Find hotels in Great Oak Landing, MD from $67

Go beyond your typical stay in Great Oak Landing

pet friendly image
Pet friendly
Pet friendly
Pool image
Pool
Pool

Check prices for these dates

Tonight
Nov 11 - Nov 12
Tomorrow
Nov 12 - Nov 13
This weekend
Nov 13 - Nov 15
Next weekend
Nov 20 - Nov 22

Filter by

Star rating

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Great Oak Landing hotels

A spacious lobby with a grand chandelier, multiple seating areas, and a piano in the background.

1. Lord Baltimore Hotel

Lord Baltimore Hotel
3.5 star property
Downtown Baltimore
8.4 out of 10, Very good, (3,395 reviews)
"Location, cleanliness and front desk staff Mr. He was very kind and helpful."
United States
Valerie E.
10 days ago
$107 nightly
The price is $126
Nov 22 - Nov 23
Total with taxes and fees
Lord Baltimore Hotel
A Northern Lights Arcade with various gaming machines and a prize shop.

2. Great Wolf Lodge Perryville

Great Wolf Lodge Perryville
2.0 star property
Perryville
8.6 out of 10, Excellent, (365 reviews)
"The food was great staff were very friendly. My children had a great time!"
United States
Shatana
29 days ago
$207 nightly
The price is $232
Nov 12 - Nov 13
Total with taxes and fees
Great Wolf Lodge Perryville
An outdoor bar area with stone seating, umbrellas, and a view of a marina.

3. Hyatt Regency Baltimore Inner Harbor

Hyatt Regency Baltimore Inner Harbor
4.0 star property
Downtown West
8.4 out of 10, Very good, (2,075 reviews)
"Good location and overall hotel. Bar was fine. Staff was mostly helpful."
United States
Scott
7 days ago
$119 nightly
The price is $140
Dec 7 - Dec 8
Total with taxes and fees
Hyatt Regency Baltimore Inner Harbor
A waterfront hotel with multiple floors, a marina with boats, and a cityscape in the background.

4. The Royal Sonesta Harbor Court Baltimore

The Royal Sonesta Harbor Court Baltimore
4.5 star property
Otterbein
8.8 out of 10, Excellent, (2,082 reviews)
"Overall a good stay. The restaurant is good enough. Staff are friendly."
United States
Jason
2 days ago
$144 nightly
The price is $169
Nov 22 - Nov 23
Total with taxes and fees
The Royal Sonesta Harbor Court Baltimore
A modern hotel room with a large gray sectional sofa, a glass coffee table, and a view of the city through large windows.

5. Renaissance Baltimore Harborplace Hotel

Renaissance Baltimore Harborplace Hotel
4.0 star property
Inner Harbor
8.4 out of 10, Very good, (2,535 reviews)
"The hotel was nice overall. The hotel room was clean."
United States
Cynthia
6 days ago
$134 nightly
The price is $158
Nov 27 - Nov 28
Total with taxes and fees
Renaissance Baltimore Harborplace Hotel
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

6. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (129 reviews)
"Clean, comfortable and in a beautiful area."
United States
William
2 days ago
$124 nightly
The price is $137
Nov 12 - Nov 13
Total with taxes and fees
The Lodge at Great Oak Landing
A modern indoor pool area with lounge chairs, a glass wall, and a skylight.

7. Hyatt Place Baltimore Inner Harbor

Hyatt Place Baltimore Inner Harbor
3.5 star property
Harbor East
8.4 out of 10, Very good, (2,690 reviews)
"Location was great to walk all around!"
United States
Steve
1 day ago
$111 nightly
The price is $131
Nov 22 - Nov 23
Total with taxes and fees
Hyatt Place Baltimore Inner Harbor
An outdoor bar area with tables and chairs, a view of the water, and buildings in the background.

8. Pier 5 Hotel Baltimore

Pier 5 Hotel Baltimore
3.5 star property
Inner Harbor
8.2 out of 10, Very good, (1,629 reviews)
"Friendly staff, beautiful room ideal location."
United States
Paul
7 days ago
$99 nightly
The price is $116
Nov 22 - Nov 23
Total with taxes and fees
Pier 5 Hotel Baltimore
A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

9. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (2,071 reviews)
"The room was very comfortable. This hotel is very close to the USNA."
United States
Joseph
2 days ago
$106 nightly
The price is $120
Dec 3 - Dec 4
Total with taxes and fees
Historic Inns of Annapolis
A long, dark wooden table with various decorative items and a bird sculpture, set against a large window with a city view.

