The Hotel Guru
20 Best Hotels on Chesapeake Bay

20 Best Hotels on Chesapeake Bay

Chesapeake Bay runs 200 miles between its northern headwaters and the Atlantic Ocean, an unusually long stretch, and an idyllic spot for anyone who enjoys pottering about on, or around, the water, because there’s just so much bay to explore. Beautiful and bountiful, this is a fantastic natural wonder, and our Gurus have come up with some appropriately fantastic recommendations for the best hotels on Chesapeake Bay. They’ve picked out a few bay-side charmers for anyone who wants to wake up and see water, and their recommendations for romantics includes a couple of exquisite historic properties. They’ve also included picks for families and sailors, so no-one should be left disappointed!

For Water Views

The Inn at Perry Cabin is a grand, colonial looking hotel with spectacular bay views, a very well regarded spa and a 200 year old garden. If you’re charmed by white timber and pillars, then this inn is for you. Inside the 78 rooms and suites are luxuriously decorated with delicate Laura Ashley fabrics and wallpapers. Our favourites have private balconies or terraces and incredible water views. The bar and restaurant also have fantastic views from floor-to-ceiling windows, and the restaurant offers a lovely afternoon tea.

For Waterside

The Oaks Waterfront Inn is a centuries old inn on the waterline of a cove just off Chesapeake Bay. There are 15 rooms snd suites and a cottage, offering a range of accommodation sizes all decorated with antiques and vintage furniture, against a calming, contemporary colour palate. Most rooms come with whirlpool baths and fireplaces too. There’s no restaurant, but they do offer a gourmet cooked breakfast in the dining room; the cottage is self catering.
Contemporary and luxurious, the Annapolis Waterfront Hotel is a great pick if you want to look out of your window of a morning and see the water. The 149 rooms and suites also take a nod to the nautical, decorated with maps, flags and other maritime imagery, but are otherwise contemporary in style. There’s a bar, seafood restaurant and courtyard in the hotel, but you’re super well located for Annapolis’ historic centre, so you’re close to lots of shops and restaurants.

For Families

The Inn at Osprey Point is an elegant, white timbered inn on the shores of Swan Creek in Rock Hall. There are just seven rooms and suites, split between three colonial-style buildings: the main inn, a four bedroom, self-catering farmhouse, and an annex. The gardens line the water, so the views are idyllic, and if you arrive by boat you’re welcome to dock here. There’s a pool and playground, and a friendly restaurant.
The Hotel Cape Charles is a chic, contemporary hotel just metres from the beach, with our favourite rooms leading out onto the gardens, courtyard, or onto private balconies with sea views. This is an incredible spot for an adventure, you’re close to facilities as varied as jet-skiing and hang gliding, and you’ve all the landscape of Chesapeake Bay to explore. There’s no restaurant, but there is a cafe, and for a fee you can access a local resort, which has a private beach, golf course, gym and two pools. The large loft rooms are ideal for families with lots of space, kitchens, living and dining areas.
The name is a handful: The Inn at Chesapeake Bay Beach Club, but informative. Because this contemporary, 77 room inn is part of the Chesapeake Beach Club, and that means access to a huge spa, a choice of pools and places to eat and drink, the private beach, and lots of water sporting facilities. The rooms and suites vary a lot in size, and some of the family cottages have multiple bedrooms and bathrooms. Decor is farm chic, with contemporary detail and big bathrooms.

For a Rural Retreat

Set right up against the shoreline, Great Oak Manor is our pick for a charming country escape. This is an historic feeling manor house, with elegant, unfussy details both inside and out. There are 13 rooms and suites for guests to choose from, all of them different, but all spacious and well lit, with wonderful views. If you’re planning a romantic break you might opt for one of the rooms with a fireplace or stand-alone bathtub. This is a great place to relax, but they also have paddle boards, kayaks and bikes for guest use.
The Hope and Glory Inn is a collection of rustic and quaint rooms and cottages set on a vineyard. This is the stuff of farmhouse dreams: open fires, chintz and florals in cheerful hues, and vintage furniture beautifully painted. The restaurant offers fabulous farm-to-fork fare, and the wine list is excellent. The cottages offer self-catering accommodation perfect for families.
The Inn at Huntingfield Creek is part of a farm estate which spreads for 70 acres along the edge of Chesapeake Bay just above Annapolis. A main manor house and a handful of separate cottages make up the accommodation; there are 12 options in all. All around them are beautiful gardens, which also surround an outdoor pool. They offer a full country breakfast each morning, and complimentary daily wine and beer receptions, but there’s no restaurant.

