Search Great Oak Landing hotels

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check Great Oak Landing hotel prices

Tomorrow night
This weekend

Filter by

Popular filters
Popular filters
Total price
Guest rating
Guest rating
Property class
Payment type
Payment type
Property type
Property type
Area
Area
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility
Traveller experience
Traveller experience

Top hotels and accommodation in Great Oak Landing

Lake
Inn at Huntingfield Creek
3.5 star property
10.0 out of 10, Exceptional, (44)
"Lovely property with wonderful owners and staff, including three very welcoming dogs. We had a perfect weekend getaway."
The price is NZ$416
per night
19 May - 20 May
Inn at Huntingfield Creek
Fridge, microwave, coffee/tea maker, toaster
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (16)
"We have been coming to Rock Hall for years and have stayed at the cottage the last two times and we have really enjoyed it. We will be back again and we will stay at this cottage again. My husband loves the sauna. Bill and Hannah"
The price is NZ$443
per night
18 May - 19 May
BAYSIDE BUNGALOW
Iron/ironing board, travel cot, free WiFi, bed sheets
Carriage House Hideaway in Middle of Chestertown
10.0 out of 10, Exceptional, (76)
"Bob and Beth's apartment was absolutely perfect for us. It was the cleanest VRBO that we have ever stayed in. All of the amenities were above and beyond what we expected. The apartment is in a great location and walkable into town and the WC campus. We will definitely stay again when we come back to town."
Carriage House Hideaway in Middle of Chestertown
Save an average of 15% on thousands of hotels when you're signed in
Interior
200 steps to the beach!
10.0 out of 10, Exceptional, (73)
"My husband and I love visiting Rock Hall and this was our first time staying at this home. It is very nicely decorated and has all of the necessary amenities. We were so pleased with this stay, this will definitely be on our favorites list"
200 steps to the beach!
Outdoor dining
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
10.0 out of 10, Exceptional, (37)
"This was the perfect landing pad for us and our dog during out 4 night visit. Very clean kitchen and bathrooms, and conveniently located. Well-stocked with all the comforts and conveniences of home. We really loved our meals out at Harbor Shack. We would definitely stay here again!"
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Property grounds
Cute waterfront apartment -- 8 min from the beach!
10.0 out of 10, Exceptional, (5)
"I raced the Waterman's tri and this location was perfect, well equipped, comfortable, clean, easy."
Cute waterfront apartment -- 8 min from the beach!
Beach nearby, sun-loungers, beach towels
Rambling Victorian Beach House on Maryland's Eastern Shore
10.0 out of 10, Exceptional, (13)
"Our group of couples + kids enjoyed our getaway to the Eastern Shore. Betterton was a great home base to visit our alma mater, Washington College, in Chestertown. There, we visited the farmers market and waterfront park & playground with the kids. Back in Betterton, the house fit our group well. Plenty of bedrooms, bathrooms and space for each family. The kids & adults enjoyed spending time lounging in the third floor living room. We were pleased that the house had plenty of games, kids toys,...
Rambling Victorian Beach House on Maryland's Eastern Shore
Exterior
This is truly a Baydream!
10.0 out of 10, Exceptional, (27)
"Close to everything. Cute quiet neighborhood. Well equipped kitchen."
This is truly a Baydream!
Fridge, microwave, oven, stovetop
Bayside Cottage steps from Rock Hall Harbor
10.0 out of 10, Exceptional, (1)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
The price is NZ$642
per night
20 May - 21 May
Bayside Cottage steps from Rock Hall Harbor
Beach towels
Charming Chestertown Waterfront Cottage
10.0 out of 10, Exceptional, (58)
"This is a great place to relax. The house had everything we needed and was very comfortable."
Charming Chestertown Waterfront Cottage
Exterior
Cozy, unique, historic registered cottage on the Corsica River!
10.0 out of 10, Exceptional, (4)
"Very nice property. Enjoy the weekend. Would recommend to anyone visiting the Chestertown and Centreville area."
Cozy, unique, historic registered cottage on the Corsica River!
Balcony
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, (28)
"I organized a large (15 person) bachelorette weekend at this property in early April. It is an absolutely gorgeous house and the host had a number of thoughtful touches - like extra firewood for the firepit, coffee supplies, and a bottle of bubbly for our bride! The beds were comfortable (even the twins!), which was lucky because one bedroom on the breakdown was not really usable, so a handful of guests relocated to one of the 'kid rooms.' We found Ashleigh very responsive both before and...
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Property grounds
Historic Downtown Garden Oasis with Private Patio
10.0 out of 10, Exceptional, (14)
"Stephen and Marianna were great hosts. The property was very clean and functional with beautiful artwork throughout the property. Great outdoor patio for relaxing plus excellent location for access to downtown Chestertown. We will be staying here again on our next visit."
Historic Downtown Garden Oasis with Private Patio
Beach nearby, sun-loungers, beach towels
BEACH WITHOUT THE BUSTLE
10.0 out of 10, Exceptional, (21)
"We needed tranquility after returning from a deployment in the Mideast. All was perfect for my team and I."
BEACH WITHOUT THE BUSTLE
Aerial view
Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD
10.0 out of 10, Exceptional, (14)
"We enjoyed our stay. The home was well stocked and clean and spacious. Perfect for our family"
Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD
Fridge, microwave, oven, stovetop
Beautiful, spacious, quiet waterfront house!
10.0 out of 10, Exceptional, (39)
"We had plenty of room for our family of 8. The weather didn't let us enjoy the outdoor activities and spaces that this house has to offer, which was disappointing, but you can't control Mother Nature! Having grown up in the area, it was fun to get to some of the local spots that have been around for years."
Beautiful, spacious, quiet waterfront house!
Property grounds
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (59)
"This was the perfect place to rest our heads along our trip down the east coast. Very comfortable, clean and quiet. We made time to visit the beautiful town and I’m glad we did!"
The price is NZ$268
per night
11 Jun - 12 Jun
First Floor Studio Apartment in Historic Chestertown
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
9.8 out of 10, Exceptional, (77)
"We had a great stay and the property is well maintained. They had a lot of extras for our convenience such as toothbrushes, snacks, and more. The dock and view was beautiful and relaxing. We plan to come back soon!"
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Pool
Waterfront Oasis w/ Private Dock, 3BR/2BA
9.8 out of 10, Exceptional, (19)
"We really enjoyed our stay. We were in town to celebrate my Dad's 80th birthday and the house was convenient to Parkville and Towson. The view from the sunroom was gorgeous. It was everything we needed for a quick weekend stay. Thank you."
Waterfront Oasis w/ Private Dock, 3BR/2BA
Fridge, microwave, oven, stovetop
Newly restored apartment in the heart of Chestertown
9.8 out of 10, Exceptional, (15)
"This was a great apartment in an excellent location. We visited Washington college and attended a sailing regatta. The Evergrain Bakery across the street was amazing. Shops and restaurants all within walking distance! Apartment was well stocked, nicely decorated and clean! Also very close to the Hodson boathouse. It was a 3 minute drive!"
Newly restored apartment in the heart of Chestertown
Don't see what you're looking for?
See all available properties in Great Oak Landing
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.

