Find hotels in Great Oak Landing, MD from $62

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Check Great Oak Landing hotel prices

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Jun 1 - Jun 2
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Jun 2 - Jun 3
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Jun 7 - Jun 9

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Compare 305 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Comfort Inn & Suites Chestertown
Lobby
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (677)
"Breakfast area and food was below expectations"
The price is $127
$141 total
includes taxes & fees
Jun 4 - Jun 5
Comfort Inn & Suites Chestertown
Red Roof 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, (273)
"nice hotel. helpful staff. stores and dining are walkable distances."
The price is $107
$119 total
includes taxes & fees
Jun 16 - Jun 17
Red Roof Inn & Suites Chestertown
The Lodge at Great Oak Landing
Private beach nearby, sun loungers, beach volleyball, beach bar
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
Jun 3 - Jun 4
The Lodge at Great Oak Landing
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Driftwood Inn
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
Jun 2 - Jun 3
Driftwood Inn
Inn at Huntingfield Creek
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 $230
$255 total
includes taxes & fees
Jun 18 - Jun 19
Inn at Huntingfield Creek
Mariners Motel
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
Jun 2 - Jun 3
Mariners Motel
BAYSIDE BUNGALOW
Fridge, microwave, coffee/tea maker, toaster
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (17)
"What a delight to have found this property. Beautiful drive to get to the Eastern Shore. Rock Hall The beautiful place that’s tucked in along the Chesapeake Bay. My fiancé and I needed a much desirable getaway. The bungalow at this property was the perfect place just for us to forget about our worries back home. The owners were kind enough to message us. Let us know if the events that were happening in town but more so anything that was happening on the property they gave us just a heads up as...
The price is $175
$272 total
includes taxes & fees
Jun 2 - Jun 3
BAYSIDE BUNGALOW
First Floor Studio Apartment in Historic Chestertown
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 $110
$164 total
includes taxes & fees
Jun 12 - Jun 13
First Floor Studio Apartment in Historic Chestertown
Carriage House Hideaway in Middle of 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
200 steps to the beach!
Interior
200 steps to the beach!
10.0 out of 10, Exceptional, (75)
"Great stay over Memorial Day weekend. Loved the location of the house...so close to the water and not crowded at all. We will definitely be back!"
200 steps to the beach!
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Outdoor dining
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
10.0 out of 10, Exceptional, (38)
"This was our second stay at your lovely cottage. I’m sure it won’t be our last. Great location!"
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Cute waterfront apartment -- 8 min from the beach!
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!
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
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
Waterfront Oasis w/ Private Dock, 3BR/2BA
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
Rambling Victorian Beach House on Maryland's Eastern Shore
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
This is truly a Baydream!
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!
Bayside Cottage steps from Rock Hall Harbor
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 $201
$396 total
includes taxes & fees
Jun 2 - Jun 3
Bayside Cottage steps from Rock Hall Harbor
Serene Waterfront Cottage with dock and gorgeous views.
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.
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
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
Charming Chestertown Waterfront Cottage
Beach towels
Charming Chestertown Waterfront Cottage
10.0 out of 10, Exceptional, (59)
"This is a great place to relax. The house had everything we needed and was very comfortable."
Charming Chestertown Waterfront Cottage
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

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

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

4 Philadelphia Ct, Rosedale, MD
The price is $95 per night from Jun 2 to Jun 3
$95
$109 total
includes taxes & fees
Jun 2 - Jun 3
7.2/10 Good! (1,004 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
5,582
Accommodation
305 hotels
Highest price
$230
Lowest price
$62
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 golf course and 3 bars. 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?

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock : This vacation home near Great Oak Landing is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation. 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 golf course 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. There are 307 hotels and other accommodations in the surrounding area. 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

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

5/5 Excellent
"This is the second time I've stayed here and both experiences were extemely positive. I don't have one bad thing to say!"
A verified traveler stayed at Fairfield Inn & Suites by Marriott White Marsh
Posted 2 days ago
Fairfield Inn & Suites by Marriott White Marsh