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Compare 23 Apartments in Great Oak Landing with updated reviews, rates, and availability.

First Floor Studio Apartment in Historic Chestertown
Back Yard
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (73)
"EasyvPeasy place."
The price is AED 360
AED 557 total
includes taxes & fees
14 Nov - 15 Nov
First Floor Studio Apartment in Historic Chestertown
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Entrance into kitchen
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
9.8 out of 10, Exceptional, (44)
"Wanted to fish Friday evening and again early Saturday morning. Eliminated the hour and a half drive back and forth. Great location and very nice accommodations"
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Room
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, (33)
"Super clean and beautiful views across the bay."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Interior
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
10.0 out of 10, Exceptional, (49)
"Wonderful hosts. Beautiful property. And a spacious yet cozy place to stay. We will book again next time we visit. "
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Cozy 2 bedroom apartment w/ free parking
Private kitchen
Cozy 2 bedroom apartment w/ free parking
8.6 out of 10, Excellent, (4)
"Very good communication, address was listed wrong on website but the host helped a lot, it wasn't his fault. It's in the basement, and it's really nice, but it's in the basement lol"
The price is AED 459
AED 1,328 total
includes taxes & fees
18 Nov - 19 Nov
Cozy 2 bedroom apartment w/ free parking
Historic Downtown Garden Oasis with Private Patio
Outdoor dining
Historic Downtown Garden Oasis with Private Patio
10.0 out of 10, Exceptional, (24)
"This is the second time I stayed here and will be back. I was able to work from here and enjoyed breakfast and lunch on the covered porch with a sweet companion (the owners' totally chill dog). Walking distance to everything. Check out the new wetland preserve at the end of the street. "
Historic Downtown Garden Oasis with Private Patio
Knot's Landing, spacious Apt. downtown Rock Hall
Apartment above the Hickory Store
Knot's Landing, spacious Apt. downtown Rock Hall
10.0 out of 10, Exceptional, (2)
"Just spent the weekend at Knot’s Landing and highly recommend it! The location is incredible with walk-ability to all of Main St and still close to the marina and the beach. The place was very clean and incredibly spacious. Check in and out was perfectly smooth and the host was responsive and helpful with the one question we had. 10/10 absolutely recommend!"
Knot's Landing, spacious Apt. downtown Rock Hall
Newly restored apartment in the heart of Chestertown
Living area
Newly restored apartment in the heart of Chestertown
9.8 out of 10, Exceptional, (18)
"We fell in love with Chestertown and are so glad we stayed in the heart of downtown at this charming vrbo. Everything was perfect. Will return and recommend "
The price is AED 643
AED 1,055 total
includes taxes & fees
14 Nov - 15 Nov
Newly restored apartment in the heart of Chestertown
Waterfront Retreat with Private Dock and Beach
Private Dock
Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (17)
"This property was exactly what we needed! The apartment was very clean and well maintained making it such a pleasant experience. Even though the property is shared with the owners, they weren’t constantly around or hovering over us allowing us to enjoy our time together. We loved having the dock and availability of the kayaks so we didn’t have to bring us along for the long trip there. We found some small shops and cute little towns along with a wonderful winery all within a short drive from...
The price is AED 643
AED 1,144 total
includes taxes & fees
14 Nov - 15 Nov
Waterfront Retreat with Private Dock and Beach
Cute waterfront apartment -- 8 min from the beach!
Your private dock to swan creek.
Cute waterfront apartment -- 8 min from the beach!
10.0 out of 10, Exceptional, (6)
"We enjoyed our stay so much. It was so private and quiet. It was also nice to be able to bike ride where ever we needed to go. It was perfect!! We plan on going back soon!!"
Cute waterfront apartment -- 8 min from the beach!
Royalty Homes - 2 bedroom apartment
Living area
Royalty Homes - 2 bedroom apartment
Royalty Homes - 2 bedroom apartment
The "Dock House"
Terrace/patio
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"
Lofty Home.
Room
Lofty Home.
Lofty Home.
Maryland Vacation Rental Near Baltimore
Living area
Maryland Vacation Rental Near Baltimore
3.0 star property
Maryland Vacation Rental Near Baltimore
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Welcome to Sharp Street Apartment!
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (4)
"A great place to chill out and enjoy what Rock Hall has to offer. It’s always great to come back to my childhood town. Rick is a great host and takes really good care of the property! We will be back."
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Spacious 3-bedroom apartment with AC and WiFi in charming Nottingham
Dining
Spacious 3-bedroom apartment with AC and WiFi in charming Nottingham
2.0 star property
Spacious 3-bedroom apartment with AC and WiFi in charming Nottingham
Beautiful Studio Bedroom Rental!
Room
Beautiful Studio Bedroom Rental!
Beautiful Studio Bedroom Rental!
Maryland Abode w/ Patio: Near Baltimore Harbor
Living area
Maryland Abode w/ Patio: Near Baltimore Harbor
3.0 star property
Maryland Abode w/ Patio: Near Baltimore Harbor
A cozy/modern private suite. Mins away from I695/95 and the heart of Baltimore.
Living area
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.
Bright & Cozy Private John's Hopkins Studio Apartment
Living area
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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Other property types in Great Oak Landing

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (44)
"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
First Floor Studio Apartment in Historic Chestertown
Back Yard
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (73)
"EasyvPeasy place."
The price is AED 360
AED 557 total
includes taxes & fees
14 Nov - 15 Nov
First Floor Studio Apartment in Historic Chestertown
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
10.0 out of 10, Exceptional, (48)
"The house was beautiful. The location was perfect. The owner was very responsive. 5 couples stayed in the house and we would all love to return. Thank you for everything!!"
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
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 39 accommodation choices including 5 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: First Floor Studio Apartment in Historic Chestertown: Located in Chestertown, 8.4 mi/13.4 km from the heart of Great Oak Landing. Includes a private pool, laundry facilities, and free WiFi. A fitness center and an outdoor pool are 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. Osprey’s Landing at Atlantic Marinas - relaxing waterfront coastal retreat: Located in Pasadena, 15.9 mi/25.6 km away. Includes free WiFi and Smart TVs. Access to an outdoor pool is available on site. Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!: Located in Annapolis, 19.4 mi/31.3 km from Great Oak Landing. Includes free WiFi, private patios, and Smart TVs. A fitness center and a game room are on site.
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 Miami Beach. Washington College and Rock Hall Harbor 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.