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?
