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

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
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 !!
First Floor Studio Apartment in Historic Chestertown
Back Yard

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (77)
"The room and bathroom were very spacious and clean! I love and appreciate the small toiletries that were left for us! The small refrigerator and table are a nice touch that we used during our stay! "
The price is AED 360
AED 579 total
includes taxes & fees
1 Jan - 2 January 2025
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
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 323
AED 1,137 total
includes taxes & fees
25 Dec - 26 Dec
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, (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
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, (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
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 1,140 total
includes taxes & fees
5 Jan - 6 January 2025
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

10.0 out of 10, Exceptional, (1)
"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
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 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!
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
Cozy 1-bedroom 2nd story apartment in center of Rock Hall
Room

Cozy 1-bedroom 2nd story apartment in center of Rock Hall

Cozy 1-bedroom 2nd story apartment in center of Rock Hall
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.
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 family resort Lodge with private pier, game room and bar
The Twin Ponds Lodge sits on over 7 acres of private waterfront property.

Waterfront family resort Lodge with private pier, game room and bar

9.8 out of 10, Exceptional, (23)
"The property was excellent for a large group. We was there for a Sailing Regatta on the lake in front of the house. The perfect house for groups."
Waterfront family resort Lodge with private pier, game room and bar
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Waterfront with private pier and great views

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (24)
"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
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.

9.8 out of 10, Exceptional, (50)
" We ( a group of 16 women) enjoyed having our annual retreat at Nauti or Knot. We stayed for a weekend and the accommodations could not have been better! The bedrooms and bathrooms were wonderful. The living room was able to sit 16 comfortably and the dining room table was big enough for all of us to have dinner together. This is an excellent house!! Our only complaint and it’s minor is that the freezer door was really hard to open."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
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 40 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?
Listed below are some of the favorite apartments in the area to choose from: WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD: Situated in Earleville, 17.1 mi/27.5 km from the heart of Great Oak Landing. Includes free WiFi and Smart TVs. Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!: Located in Annapolis, 19.4 mi/31.3 km away. Includes free WiFi, private patios, and Smart TVs. A fitness center and a game room are 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 an outdoor pool are on site. Osprey’s Landing at Atlantic Marinas - relaxing waterfront coastal retreat: Located in Pasadena, 15.9 mi/25.6 km from Great Oak Landing. Includes free WiFi and Smart TVs. Access to an outdoor pool is available 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.