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Our top choices for Oyster Harbor hotels

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
26.6 km from Oyster Harbor
8.8 out of 10, Excellent, (93 reviews)
"We were"
United States
Guevara
The price is NT$4,102
NT$5,919 total
includes taxes & fees
Apr 6 - Apr 7
Wylder Tilghman Island

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
25.8 km from Oyster Harbor
9.4 out of 10, Exceptional, (374 reviews)
"Such a marvelous retreat! And the balcony facing the boats and the Bay at sunset is so welcome after exploring St Michael’s (a short 17 mins drive). Extremely friendly staff and good breakfast. Highly recommend to any nature lovers."
United States
Nadia
The price is NT$3,199
NT$3,519 total
includes taxes & fees
Mar 29 - Mar 30
Knapps Narrows Marina & Inn

George Brooks House B&B

George Brooks House B&B
3.0 star property
25.4 km from Oyster Harbor
8.8 out of 10, Excellent, (70 reviews)
"A beautiful renovated historical house with charm, clean rooms, decorative furnishings and a wonderful hot breakfast. What we enjoyed the most was the warm hospitality of Willard, Valerie, and the other staff. Very close to downtown St. Michael’s, but just far enough away to give a nice feel of natural serenity. Great for a quick getaway from the city. We will be back. "
United States
Charles
The price is NT$5,117
NT$5,629 total
includes taxes & fees
Mar 30 - Mar 31
George Brooks House B&B

Kent Island Resort

Kent Island Resort
3.5 star property
13.8 km from Oyster Harbor
9.2 out of 10, Wonderful, (134 reviews)
"Beautiful hotel, nice staff"
United States
Kim
The price is NT$3,806
NT$5,184 total
includes taxes & fees
Mar 31 - Apr 1
Kent Island Resort

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
26.8 km from Oyster Harbor
8.4 out of 10, Very Good, (1,003 reviews)
"Great place to stay with lovely views"
United States
David
The price is NT$3,426
NT$4,443 total
includes taxes & fees
Mar 29 - Mar 30
Rod 'N' Reel Resort

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
30.3 km from Oyster Harbor
The price is NT$4,959
NT$5,504 total
includes taxes & fees
Apr 21 - Apr 22
Haven Point Inn and Gallery

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
23.2 km from Oyster Harbor
7.8 out of 10, Good, (884 reviews)
"Staff was nice and room was clean "
United States
Lauren
The price is NT$3,398
NT$3,772 total
includes taxes & fees
Apr 1 - Apr 2
Quality Inn Grasonville near Kent Island

Parsonage Inn

Parsonage Inn
3.5 star property
26.1 km from Oyster Harbor
9.2 out of 10, Wonderful, (131 reviews)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is NT$4,767
NT$5,243 total
includes taxes & fees
Mar 31 - Apr 1
Parsonage Inn

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
29.4 km from Oyster Harbor
10.0 out of 10, Exceptional, (62 reviews)
"The owners and staff were very courteous and nice. The room layout was great and thoughtfully designed and decorated."
United States
Sandra
The price is NT$4,482
NT$4,976 total
includes taxes & fees
Mar 29 - Mar 30
Inn at Huntingfield Creek

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
20.3 km from Oyster Harbor
8.0 out of 10, Very Good, (1,002 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is NT$3,438
NT$3,816 total
includes taxes & fees
Mar 31 - Apr 1
Best Western Kent Narrows Inn

The Wildset

The Wildset
2.5 star property
26.2 km from Oyster Harbor
9.8 out of 10, Exceptional, (425 reviews)
"Best HOTEL EVER!!!"
United States
Ama
The price is NT$6,686
NT$8,059 total
includes taxes & fees
Apr 2 - Apr 3
The Wildset

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
19.7 km from Oyster Harbor
9.4 out of 10, Exceptional, (12 reviews)
"Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend *****"
United States
Todd
The price is NT$8,244
NT$9,399 total
includes taxes & fees
Apr 5 - Apr 6
The Inn at Tacaro Estate