For Getting out on the Water

An incredible spot to watch the sunset, Wades Point Inn on the Bay is a collection of four buildings set on a sloping lawn overlooking the bay. Inside are 26 rooms and suites, all spacious and carefully decorated, with windows offering spectacular ocean views and plenty of natural light. This is the perfect spot from which to try sailing, kayaking or fishing (you can arrange it all from the inn); alternatively, there are three golf clubs nearby and a birding club.
The Wylder Tilghman Island resort is a chic, nautical themed historic conversion, on a nine and a half acre estate on Tilghman Island. Originally built in 1898 as a boarding house, this building now has 54 hotel rooms and suites, all simply, but chicly decorated, with that nautical edge. The restaurants are more ship-shape, decked out in wood, brass, rattan and maritime colours, and both specialise in seafood. The views are really something, there’s a pool and private marina, and lots of watersports facilities on hand.

For Romantics

The Inn at Warner Hall has been converted from a grand plantation house with roots that go back to 1642. Complete with all the Gone with the Wind details, like pillars and broad verandahs, this is an elegant place to stay. Sip mint juleps on the porch while you watch the river, play card games in the elegant drawing room, and sleep under a four-poster canopy. Then in the morning enjoy a leisurely three course breakfast. And on Friday and Saturday evening they serve a five course meal as well. There are 15 rooms and suites.
The Sandaway Waterfront Lodging is a lovers’ hideaway on a particularly scenic stretch of shoreline overlooking the bay. Each of the 18 rooms has a private outdoor seating area, with its own view of paradise. They also have a private beach, with a collection of watersports facilities. There’s a communal dining room, or you can eat al fresco; otherwise, take a leisurely stroll into Oxford where there are restaurants to choose from.
The Swanendele Inn is a fantastic, timber-clad mansion on a stunning waterfront plot with direct access to St. Jerome’s Creek. Its seven guest rooms rooms are all individual, with the more luxurious end featuring a whirlpool bath with a built in marble wine bucket. Even if you don’t opt for that level of comfort you’ll have antiques, a cosy fireplace, water views, and either a private deck, or one shared with one other room. Remote and romantic.

For Urban Comforts

The Graduate Annapolis is a funky, arty pick in the heart of the Annapolis Arts District. There are 215 rooms and suites, but they’re anything but cookie cutter, with plenty of unique and unusual touches, from crab print wall papers to large stripes, and a joyful feel. Rooms and communal spaces, like the buzzy restaurant and business centre, are arranged around a central courtyard and atrium, and there’s also a 24 hour gym and complimentary bike hire.
The Tidewater Inn is a luxurious, colonial style — but Victorian built — hotel in downtown Easton. The inn has 86 rooms and suites, and a stand-alone five bedroom house, all recently renovated to make the most of the huge windows and the hotel’s elegant dimensions. The restaurant blends fine dining cuisine with an informal setting, and is one of the best places to eat in town. The inn also has ballrooms, business spaces and conference rooms, and expansive gardens. Easton is known for its sailing, but also hosts the Chesapeake Music Festival, the Chesapeake Film Festival and a Jazz Festival.
The Historic Inns of Annapolis are a collection of three historic townhouses: Governor Calvert House, Robert Johnson House and the Maryland Inn. Each building has its own history and personality, but the 124 rooms, which are split between them, are all decorated with the same classical style. The Maryland Inn has a friendly pub, and the Governor Calvert has a restaurant. There’s also a shared gym and business centre.

For Foodies

The Charlotte in Onancock is a quaint restaurant with rooms — eight rooms to be precise. While the award-winning restaurant specialising in local produce and whiskies is the ‘main event’ the rooms have plenty to recommend them too: they’re simply, tasteful decorated with rustic antiques and vintage treasures, and affordable with it.

