11 Best Places To Stay In Maryland Eastern Shore
With so many world-class Maryland Eastern Shore hotels, B&Bs, and vacation rentals, finding accommodation that offers beautifully appointed rooms, incredible amenities, a great location, and value for money all rolled up in one is daunting at times!
Eastern Shore is a perfect place for some of the most Unforgettable Maryland Road Trips to take with Kids
The best places to stay in Maryland Eastern Shore
Searching for a high-end hotel with luxurious amenities and family-friendly activities or a quirky B&B with outstanding cuisine that even includes a private garden clawfoot tub? Well then, read on if you want to know about the best places to stay in Maryland Eastern Shore and its hidden gems.
11 Best Places To Stay On The Chesapeake Bay
Epic Chesapeake Bay, with its endless breathtaking shoreline, navy-blue waters, sun-kissed beaches, and laid-back coastal atmosphere from Maryland to Virginia, has become a prime vacation destination with great outdoor activities and the best seafood on the planet!
So, if you are looking for the best places to stay in Maryland Eastern Shore, here are a few carefully selected great places in the Chesapeake Bay area ranging from budget-friendly, historic hotels and family-friendly Inns to high-end establishments that are the epitome of luxury.
1. Tides Inn
The Tides Inn is a stunning waterside, family-friendly establishment with stunning views, high-end amenities, and several outdoor activities. In addition, its also a prime destination for avid golfers due to the Inn’s Golden Eagle Golf Course, which George W. Cobb designed.
The Inn also caters to kids with a fun children’s vacation program, a par-3 golf course, a sailing school, and bicycles to keep them well-occupied. Furthermore, there are several family-friendly local attractions to explore.
Other notable amenities visitors can expect at this immaculate Inn include a refreshing pool, relaxing spa, a well-maintained tennis court, and an outstanding seafood restaurant with a delicious array of fresh local seafood and moreish oysters.
Guests can expect luxurious, well-appointed rooms with ultra-soft linens and stately mahogany furniture, including spectacular private patios with panoramic views of Carter’s Creek and the Inn’s manicured lush gardens.
2. The Cavalier Hotel & Beach Club
Born in the Big Band era, the stately, award-winning Cavalier Hotel, situated in Virginia Beach with its breathtaking panoramic views of the Atlantic Ocean, is steeped in history and brims with the elegance of a bygone era as a proud former host to several notable Presidents.
While its former old-world charm and warm hospitality remain, this historic hotel has undergone extensive renovations. As a result, it includes all the modern amenities travel-savvy visitors expect in a luxurious hotel.
This historic grand hotel features 85 opulent and well-curated rooms, high-end spa amenities, three top restaurants, an onsite bourbon distillery, Beach Club, and a spectacular pool, including easy access to a hidden beach, coupled with exemplary service and unrivaled luxury.
There are also numerous fun local attractions and activities in Virginia Beach, ranging from surfing, and enjoying a Pleasure House Oysters Boat Tour, to climbing the 191 historic steps of the Cape Henry Lighthouse for panoramic views of the breathtaking Chesapeake Bay and the ocean.
3. Delta Hotels By Marriott Virginia Beach Bayfront Suites
The Virginia Beach Hotel, with its breathtaking views of Chesapeake Bay, offers guests world-class, beautifully appointed high-end suites with comfortable beds and luxurious linens, signature amenities, including rest and relaxation on a private beach or a sparkling pool.
This spectacular hotel is conveniently located near a diverse range of fun Chesapeake Bay water activities, the Virginia Beach Sportsplex, and it’s near the First Landing State Park, with great picnic spots, crabbing, and fishing activities, including breathtaking nature trails for hiking and biking.
So, it’s hands down one of the best places to stay in Maryland Eastern Shore for visitors who prefer a touch of class and sophistication!
4. Inn at Perry Cabin
If you’re looking around for a truly iconic hotel set on an exquisite colonial estate with old southern charm and exceptional service levels, look no further!