More cheap accommodation in Great Oak Landing

Stay near top Great Oak Landing attractions

Great Oak Landing hotels information

Number of reviews
5,549
Accommodation
307 hotels
Lowest Price
NZ$114
Highest Price
NZ$643

Frequently asked questions

If I need to cancel my hotel reservation in Great Oak Landing, will I receive a refund?

Yes! You'll find that most hotel reservations are fully refundable if you cancel before the hotel’s cancellation deadline, which is usually within 24-48 hours of check in. If your reservation is non-refundable, it might still be possible to cancel it and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Great Oak Landing.

What are some accommodation options with pools in Great Oak Landing?

Home2 Suites by Hilton Baltimore/White Marsh: 3-star aparthotel located near White Marsh Mall. Features a children's pool, an indoor pool and a snack bar. Best Western Plus Hotel & Conference Center and Fairfield Inn & Suites by Marriott White Marsh are a couple of other choices with an on-site pool. View all hotels with pools in Great Oak Landing.

What is the best spa hotel in Great Oak Landing?

Great Oak Manor is a top spa hotel featuring a private beach and a fitness centre.

How is it to stay in Great Oak Landing?

Visitors can enjoy all that Great Oak Landing has to offer, including its restaurants. Tourists to the city can also enjoy its welcoming locals. In Great Oak Landing, there are 2 hotels and other accommodation options to choose from. Find out more about Great Oak Landing.

What is there to see in Great Oak Landing?

Places to visit in the wider area include Rock Hall Harbor, Miami Beach and Gunpowder Falls State Park. You'll also find Betterton Beach and Rolphs Wharf Marina in the area. Take a look at what more there is to see and do in Expedia's Great Oak Landing guide.

What's the weather like in Great Oak Landing?

The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Great Oak Landing is 1223 mm.

Recent Reviews in Great Oak Landing
Expedia verified reviews