10. Hilton Baltimore Inner Harbor

Hilton Baltimore Inner Harbor
4.0 star property
Downtown West
8.6 out of 10, Excellent, (1,000 reviews)
"Room was clean. Staff were great!"
United States
Chanel
19 days ago
$139 nightly
The price is $163
Nov 27 - Nov 28
Total with taxes and fees
Hilton Baltimore Inner Harbor
A multi-story hotel with a classic architectural style, featuring arched windows and decorative trim.

11. Hotel Indigo Baltimore Downtown by IHG

Hotel Indigo Baltimore Downtown by IHG
4.0 star property
Mount Vernon
9.2 out of 10, Wonderful, (1,139 reviews)
"The hotel was lovely. Staff was really nice. The food was also good."
United States
Tania
5 days ago
$106 nightly
The price is $125
Nov 23 - Nov 24
Total with taxes and fees
Hotel Indigo Baltimore Downtown by IHG
A modern interior with large windows, wooden slats, and green-striped seating.

12. Hotel Revival Baltimore

Hotel Revival Baltimore
4.0 star property
Mount Vernon
9.4 out of 10, Exceptional, (1,169 reviews)
"I had a great experience at Hotel Revival. Definitely enjoyed my stay."
United States
Rudolph
1 day ago
$127 nightly
The price is $149
Nov 22 - Nov 23
Total with taxes and fees
Hotel Revival Baltimore
A multi-story hotel with illuminated windows, a prominent entrance with a canopy, and a statue above the entrance.

13. Kimpton Hotel Monaco Baltimore Inner Harbor by IHG

Kimpton Hotel Monaco Baltimore Inner Harbor by IHG
4.5 star property
Downtown Baltimore
8.8 out of 10, Excellent, (532 reviews)
"The hotel is BEAUTIFUL. I stayed with our kids. We had a wonderful experience."
United States
Neshka
24 days ago
$127 nightly
The price is $149
Dec 7 - Dec 8
Total with taxes and fees
Kimpton Hotel Monaco Baltimore Inner Harbor by IHG
An outdoor patio with tables and chairs, string lights, and large planters.

14. Baltimore Marriott Waterfront

Baltimore Marriott Waterfront
3.5 star property
Harbor East
9.2 out of 10, Wonderful, (1,045 reviews)
"Overall great stay. Great location on the harbor within walking distance to shopping."
United States
Autumn
4 days ago
$125 nightly
The price is $147
Nov 22 - Nov 23
Total with taxes and fees
Baltimore Marriott Waterfront
A bar area with a brick counter, bar stools, and a graffiti wall.

15. Residence Inn by Marriott Baltimore Inner Harbor

Residence Inn by Marriott Baltimore Inner Harbor
3.0 star property
Downtown Baltimore
9.0 out of 10, Wonderful, (1,222 reviews)
"My room was clean. The front desk staff was polite."
United States
Sarita
2 days ago
$104 nightly
The price is $122
Nov 29 - Nov 30
Total with taxes and fees
Residence Inn by Marriott Baltimore Inner Harbor
A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

16. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,274 reviews)
"I visited with my young daughter. Everything about the facility made me feel safe."
United States
Rebecca
6 days ago
$89 nightly
The price is $102
Nov 23 - Nov 24
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
A modern living room with a fireplace, two sofas, a coffee table with a book, and a view of the sea.

17. Pendry Baltimore

Pendry Baltimore
5.0 star property
Fells Point
9.4 out of 10, Exceptional, (1,000 reviews)
"Their warm hospitality made an already wonderful stay even more memorable."
United States
Sherry A.
24 days ago
$422 nightly
The price is $496
Dec 10 - Dec 11
Total with taxes and fees
Pendry Baltimore
A swimming pool with a clear blue water, surrounded by lounge chairs and a glass wall.

18. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,015 reviews)
"But the staff was helpful, the rooms were big and clean."
United States
Brian
1 day ago
$110 nightly
The price is $125
Nov 15 - Nov 16
Total with taxes and fees
Crowne Plaza Annapolis by IHG
A high-rise building with a glass facade, a waterfront view, and a small park with white tents.