Best B&Bs

The Hummingbird Inn is a memorable looking Victorian B&B on a quiet street in Easton. Inside are six rooms and suites, all different shapes and sizes, with some sleeping between three and six. The room decor varies too, some are decked out beautifully in period style, with antiques, and some are much more contemporary. A three course, gourmet breakfast is served in a pretty, period dining room and there’s a guest parlour, a large verandah and a garden.
The Hornsby House Inn is a generously proportioned, five room B&B, just outside Yorktown’s main historic centre, and built in the colonial era. This is a warm and welcoming place to stay, with inviting shared spaces and and homely touches. The rooms are all different, but all feature antiques and charming views.

Still not sure where to book?

You could refine your search to the best places to stay in Annapolis
Or browse our recommendations for all the best places to stay in Maryland or Virginia
Or you could contact one of our friendly Gurus for personalised advice.
- Inn at Perry Cabin St Michaels (Maryland) 78 rooms from £130
  
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  Total relaxation  -  The peaceful gardens, exquisite spa, outdoor pool and views over Chesapeake Bay- the perfect relaxing break
  Active Holiday  -  The Offshore Sailing School on the inn's grounds offers lessons between April and November
  Spa  -  Linden Spa offers an array of spa treatments, including massages, exfoliation treatments, yoga classes, facials and pedicures
  Restaurant  -  Stars, a riverfront dining room with floor-to-ceiling windows, serving local fare, and offering afternoon tea in the day
  Recommended by  -  Tablet, Mr & Mrs Smith
  
  Beautiful colonial hotel with spectacular views of Chesapeake Bay, a 200-year-old garden and a renowned spa. The spacious and elegant rooms feature Laura Ashley designer fabrics and wallpapers. The bar, restaurant, gardens and spa all conspire to provide a relaxed yet stylish atmosphere. See More
  
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- The Oaks Waterfront Inn St Michaels, Maryland 15 rooms from £125
  
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  Local exploring  -  Relaxed and scenic base from which to explore the bay. Visit small local towns, go sailing, fishing or kayaking
  Weddings  -  Offers one of the best wedding venues in the Chesapeake Bay; secluded waterfront backfrop is to die for
  Birdwatching  -  Spot Great Blue Herons, Ospreys, transient Canada Geese and Bald Eagles from the shoreline
  Swimming Pool  -  It's tempting not to leave the property and just sunbathe by the large outdoor pool
  
  Centuries-old waterfront inn set on the cove off Chesapeake Bay. Rooms, suites and a stand-alone cottage blend traditional period decor with fresh colour schemes and modern touches. After a home-cooked breakfast, explore the area's natural beauty or relax by the pool. Designed for weddings & events. See More
  
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- Wades Point Inn on the Bay St Michaels (Maryland) 26 rooms from £140
  
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  Sailing  -  Lady Patty sets sail from Knapp’s Narrows Marina onto the Chesapeake Bay and the Choptank River- discounts for hotel guests.
  Fishing  -  Have a certified Orvis guide take you out in a 19 foot Hewes flatboat, or simply enjoy the complimetary lines provided.
  Kayaking  -  Kayaks onsite for exploring the The American Canoe Association recommended Tilghman Island Water Trail.
  Birdwatching  -  Check out the “Birds of Wades Point B & B" list- regularly updated by Talbot Bird Club.
  
  Four elegant buildings, surrounded by slopping lawns and porches overlooking the bay. Spacious and beautifully decorated bedrooms with large windows commanding spectacular ocean views, provide plenty of natural light. Sit back and enjoy the Chesapeake Bay sunsets! See More
  
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- Hotel Cape Charles Cape Charles, Virginia 16 rooms from £140
  
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  Local exploring  -  Explore the shores of the Chesapeake Bay; there are nature reserves, oyster farms, great golf, sailing and Victorian monuments
  Active Holiday  -  There are plenty of outdoor activities available include kayaking, hang-gliding, jet-skiing fishing, sailing and birding
  Families  -  The large Loft Rooms are great for families with lots of space, kitchens, living and dining areas
  Beach Life  -  The town's mile-long family-friendly sandy beach is just steps from the hotel
  
  Contemporary-style boutique hotel offering spacious and comfortable rooms metres from the beach. Rooms lead out onto the gardens, courtyard, veranda and private balconies offering sea views. Cafe and wine bar on-site, access to local health club included and close to everything in town. See More
  
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- The Tidewater Inn Easton, Maryland 86 rooms from £145
  