St Michaels Inn

St Michaels Inn
2.5 star property
28.7 km from Oyster Harbor
8.2 out of 10, Very Good, (1,000 reviews)
" Great place,great location, was in town for St Michael Chocolate fest "
United States
Katherine
The price is NT$4,328
NT$4,761 total
includes taxes & fees
Apr 5 - Apr 6
St Michaels Inn

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
20.3 km from Oyster Harbor
9.0 out of 10, Wonderful, (1,000 reviews)
"Beautiful area"
United States
Dan
The price is NT$4,694
NT$5,211 total
includes taxes & fees
Apr 1 - Apr 2
Hilton Garden Inn Kent Island Marina

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
22.1 km from Oyster Harbor
9.0 out of 10, Wonderful, (1,046 reviews)
"We stayed here while visiting our kids in the area! Very nice staff and clean hotel. Good place to stay for the money! "
United States
Lonnie
The price is NT$2,735
NT$3,118 total
includes taxes & fees
Apr 19 - Apr 20
Microtel Inn & Suites by Wyndham Gambrills

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
17.4 km from Oyster Harbor
9.4 out of 10, Exceptional, (478 reviews)
"The Anchored Inn at Hidden Harbour Marina is a small gem of a hotel in Deale, Maryland. The staff was incredibly kind and professional. We were there "off season" and enjoyed the quiet. The room was a little small, but the bed was very comfortable. We would stay at the Anchored Inn again in a heartbeat!"
United States
Katey
The price is NT$4,865
NT$5,546 total
includes taxes & fees
Mar 30 - Mar 31
Anchored Inn at Hidden Harbour Marina

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
25.6 km from Oyster Harbor
9.6 out of 10, Exceptional, (125 reviews)
"A wonderful property with a fantastic location. Super friendly staff. Couldn't ask for a more pleasant stay anywhere. You should book right now."
United States
Timothy
The price is NT$7,516
NT$8,268 total
includes taxes & fees
Apr 7 - Apr 8
The Tilghman Island Inn

Flag House Inn

Flag House Inn
3.5 star property
Historic District, 6.1 km from Oyster Harbor
9.2 out of 10, Wonderful, (90 reviews)
"The B&B website and other on-line links claims "...excellent breakfast" and "the best breakfast in Annapolis". What was served were mini grocery store bought pastry, no fresh coffee, no juice, no plates, no one around. In addition, they state that for a large fee you can have valet parking on-site. There was no valet. I requested a refund for the valet parking and used that money to have a decent breakfast elsewhere. "
United States
Linda
The price is NT$5,809
NT$6,623 total
includes taxes & fees
Mar 29 - Mar 30
Flag House Inn

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
26.2 km from Oyster Harbor
9.6 out of 10, Exceptional, (374 reviews)
"Fantastic - loved our stay!"
United States
Emily
The price is NT$13,204
NT$14,525 total
includes taxes & fees
Apr 19 - Apr 20
Inn at Perry Cabin

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
8.5 km from Oyster Harbor
8.8 out of 10, Excellent, (220 reviews)
"Hotel was clean staff was friendly"
United States
Kim
The price is NT$3,327
NT$3,951 total
includes taxes & fees
Mar 29 - Mar 30
Candlewood Suites Annapolis by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Where to stay in Oyster Harbor

Find the best Oyster Harbor areas and neighborhoods for the activities you enjoy most. Learn more about Oyster Harbor
Learn more about Oyster Harbor

Historic District

Discover a well-preserved historic district with elements of the original town plan, featuring landmarks like the Maryland State House, St. Ann's Church, and Paca House and Gardens. The neighborhood features prestigious educational institutions like St. John's College and the U.S. Naval Academy.

Eastport

While visiting Eastport, you might make a stop by sights like Annapolis Maritime Museum and Annapolis Harbor.

Murray Hill

While visiting Murray Hill, you might make a stop by sights like Spa Creek and Ballet Theater of Maryland.