19. Four Seasons Hotel Baltimore

Four Seasons Hotel Baltimore
5.0 star property
Harbor East
9.4 out of 10, Exceptional, (1,001 reviews)
"Harbor views. The hotel bedding was plush. The room was spacious."
United States
TALILA
10 days ago
$446 nightly
The price is $524
Dec 11 - Dec 12
Total with taxes and fees
Four Seasons Hotel Baltimore
An outdoor seating area with a fire pit, blue sofas, and tables.

20. Hampton Inn Towson Downtown

Hampton Inn Towson Downtown
3.5 star property
Towson
9.2 out of 10, Wonderful, (1,008 reviews)
"Many food options walking distance. Staff was super friendly."
Canada
Nicole
3 days ago
$113 nightly
The price is $131
Nov 24 - Nov 25
Total with taxes and fees
Hampton Inn Towson Downtown
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.
View all properties

Stay near popular Great Oak Landing attractions

Discover the charm of Great Oak Landing, where outdoor adventures await at the stunning Chesapeake Bay. Enjoy the serene beaches, explore the local marina, and immerse yourself in the history with the Great Oak Historical Society. This destination promises unforgettable experiences for every traveler.

Washington College

8.6/10 (87 reviews)
Set the stage for your cultural exploration at Washington College, a historic institution in Chestertown, Maryland. With its rich history and vibrant atmosphere, it offers a unique glimpse into American academia. It’s about 11 miles by car from Great Oak Landing, making it a convenient stop on your journey.
See properties

Top Great Oak Landing Hotel Reviews

A hotel lobby with a fireplace, seating area, and a television.
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown

10/10 Excellent

Inside the building it was clean, quiet and nice. In the back parking lot, it was very dirty. The grounds surrounding the lot was littered with trash and debris. One person looked to be sleeping in his car. I did appreciate the very bright lighting in that lot. A small clean up of the back lot would make a big difference in first impressions!!
United States
Laura
Reviewed April 12, 2025
Comfort Inn & Suites Chestertown

Find out more about Great Oak Landing

Top reasons to visit Great Oak Landing

  • Stunning Marina Views: Great Oak Landing features a large marina with safe harbor, perfect for water activities and enjoying beautiful scenery.
  • Outdoor Adventure: The area is ideal for outdoor enthusiasts, offering a dog park, town park, and access to local beaches.
  • Family-Friendly Atmosphere: With a welcoming vibe, Great Oak Landing is perfect for family outings and relaxation.
  • Local Events and Activities: Visitors can engage in local events and explore nearby towns for historical charm.
  • Diverse Accommodations: A variety of lodging options cater to different traveler needs, including pet-friendly and LGBTQIA-inclusive stays.

Find great hotels near Great Oak Landing

Explore a variety of hotel accommodations in Great Oak Landing, Maryland, catering to diverse traveler needs. Whether you're seeking a cozy beach lodge, a welcoming pet-friendly hotel, or a business-friendly motel, you'll find options that promise a comfortable stay. Enjoy a vacation experience that embraces inclusivity and caters to everyone, including LGBTQIA travelers, ensuring a memorable time in this charming destination.

  • WoodSpring Suites Baltimore White Marsh - Nottingham: WoodSpring Suites Baltimore White Marsh - Nottingham is a budget-friendly hotel located 16 miles from Great Oak Landing, perfect for travelers seeking a practical and pet-friendly accommodation. This hotel offers a distinctive home-like atmosphere with spacious rooms equipped with kitchenettes, making it ideal for extended stays or business travelers. Its pet-friendly policy allows dogs, with specific weight limits and cleaning fees, ensuring a welcoming environment for furry companions. Guests can enjoy conveniences such as on-site laundry facilities and free parking, making it a smart choice for those on a budget.
  • Best Western Plus Hotel & Conference Center: Situated 18 miles from Great Oak Landing, Best Western Plus Hotel & Conference Center is an excellent choice for families and business travelers alike. This budget-friendly hotel offers a range of amenities including free cribs for children and a pet-friendly policy that permits dogs, creating a welcoming environment for guests with family pets. With an on-site conference center, this hotel is well-equipped for business needs, while leisure travelers can take advantage of its comfortable accommodations and family-oriented services. The friendly atmosphere and convenient location make it a standout option.
  • Americas Best Value Inn Baltimore: Also located 18 miles from Great Oak Landing, Americas Best Value Inn Baltimore provides budget-conscious travelers with essential amenities and a family-friendly environment. This hotel features child safety measures such as window guards and free cribs, ensuring peace of mind for parents. The property caters well to business travelers while maintaining a welcoming atmosphere for families. With its affordable rates and focus on comfort, this hotel stands out as a practical choice for those looking to explore the Baltimore area.

