Find hotels in Oyster Harbor, Annapolis from $91

Top reasons to visit Oyster Harbor

• Outdoor Activities: Enjoy fishing at the pier, boating, and exploring nearby golf courses for a fun-filled adventure.
• Family-Friendly Environment: Oyster Harbor is perfect for families, offering activities suitable for all ages.
• Charming Coastal Community: Experience the beautiful community beach and picturesque streets of Osterville.
• Diverse Accommodations: Choose from charming bed & breakfasts to modern hotels, including pet-friendly options.
• Cultural Experiences: Immerse yourself in local attractions and historic sites for a well-rounded vacation.

Find great hotels near Oyster Harbor

Oyster Harbor, nestled in Annapolis, Maryland, offers a delightful selection of accommodations ranging from charming bed & breakfasts to modern hotels. Travelers can enjoy pet-friendly options and LGBTQIA welcoming stays, perfect for both leisure and business. With nearby attractions like the Oyster Harbor Club and the scenic marina, your visit promises a memorable experience in this picturesque coastal community.

• Country Inn & Suites by Radisson, Annapolis, MD: Emphasizing a welcoming and home-like atmosphere, Country Inn & Suites offers a comfortable retreat for both business and leisure travelers. Located 6 miles from Oyster Harbor, this 3-star hotel is perfect for guests seeking a pet-friendly environment with LGBTQIA inclusivity. Business travelers will appreciate the 24-hour accessible business center, multiple meeting rooms, and conference spaces designed for productivity. With a pet policy that includes a dog exercise area and waived fees for service animals, furry companions are well-catered to, ensuring a stress-free stay for all.
• Graduate by Hilton Annapolis: This vibrant 4-star hotel captures the spirit of collegiate charm while providing modern amenities for a stylish stay. Situated 4 miles from Oyster Harbor, Graduate by Hilton Annapolis is ideal for those looking for a business-oriented yet pet-friendly atmosphere, complete with LGBTQIA-friendly policies. Guests can utilize well-equipped meeting rooms and conference spaces, all while enjoying the unique decor that celebrates local history. The hotel’s pet policy accommodates both dogs and cats, offering food and water bowls, making it a convenient choice for pet owners.
• Comfort Inn Conference Center: Located 13 miles from Oyster Harbor, Comfort Inn Conference Center is a family-friendly destination that merges business convenience with comfort. This hotel features multiple meeting rooms and a 24-hour business center, making it suitable for corporate travelers. Families will appreciate the child-friendly amenities, including a pool gate for safety. Pet owners will find a welcoming environment with permitted pets and waived fees for service animals, ensuring that the whole family, including pets, can enjoy a relaxing getaway.

Where to stay near Oyster Harbor

Oyster Harbor, nestled in the charming village of Osterville, offers a delightful blend of coastal beauty and family-friendly activities. Explore the serene community beach, perfect for relaxing days in the sun, or wander through the picturesque streets of Osterville to experience its warm, welcoming atmosphere. Nearby, you can enjoy outdoor adventures and charming local shops, making this a perfect destination for a memorable vacation filled with relaxation and romance.

• Annapolis: Nestled along the Chesapeake Bay, Annapolis is a vibrant city known for its rich maritime history and charming colonial architecture. Visitors flock here for a variety of experiences, from family-friendly activities to outdoor adventures. The city's bustling downtown area features a mix of shopping malls, unique boutiques, and inviting dining options. Key attractions include the Naval Academy, picturesque waterfront, and lush parks where you can enjoy leisurely strolls or picnics. Peak travel season runs from May to July, making it an ideal time to soak in the lively atmosphere.
• Highland Beach: A quaint village located just 0.4 miles from Oyster Harbor, Highland Beach is a hidden gem perfect for those seeking outdoor and scenic experiences. This seasonal destination sees a surge of visitors from May to July, drawn by its beautiful beaches and recreational areas. The village features a relaxing boardwalk and local shopping spots, allowing travelers to unwind and soak in the coastal views. Highland Beach is also home to a national state park, offering trails and natural beauty that are ideal for family outings and nature lovers.
• Arundel on the Bay: Just 0.7 miles from Oyster Harbor, Arundel on the Bay is a charming neighborhood that attracts visitors year-round, with peak traffic occurring from May to July. This area is perfect for families and city enthusiasts alike, with access to shopping centers, recreational areas, and local attractions. Nearby, you can explore beautiful beaches, a national state park, and notable monuments, providing a blend of relaxation and exploration. The laid-back atmosphere and scenic landscapes make Arundel on the Bay a delightful stop on your journey.

Things to do near Oyster Harbor

Oyster Harbor in Annapolis, Maryland, is perfect for family-friendly vacations filled with outdoor activities. Visitors can enjoy fishing at the pier or creek, explore nearby golf courses, and take advantage of water boating opportunities. Additionally, the area features educational attractions and shopping malls, ensuring a well-rounded experience for all. Whether you're looking to relax or engage in fun activities, Oyster Harbor has something for everyone.

