The 7 Best Chesapeake Bay Hotels

The Tides Inn is the best stay within the Chesapeake region

New Cape Henry Lighthouse in Virginia

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The Rundown

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

Tides Inn

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

Inn at Perry Cabin

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

Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina

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

The Hope and Glory Inn

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

Kent Manor Inn

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

Anchored Inn at Hidden Harbor

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

Brampton Inn

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.

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