Arundel on the Bay

Former post village turned residential area, Arundel-on-the-Bay boasts a private beach, pier, boat ramp, and boat launch for community use, with the picturesque Thomas Point Lighthouse just a short boat ride away.

Hillsmere

If you're spending some time in Hillsmere, Maryland Quiet Waters Park and Great Frogs Winery are top sights worth seeing.

Top Oyster Harbor Hotel Reviews

Find out more about Oyster Harbor

Top reasons to visit Oyster Harbor

  • Outdoor Activities: Oyster Harbor offers a variety of outdoor experiences, including fishing, boating, and golfing, perfect for family vacations.
  • Scenic Beaches: Relax at the inviting community beach, where stunning coastal views create a picturesque setting.
  • Charming Local Shops: Discover quaint shops and delightful eateries nearby, adding a touch of local flavor to your visit.
  • Rich History: Explore historic houses and cultural sites that showcase the area's unique heritage.
  • Diverse Accommodations: Choose from cozy bed & breakfasts to modern hotels, catering to various traveler needs.

Find great hotels near Oyster Harbor

Discover a range of hotel accommodations in Oyster Harbor, Annapolis, Maryland, perfect for your getaway. Whether you prefer a cozy bed & breakfast or a modern hotel, you'll find pet-friendly options and services tailored for business travelers and LGBTQIA guests. Enjoy proximity to local attractions like Oyster Harbor's marina, the Oyster Harbor Club, and the Boat Yard, ensuring a memorable stay by the water.

  • Country Inn & Suites by Radisson, Annapolis, MD: Nestled 9.7km from Oyster Harbor, Country Inn & Suites by Radisson offers a welcoming atmosphere perfect for pet lovers and business travelers alike. This 3-star hotel embraces diversity, being LGBTQIA-friendly and affiliated with LGBTQI travel guides. Guests can enjoy amenities like a designated dog exercise area and flexible pet policies, making it a great choice for those traveling with furry companions. The hotel’s comfortable rooms and convenient business facilities cater to a variety of needs, ensuring an enjoyable stay for all.
  • Comfort Inn Conference Center: Located 20.9km from Oyster Harbor, Comfort Inn Conference Center is ideal for business travelers seeking a comfortable and pet-friendly environment. This hotel offers essential amenities and a welcoming atmosphere for both work and relaxation. With its pet policy allowing for service animals and permitted pets, guests can travel with peace of mind. The hotel is equipped with essential business facilities, making it a practical choice for those on a work trip who also want the option to bring their pets along.
  • Historic Inns of Annapolis: Just 6.4km from Oyster Harbor, Historic Inns of Annapolis stands out with its unique blend of history and charm. Set within a national historic building, this 3.5-star hotel offers a city-themed experience that allows guests to immerse themselves in Annapolis’s rich heritage. With pet-friendly policies, including accommodations for dogs, guests can enjoy their stay without leaving their pets behind. The central location makes it easy to explore the vibrant surroundings, while the historic ambiance enhances your vacation experience.

Where to stay near Oyster Harbor

Oyster Harbor, nestled in the charming village of Osterville, offers a perfect blend of coastal beauty and family-friendly activities. Explore the inviting community beach, where relaxation meets stunning scenery. Nearby, you'll find quaint shops and delightful eateries, making it an ideal spot for both leisure and romance. Enjoy the warm atmosphere and friendly locals as you experience the best of what this beautiful region has to offer.

