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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 27 Apartments in Great Oak Landing with updated reviews, rates, and availability.

Newly restored apartment in the heart of Chestertown
Fridge, microwave, oven, stovetop

Newly restored apartment in the heart of Chestertown

9.8 out of 10, Exceptional, (24)
"Wonderful spot in the center of historical Chestertown,"
Newly restored apartment in the heart of Chestertown
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (31)
"Very nice place. Great location, close to dining, etc. No TVs. Would have liked to know that going in. Otherwise, prefect spot."
Historic Downtown Garden Oasis with Private Patio
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (85)
"Quiet neighborhood and the best place to stay."
The price is AED 404
AED 628 total
includes taxes & fees
19 May - 20 May
First Floor Studio Apartment in Historic Chestertown
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Fridge, microwave, oven, stovetop

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

9.8 out of 10, Exceptional, (49)
"The location and unit did not disappoint! "
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Marina

Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!

10.0 out of 10, Exceptional, (49)
"Everything about our stay was outstanding. Beautiful, just like the pictures show. We highly recommend this property."
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Apartment in Perry Hall area
Fridge, microwave, oven, stovetop

Apartment in Perry Hall area

2.0 star property
10.0 out of 10, Exceptional, (1)
"We are so excited to have such a lovely place to stay that’s close to family!"
Apartment in Perry Hall area
Home in Perry Hall area
Fridge, microwave, oven, stovetop

Home in Perry Hall area

2.0 star property
10.0 out of 10, Exceptional, (2)
"Excellent Spot "
Home in Perry Hall area
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

10.0 out of 10, Exceptional, (37)
"Great location, wonderful place and fantastic owner. Recommendations on restaurants and things to do were perfect. We had a great time and Betty Ann was very kind and responsive in communications. Will definitely visit again!"
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Waterfront Retreat with Private Dock and Beach
Miscellaneous

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (19)
"Everything about the place was great! Easy check in and super clean and homey feeling spot. Would recommend to anyone looking for a quiet and comfy place on the eastern shore. We will definitely be booking again if we come back to the area!"
The price is AED 826
AED 1,352 total
includes taxes & fees
19 May - 20 May
Waterfront Retreat with Private Dock and Beach
Royalty Homes - 2 bedroom apartment
Exterior

Royalty Homes - 2 bedroom apartment

8.0 out of 10, Very Good, (2)
"Property location and size were good. Unit smelled like smoke the entire stay. "
Royalty Homes - 2 bedroom apartment
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Miscellaneous

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

10.0 out of 10, Exceptional, (6)
"Perfection"
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A cozy/modern private suite. Mins away from I695/95 and the heart of Baltimore.
Smart TV

A cozy/modern private suite. Mins away from I695/95 and the heart of Baltimore.

A cozy/modern private suite. Mins away from I695/95 and the heart of Baltimore.
11 Mi to Downtown Baltimore: Middle River Townhome
Interior

11 Mi to Downtown Baltimore: Middle River Townhome

3.5 star property
11 Mi to Downtown Baltimore: Middle River Townhome
Knot's Landing, spacious Apt. downtown Rock Hall
Property grounds

Knot's Landing, spacious Apt. downtown Rock Hall

10.0 out of 10, Exceptional, (2)
"Spent the weekend here. Great location close to everything. Bikes were provided and you can ride to anything in Rock Hall. We would definitely rent here again."
Knot's Landing, spacious Apt. downtown Rock Hall
Beautiful Studio Bedroom Rental!
Interior

Beautiful Studio Bedroom Rental!

Beautiful Studio Bedroom Rental!
The "Dock House"
Outdoor dining

The "Dock House"

10.0 out of 10, Exceptional, (3)
"We couldn't have been happier with our stay. Gary and Diane were wonderful hosts, as well as their dog Lucy! They couldn't have been nicer and more accommodating, so we' are looking forward to booking another stay in the future!"
The "Dock House"
Cute waterfront apartment -- 8 min from the beach!
Outdoor dining

Cute waterfront apartment -- 8 min from the beach!

10.0 out of 10, Exceptional, (6)
"Nice and quiet with a great location and amazing view!!!"
Cute waterfront apartment -- 8 min from the beach!
Maryland Vacation Rental Near Baltimore
Apartment (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Maryland Vacation Rental Near Baltimore

3.0 star property
Maryland Vacation Rental Near Baltimore
Bright & Cozy Private John's Hopkins Studio Apartment
Fridge, microwave, oven, stovetop

Bright & Cozy Private John's Hopkins Studio Apartment

Bright & Cozy Private John's Hopkins Studio Apartment
A cozy short-term lower level rental in quiet area of Baltimore City
Interior

A cozy short-term lower level rental in quiet area of Baltimore City

A cozy short-term lower level rental in quiet area of Baltimore City
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.
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Other property types in Great Oak Landing

BAYSIDE BUNGALOW
Exterior detail

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (35)
"Beautiful, cozy cottage. So peaceful and pretty. Owners are on site and are great people. We have stayed here several times and look forward to coming back soon."
The price is AED 735
AED 1,102 total
includes taxes & fees
19 May - 20 May
BAYSIDE BUNGALOW
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach nearby, sun loungers

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (47)
"Great little home away from home. A small orientation list for newcomers would be helpful. Closest groceries, gas and such. Outside of that all and all VERY pleasing. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outdoor dining

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (186)
"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
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.

Frequently asked questions

What's it like to stay at an apartment in Great Oak Landing?
There are plenty of places to stay with in Chestertown, with 44 accommodation choices including 8 apartments.
How do you know if an apartment is a good option for you?
Often more spacious than a traditional hotel room, an apartment comes equipped with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home but also for couples who want something in a quieter part of town.
What's a favorite apartment I should consider for a stay in Great Oak Landing?
Here are some of the top apartments in the area to choose from: Osprey’s Landing at Atlantic Marinas - relaxing waterfront coastal retreat: Located in Pasadena, 15.9 mi/25.6 km from the heart of Great Oak Landing. Includes free WiFi and Smart TVs. Access to an outdoor pool is available on site. WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD: Located 17.1 mi/27.5 km away in Earleville. Free WiFi and Smart TVs are included. First Floor Studio Apartment in Historic Chestertown: Located in Chestertown, 8.4 mi/13.4 km away. Includes a private pool, laundry facilities, and free WiFi. A fitness center and onsite laundry facilities are on site. Studio apartment in water view Historic home with WiFi, separate AC/heat: 13.4 mi/21.6 km away in Essex. Free WiFi and Smart TVs are included. Waterfront Retreat with Private Dock and Beach: It’s located in Worton, 6.1 mi/9.7 km from Great Oak Landing. Includes free WiFi, sofa beds, and Smart TVs.
What can I expect from the weather during my trip to Great Oak Landing?
Though weather is just one factor, it can really affect your travel plans, especially if you’re planning an extended stay 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.
What should I see in Great Oak Landing?
Explore the area and family-friendly sights such as Crumpton Auction, or get out into nature at a spot like Ferry Park. Washington College and River Arts Chestertown are a couple of places you’ll find in the larger area.
What's the best way to get to and around Great Oak Landing?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Baltimore, MD (MTN-Martin State), which is located 12.5 mi (20.2 km) from the city center. Otherwise, you can search for flights to Baltimore Washington Intl. Airport (BWI), which is 25.7 mi (41.3 km) away. If you’d like to explore around the area, you may want a rental car for your journey.