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  Business meetings  -  Offers a fantastic array of meeting and event spaces across meeting rooms, the carriage house, ballrooms and hospitality suites
  Local exploring  -  Located within downtown; walk to shops, art galleries, museum & restaurants or head to Oxford & Kent Island for day trips
  Weddings  -  Fab choice for classic weddings. Venues include ballrooms, gardens, tented courtyard and even outdoor ceremonies
  Short break  -  Less than two hours from Washington DC, Baltimore and Wilmington - this makes for lovely Eastern Shore getaways
  
  Deluxe colonial-style hotel & a stand-alone 5-bedroom house in downtown Easton. Dating from Victorian times, a recent renovation has brought elegant airy spaces to life. Enjoy an indulgent spa, a tavern specializing in seafood & lots of outdoor space. Perfect for events and Chesapeake Bay getaways. See More
  
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- Sandaway Waterfront Lodging Oxford, Maryland 18 rooms from £148
  
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  Cooking classes  -  Cooking demonstrations with Master Chef Mark Salter in nearby town Oxford.
  Hideaway  -  Each room comes with a private seating area commanding spectacular views.
  Views  -  Views of the Tred Avon River, Choptank River, & Chesapeake Bay
  Fishing  -  Nearby Chesapeake Bay offers a variety of fishing charters.
  
  Elegant rooms and suites commanding spectacular views of Chesapeake Bay. Designed as a lovers' hideaway, each room comes with private seating area and a team of masseurs on call! For the more active couples, water sports facilities on site. A chic romantic getaway. See More
  
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- Graduate Annapolis Annapolis (Maryland) 215 rooms from £149
  
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  Local exploring  -  Good base to explore Chesapeake Bay; walk coastal paths, eat at great restaurants or browse antique stores and art galleries
  Business meetings  -  20,000 square feet of flexible meeting space make this perfect for events and functions of up to 500 people
  City Style  -  The smartest place to stay in this small seaside town
  Restaurant  -  Tuck into coffees, healthy snacks and salads at Poindexter or indulge in nostalgic American comfort food at Trophy Room
  
  Funky boutique-style hotel in the heart of Annapolis Arts District. Luxuriously decorated in joyful primary tones, rooms and public spaces centre around a spectacular light-filled atrium and feature locally inspired touches. Enjoy a coffee bar, buzzing restaurant, 24-hour gym, bikes and dog park. See More
  
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- The Inn at Osprey Point Rock Hall, Maryland 7 rooms from £94
  
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  Groups  -  Groups or families will love the 4 bedroom Farmhouse which comes with kitchen, pool table, fire-pit and screened porch
  Back to Nature  -  Breathe in fresh sea air as you sail, kayak, fish or simply relax on the water-facing lawn
  Sailing  -  Those arriving by boat can dock at the marina and receive 50% off of transient fees
  Fishing  -  Charter a boat out into Swan Creek for fishing or simply a sunset cruise
  
  Elegant inn, restaurant and marina located on the shores of Swan Creek in Rock Hall. Rooms are split over 3 colonial-style buildings; the main inn, farmhouse and annexe. There is an outdoor pool, extensive waterfront grounds and children's playground. Rooms are traditional and offer panoramic views. See More
  
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- The Charlotte Virginia 8 rooms from £109
  
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  Local exploring  -  Set in the heart of Onancock surrounded by boutique stores, cafes, jazz bars, and just a stroll from the coast
  Foodies  -  An award-winning restaurant features a menu that is prepared using many Eastern Shore products
  Great walks  -  Take a stroll on the Nature Trail that runs along the Onancock Creek
  Kayaking  -  Head out on a kayak (or a boat) from the town wharf
  
  A quaint restaurant with rooms set in historic Onancock. A handful of charming rooms are packed full of character with antiques & traditional artwork while the towels are Egyptian cotton and linens luxurious. The award-winning restaurant uses local produce and the bar specialises in whiskys. See More
  
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- Great Oak Manor Chestertown, Maryland 13 rooms from £140
  
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  Back to Nature  -  Enjoy the outdoors with the inn's complimentary cruiser bikes, kayaks, paddle boards, hammocks, binoculars, fire-pit and more
  Local markets  -  Visit Chestertown's Farmer’s Market which opens every Saturday morning
  Restrictions on children  -  Children over the age of 12 are welcome
  Sailing  -  Go on sunset cruise and spot dolphins
  
