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Check prices for these dates

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1 Aug - 3 Aug
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22 Aug - 24 Aug
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19 Sep - 21 Sep

Apartments in Great Oak Landing

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

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

9.8 out of 10, Exceptional, (58)
"The location and unit did not disappoint! "
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (91)
"Very pretty location. Few minutes drive to town center."
The price is SAR 371
SAR 596 total
includes taxes & fees
4 Aug - 5 Aug
First Floor Studio Apartment in Historic Chestertown
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, (52)
"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 !!
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Beach

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

10.0 out of 10, Exceptional, (10)
"Perfection"
The price is SAR 465
SAR 1,106 total
includes taxes & fees
27 Jul - 28 Jul
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (35)
"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "
Historic Downtown Garden Oasis with Private Patio
Waterfront Retreat with Private Dock and Beach
Beach

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (22)
"I stayed with 3 friends and it was lovely! The apartment was clean and tidy. The view was spectacular. The host was very communicative and kind leading up to and during our stay. There are great restaurants and things to do in the area as well. "
The price is SAR 844
SAR 1,420 total
includes taxes & fees
27 Jul - 28 Jul
Waterfront Retreat with Private Dock and Beach
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

9.8 out of 10, Exceptional, (43)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
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!
Knot's Landing, spacious Apt. downtown Rock Hall
Property grounds

Knot's Landing, spacious Apt. downtown Rock Hall

9.0 out of 10, Wonderful, (4)
"This property is near many of the downtown places you want to visit, and all are within walking distance. "
Knot's Landing, spacious Apt. downtown Rock Hall
Chic and cozy apartment with WiFi and AC in Parkville
Living area

Chic and cozy apartment with WiFi and AC in Parkville

Chic and cozy apartment with WiFi and AC in Parkville
Studio apartment in water view Historic home with WiFi, separate AC/heat
Property grounds

Studio apartment in water view Historic home with WiFi, separate AC/heat

10.0 out of 10, Exceptional, (2)
"SMALL BUT EFFICIENT"
Studio apartment in water view Historic home with WiFi, separate AC/heat
Royalty Homes - 2 bedroom apartment
Living area

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
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Fridge, microwave, oven, stovetop

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

10.0 out of 10, Exceptional, (3)
"The house was clean and the beds were comfortable. "
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
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, (26)
"Nice downtown location."
Newly restored apartment in the heart of Chestertown
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"
Beautiful Studio Bedroom Rental!
Interior

Beautiful Studio Bedroom Rental!

Beautiful Studio Bedroom Rental!
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
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.
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
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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Top Great Oak Landing Hotel Reviews

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

10/10 Excellent
"Our check-in quicl Staff was quick. The rooms have a very spacious area it was clean and the beds were comfortable just for a night to crash. "
Marie Paz 1-night trip
Posted 3 days ago
Red Roof Inn & Suites Chestertown

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 9 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. First Floor Studio Apartment in Historic Chestertown: Located 8.4 mi/13.4 km away in Chestertown. A private pool, laundry facilities, and free WiFi are included. A fitness center and onsite laundry facilities are on site. Waterfront Retreat with Private Dock and Beach: 6.1 mi/9.7 km away in Worton. Free WiFi, sofa beds, and Smart TVs are included.
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 Chestertown Dog 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.