Where to stay near Great Oak Landing

Great Oak Landing, Maryland, offers an idyllic escape for outdoor enthusiasts and beach lovers alike. Nestled near the picturesque Chesapeake Bay, travelers can enjoy stunning marina views and serene picnic areas. The village's friendly atmosphere and family-friendly vibe make it perfect for a relaxing getaway. Explore nearby towns for a blend of historical charm and budget-friendly experiences, ensuring a memorable vacation in this scenic part of the Eastern Shore.

  • Georgetown: Nestled a mere 3 miles from Great Oak Landing, Georgetown is a charming village that offers a blend of outdoor adventures and romantic settings. The travel experience in Georgetown peaks during the summer months, attracting visitors for its recreational activities, educational opportunities, and scenic hiking trails. You can enjoy local landmarks like the beach and marina while immersing yourself in the vibrant community. Whether you're looking to unwind or seek entertainment, Georgetown provides a delightful escape.
  • Fairlee: Also located 3 miles away from Great Oak Landing, Fairlee is a picturesque village where family-friendly experiences abound. This destination draws visitors year-round, with a noticeable surge during the summer. Fairlee boasts a range of activities including shopping at local centers, golfing, and enjoying the recreational areas. The nearby beach and urban park offer perfect spots for relaxation and family fun. With its welcoming atmosphere, Fairlee is an ideal place for families to create lasting memories.
  • Tolchester Beach: Situated just 4 miles from Great Oak Landing, Tolchester Beach is a scenic village perfect for outdoor enthusiasts and beach lovers. This destination maintains a steady flow of visitors, particularly during the summer months. Enjoy a variety of activities, including skiing at nearby resorts and exploring educational venues. Tolchester Beach is renowned for its stunning family-friendly beach and marina, making it a fantastic spot for a leisurely day in the sun. Its captivating scenery and laid-back vibe make it a must-visit during your vacation.

Things to do in Great Oak Landing

Great Oak Landing, Maryland, is perfect for outdoor enthusiasts and beach lovers, offering stunning scenery and a range of activities. Visitors can enjoy family outings, explore local events, and indulge in outlet shopping. The area also features a dog park and a town park, making it an ideal destination for relaxation and recreation.

Shopping

In Great Oak Landing, enjoy local shops and charming boutiques for unique gifts and souvenirs. If you're up for a drive, visit the nearby Easton Shopping Center, about 12 miles away, featuring a variety of retail stores and dining options for a delightful shopping experience.

Recreation

In Great Oak Landing, indulge in rejuvenating treatments at the serene wellness centers that offer massages and holistic therapies. Enjoy nature walks along scenic trails, or participate in yoga sessions by the water, providing a perfect blend of relaxation and recreation for your vacation.

Adventure

In Great Oak Landing, explore the scenic waterfront with thrilling kayaking adventures or enjoy fishing trips in the Chesapeake Bay. Discover beautiful hiking trails nearby, perfect for immersing yourself in nature while spotting local wildlife.

Nightlife

In Great Oak Landing, enjoy lively evenings at local pubs featuring live music and friendly atmospheres. Nearby, charming waterfront restaurants provide scenic views and delicious dining options, while cozy lounges offer relaxed vibes for unwinding after a busy day exploring the area.

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

Booking tips and Expedia advantages for Great Oak Landing

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Great Oak Landing are December to February, where the prices are slightly lower. This is in comparison to May and September to October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Great Oak Landing is Monday. The most expensive day to stay in Great Oak Landing is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia's search tool to customize your travel preferences, such as your budget, desired location, and type of hotel you’re looking for. For instance, selecting the Eco-certified filter will show you sustainable and environmentally-friendly hotels that are currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Great Oak Landing hotel reservation with your flights and activities through an Expedia package deal.

Find the best attractions near Great Oak Landing

Great Oak Landing, Maryland, is perfect for outdoor and beach vacations, offering stunning scenery and adventure. Visitors can explore a large marina and enjoy the safe harbor, making it ideal for water activities. Popular attractions include local parks and beautiful beaches, catering to those seeking a blend of relaxation and excitement. Whether you're looking to unwind or embark on an adventure, Great Oak Landing has something for everyone.