  • Annapolis: As the capital of Maryland, Annapolis is a vibrant city filled with rich history and culture. Nestled along the Chesapeake Bay, it offers a unique blend of urban life and coastal charm. Visitors can explore the historic downtown area, packed with colonial architecture, shops, and restaurants. Annapolis is renowned for its sailing heritage, making it a perfect destination for water enthusiasts. Key attractions include the United States Naval Academy, the Maryland State House, and picturesque waterfront parks. The city thrives year-round, but expect a bustling atmosphere during summer months when festivals and outdoor events take center stage.
  • Highland Beach: A quaint village located just 644m from Oyster Harbor, Highland Beach is a hidden gem known for its serene beaches and charming community vibe. This idyllic spot is ideal for outdoor lovers, offering beautiful shoreline views and recreational activities. Perfect for romantic getaways or family outings, visitors can enjoy leisurely strolls along the boardwalk and spend time at local parks. The village's seasonal appeal peaks in late spring and summer, making it a popular destination for those looking to unwind by the water and soak up the sun.
  • Arundel on the Bay: Situated 1.1km from Oyster Harbor, Arundel on the Bay is a picturesque neighborhood that combines natural beauty with a friendly atmosphere. This area is popular among families and business travelers alike, offering easy access to local beaches and recreational activities. Visitors can explore the nearby lake and enjoy the historic charm of local landmarks. With its unique blend of outdoor experiences and community spirit, Arundel on the Bay is a delightful stop for those looking to escape the hustle and bustle while still being close to the heart of Annapolis.

Things to do near Oyster Harbor

Oyster Harbor in Annapolis, Maryland, is perfect for outdoor family vacations, offering a variety of activities. Enjoy the scenic recreational areas, visit local educational sites, or shop at nearby malls. Popular attractions include a fishing pier, a golf course, fishing in the creek, water boating, and guided tours, ensuring a memorable experience for all visitors.

Shopping

Experience shopping in Oyster Harbor with Westfield Annapolis Mall, just 9.7km away, offering a vibrant mix of entertainment and family-friendly options. Don't miss the Wild Bird Center, 4.8km away for unique gifts, and Annapolis Harbor Center, 8.0km away, featuring a variety of stores.

Recreation

At the Navy-Marine Corps Memorial Stadium, immerse yourself in the energetic atmosphere of local sports events, just a short drive from Oyster Harbor. Experience the great outdoors at Annapolis Golf Club, where you can enjoy a round of golf surrounded by beautiful scenery. Lastly, indulge in the arts at the Ballet Theater of Maryland, celebrating culture and romance through captivating dance performances.

Adventure

At Annapolis Sailing School, located 4.8km from Oyster Harbor, embrace the thrill of sailing in a vibrant outdoor environment. Chesapeake Beach Water Park, 27.4km away, offers family-friendly water fun and exciting attractions. For a scenic escape, hike the B&A Trail, situated 14.8km from Oyster Harbor, surrounded by nature.

Nightlife

Experience the vibrant nightlife in Oyster Harbor by catching a show at The Colonial Players, just 6.4km away, for a taste of local culture. For family fun, visit Annapolis Bowl 9.7km away or Crofton Bowl 20.9km away, where adventure awaits in an arcade atmosphere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Oyster Harbor

To save money during your visit to Oyster Harbor, plan your trip between December and February when hotel prices are lower, and try to book your stay on a Monday for the best deals. Utilize Expedia's search tool to find budget-friendly accommodations, especially by filtering for Eco-certified hotels. Combining your hotel, flights, and activities into one package can also lead to significant savings. For transportation, consider using public transport options or walking to explore the area, as it is pedestrian-friendly and offers free activities to enjoy the beautiful surroundings.

  • 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: Expedia's search tool enables you to choose your budget, desired location, and additional preferences. You can easily arrange your search results by price, starting with the most affordable hotels. Additionally, you have the option to narrow your choices by hotel type—if you select the Eco-certified filter, you'll find a selection of sustainable and environmentally friendly hotels ready for booking.
  • Consider bundling your trip: You can save money by combining your hotel stay at Oyster Harbor with your flights and activities when you book an Expedia package.

Find the best attractions near Oyster Harbor

Oyster Harbor in Annapolis, Maryland, is an ideal destination for outdoor enthusiasts and families alike. Visitors can explore a variety of attractions, including marinas, urban parks, and historic houses. Whether you're interested in cultural experiences or simply enjoying the beautiful scenery, Oyster Harbor has something for everyone. Don't miss the chance to discover the charming nearby areas like Oyster Creek and the local golf community, making your vacation truly memorable.

