Great Oak Landing Holiday 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
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Great Oak Landing holiday rentals

Property grounds

Apartment in Chestertown

First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"Everything was clean and neat and welcoming "
United States
Iriana J.
The price is HK$774
HK$1,242 total
includes taxes & fees
10 Mar - 11 Mar
First Floor Studio Apartment in Historic Chestertown
Property grounds

Cottage in Pasadena

Chesapeake Cottages- 2 Quaint Waterfront Retreats
9.6 out of 10, Exceptional, (22 reviews)
"Excellent Property"
United States
Buu T.
The price is HK$2,815
HK$5,197 total
includes taxes & fees
9 Mar - 10 Mar
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Terrace/patio

Apartment in Kent County

High Tide Haven Suite
The price is HK$1,355
HK$1,561 total
includes taxes & fees
8 Mar - 9 Mar
High Tide Haven Suite
Beach

Apartment in Worton

Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (25 reviews)
"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "
United States
Debbie S.
The price is HK$1,368
HK$2,452 total
includes taxes & fees
10 Mar - 11 Mar
Waterfront Retreat with Private Dock and Beach
Dining

Holiday Home in Abingdon

Luxury Waterfront Home Built for Entertaining!
9.0 out of 10, Wonderful, (9 reviews)
"Excellent communication with host, we had everything we needed"
United States
Kelly W.
The price is HK$6,255
HK$9,465 total
includes taxes & fees
8 Mar - 9 Mar
Luxury Waterfront Home Built for Entertaining!
Dining

Cottage in Betterton

Grandma’s Cottage will wrap around you like a warm hug
The price is HK$1,759
HK$3,299 total
includes taxes & fees
22 Mar - 23 Mar
Grandma’s Cottage will wrap around you like a warm hug
Beach

Apartment in Rock Hall

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (18 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is HK$970
HK$2,288 total
includes taxes & fees
8 Mar - 9 Mar
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
TV

Holiday Home in Aberdeen

Charming 2-bedroom house in Aberdeen with WiFi and AC
7.6 out of 10, Good, (13 reviews)
"Pleasant stay"
United States
Yommali G.
The price is HK$528
HK$725 total
includes taxes & fees
15 Mar - 16 Mar
Charming 2-bedroom house in Aberdeen with WiFi and AC
Property grounds

Houseboat in Pasadena

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
The price is HK$1,306
HK$3,433 total
includes taxes & fees
8 Mar - 9 Mar
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Smart TV

Holiday Home in Rock Hall

Bayside Cottage steps from Rock Hall Harbor
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 HK$1,478
HK$2,926 total
includes taxes & fees
1 Apr - 2 Apr
Bayside Cottage steps from Rock Hall Harbor
Interior

Holiday Home in Abingdon

Abingdon Haven Hideaway
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 HK$915
HK$3,009 total
includes taxes & fees
8 Mar - 9 Mar
Abingdon Haven Hideaway
Dining

Holiday Home in Overlea

Spacious 4-bedroom retreat house with plenty of parking
10.0 out of 10, Exceptional, (1 review)
"Property was comfortable. TV streaming isnt a preferred way to watch, "
United States
Joseph M. G.
The price is HK$2,268
HK$4,290 total
includes taxes & fees
22 Mar - 23 Mar
Spacious 4-bedroom retreat house with plenty of parking
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

8/10 Good
"Staff was helpful but the hotel was average. "
Stephen 1-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 holiday rentals in Great Oak Landing?

Yes, there are holiday rentals close to the most popular sights in Great Oak Landing, or you can select a more secluded option if you're looking for a relaxing stay. Great Oak Landing is known for its restaurants.

What are some of the best holiday rentals that Great Oak Landing has to offer?

240' Private Beachfront @Kent Island Love Point - Great for Families: This holiday home rental outside of Great Oak Landing is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 wider area.

What are holiday rentals like in Great Oak Landing?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Great Oak Landing. Holiday rentals feature amenities such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family trip.