Great Oak Landing Vacation Rentals

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Our top choices for Great Oak Landing vacation rentals

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
8.0 out of 10, Very good, (12 reviews)
"Pleasant stay"
United States
Yommali G.
The price is CA $92
CA $126 total
includes taxes & fees
Feb 19 - Feb 20
Charming 2-bedroom house in Aberdeen with WiFi and AC

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is CA $135
CA $216 total
includes taxes & fees
Feb 17 - Feb 18
First Floor Studio Apartment in Historic Chestertown

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, (17 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is CA $160
CA $388 total
includes taxes & fees
Feb 17 - Feb 18
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

5 Mi to Downtown Baltimore: Quiet Home w/ Porch
3.0 star property
Rosedale
9.0 out of 10, Wonderful, (2 reviews)
"It took a whole day for the house to get warm.No utensils.And last but not least the heat was turned off in the middle of the night.Monday morning was very cold,that’s why we left at nine thirty. "
United States
Cathy
The price is CA $249
CA $716 total
includes taxes & fees
Feb 28 - Mar 1
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
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 CA $238
CA $428 total
includes taxes & fees
Feb 17 - Feb 18
Waterfront Retreat with Private Dock and Beach

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is CA $214
CA $578 total
includes taxes & fees
Feb 17 - Feb 18
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

Hobbit House one of a kind home

Hobbit House one of a kind home
Bel Air
10.0 out of 10, Exceptional, (9 reviews)
"We had a great stay! "
United States
Courtney H.
The price is CA $131
CA $384 total
includes taxes & fees
Feb 22 - Feb 23
Hobbit House one of a kind home

Spacious Private 2BR Suite in Abingdon with Separate Entrance

Spacious Private 2BR Suite in Abingdon with Separate Entrance
Bel Air South
The price is CA $119
CA $184 total
includes taxes & fees
Feb 22 - Feb 23
Spacious Private 2BR Suite in Abingdon with Separate Entrance

High Tide Haven Suite

High Tide Haven Suite
Kent County
The price is CA $236
CA $276 total
includes taxes & fees
Feb 27 - Feb 28
High Tide Haven Suite

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

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
Chestertown
10.0 out of 10, Exceptional, (3 reviews)
"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."
United States
Jason
The price is CA $342
CA $575 total
includes taxes & fees
Feb 21 - Feb 22
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

Grandma’s Cottage will wrap around you like a warm hug

Grandma’s Cottage will wrap around you like a warm hug
Betterton
The price is CA $306
CA $574 total
includes taxes & fees
Feb 19 - Feb 20
Grandma’s Cottage will wrap around you like a warm hug

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 CA $159
CA $521 total
includes taxes & fees
Mar 1 - Mar 2
Abingdon Haven Hideaway

Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!
Abingdon
8.8 out of 10, Excellent, (8 reviews)
"Excellent communication with host, we had everything we needed"
United States
Kelly W.
The price is CA $749
CA $1,237 total
includes taxes & fees
Feb 17 - Feb 18
Luxury Waterfront Home Built for Entertaining!

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 $490
CA $894 total
includes taxes & fees
Mar 2 - Mar 3
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Spacious 4-bedroom retreat house with plenty of parking

Spacious 4-bedroom retreat house with plenty of parking
Overlea
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 CA $395
CA $761 total
includes taxes & fees
Feb 17 - Feb 18
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.

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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?

240' Private Beachfront @Kent Island Love Point - Great for Families: Visitors like this Great Oak Landing vacation home rental. It is located on the beach and has a fireplace, a patio, and a barbecue grill 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 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 Garfield Center for the Arts at the Prince Theater 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.