Go to Map View
Want travel alerts for this area?

Enter your name and email to receive alerts when new vacation deals are added to any property in this region.

By clicking "Submit" you are agreeing to the
Terms of Service.

Alert successfully created!

Filters

Resort Type
Activities
Amenities
Avg. Daily Rate

Showing 16-30 of 65 Resorts and Lodges

Combsberry Inn

Oxford, Maryland, United States
93
Excellent
12 Reviews
More Info
Compare
$250

Overlooking beautiful Bringman's Cove on the outskits of Oxford and St. Michaels, the Combsberry Inn is an extraordinary Eastern Shore experience. Rest in one of the Carriage House's signature waterfront rooms, featuring whirlpool tubs and gas fireplaces, or enjoy the stunning garden views from the Manor House. And, if you're feeling a little... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size N/A
  • Conference Facility
  • Kids Allowed
  • Nearby City Oxford
  • Nearby Water Bringman's Cove
  • Open Dates All Year
RESORT TYPE(S):
  • Historical
  • Romantic
  • Bed & Breakfasts, Inns

Lowes Wharf Marina Inn

St. Michaels, Maryland, United States
More Info
Compare
$76

At Lowes Wharf Marina Inn in Sherwood, Maryland, a cross road connects you with your awaiting sunset island on the Chesapeake Bay. Our accommodations feature new waterfront guestrooms, transient slips, fishing, crabbing,kayaking, or just sitting back in the yacht club having a cool drink while watching the sunset. We are only 7 miles from St.... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size N/A
  • Conference Facility
  • Kids Allowed
  • Nearby City St Michaels
  • Nearby Water N/A
  • Open Dates All Year
RESORT TYPE(S):
  • Bed & Breakfasts, Inns

Driftwood Inn

Chestertown, Maryland, United States
More Info
Compare
$60

Rest and relax at this 28-room Inn, conveniently located in peaceful Chestertown. Lounge on your spacious colonial-style bed or splash in the outdoor pool. Some rooms even feature a jacuzzi style tub! And Driftwood Inn is within easy distance of all... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 28 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Chestertown
  • Nearby Water Chester River
  • Open Dates All Year
RESORT TYPE(S):
  • Family
  • Romantic
  • Bed & Breakfasts, Inns

Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina

Cambridge, Maryland, United States
83
Very Good
240 Reviews
More Info
Compare
$135

The pristine white walls of Hyatt Regency shine on Choptank River as a beacon for luxury travelers. Along Maryland's eastern shore, Hyatt Regency Chesapeake Bay Golf Resort offers four-diamond accommodations and diversions by land and sea. Plush, patterned pillows, step out balconies overlooking the water, and marble baths are among some of the... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 400 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Cambridge
  • Nearby Water Chesapeake Bay
  • Open Dates All Year
RESORT TYPE(S):
  • Meetings
  • Family
  • Golf
  • Pet Friendly
  • Villas and Condos

Tarr House

St. Michaels, Maryland, United States
More Info
Compare
$151

The Tarr House, circa 1667, recalls the quiet elegance of a time past. Guests are lavished with English fabrics and antiques in the richly decorated home of a professiona interior designer. The cozy sitting room features original heart-of-pine floors, a fireplace and windows framing a view of picturesque St. Michaels Harbor. Lodging rates in-... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size N/A
  • Conference Facility
  • Kids Allowed
  • Nearby City St Michaels
  • Nearby Water N/A
  • Open Dates All Year
RESORT TYPE(S):
  • Bed & Breakfasts, Inns

The Old Brick Inn

St. Michaels, Maryland, United States
More Info
Compare
$125

Welcome to Old Brick Inn, a Maryland boutique hotel in the tradition of a bed and breakfast. Start off your day with a tantalizing homemade breakfast and then head out to explore shopping, museums, golf and area sights, like Hooper Strait Lighthouse. Lavish rooms and suites have their own private bath and many have fireplaces and Jacuzzis. Make... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 20 units
  • Conference Facility
  • Kids Allowed
  • Nearby City St. Michaels
  • Nearby Water N/A
  • Open Dates All Year
RESORT TYPE(S):
  • Historical
  • Romantic

Castle in the Sand Hotel

Ocean City, Maryland, United States
81
Very Good
467 Reviews
More Info
Compare
  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 179 units
  • Conference Facility
  • Kids Allowed
  • Nearby City N/A
  • Nearby Water N/A
  • Open Dates All Year