While this luxurious hotel is on the pricey end, it’s one of the region’s best-kept secrets and a world away from all the stresses and strains of modern living with beautifully manicured grounds, fine dining restaurants, an onsite pub, and exquisite well-appointed rooms.
Visitors have all the amenities one would expect from a high-end hotel, like spas, a pool, a fitness center, bicycles to explore the estate, an immaculate golf course, tennis courts, waterfront activities, and sailing lessons.
Oh, and if the hotel looks vaguely familiar, it’s because this iconic hotel was featured in the 2005 smash comedy Wedding Crashers. So, if you are looking for a well-known hotel that is close to all the local attractions, this Inn is one of the best places to stay on the Maryland Eastern Shore!
5. Bay Creek Vacation Rentals
Renting a privately owned vacation home in the Bay Creek, Chesapeake Bay area is a fantastic option for visitors who prefer to stay in a home-away-from-home and not a typical chain hotel.
All the vacation rentals are all fully equipped with all the modern amenities needed for a comfortable stay, including fun extras like stunning decks with breathtaking sea views, sundowner cocktails, and outdoor barbeque grills for fresh seafood family dinners.
As it can be found on the shore of the Chesapeake Bay, visitors can explore laid-back Bay Creek and all the surrounding attractions in the charming Cape Charles seaport with its 19th-century charm, contemporary amenities, and spectacular marina sunsets.
The Bay Creek area is also one of the best places to stay in Maryland Eastern Shore for avid golfers, as Palmer and Nicklaus expertly designed the Golf District greens and fairways, and those in the know consider it one of the best in the region.
6. Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina
The gorgeous Hyatt Regency Chesapeake Bay Golf Resort, Spa, and Marina are perfect if you are looking for a great family-friendly hotel that will keep your kiddos well entertained. The kid-friendly amenities include a games room, Camp Hyatt babysitting facilities, and even your fur-baby can tag along!
Apart from having a spectacular marina, kayaks, fitness center, outstanding restaurants, an excellent 18-hole golf course, pool, and a luxurious spa, there are numerous offsite Cambridge city activities to enjoy if you feel the need to venture out.
7. The Hope and Glory Inn
Foodies, take note – The Hope and Glory Inn is one the best places to stay on Maryland Eastern Shore! It has one of the most outstanding onsite restaurants for fresh local dishes under the expert management of Chef Crockett, who was born in Ethiopia and trained in France.
While the Hope and Glory Inn is more inland, the area has several great attractions to explore, like the adjacent vineyard. This foodie haven that is also pet-friendly features a stunning garden and patio, incredible décor, a sparkling pool, and a lively, fun atmosphere.
However, what truly sets the Hope and Glory Inn apart from other places, besides its elegantly decorated bedrooms, and delicious complimentary breakfasts, is the fact that all guests have access to their own secluded garden clawfoot tubs and showers. Now that’s unique!
8. Kent Manor Inn
The Kent Manor Inn boutique hotel, dating back to 1898, is a stunning resort set on 226 acres of land alongside Thomas Creak near the Chesapeake Bay Bridge on the picturesque Kent Island. This little paradise offers guests luxurious amenities at more affordable rates that won’t max your credit card.
With beautifully appointed rooms, a lush waterfront lawn, kayaks, bicycles, a pool, and a fire pit, the historic 19th-century Kent Manor Inn offers a cozy home-away-from-home that is close to all the area’s main attractions.
Some manor hotel rooms include stately Italian marble fireplaces and elegant window seats, including semi-private verandas with stunning views on the upper floors.
While the Kent Manor Inn has a peaceful and relaxing atmosphere, there are several easily accessible vibe restaurants, bars, and quirky shops to explore on a fun day out.
9. The Anchored Inn At Hidden Harbor
Located in the scenic Hidden Harbor, the Anchored Inn is one of the best places to stay on the Maryland Eastern Shore for budget travelers who are looking for a clean yet comfortable alternative to high-end hotels that is also pet-friendly.
