Find hotels in Great Oak Landing, MD from $64

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Check Great Oak Landing hotel prices

Tonight
May 2 - May 3
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May 3 - May 4
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May 3 - May 5
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May 10 - May 12

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Compare 312 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Lobby
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (666)
"We arrived late but the lady at the front desk was so nice. Our room was spacious, clean and the bed was so comfortable. We didn’t get to heave breakfast due to heading home but we really enjoyed our short stay and plan to come back. "
The price is $114
$126 total
includes taxes & fees
May 5 - May 6
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board
Red Roof Inn & Suites Chestertown
2.0 star property
7.4 out of 10, Good, (261)
"This is a conveniently located and comfortable Inn/Hotel. It was perfect for a one night stay. The only deficit was the lack of a simple, continental breakfast room necessitating a walk to the local DD/Dunkin'."
The price is $94
$105 total
includes taxes & fees
May 9 - May 10
Red Roof Inn & Suites Chestertown
Private beach, sun loungers
The Lodge at Great Oak Landing
3.0 star property
7.6 out of 10, Good, (4)
"The place is beautiful. The rooms are little small and could use updating. When I turned the air on the windows rattled so loud. I had to keep it on low to avoid the noise. No microwave in the room and be prepared for the slamming door at 6am. Other than those things we really enjoyed our time. "
The price is $132
$151 total
includes taxes & fees
May 6 - May 7
The Lodge at Great Oak Landing
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Lobby
Driftwood Inn
2.0 star property
5.0 out of 10, (159)
"It was clean and everything worked--more than I could say for many other more expensive rooms I've stayed in. The shower was exceptionally good. Watch out for the hot water: very hot! The TV had Netflix, Hulu, Roku, & Vudu. And they worked. On the downside, the furnishings and carpet were worn, but not terrible. "
The price is $64
$70 total
includes taxes & fees
May 5 - May 6
Driftwood Inn
Lake
Inn at Huntingfield Creek
3.5 star property
10.0 out of 10, Exceptional, (43)
"Beautiful inn, staff is friendly, beautiful location and friendly dogs but since we were there in the off season the town Rock hall wasn’t very interesting "
The price is $224
$249 total
includes taxes & fees
May 4 - May 5
Inn at Huntingfield Creek
Outdoor pool
Mariners Motel
2.0 star property
9.4 out of 10, Exceptional, (85)
"Really cute property and rooms. The rooms are small but exceptionally clean and nicely decorated. Pretty grounds with a pool, fire pit, hammocks and yard games available. Easy walking distance to a few restaurants. Staff was very pleasant. "
The price is $167
$185 total
includes taxes & fees
May 5 - May 6
Mariners Motel
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 $175
$269 total
includes taxes & fees
May 4 - May 5
BAYSIDE BUNGALOW
Property grounds
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (56)
"This was our second stay and we will most definitely be repeat visitors. Spacious room, easy check in and communication with owner, lovely property and area!"
The price is $98
$152 total
includes taxes & fees
May 6 - May 7
First Floor Studio Apartment in Historic Chestertown
Iron/ironing board, travel crib, 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
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!
Pool
Waterfront Oasis w/ Private Dock, 3BR/2BA
9.8 out of 10, Exceptional, (19)
"We have our sailboat in a marina close by. Friends came, we all stayed at the house and day sailed. Nice day on the bay and a relaxing evening overlooking the river. Worked great! Beautiful place to kickback. Incredible view of the river. Will do it again!"
Waterfront Oasis w/ Private Dock, 3BR/2BA
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, stovetop, dishwasher
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 $201
$394 total
includes taxes & fees
May 5 - May 6
Bayside Cottage steps from Rock Hall Harbor
Fridge, microwave, dishwasher, coffee/tea maker
Serene Waterfront Cottage with dock and gorgeous views.
9.6 out of 10, Exceptional, (35)
"Nice place with everything I could want. Would stay there again!"
Serene Waterfront Cottage with dock and gorgeous views.
Beach nearby, sun loungers, beach towels
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
9.4 out of 10, Exceptional, (26)
"This was our second stay here. The property is well appointed for a relaxing stay with 5-star views! Lots of room for family to spread out and relax, and the kitchen has everything you need to make delicious meals. Betterton is extra relaxing with its beautiful views and quiet stillness. We'll be back!"
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
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!
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 stays in Great Oak Landing

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

5625 O'Donnell Street, Baltimore, MD
The price is $107 per night from May 19 to May 20
$107
$125 total
includes taxes & fees
May 19 - May 20
7.6/10 Good! (1,000 reviews)

Stay near popular Great Oak Landing attractions

Image for Washington College

Washington College

4/5(13 reviews)

Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

See properties
Washington College

Great Oak Landing Travel Info

Number of reviews
5,535
Accommodation
312 hotels
Highest price
$224
Lowest price
$64
Reasons to visit
Historical Society of Kent County Maryland, Garfield Center for the Arts at the Prince Theater and Washington College
Hotels with ocean views
2

Frequently asked questions

Where is the best place for a stay in Great Oak Landing?

The Lodge at Great Oak Landing is one of the top choices for your stay based on our traveler data. This lodge offers a private beach and a golf course. Two other choices for your stay in the area are Best Western Plus Hotel & Conference Center and La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh. See all available top hotels, or vacation rentals in Great Oak Landing.

What are some of the best vacation home rentals that Great Oak Landing has to offer?

Stunning Home Steps minutes from Cal Ripken Stadium!!!: You might like this vacation home rental near Great Oak Landing. It offers a fireplace, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a spa tub. See all vacation rentals in Great Oak Landing.

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

Yes! Most room reservations are refundable if you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If you have a reservation that's non-refundable, you might be able to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Great Oak Landing.

Where can I learn more about changing or cancelling my trip to Great Oak Landing?

To find more details about changing or cancelling your trip to Great Oak Landing, head over to our customer service page.

What's the best LGBTQ-friendly accommodation in Great Oak Landing?

The Lodge at Great Oak Landing is a top LGBTQ-friendly lodge, and features a private beach and free WiFi. See all available hotels listed as LGBTQ-friendly in Great Oak Landing.

What are some accommodations 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 onsite 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 center.

What's the best hotel for staying near Salisbury - Ocean City Wicomico Regional Airport (SBY)?

Country Inn & Suites by Radisson, Salisbury, MD is one of the top choices for your stay and is a popular 3-star hotel featuring free breakfast and an indoor pool. It's located 2.2 mi (3.6 km) from Salisbury - Ocean City Wicomico Regional Airport. Other options close to the airport include Microtel Inn & Suites by Wyndham Salisbury and Sleep Inn Salisbury.

How is it staying 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 accommodations to choose from. Find out more about Great Oak Landing.

What are the top places to visit 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. Check out what more to see and do in Expedia's Great Oak Landing guide.

What's the seasonal weather like in Great Oak Landing?

The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Great Oak Landing is 48 inches.

Recent reviews of Great Oak Landing hotels
Expedia verified reviews

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

5/5 Excellent
"Very happy with condition and service. "
A verified traveler stayed at La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Posted 23 hours ago
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh