Apartments in Great Oak Landing for Rent

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

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, 22 reviews
"Especially nice for summer visits."
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
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, 19 reviews
"Cozy & elegant ☀️ a clean bright space."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Carriage House Hideaway in Middle of Chestertown
Iron/ironing board, travel crib, free WiFi, bed sheets
Carriage House Hideaway in Middle of Chestertown
10.0 out of 10, Exceptional, 76 reviews
"Bob and Beth's apartment was absolutely perfect for us. It was the cleanest VRBO that we have ever stayed in. All of the amenities were above and beyond what we expected. The apartment is in a great location and walkable into town and the WC campus. We will definitely stay again when we come back to town."
Carriage House Hideaway in Middle of Chestertown
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Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Pool
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
10.0 out of 10, Exceptional, 35 reviews
"Super clean and easy to find. I encourage anyone to rent this space"
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
First Floor Studio Apartment in Historic Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, 59 reviews
"This was the perfect place to rest our heads along our trip down the east coast. Very comfortable, clean and quiet. We made time to visit the beautiful town and I’m glad we did!"
The price is $110
$164 total
includes taxes & fees
Jun 11 - Jun 12
First Floor Studio Apartment in Historic Chestertown
Serenity on the Water
Property grounds
Serenity on the Water
10.0 out of 10, Exceptional, 2 reviews
"My partner and I rented the beautiful "serenity on the water" to celebrate our anniversary over the Memorial Day holiday. We found the rental in immaculate condition. It is very large, and well appointed, even including a ping pong table. The place is beautifully decorated and located very close to all the amenities you could ask for. It was an awesome stay, and we were so happy with the recommendations for activities. You can even WALK to the near by vineyard."
Serenity on the Water
Historic Downtown Garden Oasis with Private Patio
Property grounds
Historic Downtown Garden Oasis with Private Patio
10.0 out of 10, Exceptional, 15 reviews
"A perfect stay in lovely, comfortable private guest quarters. Perfect for a couple. Well designed layout. Kitchen includes a toaster oven, microwave and coffee machine (capsules provided). Extremely well located, close to the superb Watershed Alley and Modern Stone Age Kitchen as well as the brand new Lawrence Wetlands Preserve (ideal if you are a birder!). Will definitely return to enjoy Stephen's and Marianna's guest suite. "
Historic Downtown Garden Oasis with Private Patio
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, 15 reviews
"This was a great apartment in an excellent location. We visited Washington college and attended a sailing regatta. The Evergrain Bakery across the street was amazing. Shops and restaurants all within walking distance! Apartment was well stocked, nicely decorated and clean! Also very close to the Hodson boathouse. It was a 3 minute drive!"
Newly restored apartment in the heart of Chestertown
Waterfront Retreat with Private Dock and Beach
Property grounds
Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, 1 review
"Loved sitting on the dock, peaceful, quiet; house has everything you need"
The price is $225
$374 total
includes taxes & fees
Jun 9 - Jun 10
Waterfront Retreat with Private Dock and Beach
Royalty Homes - 2 bedroom apartment
Exterior
Royalty Homes - 2 bedroom apartment
Royalty Homes - 2 bedroom apartment
Knot's Landing, spacious Apt. downtown Rock Hall
Property grounds
Knot's Landing, spacious Apt. downtown Rock Hall
Knot's Landing, spacious Apt. downtown Rock Hall
Spacious Dundalk Townhome: 8 Mi to Inner Harbor!
Interior
Spacious Dundalk Townhome: 8 Mi to Inner Harbor!
3.0 star property
8.0 out of 10, Very Good, 1 review
"The interior of the property is very nicely decorated and feels homey. It easily accommodated our family of 6, with three bedrooms on top floor sharing one full bath, and two bedrooms on basement level sharing one full bath. The kitchen had everything we needed, including ample space to cook and a dining room table with six chairs. The living room was a sizeable space for socializing. We truly enjoyed our stay here. Unfortunately, we encountered just a few small inconveniences such as the...
Spacious Dundalk Townhome: 8 Mi to Inner Harbor!
Cute waterfront apartment -- 8 min from the beach!
Property grounds
Cute waterfront apartment -- 8 min from the beach!
10.0 out of 10, Exceptional, 5 reviews
"I raced the Waterman's tri and this location was perfect, well equipped, comfortable, clean, easy."
Cute waterfront apartment -- 8 min from the beach!
The "Dock House"
Property grounds
The "Dock House"
10.0 out of 10, Exceptional, 2 reviews
"The Dock House was the best place for a weekend getaway! The hosts, Gary and Diane were the most pleasurable people to meet and interact with. They welcomed us with open arms, (literally.) The space was so clean and quaint and had everything we needed. Access to the pier was perfect for morning coffee and floating in the river in the afternoon. The neighborhood is super quiet and friendly. The marina down the street had amazing food and was a perfect place to meet the locals. The Dock House ia...
The "Dock House"
Lofty Home.
1 bedroom, desk, free WiFi, bed sheets
Lofty Home.
Lofty Home.
Maryland Vacation Rental Near Baltimore
Interior
Maryland Vacation Rental Near Baltimore
3.5 star property
Maryland Vacation Rental Near Baltimore
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Property grounds
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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.
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
Smart TV
Bright & Cozy Private John's Hopkins Studio Apartment
Bright & Cozy Private John's Hopkins Studio Apartment
The Buck: modern farmhouse style Dundalk apartment
Exterior
The Buck: modern farmhouse style Dundalk apartment
The Buck: modern farmhouse style Dundalk apartment
Don't see what you're looking for?
See all available properties in Great Oak Landing
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.

Other property types in Great Oak Landing

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, 36 reviews
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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, 22 reviews
"Especially nice for summer visits."
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Interior
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, 15 reviews
"My friends, our wives, and kids loved our stay. Everything exceeded expectations. We especially enjoyed the backyard where we played yard games, grilled, and enjoyed the river."
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
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.

Great Oak Landing Apartments information

Number of reviews
Accommodation
 Apartments
Lowest Price
Highest Price

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 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: 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. 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 in Chestertown, 8.4 mi/13.4 km from Great Oak Landing. Includes a private pool, laundry facilities, and free WiFi. A fitness center and an outdoor pool 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.

Recent reviews of Great Oak Landing hotels
Expedia verified reviews

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

5/5 Excellent
"Came in out of a storm. Very nice and accommodating Room and facility very nice and comfortable"
A verified traveler from Burbank stayed at Hampton Inn & Suites Edgewood/Aberdeen-South
Posted 2 days ago
Hampton Inn & Suites Edgewood/Aberdeen-South