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Check prices for these dates

In two weeks
26 Sep - 28 Sep
In one month
10 Oct - 12 Oct
In two months
7 Nov - 9 Nov
In three months
5 Dec - 7 Dec

Apartments in Great Oak Landing

Our top choices for Great Oak Landing apartments

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, (64)
"Awesome place!"
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, (100)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is SAR 371
SAR 596 total
includes taxes & fees
15 Sep - 16 Sep
First Floor Studio Apartment in Historic Chestertown
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, (13)
"A very well maintained and comfy apartment that is just a short walk to the heart of Rock Hall. My family especially enjoyed the large private backyard. Rick made sure we had everything we needed."
The price is SAR 465
SAR 1,098 total
includes taxes & fees
14 Sep - 15 Sep
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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, (46)
"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
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, (5)
The price is SAR 507
SAR 849 total
includes taxes & fees
16 Sep - 17 Sep
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (39)
"Loved the location and ease of access to downtown. Property was super clean, organized and beautifully appointed with original art too. "
Historic Downtown Garden Oasis with Private Patio
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
Property grounds

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

10.0 out of 10, Exceptional, (2)
"We had a great stay. Property was updated, clean and in a nice part of town walkable to everything. We would definitely stay here again and are looking forward to it."
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
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
Waterfront Retreat with Private Dock and Beach
Beach

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (24)
"Quiet and relaxing spot right on the water"
Waterfront Retreat with Private Dock and Beach
Charming 2-bedroom apartment in fantastic Overlea with AC
Microwave, oven, stovetop, dishwasher

Charming 2-bedroom apartment in fantastic Overlea with AC

The price is SAR 469
SAR 867 total
includes taxes & fees
14 Sep - 15 Sep
Charming 2-bedroom apartment in fantastic Overlea with AC
Royalty Homes - 2 bedroom apartment
Exterior

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
Chic and cozy apartment with WiFi and AC in Parkville
Living area

Chic and cozy apartment with WiFi and AC in Parkville

6.0 out of 10, (2)
"The apartment was very well appointed with top of the line appliances & access to the washer & dryer! We were very comfortable in this beautiful space. Thank you to the hosts for sharing your home with us!"
Chic and cozy apartment with WiFi and AC in Parkville
Knot's Landing, spacious Apt. downtown Rock Hall
Property grounds

Knot's Landing, spacious Apt. downtown Rock Hall

9.2 out of 10, Wonderful, (5)
"Spent the weekend here. Great location close to everything. Bikes were provided and you can ride to anything in Rock Hall. We would definitely rent here again."
Knot's Landing, spacious Apt. downtown Rock Hall
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
Cute waterfront apartment -- 8 min from the beach!
Outdoor dining

Cute waterfront apartment -- 8 min from the beach!

9.6 out of 10, Exceptional, (7)
"Nice and quiet with a great location and amazing view!!!"
Cute waterfront apartment -- 8 min from the beach!
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"
Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River
Outdoor dining

Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River

Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River
Beautiful Studio Bedroom Rental!
Interior

Beautiful Studio Bedroom Rental!

Beautiful Studio Bedroom Rental!
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, (54)
"Wonderful place!"
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Home away from home with WiFi and AC in delightful Parkville
Living area

Home away from home with WiFi and AC in delightful Parkville

Home away from home with WiFi and AC in delightful Parkville
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

Hampton Inn Baltimore Bayview Campus

Hampton Inn Baltimore Bayview Campus

10/10 Excellent
"In general we were satisfied with our stay in the hotel"
Sintec 3-night trip
Posted 19 hours ago
Hampton Inn Baltimore Bayview Campus

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 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. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!: Located 9 mi/14.5 km away in Rock Hall. Free WiFi and Smart TVs are included. Access to onsite laundry facilities is available on site. First Floor Studio Apartment in Historic Chestertown: Located in Chestertown, 8.4 mi/13.4 km away. Includes a private pool, laundry facilities, and free WiFi. A fitness center and onsite laundry facilities are on site. Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC: Located 19 mi/30.6 km away in Baltimore. Free WiFi, private patios, and Smart TVs are included. Access to onsite laundry facilities is available on site. WORLD'S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD: It's located in Earleville, 17.1 mi/27.5 km from Great Oak Landing. Includes free WiFi and Smart TVs.
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.