Great Oak Landing Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Great Oak Landing vacation rentals

Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (111 reviews)
"Every thing was great"
United States
lesia k.
The price is ￥15,759
￥25,284 total
includes taxes & fees
May 25 - May 26
First Floor Studio Apartment in Historic Chestertown
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
8.2 out of 10, Very Good, (17 reviews)
"Nice place"
United States
christine
The price is ￥10,745
￥14,764 total
includes taxes & fees
May 25 - May 26
Charming 2-bedroom house in Aberdeen with WiFi and AC
Beach

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (21 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is ￥19,716
￥46,523 total
includes taxes & fees
May 31 - Jun 1
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Beach

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is ￥35,775
￥60,194 total
includes taxes & fees
Jun 15 - Jun 16
Waterfront Retreat with Private Dock and Beach
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (55 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ￥31,800
￥48,202 total
includes taxes & fees
Jun 9 - Jun 10
BAYSIDE BUNGALOW
Terrace/patio

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is ￥38,108
￥84,090 total
includes taxes & fees
May 26 - May 27
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Smart TV

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
The price is ￥27,857
￥57,875 total
includes taxes & fees
Jun 10 - Jun 11
Bayside Cottage steps from Rock Hall Harbor
Exterior

Spacious Private 2BR Suite in Abingdon with Separate Entrance

Spacious Private 2BR Suite in Abingdon with Separate Entrance
Bel Air South
The price is ￥12,750
￥19,421 total
includes taxes & fees
May 27 - May 28
Spacious Private 2BR Suite in Abingdon with Separate Entrance
WiFi, bed sheets

Turtle Cove Room

Turtle Cove Room
Kent County
The price is ￥24,068
￥29,609 total
includes taxes & fees
May 26 - May 27
Turtle Cove Room
Smart TV, books

Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
9.8 out of 10, Exceptional, (28 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
The price is ￥39,795
￥61,315 total
includes taxes & fees
Jun 22 - Jun 23
Newly restored apartment in the heart of Chestertown
Terrace/patio

Beachcomber Suite

Beachcomber Suite
Kent County
The price is ￥23,182
￥28,639 total
includes taxes & fees
Jun 8 - Jun 9
Beachcomber Suite
Interior

Abingdon Haven Hideaway

Abingdon Haven Hideaway
Abingdon
7.0 out of 10, Good, (2 reviews)
"We made good use of this rental, it was convenient to all our family & activities. Host is very kind & quickly helpful on request. The main problem with a basement apt is that the thermostat is usually upstairs in the main house, but host was most accommodating about temperature control. We rested well here and had a nice week."
United States
Pam L.
The price is ￥18,624
￥60,406 total
includes taxes & fees
May 25 - May 26
Abingdon Haven Hideaway
Property grounds

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (22 reviews)
"Excellent Property"
United States
Buu T.
The price is ￥57,240
￥105,675 total
includes taxes & fees
Jun 4 - Jun 5
Chesapeake Cottages- 2 Quaint Waterfront Retreats
1 bedroom, in-room safe, desk, iron/ironing board

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Nottingham City
The price is ￥20,375
￥34,564 total
includes taxes & fees
Jun 15 - Jun 16
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Property grounds

Charming Hideaway By The Water

Charming Hideaway By The Water
Middle River
10.0 out of 10, Exceptional, (1 review)
"Incredibly beautiful home, very clean and nicely decorated. Fully stocked with basic amenities. Fire pit and water views were absolute perfection! And the management company was quickly responsive to the minor issues we had! Will definitely book again! Thank you! "
United States
Nicole J.
The price is ￥39,750
￥78,785 total
includes taxes & fees
Jun 4 - Jun 5
Charming Hideaway By The Water
Dining

Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!
Abingdon
9.0 out of 10, Wonderful, (10 reviews)
"Excellent communication with host, we had everything we needed"
United States
Kelly W.
The price is ￥127,200
￥192,473 total
includes taxes & fees
Jun 10 - Jun 11
Luxury Waterfront Home Built for Entertaining!
Interior

The Sparrows Nest - in downtown Sparrows Point

The Sparrows Nest - in downtown Sparrows Point
Edgemere
The price is ￥12,177
￥34,841 total
includes taxes & fees
Jun 7 - Jun 8
The Sparrows Nest - in downtown Sparrows Point
Dining

Spacious 4-bedroom retreat house with plenty of parking

Spacious 4-bedroom retreat house with plenty of parking
Overlea
9.4 out of 10, Exceptional, (3 reviews)
"Great visit wonderful host. "
United States
Jeton E.
The price is ￥46,110
￥87,967 total
includes taxes & fees
Jun 4 - Jun 5
Spacious 4-bedroom retreat house with plenty of parking
Fridge, microwave, oven, stovetop

Gorgeous 3-bedroom townhome with AC in friendly Dundalk

Gorgeous 3-bedroom townhome with AC in friendly Dundalk
Dundalk
4.0 out of 10, (1 review)
"I think we were the first people to stay at this property. It was a little risky because there wasn’t any reviews yet, but you get what you paid for. It lacked a lot of basic necessities. It was not ready for guests, there were no towels, toilet paper, napkins, etc. One of the beds was missing a blanket, there was a full load of dirty laundry in the washer. The first shower had a body wash and a kids detangle shampoo and the second shower had nothing, so be prepared for that. (Despite the fact...
United States
Anastasia S.
The price is ￥17,908
￥32,634 total
includes taxes & fees
Jun 1 - Jun 2
Gorgeous 3-bedroom townhome with AC in friendly Dundalk
Property grounds

Cozy Waterfront Retreat w/ Dock, Hot Tub, Fire Pit, Game Room, Pet Friendly

Cozy Waterfront Retreat w/ Dock, Hot Tub, Fire Pit, Game Room, Pet Friendly
Lake Shore
The price is ￥87,231
￥196,527 total
includes taxes & fees
May 26 - May 27
Cozy Waterfront Retreat w/ Dock, Hot Tub, Fire Pit, Game Room, Pet Friendly
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Great Oak Landing Hotel Reviews

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

6/10 Okay
"Saturday night very disruptive."
Fred 4-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

Find out more about Great Oak Landing

Search for holiday rentals in Great Oak Landing on Expedia! You can easily find your home rentals, villas, holiday apartments in Great Oak Landing using one of the methods below:

  • View our selection of featured holiday rentals in Great Oak Landing
  • Use the map to find apartments and other holiday homes in the Great Oak Landing neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Great Oak Landing while they last

Look no further and take a look at our great range of rental properties in Great Oak Landing!

Frequently asked questions

Are there vacation rentals in Great Oak Landing?

Yes, we have vacation rentals close to popular sights in Great Oak Landing, or you can select a more remote option if you're looking for relaxation. Great Oak Landing is known for its restaurants.

What's the top vacation rental that Great Oak Landing has to offer?

Waterfront Oasis w/ Private Dock, Firepit, Arcade & Sunset Views: Visitors like this Great Oak Landing vacation home rental. It is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the arcade game room in this rental home to help you unwind.

What can I see and do in Great Oak Landing?

Northern Chesapeake Bay and Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. Washington College and River Arts Chestertown are a couple of places you'll find in the larger area.

What are vacation rentals like in Great Oak Landing?

Vacation rentals are private accommodations you can stay in for a short or long stay in Great Oak Landing. Vacation rentals offer amenities like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a small group gathering.