee With waterfront views, a sailing school, and even a children’s program, the whole family will be happy here. But golfers, in particular, will delight in the Inn’s George W. Cobb-designed Golden Eagle Golf Course. There’s even a par-3 course for the family to enjoy. Seafood lovers will also be drawn to the Tides, as oysters and other local fare are mainstays on the menu. As for the rooms and luxury suites, guests can expect soft and sumptuous linens accented by rich mahogany furniture, private patios overlooking lush gardens and Carter's Creek, and the option (depending on the type of room or suite) for pets, sleeper sofas, and in-suite wet bars. Notable Amenities Sailing, tennis, and golf Exceptional seafood Spa and pool Bicycles on-site for guest use 02 of 07 Best Luxury: Inn at Perry Cabin Inn at Perry Cabin See Rates on Tripadvisor.com Why We Chose It This hotel is what should come to mind when imagining the upscale, slightly southern charms of Maryland's Eastern Shore—and insiders have loved the spot for decades, so you know it's worth the splurge. Pros Gorgeous grounds Waterfront activities Restaurant and pub on-site Close proximity to dozens of local attractions Cons Pricey The Inn at Perry Cabin offers a luxury bayside experience unlike any other. Take a morning sailing lesson and then relax on the expansive lawn’s Adirondack chairs before an afternoon of golf. Then enjoy a cocktail at on-site Purser’s Pub before an upscale dinner at the property’s STARS restaurant. And do it all in a beautiful, colonial-style estate that you just might recognize from its appearance in 2005 comedy smash Wedding Crashers. Of all the Chesapeake Bay hotels, this is surely the most iconic. Notable Amenities Sailing, tennis, and golf Great on-site dining Spa and pool Fitness center Bicycles on-site for guest use 03 of 07 Best for Families: Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina See Rates on Tripadvisor.com Why We Chose It Truly the best option for the kids. the energy and activity at this hotel make it a destination the young ones will want to visit again. Pros Full-service, on-site spa Marina 18-hole golf course Babysitting Pet friendly Hyatt reliability Cons Large-chain feel Resort fee A safe bet at a reasonable price, the Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina is a premier AAA Four Diamond property. Its spa and waterfront setting set it apart, and the massive property gives visitors plenty to explore. Camp Hyatt (temporarily suspended as of April 2021) means the kids are taken care of, and onsite golf means you don’t even need to leave the property to hit the links—though the nearby city of Cambridge offers plenty of offsite activities. Notable Amenities Marina and kayaks On-site restaurants Spa and pool Babysitting Golf course Game room Fitness center 04 of 07 Best for Foodies: The Hope and Glory Inn The Hope and Glory Inn See Rates on Tripadvisor.com Why We Chose It The pretty gardens, eclectic decor, fun patio scene, and fantastic menu make this place ideal for those on the hunt for local delicious cuisine in a lively atmosphere Pros Terrific on-site restaurant with accomplished chef Vineyard nearby Pet friendly Beautiful gardens Cons A bit inland from the water Ethiopian-born, French-trained chef Meseret Crockett brings fresh ingredients and exceptional talent to her regularly updated menus at the inn’s restaurant, so you can rest assured that you’ll eat well. The grounds here are simply beautiful, and guests will notice that the meticulously tended gardens complement tastefully decorated rooms. You’ll also find a pool and even a private garden bath and shower (ahem, there's a clawfoot tub!)—perhaps the only amenity of its kind on Virginia’s eastern shore, or elsewhere, for that matter. Notable Amenities Breakfast included Pool Bicycle on-site for guests use Private garden bath and shower Continue to 5 of 7 below. 05 of 07 Best Boutique Hotel: Kent Manor Inn Kent Manor Inn See Rates on Tripadvisor.com Why We Chose It Classic Eastern Shore luxury at a more affordable price point makes this an attractive choice for those not looking to break the bank while still kicking back in style. Pros Beautiful rooms Waterfront lawn Close proximity to dozens of local attractions Cons Food can be hit or miss Located not too far from the Chesapeake Bay Bridge, the inn sits on Kent Island, one of the region’s iconic examples of Eastern Shore Maryland living. A beautiful waterfront setting just minutes from lively restaurants, bars, and shops means the Kent Manor Inn is peaceful while near the action, and the 19th-century building’s cozy rooms give the large property a boutique feel. Notable Amenities Pool Firepit Kayaks and bicycles on-site for guest use 06 of 07 Best Budget Hotel: Anchored Inn at Hidden Harbor Anchored Inn at Hidden Harbor See Rates on Tripadvisor.com Why We Chose It An excellent value for the price point, the Anchored Inn at Hidden Harbor gives visitors everything they need to be comfortable in a beautiful setting. Pros Water views Pet friendly On-site restaurant Close proximity to dozens of local attractions Balconies Cons Feels like a chain The Anchored Inn at Hidden Harbor offers new, clean accommodations on a smaller scale than major chain properties and at an affordable price. It is located near a handful of fun waterfront restaurants and even has its own small bar. If you’re looking for a place to base yourself while you spend your time on the water, the Anchored Inn at Hidden Harbour is a great option. Notable Amenities Pool Paddleboards for guest use On-site dining 07 of 07 Best B&B: Brampton Inn Brampton Inn See Rates on Tripadvisor.com Why We Chose It It's hard to beat these gorgeous accommodations just outside of charming and historic Chestertown, Maryland. Pros Award-winning spa Electric vehicle charging stations Complimentary breakfast Close proximity to dozens of local attractions Pet friendly Cons Not directly on the water Thoughtful innkeepers and attention to detail make the Brampton Inn stand out as an excellent place to stay, and its proximity to Chestertown, Maryland, makes it even more appealing. Daily tea time provides guests with a pleasant treat, and a high-quality breakfast is also included with your visit. Most rooms and suites at the inn have working fireplaces and luxurious baths, making it an especially cozy choice in the winter for those looking for an offseason stay. Notable Amenities Fireplaces Jetted bathtubs Firepit Breakfast and tea time included with room EV charging stations Final Verdict Chesapeake Bay hotels run the gamut from elegant resorts to big chain hotels and quaint B&Bs. The area is great for those who love to be on the water but also offers terrific on-shore activities like golfing and tennis. Be sure to make time to discover the charming local towns and the area's fascinating history. While spring and fall are ideal times to go, the Chesapeake Bay region offers outstanding accommodations any time of year. If you're not sure where to start, the Inn at Perry Cabin epitomizes the Chesapeake lifestyle and offers all the luxuries any traveler could hope for. Compare The Best Chesapeake Bay Hotels Property Resort Fee Starting Rate Rooms Free WiFI Tides Inn Best Overall $40 $$ 70 With resort fee The Inn at Perry Cabin Best Luxury $45.90 $$$$ 79 Yes Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina Best for Families $42.34 $$ 400 Yes The Hope and Glory Inn Best for Foodies None $$ 12 Yes Kent Manor Inn Best Boutique Hotel None $$ 24 Yes Anchored Inn at Hidden Harbor Best Budget Hotel None $ 16 Yes Brampton Inn Best B&B None $$ 13 Yes Methodology We evaluated nearly two dozen Chesapeake Bay hotels, resorts, and B&Bs in Virginia and Maryland. We spoke to locals, combed through reviews, and considered a number of elements before selecting the best accommodations in each category. We assessed such things as the property’s reputation and quality of service, its proximity to major local attractions, and notable amenities. We also considered the property's dining options, extra fees, and what kinds of experiences (meals, on-site activities, etc.) are available to guests. Was this page helpful? Thanks for letting us know! Share Pin Email Tell us why! Submit