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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

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, (78)
"Very clean, excellent communications,"
The price is SAR 368
SAR 592 total
includes taxes & fees
22 Feb - 23 Feb
First Floor Studio Apartment in Historic Chestertown
Cozy 2 bedroom apartment w/ free parking
Private kitchen

Cozy 2 bedroom apartment w/ free parking

8.8 out of 10, Excellent, (5)
"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 SAR 544
SAR 1,434 total
includes taxes & fees
20 Feb - 21 Feb
Cozy 2 bedroom apartment w/ free parking
Newly restored apartment in the heart of Chestertown
Living area

Newly restored apartment in the heart of Chestertown

9.8 out of 10, Exceptional, (19)
"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 "
Newly restored apartment in the heart of Chestertown
Apartment in Perry Hall area
Dining

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
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, (45)
"The location and unit did not disappoint! "
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, (34)
"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
Lofty Home.
Room

Lofty Home.

Lofty Home.
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 SAR 656
SAR 1,164 total
includes taxes & fees
20 Feb - 21 Feb
Waterfront Retreat with Private Dock and Beach
Historic Downtown Garden Oasis with Private Patio
Outdoor dining

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (25)
"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
Home in Perry Hall area
Exterior

Home in Perry Hall area

2.0 star property
10.0 out of 10, Exceptional, (1)
"Excellent Spot "
Home in Perry Hall area
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.
Royalty Homes - 2 bedroom apartment
Living area

Royalty Homes - 2 bedroom apartment

8.0 out of 10, Very Good, (2)
"Freshly remodeled apartment with a clean bathroom and linens! Easy and clear instructions for entry and even a coin washer available on site. Kitchen needs a pot for the stove or just a glass mixing bowl for heating things in the microwave. "
Royalty Homes - 2 bedroom apartment
Beautiful Studio Bedroom Rental!
Room

Beautiful Studio Bedroom Rental!

Beautiful Studio Bedroom Rental!
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 !!
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Welcome to Mermaid's Getaway!

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!
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
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"
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!
Maryland Vacation Rental Near Baltimore
Living area

Maryland Vacation Rental Near Baltimore

3.0 star property
Maryland Vacation Rental Near 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

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Guest Lodge | Private Pool | Outdoor Dining | Game Room
Exterior

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Guest Lodge | Private Pool | Outdoor Dining | Game Room
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
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 42 accommodation choices including 7 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. Cozy 2 bedroom apartment w/ free parking: Located 13.5 mi/21.7 km away in Essex. Free WiFi, sofa beds, and Smart TVs are included. Access to onsite laundry facilities is available on site. 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. WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD: 17.1 mi/27.5 km away in Earleville. Free WiFi 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 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.