Great Oak Landing Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Great Oak Landing

Property grounds
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Pasadena
9.4 out of 10, Exceptional, (89)
"This property was a great place for a family to all relax together, play games, and enjoy the water!"
United States
Armando V.
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
6 bedrooms, iron/ironing board, WiFi, bed sheets
Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!

Abingdon
8.4 out of 10, Very Good, (6)
"Quite lovely house with a gorgeous view over the water. It is definitely a good spot to stay with a large family or friends for a few days with plenty to do (relaxing on the dock, play games inside, not too far from Baltimore and other nice towns, etc). The host was great and very communicative as well.The only downsides were details around cleanliness and the check-out procedures. The house itself was overall fine, but there dishes left in the dishwasher that we had to put away, the bottom...
United States
Benjamin J.
$784 nightly
The price is $831
Dec 8 - Dec 9
Total with taxes and fees
Luxury Waterfront Home Built for Entertaining!
Interior
200 steps to the beach!

200 steps to the beach!

Rock Hall
10.0 out of 10, Exceptional, (93)
"Beautiful, comfortable home in a great location. "
United States
Stephanie C.
200 steps to the beach!
Dining
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Rock Hall
9.8 out of 10, Exceptional, (40)
"Ashleigh was amazing as a host, got right back to us on all questions and needs. "
United States
Tim B.
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Property grounds
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Pasadena
9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
$583 nightly
The price is $665
Dec 8 - Dec 9
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Outdoor dining
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

stevensville
10.0 out of 10, Exceptional, (197)
"This home was the perfect get-away for a group of friends!The accommodations were wonderful and the host went out of their way to ensure our stay was full of fun activities."
United States
David N.
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outdoor dining
BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

Rock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
$262 nightly
The price is $278
Jan 1 - Jan 2, 2026
Total with taxes and fees
BAYSIDE BUNGALOW
Interior
Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Bel Air
10.0 out of 10, Exceptional, (5)
"I appreciated how clean and pleasant it smelled! Then it was a beautiful location with lots of places to eat nearby. My only improvement would have been window curtains, especially in the master bath. "
United States
Leah M.
$266 nightly
The price is $282
Jan 5 - Jan 6, 2026
Total with taxes and fees
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
Smart TV, books
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville
9.8 out of 10, Exceptional, (59)
"We had an amazing weekend at the cottage. It’s very clean and beautiful! The close walk to the beach is perfect and we had great weather. Would love to stay here again! "
United States
Angela F.
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Exterior
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Chestertown
10.0 out of 10, Exceptional, (12)
"Kayaks were a great plus! Ideal spot for a small family with easy access to the the beautiful Chester River. Our grandchildren had a blast, visiting the pigs, chickens, and sheep that were within easy walking distance."
United States
Douglas N.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Terrace/patio
Close to Hospital & White Marsh! Rosedale Townhome

Close to Hospital & White Marsh! Rosedale Townhome

2.0 star property
Nottingham
$459 nightly
The price is $526
Dec 14 - Dec 15
Total with taxes and fees
Close to Hospital & White Marsh! Rosedale Townhome
Fridge, microwave, oven, stovetop
Waterfront CHeerful 2 with Private Pier

Waterfront CHeerful 2 with Private Pier

Gibson Island
9.8 out of 10, Exceptional, (19)
"Great place we stayed while visiting family in the area. Great to decompress from all the chaos."
United States
Karolyn M.
Waterfront CHeerful 2 with Private Pier
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (107)
"Amazing and neat and very private "
United States
Alexander M.
$144 nightly
The price is $159
Dec 8 - Dec 9
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Marina
Waterfront Oasis w/ Private Dock, 3BR/2BA

Waterfront Oasis w/ Private Dock, 3BR/2BA

Middle River
9.4 out of 10, Exceptional, (39)
"Perfect place, close to the park and the most amazing sunset "
United States
Nicoleta E.
Waterfront Oasis w/ Private Dock, 3BR/2BA
Private kitchen
Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Chestertown
10.0 out of 10, Exceptional, (3)
"Overall a beautiful and well maintained place to stay! The location was perfect…within walking distance to everything! A very charming home! We were so happy we chose this property!"
United States
Dawn B.
Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!
Beach
Stay in the landmark Lighthouse!

Stay in the landmark Lighthouse!

Rock Hall
10.0 out of 10, Exceptional, (107)
"Beautiful home. Wish I could of stayed longer "
United States
Pat R.
Stay in the landmark Lighthouse!
House (3 Bedrooms) | Interior
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
Rosedale
10.0 out of 10, Exceptional, (1)
$431 nightly
The price is $498
Dec 8 - Dec 9
Total with taxes and fees
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Microwave, stovetop, dishwasher
Spacious 4-bedroom retreat house with plenty of parking

Spacious 4-bedroom retreat house with plenty of parking

2.0 star property
Overlea
$472 nightly
The price is $545
Dec 8 - Dec 9
Total with taxes and fees
Spacious 4-bedroom retreat house with plenty of parking
Outdoor dining
Chesapeake Bay Harbor View in a central location to events/restaurants

Chesapeake Bay Harbor View in a central location to events/restaurants

2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
$257 nightly
The price is $272
Dec 8 - Dec 9
Total with taxes and fees
Chesapeake Bay Harbor View in a central location to events/restaurants
Outdoor dining
Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Rock Hall
10.0 out of 10, Exceptional, (73)
"This trip was a girls get away & we thoroughly enjoyed ourselves .. the house was by far the best I’ve ever rented .. clean, well appointed, & decor was gorgeous … the owner was so attentive & acted on anything we needed right away .. I highly recommend this property & we will definitely be returning …"
United States
Denise O.
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
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

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

10/10 Excellent
"Clean yes "
Gary 1-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Aberdeen-APG

Find out more about Great Oak Landing

Everything you need to know about Great Oak Landing vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Great Oak Landing vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Great Oak Landing vacation 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 low season months. For more hustle and bustle, you may prefer to visit Great Oak Landing in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !: Visitors like this Great Oak Landing vacation home rental. It is located on the beach and has a fireplace, a patio, and air-conditioning 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. You can relax into your vacation 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 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.