Great Oak Landing Vacation Rentals

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Our top choices for Great Oak Landing vacation rentals

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 CA $137
CA $219 total
includes taxes & fees
Jun 8 - Jun 9
First Floor Studio Apartment in Historic Chestertown

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 traveller
The price is CA $345
CA $531 total
includes taxes & fees
Jun 3 - Jun 4
Newly restored apartment in the heart of Chestertown

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 CA $497
CA $917 total
includes taxes & fees
Jun 2 - Jun 3
Chesapeake Cottages- 2 Quaint Waterfront Retreats

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 CA $248
CA $380 total
includes taxes & fees
Jun 7 - Jun 8
BAYSIDE BUNGALOW

2 Mi to Apg: Edgewood Family Home w/ Fenced Yard

2 Mi to Apg: Edgewood Family Home w/ Fenced Yard
3.0 star property
Edgewood
The price is CA $201
CA $656 total
includes taxes & fees
Jun 25 - Jun 26
2 Mi to Apg: Edgewood Family Home w/ Fenced Yard

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 CA $81
CA $115 total
includes taxes & fees
Jun 4 - Jun 5
Charming 2-bedroom house in Aberdeen with WiFi and AC

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 CA $400
CA $771 total
includes taxes & fees
Jun 2 - Jun 3
Spacious 4-bedroom retreat house with plenty of parking

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is CA $229
CA $604 total
includes taxes & fees
Jun 2 - Jun 3
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

Turtle Cove Room

Turtle Cove Room
Kent County
The price is CA $238
CA $293 total
includes taxes & fees
Jun 4 - Jun 5
Turtle Cove Room

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 CA $310
CA $522 total
includes taxes & fees
Jun 15 - Jun 16
Waterfront Retreat with Private Dock and Beach

Beachcomber Suite

Beachcomber Suite
Kent County
The price is CA $201
CA $248 total
includes taxes & fees
Jun 8 - Jun 9
Beachcomber Suite

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 CA $199
CA $339 total
includes taxes & fees
Jun 14 - Jun 15
Gorgeous 3-bedroom townhome with AC in friendly Dundalk

Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!
Abingdon
9.0 out of 10, Wonderful, (10 reviews)
"Very clean, spacious and quiet!!!!! Beautiful home! "
United States
Jennifer M.
The price is CA $1,103
CA $1,667 total
includes taxes & fees
Jun 7 - Jun 8
Luxury Waterfront Home Built for Entertaining!

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 CA $241
CA $501 total
includes taxes & fees
Jun 2 - Jun 3
Bayside Cottage steps from Rock Hall Harbor

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 CA $162
CA $397 total
includes taxes & fees
Jun 2 - Jun 3
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

The Sparrows Nest - in downtown Sparrows Point

The Sparrows Nest - in downtown Sparrows Point
Edgemere
The price is CA $128
CA $329 total
includes taxes & fees
Jun 7 - Jun 8
The Sparrows Nest - in downtown Sparrows Point

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 CA $159
CA $279 total
includes taxes & fees
Jun 15 - Jun 16
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals

2 Mi to APG: Edgewood Family Home w/ Fenced Yard

2 Mi to APG: Edgewood Family Home w/ Fenced Yard
Edgewood
4.0 out of 10, (1 review)
"The house was okay. Definitely wasnt cleaned thoroughly as there was still food stains in the fridge and peices of food in the butter tray inside the fridge. The stove would not work until i set the time to the correct time so that was a bit of a question mark as to why that was. There was ants all over inside the house which personally was very disgusting. Both me and my son woke up with ants crawling on us in both the master bedroom and back bedroom. So that is something that should be...
United States
Sean G.
2 Mi to APG: Edgewood Family Home w/ Fenced Yard
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

Find out more about Great Oak Landing

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Great Oak Landing. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.