  A charming and historic waterfront inn set on a country estate near Chestertown. Rooms are spacious and elegant with antique furniture, skylights, cosy fireplaces and stand-alone tubs. Relax in a hammock shaded by stately old walnut trees or use the paddleboards, kayaks and bicycles. A homely stay. See More
  
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- The Hope and Glory Inn Irvington, Virginia 12 rooms from £110
  
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  Country Escape  -  Dine on rustic fare, unwind in the quaint rooms, partake in outdoor pursuits, and sample wines - perfect rural escape material
  Families  -  Cottages provide a cosy and secluded space for families
  Sailing  -  Discover the scenic coves of Carter’s Creek on a boat cruise
  Fishing  -  Rappahannock River offers numerous opportunities for fishing
  Recommended by  -  Frommers
  
  A charming hotel comprising of quaint cottages and rooms set on a picturesque vineyard. Traditional rooms feature fireplaces and chintz fabrics plus indulgent Gilchrist & Soames soaps. A rustic restaurant serves farm to fork fare while the wine selection is unsurprisingly good. A rural idyll. See More
  
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- The Inn at Huntingfield Creek Rock Hall, Maryland 12 rooms from £250
  
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  Weddings  -  Ideal venue for country weddings: 70 acres of land, 5000-square-foot farmhouse and country-chic barn make for a dream venue
  Back to Nature  -  Admire the stunning natural scenery of Chesapeake Bay area and soak in peaceful and tranquil environment
  Romantic Break  -  Cottages are ideal for romantic retreats. Cuddle up by the fire, soak in a spa tub or watch the sunset
  Birdwatching  -  The inn offers fantastic birdwatching; Upper Chesapeake Bay is home to a multitude of resident and migratory birds
  
  Rural 70-acre farm estate on the water's edge. Made up of rooms in the main house and separate self-catered cottages. There's an outdoor pool, beautiful gardens and farm-fresh breakfast. Contemporary cottages have a romantic feel with cosy fireplaces. Perfect for weddings or quiet country weekends. See More
  
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- The Inn at Chesapeake Bay Beach Club Stevensville, Maryland 77 rooms from £160
  
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  Families  -  Wide range of multi-bedrooms suites with spacious living areas, plus stand-alone cottages, offer great options for families
  Total relaxation  -  Perfect place to come and chill out; spend days at the beach, enjoying the spoiling spa or sunbathing by the pool
  Short break  -  Located less than an hour from both Washington D.C. and Baltimore, this makes an ideal weekend break
  Beach Life  -  Enjoy a small private beach and waterfront nearby, for use only by hotel guests
  
  Contemporary inn with large grounds and fab amenities walking distance to the beach. Light-filled spaces feel airy and fresh with soft hues and polished farm-inspired furnishings; suites & cottages are to die for. Relax on-site with swimming pools, a spa, outdoor dining and a fire pit terrace. See More
  
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- Wylder Tilghman Island Saint Michaels, Maryland 54 rooms from £117
  
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  Weddings  -  Arrive by boat to a ceremony on the creek-facing lawn. Excellent dining and outdoor fire-pits make this a memorable venue
  Country Escape  -  A weekend by the sea doesn't get more wholesome; eat well, sail, kayak, enjoy the views and breathe in that salty air
  Total relaxation  -  You can easily while away a stay soaking in the heated salt water pool or reading a book on the sea-facing lawn
  Sailing  -  Charter a fishing boat or a sunset cruise on Harris Creek
  Recommended by  -  Tablet
  
  Seaside hotel located on a 9.5-acre estate on Tilghman Island. The 1898 boarding house has been converted into a chic nautical-themed resort with a private marina, pool and 2 seafood dining venues. 54 rooms have sea views and balconies and are decked out in maritime colours, brass, rattan and wood. See More
  
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- Hummingbird Inn, Maryland Easton, Maryland 6 rooms from £163
  
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  Suites  -  Sleek Crisfield Room is more of a suite. Recently renovated, it offers clean contemporary aesthetic and Vera Wang bedding
  Local exploring  -  Tranquil base to return to after idyllic days exploring the area's charming small towns, sites and beaches
  Fishing  -  The Eastern Shores offer fantastic fishing. The area is known for Maryland Blue Crab, rockfish (striped bass), oysters and clams
  Sailing  -  Head to Oxford, one of the oldest towns in America, for excellent boating and historical sightseeing
  