  • U.S. Naval Academy: Located 6.4km from Oyster Harbor, this prestigious institution offers a glimpse into naval history and training. Explore its stunning architecture and beautiful grounds while soaking in the rich maritime heritage of the United States.
  • Chesapeake Bay Bridge: A modern marvel situated 11.3km away, this iconic bridge connects the Eastern and Western shores of Maryland. Experience breathtaking views of the Chesapeake Bay and enjoy the vibrant city atmosphere surrounding the area.
  • Maryland Quiet Waters Park: Just 3.2km from Oyster Harbor, this urban park is a peaceful retreat featuring scenic trails and art installations. It's perfect for family outings and outdoor activities amidst the charm of nature and city vibes.

Best time to go to Oyster Harbor

The best time to visit Oyster Harbor can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Oyster Harbor falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature around Oyster Harbor falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly SunnySlightly LowSlightly Low
February37.9°F (3.3°C)Light RainMostly SunnySlightly LowSlightly Low
March44.6°F (7.0°C)Light RainMostly SunnyAverageAverage
April55.0°F (12.8°C)Light RainMostly SunnyAverageAverage
May64.2°F (17.9°C)Light RainMostly SunnyAverageSlightly High
June73.0°F (22.8°C)Light RainMostly SunnySlightly HighSlightly High
July78.4°F (25.8°C)Light RainMostly SunnySlightly HighAverage
August76.8°F (24.9°C)Light RainMostly SunnySlightly HighAverage
September70.7°F (21.5°C)Light RainMostly SunnyAverageSlightly High
October60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
November48.7°F (9.3°C)Light RainMostly SunnyAverageAverage
December41.5°F (5.3°C)Light RainMostly SunnySlightly LowSlightly Low

The nearest major airports for your trip to Oyster Harbor

Traveling to Oyster Harbor, Annapolis, is convenient with three major airports nearby. Baltimore/Washington International Thurgood Marshall Airport (BWI) is 32.2km away, with excellent hotel options like the 5-star Sagamore Pendry Baltimore and Four Seasons Hotel Baltimore, both 12.9km from the airport. Washington, D.C. (Ronald Reagan Washington National Airport - DCA) is 49.9km away, featuring luxurious stays at Salamander Washington DC, Riggs Washington DC, and Pendry Washington DC - The Wharf, all within 4.8km. Finally, Washington Dulles International Airport (IAD) is 54.8km from Oyster Harbor, with nearby hotels like the 4-star Hyatt Regency Dulles and Hilton Washington Dulles Airport, both just a couple of miles away.

Frequently asked questions

What's it like in Oyster Harbor?
Travelers to the Oyster Harbor neighborhood in Annapolis will be sure to enjoy their stay. Be sure to check out Northern Chesapeake Bay and Chesapeake Bay as part of your Oyster Harbor travel plans.
How many hotels can I expect to find in the Oyster Harbor area?
Expedia has 6 Oyster Harbor hotels and other accommodations, and one might make a good home base for venturing out into the greater Annapolis area.
If I need to cancel my hotel reservation in Oyster Harbor, will I receive a refund?
Yes! Most room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a non-refundable reservation, it may still be possible to cancel it and be given a refund within a 24-hour period of your booking. Add dates, click "Search", then use the filter option "fully refundable" to get the best options available in Oyster Harbor.
Where can I learn more about changing or cancelling my trip to Oyster Harbor?
To access more information about rescheduling or cancelling your trip to Oyster Harbor, go to https://www.expedia.com/service/.
What is there to do around this Annapolis neighborhood?
A few attractions you might want to check out while you're in Oyster Harbor are Northern Chesapeake Bay and Chesapeake Bay. While you're out sightseeing, Bay Ridge Beach and Annapolis Golf Club are a couple of additional sights to visit in Annapolis.

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