  • CopperPlex: Experience the excitement of live sports at CopperPlex, a vibrant stadium located 12 miles from Great Oak Landing. With a lively atmosphere and passionate fans, it’s a perfect spot to catch a game or event and soak in the competitive spirit.
  • Rock Hall Harbor: Just 9 miles away, Rock Hall Harbor offers picturesque views and a relaxing beach vibe. Enjoy scenic strolls along the waterfront, or take part in water activities while soaking in the charm of this quaint harbor.
  • Betterton Beach: Located 10 miles from Great Oak Landing, Betterton Beach is a delightful sandy escape. With its tranquil waters and inviting shoreline, it’s an ideal spot for sunbathing, swimming, and enjoying a laid-back day by the sea.

Best time to go to Great Oak Landing

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

Calendar MonthTemperaturePrecipitationCloudinessOccupancyPricing
January34.2°F (1.2°C)Light RainMostly SunnySlightly LowSlightly Low
February36.9°F (2.7°C)Light RainMostly SunnySlightly LowSlightly Low
March43.7°F (6.5°C)Light RainMostly SunnyAverageAverage
April54.3°F (12.4°C)Light RainMostly SunnyAverageAverage
May63.7°F (17.6°C)Light RainMostly SunnyAverageSlightly High
June72.1°F (22.3°C)Light RainMostly SunnySlightly HighAverage
July77.4°F (25.2°C)Light RainMostly SunnySlightly HighAverage
August75.6°F (24.2°C)Light RainMostly SunnySlightly HighAverage
September69.4°F (20.8°C)Light RainMostly SunnyAverageSlightly High
October59.2°F (15.1°C)Light RainMostly SunnyAverageSlightly High
November47.3°F (8.5°C)Light RainMostly SunnyAverageAverage
December39.9°F (4.4°C)Light RainMostly SunnySlightly LowSlightly Low

The nearest major airports for your trip to Great Oak Landing

Traveling to Great Oak Landing, Maryland, is convenient with access to several major airports. Philadelphia International Airport (PHL) is approximately 66 miles away, with nearby hotels like the 5-star W Philadelphia and The Rittenhouse, both 6 miles from the airport. Ronald Reagan Washington National Airport (DCA) is 53 miles away, offering luxurious accommodations such as the InterContinental Washington D.C. - The Wharf and Salamander Washington DC, both just 2 miles from the airport. Washington Dulles International Airport (IAD) is about 70 miles away, with excellent hotel options including The Westin Washington Dulles Airport and Hyatt Regency, both only 1 mile away, providing easy access to the airport.

Frequently Asked Questions

What is the best area to stay in Great Oak Landing?

The best area to stay in Great Oak Landing is within the Great Oak Landing resort complex itself, as it's a self-contained destination offering an extensive experience.

This resort is situated directly on the picturesque Chesapeake Bay, providing guests with immediate access to waterfront activities and views. The main area of the resort is designed for convenience, with accommodations, dining, and recreational facilities all within walking distance or a short shuttle ride. You'll find everything from the marina, which is a focal point for boating and watersports, to various dining establishments and a golf course.

Families will find Great Oak Landing particularly appealing due to the wide array of activities available on-site. There are swimming pools, playgrounds, and organized children's programs, ensuring entertainment for all ages. The resort's layout means that children can move between activities easily, and parents can relax knowing everything is nearby.

Couples looking for a relaxing getaway will also appreciate the resort's amenities. They can enjoy leisurely strolls along the waterfront, dine at the upscale restaurants, or spend time on the golf course.

When is the best time to go to Great Oak Landing?

The best time to go to Great Oak Landing is during the spring and fall seasons, specifically from April to May and September to October. These months offer pleasant weather conditions, making it ideal for outdoor activities and enjoying the natural beauty of the area.

During the spring, the weather is mild, with blooming flowers and lush greenery, creating a scenic backdrop for outdoor adventures. This season is great for couples looking for a romantic getaway, with opportunities for kayaking, paddleboarding, or simply relaxing by the water. The cooler temperatures make it comfortable for exploring the walking trails around the landing.

The fall season brings comfortable temperatures and vibrant foliage, making it an excellent time for those who appreciate scenic views. It's a great time for families to visit, as the cooler weather is conducive to outdoor play and exploring the natural surroundings without the summer heat.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Great Oak Landing.

How much is the nightly rate at a Great Oak Landing hotel?

Prices for hotels in Great Oak Landing often vary, but you can find a great deal from $67 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

Explore a world of travel with Expedia