  Owner-run Victorian-era B&B on a quiet leafy Easton street. Lovely rooms feature impressive modern comforts; think top of the range bedding and sound systems. Breakfast is served in a pretty dining room and there's a guest parlour, large garden & wrap-around porch. Beautiful base for exploring. See More
  
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- Historic Inns of Annapolis Annapolis (Maryland) 124 rooms from £117
  
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  Sailing  -  Sailing in Annapolis is a popular past time.
  Sights nearby  -  National Maritime Museum.
  Full of character
  Restaurant  -  Recommended.
  
  Hotel consists of 3 townhouses in central Annapolis. Modern rooms offer en suite bathrooms and all facilities. The Treaty of Paris Restaurant offers seasonal fish, an extensive wine list and American cuisine. Location is great for Maryland's history and Washington DC. Business and gym facilities. See More
  
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- Annapolis Waterfront Hotel Annapolis (Maryland) 149 rooms from £167
  
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  Local exploring  -  The prime location means that the historic downtown's shops, attractions and restaurants, plus the harbour, are walking distance
  Weddings  -  Enjoy a waterfront wedding; the property's venues range from a traditional ballroom and harbour-view rooms to outdoor patios
  Restaurant  -  All-day Pusser's Caribbean Grille serves fresh seafood with wonderful harbour and bay views; it's a firm favourite with locals
  Sights nearby  -  Take a trolley tour of Annapolis, covering 350 years of history in an hour; drive past colonial mansions and Victorian homes
  
  Contemporary luxury waterfront hotel located in the historic downtown. Views are everywhere, from fresh nautical-themed rooms and private balconies to harbour-front restaurant and outdoor patio. Decor combines sleek furnishings with homely touches and a cosy feel. Stylish well-connected city base. See More
  
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- Swanendele Inn Ridge, Maryland 7 rooms from £187
  
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  Romantic Break  -  Both suites offer two-person whirlpools with champagne holders and sunset views over St. Jerome’s Creek and Chesapeake Bay
  Local exploring  -  The area is home to some of the country's oldest colonial sites, in addition to a rich Civil War and naval history
  Hideaway  -  The place to do very little. Sit on your deck or the private porch and admire the view from sunrise to sunset
  Views  -  Stunning views from rooms include St. Jerome’s Creek, gardens, forest, Chesapeake Bay, sunrise and sunset
  
  Stunning waterfront plot with direct access to St Jermone's Creek. A southern-style mansion surrounded by landscaped gardens boasts endless wraparound porches, private decks & water views from each window. Homely individually decorated rooms feature antiques & fireplaces. Secluded seaside hideaway. See More
  
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- Inn at Warner Hall Gloucester Courthouse, Virginia 15 rooms from £152
  
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  Fishing  -  Take one of the boats onto the lake and embark on an afternoon of fishing in a stunning setting.
  Great walks  -  Seen from the porch the Severn River is a great guide for a walk.
  Birdwatching  -  Nature at its finest.
  Sights nearby  -  Rosewell Ruins.
  
  Warner Hall Plantation welcomes guests with true southern hospitality. An elegant drawing room, wrap around river view porch & classically restored rooms ensure your every comfort. Fabulous views over the lake and Severn River. A three course breakfast starts the day just right! See More
  
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- Hornsby House Inn Yorktown 5 rooms from £124
  
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  Families  -  The Monument Grand Suite offers the perfect family apartment with double bed, two twin beds, large living area and fireplace
  Local exploring  -  Walking distance from the Yorktown battlefields, York Monument, historic downtown, shops and waterfront restaurants
  Total relaxation  -  After a day of sightseeing, relax in the sunroom or front patio with a book, glass of wine or cup of tea
  Beach Life  -  It's less than 50 metres to white-sand family-friend Yorktown Beach and fishing pier
  
  Large colonial-era B&B walking distance to Yorktown's sites. Inside the grand exterior, shared spaces are warm and inviting with fireplaces, period furnishings, homely touches and friendly hosts. Cosy rooms with impressive views, antiques and canopy beds suit all set-ups from couples to families. See More
  
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