Hambleton Inn

St. Michaels, Maryland, United States
More Info
Compare
$251

The Hambleton Inn offers distinctive lodging in the heart of St. Michaels' historic residential district. The inn is located on the harbor and is a short stroll from the finest of restaurants, antique shops, boutiques, and the Chesapeake Bay Maritime Museum. The inn is open year-round.... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size N/A
  • Conference Facility
  • Kids Allowed
  • Nearby City St Michaels
  • Nearby Water N/A
  • Open Dates All Year
RESORT TYPE(S):
  • Bed & Breakfasts, Inns

Knapp's Narrows Marina & Inn

Tilghman Island, Maryland, United States
More Info
Compare
$80

Knapp's Narrows Marina and Inn is located on Tilghman Island, Maryland, offering perfect access to the Chesapeake Bay.... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 20 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Tilghman
  • Nearby Water Chesapeake Bay
  • Open Dates All Year
RESORT TYPE(S):
  • Bed & Breakfasts, Inns

St. Michaels Harbour Inn & Marina

St. Michaels, Maryland, United States
More Info
Compare

Located off the Miles River in the quaint town of St. Michael's, the St. Michaels Harbour Inn, Marina & Spa is the perfect place to relax, rejuvenate, and restore! Enjoy the panoramic view from your room's private balcony, cruise the 56-slip transient marina, have a cocktail in The Clubroom, unwind in the boutique spa, and fine dine at the... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 46 units
  • Conference Facility
  • Kids Allowed
  • Nearby City St. Michaels
  • Nearby Water Miles River
  • Open Dates All Year
RESORT TYPE(S):
  • Meetings
  • Pet Friendly
  • Spa

Comfort Suites

Chestertown, Maryland, United States
More Info
Compare
$93

Stay at Comfort Suites and experience the eastern shore of Maryland! Start your day with a free hot breakfast, then take a dip in the hot tub or splash in the pool. Venture out into Chestertown and enjoy nearby attractions like the Eastern Neck National Wildlife Refuge, Betterton Beach, and the Waterman's Museum. At the end of the day, return to... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 53 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Chestertown, Maryland
  • Nearby Water Chester River
  • Open Dates All Year

Widow's Walk Inn

Chestertown, Maryland, United States
More Info
Compare
$105

Located in historic Chestertown on Maryland’s upper eastern shore, Widow’s Walk Inn provides comfortable lodging in its five rooms with the warm atmosphere of a family home. Whether you play a game or read a book in the parlor or relax... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 5 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Chestertown, Maryland
  • Nearby Water Chester River
  • Open Dates All Year
RESORT TYPE(S):
  • Historical
  • Romantic
  • Bed & Breakfasts, Inns

Grand Hotel & Spa

Ocean City, Maryland, United States
More Info
Compare

Boasting a prime oceanfront location on Ocean City's boardwalk, the Grand Hotel & Spa offers an affordable vacation spot equipped with the contemporary comforts and relaxing resort-style amenities catered for both families and leisure travelers alike. Just outside the doors of the hotel and beyond the famed boardwalk is a 10-mile stretch of... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 251 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Ocean City
  • Nearby Water Atlantic Ocean
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Meetings
  • Family
  • Golf
  • Holiday
  • Honeymoon
  • Luxury
  • Nature
  • Pet Friendly
  • Romantic
  • Spa
  • Wedding

NorthBay

North East, Maryland, United States
More Info
Compare

In MD's scenic Elk Neck State Park, NorthBay is the pinnacle of high adventure and accommodation! Conveniently located between Philadelphia and Baltimore on the scenic Chesapeake Bay, NorthBay's guest house is the ideal location for your next planning meeting or corporate retreat. Situated just feet from the bay the guest house is the perfect place... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 11 units
  • Conference Facility
  • Kids Allowed
  • Nearby City North East
  • Nearby Water Chesapeake Bay
  • Open Dates All Year
RESORT TYPE(S):
  • Meetings
  • Lake
  • Nature

Osprey Point

Rock Hall, Maryland, United States
More Info
Compare

Osprey Point on Maryland's Eastern Shore prrovides a luxurious northern Chesapeake Bay adventure destination located on 30 lush acres of waterfront solitude in the village of Rock Hall. The Inn provides elegant lodging and gourmet dining just a few feet away from our modern world class marina on the Chesapeake Bay's eastern shore, with the... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size N/A
  • Conference Facility
  • Kids Allowed
  • Nearby City N/A
  • Nearby Water N/A
  • Open Dates All Year
RESORT TYPE(S):
  • Bed & Breakfasts, Inns

Showing 16-30 of 65 Resorts and Lodges

statsstats