Great Oak Landing Holiday Rentals

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Our top choices for Great Oak Landing holiday 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 NZ$271
includes taxes & fees
8 June - 9 June
First Floor Studio Apartment in Historic Chestertown

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 NZ$209
includes taxes & fees
27 June - 28 June
Charming 2-bedroom house in Aberdeen with WiFi and AC

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 NZ$483
includes taxes & fees
28 May - 29 May
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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 NZ$639
includes taxes & fees
21 June - 22 June
Waterfront Retreat with Private Dock and Beach

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 NZ$470
includes taxes & fees
10 June - 11 June
BAYSIDE BUNGALOW

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is NZ$722
includes taxes & fees
1 June - 2 June
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

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 NZ$616
includes taxes & fees
10 June - 11 June
Bayside Cottage steps from Rock Hall Harbor

Spacious Private 2BR Suite in Abingdon with Separate Entrance

Spacious Private 2BR Suite in Abingdon with Separate Entrance
Bel Air South
The price is NZ$216
includes taxes & fees
31 May - 1 June
Spacious Private 2BR Suite in Abingdon with Separate Entrance

Turtle Cove Room

Turtle Cove Room
Kent County
The price is NZ$361
includes taxes & fees
28 May - 29 May
Turtle Cove Room

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 NZ$651
includes taxes & fees
22 June - 23 June
Newly restored apartment in the heart of Chestertown

Beachcomber Suite

Beachcomber Suite
Kent County
The price is NZ$307
includes taxes & fees
1 June - 2 June
Beachcomber Suite

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 NZ$641
includes taxes & fees
28 May - 29 May
Abingdon Haven Hideaway

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 NZ$1,115
includes taxes & fees
28 May - 29 May
Chesapeake Cottages- 2 Quaint Waterfront Retreats

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 NZ$370
includes taxes & fees
15 June - 16 June
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals

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 NZ$826
includes taxes & fees
31 May - 1 June
Charming Hideaway By The Water

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 NZ$2,010
includes taxes & fees
2 June - 3 June
Luxury Waterfront Home Built for Entertaining!

The Sparrows Nest - in downtown Sparrows Point

The Sparrows Nest - in downtown Sparrows Point
Edgemere
The price is NZ$392
includes taxes & fees
8 June - 9 June
The Sparrows Nest - in downtown Sparrows Point

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 NZ$928
includes taxes & fees
9 June - 10 June
Spacious 4-bedroom retreat house with plenty of parking

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 NZ$357
includes taxes & fees
1 June - 2 June
Gorgeous 3-bedroom townhome with AC in friendly Dundalk

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
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.
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Find out more about Great Oak Landing

Everything you need to know about Great Oak Landing holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Great Oak Landing holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Great Oak Landing holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Great Oak Landing holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Great Oak Landing. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Great Oak Landing holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Great Oak Landing holiday rentals we have selected for you start as low as NZ$209 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Great Oak Landing rentals

At Expedia, we put the best Great Oak Landing holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Great Oak Landing rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Great Oak Landing holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Great Oak Landing. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Waterfront Oasis w/ Private Dock, Firepit, Arcade & Sunset Views: This holiday home rental outside of Great Oak Landing is located on a river, and has a patio, a garden and a BBQ 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 that you can cook with friends or family. Make the most of an arcade/games 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 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.