Shopping

In Oyster Harbor, you can visit Annapolis Mall Shopping Center and Westfield Annapolis Mall, both 6 miles away, offering entertainment and family-friendly vibes. For a unique find, check out the Wild Bird Center, located 3 miles away, perfect for nature enthusiasts seeking memorable gifts.

Recreation

At the Navy-Marine Corps Memorial Stadium, experience the thrill of the game while soaking in the energetic atmosphere. Enjoy a round of golf at the Annapolis Golf Club, surrounded by beautiful landscapes. For a touch of culture, visit the Ballet Theater of Maryland for a captivating performance.

Adventure

At Annapolis Sailing School, located 3 miles from Oyster Harbor, you can immerse yourself in thrilling water sports while enjoying the beautiful Chesapeake Bay. For family fun, Chesapeake Beach Water Park, 17 miles away, offers exciting water attractions. Don’t miss the scenic B&A Trail, perfect for hiking 13 miles from Oyster Harbor.

Nightlife

In Oyster Harbor, The Colonial Players offers an intimate theater experience just 4 miles away, perfect for culture and romance. For adventure, head to Annapolis Bowl, located 6 miles away, where you can enjoy arcade fun, or visit Crofton Bowl, 13 miles away, for more exciting arcade activities.

Booking tips and Expedia advantages for Oyster Harbor

To save money on your trip to Oyster Harbor, consider visiting between December and February when prices are lower. Booking your stay on a Monday can also help you avoid higher weekend rates. Use Expedia to find budget-friendly accommodations by filtering for eco-certified hotels and arranging options from lowest to highest price. Combining your hotel, flights, and activities in an Expedia package can lead to further savings. Additionally, join Expedia's One Key membership for exclusive discounts and the opportunity to earn OneKeyCash for future bookings.

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Oyster Harbor are December to February, where the prices are slightly lower. This is in comparison to May to June and September, where prices are slightly higher.
• The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Oyster Harbor is Monday. The most expensive day to stay around Oyster Harbor is Saturday.
• Find cheap hotels on Expedia: Utilize Expedia’s search tool to tailor your options based on your budget, desired location, and preferred hotel type. For instance, selecting the Eco-certified filter will show you a range of sustainable and eco-friendly hotels that are currently available. To find the best prices and deals, simply arrange the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your hotel stay in Oyster Harbor with your flights and activities through an Expedia package.
• Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Oyster Harbor

Oyster Harbor in Annapolis, Maryland, is perfect for families and outdoor enthusiasts, offering a blend of urban parks, marinas, and historic houses. Visitors can immerse themselves in cultural experiences or enjoy outdoor activities. Explore local attractions and nearby points of interest, such as Oyster Creek and the golf community, for a well-rounded vacation. Whether you seek adventure or relaxation, Oyster Harbor has something for everyone.

• U.S. Naval Academy: Located 4 miles from Oyster Harbor, the U.S. Naval Academy offers a unique glimpse into American naval history. Explore its stunning campus, filled with historical buildings and beautiful scenery, and learn about the traditions and training of future naval officers.
• Chesapeake Bay Bridge: Just 7 miles away, this iconic bridge is a modern engineering marvel that connects the Eastern and Western Shores of Maryland. Enjoy breathtaking views of the Chesapeake Bay and the vibrant city atmosphere as you cross this impressive structure.
• Maryland Quiet Waters Park: Situated 2 miles from Oyster Harbor, this urban park is perfect for families and outdoor enthusiasts. Stroll through scenic trails, enjoy wildlife, and take in the peaceful surroundings that make it an ideal retreat within the city.

Best time to go to Oyster Harbor

The best time to visit Oyster Harbor is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	35.6°F (2.0°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	37.9°F (3.3°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
March	44.6°F (7.0°C)	Light Rain	Mostly Sunny	Average	Average
April	55.0°F (12.8°C)	Light Rain	Mostly Sunny	Average	Average
May	64.2°F (17.9°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
June	73.0°F (22.8°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	78.4°F (25.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	76.8°F (24.9°C)	Light Rain	Mostly Sunny	Average	Average
September	70.7°F (21.5°C)	Light Rain	Mostly Sunny	Average	Slightly High
October	60.4°F (15.8°C)	Light Rain	Mostly Sunny	Average	Average
November	48.7°F (9.3°C)	Light Rain	Mostly Sunny	Average	Average
December	41.5°F (5.3°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low

The nearest major airports for your trip to Oyster Harbor

When visiting Oyster Harbor in Annapolis, Maryland, you have several airport options. Ronald Reagan Washington National Airport (DCA) is about 31 miles away, with nearby hotels such as the 5-star InterContinental Washington D.C. - The Wharf and Riggs Washington DC, both within 3 miles. Washington Dulles International Airport (IAD) is located 53 miles away, offering accommodations like the 4-star Hyatt Regency Dulles and Hilton Washington Dulles Airport, both just a couple of miles from the airport. The closest airport is Baltimore Washington International Airport (BWI), situated 20 miles away, with luxurious options like the 5-star Sagamore Pendry Baltimore and Four Seasons Hotel Baltimore, both 8 miles from BWI.