All the rooms have stunning views from their balconies, and guests can enjoy dining at the Inn’s onsite restaurant, relaxing in the bar, swimming in the refreshing pool, or using the complimentary paddleboards.
Apart from being near various restaurants and local attractions, the Inn is perfect if you want to spend most of your day enjoying water activities without having to spend too much on accommodation or travel far.
While in Eastern shore, check out Pocomoke River Trail which is one of the 19 Great State Parks in Maryland to visit with Kids.
10. Brampton Inn
Located on the outskirts of the historic Chestertown, Maryland, the charming Brampton Inn is one of the best places to stay on the Maryland Eastern Shore if you are looking for a cozy B&B!
While the pet-friendly Inn is not a waterside establishment, it is closely located near several fun attractions. The pristine Inn has numerous great amenities, including an award-winning luxurious spa and a cozy firepit to watch the stars.
Brampton Inn also offers delicious complimentary breakfasts, old-fashioned tea-time treats, and all those thoughtful little touches that make an excellent B&B great!
Most of the Inn’s suites and rooms include fireplaces which are ideal for cold winter nights, comfortable beds, and luxurious jetted bathtubs so that you can be assured of a great stay in this gorgeous B&B!
And visitors are really spoilt for choice with a wide range of conveniently located attractions like the spectacular Eastern Neck Wildlife Refuge, Tuckahoe State Park, the Millington Wildlife Management Area, the Betterton Beach, Mount Harmon Plantation, including Blue Crab Sailing Charters.
If you are in Chestertown in the fall, check out 18 Best Places to See Fall Foliage in Maryland (Updated for 2022). Chestertown is a perfect place for animal lovers to get up close and personal with an array of birds while taking in the fall foliage.
11. Bethpage Camp Resort
While the Bethpage Camp Resort, located in Urbanna, is not a hotel or B&B, it simply had to be included in the best places to stay in Maryland Eastern Shore for families with a wide range of budget-friendly camping, RV sites, and fully equipped cottages.
It’s truly one of those rare places where kids can be kids and enjoy the thrill of gliding down a slide in the water park, careening around in a golf cart, looking for scavenger hunts treasures, or enjoying a paddleboat ride.
Other great family activities include arts and crafts, fun movie nights, hay wagon rides, kayaking, fishing, crabbing, playing volleyball, and practicing yoga in peace and quiet, knowing that the kids are well entertained.
The only potential downside of staying at the Bethpage Camp Resort is that most parents don’t see their kids for too long as they are too busy having fun, although that is one of the great perks of a truly relaxing family vacation.
What Is Maryland Eastern Shore Known For?
Maryland Eastern Shore is comprised of a stunning peninsula that stretches all the way from the Chesapeake Bay to the icy Atlantic Ocean waters and offers visitors a wide range of summer vacation recreational activities.
The region is known for its pristine beaches, outstanding natural beauty, interesting historic towns, golfing, biking, fishing, fantastic seafood, and fun water activities like swimming and boating.
The Eastern Shore resort communities also host several incredible annual events like seafood festivals, waterside festivals, fishing tournaments, arts, and craft exhibitions, boating regattas, and museum events.
However, the Maryland Eastern Shore is the most well-known as a prime birdwatching region, especially at the Eastern Neck Wildlife Refuge, located close to Rock Hall, which is a budding ornithologist’s paradise!
Another main attraction for birdwatchers is the 27,000-acre Blackwater National Wildlife Refuge in Cambridge, which is home to 250 bird species, a prime waterfowl feeding area, and home to 165 endangered plant species, and 35 amphibians and reptiles.
Conclusion on Best Places To Stay In Maryland Eastern Shore
The best places to stay in Maryland Eastern Shore have so much in common as they all showcase the region’s outstanding natural beauty as proud ambassadors for one of the most stunning regions in the country. There is no doubt that visitors will all leave with cherished memories.
