Great Oak Landing Vacation Rentals

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Check prices for these dates

Tonight
Dec 24 - Dec 25
Tomorrow
Dec 25 - Dec 26
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Great Oak Landing vacation rentals

House (3 Bedrooms) | Interior
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Cottage in Rosedale

5 Mi to Downtown Baltimore: Quiet Home w/ Porch
3.0 star property
9.0 out of 10, Wonderful, (2)
"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 ￥24,823
￥77,749 total
includes taxes & fees
Jan 4 - Jan 5, 2026
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Property grounds
First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown

First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
The price is ￥15,456
￥24,798 total
includes taxes & fees
Dec 25 - Dec 26
First Floor Studio Apartment in Historic Chestertown
Property grounds
Hobbit House one of a kind home

Vacation Home in Bel Air

Hobbit House one of a kind home
10.0 out of 10, Exceptional, (8)
"We had a great stay! "
United States
Courtney H.
The price is ￥18,149
￥46,532 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Hobbit House one of a kind home
Microwave, oven, stovetop
Spacious Private 2BR Suite in Abingdon with Separate Entrance

Vacation Home in Bel Air South

Spacious Private 2BR Suite in Abingdon with Separate Entrance
2.0 star property
The price is ￥12,864
￥20,255 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Spacious Private 2BR Suite in Abingdon with Separate Entrance
Beach
Waterfront Retreat with Private Dock and Beach

Apartment in Worton

Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (25)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
United States
Andrea M.
The price is ￥27,321
￥48,619 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Waterfront Retreat with Private Dock and Beach
Terrace/patio
Grandma’s Cottage will wrap around you like a warm hug

Cottage in Betterton

Grandma’s Cottage will wrap around you like a warm hug
The price is ￥35,127
￥65,036 total
includes taxes & fees
Dec 30 - Dec 31
Grandma’s Cottage will wrap around you like a warm hug
Marina
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

Houseboat in Pasadena

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
The price is ￥24,589
￥65,941 total
includes taxes & fees
Dec 25 - Dec 26
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Interior
Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Vacation Home in Bel Air

Modern and Cozy Home in Bel Air with a Home Office and Fireplace
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.
The price is ￥31,068
￥45,013 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
Terrace/patio
High Tide Haven Suite

Vacation Home in Kent County

High Tide Haven Suite
The price is ￥27,048
￥31,170 total
includes taxes & fees
Dec 29 - Dec 30
High Tide Haven Suite
Terrace/patio
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Vacation Home in Centreville

HGTV quality, private guest suite, country getaway with hot tub & fire pit
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is ￥30,771
￥69,522 total
includes taxes & fees
Jan 5 - Jan 6, 2026
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Outdoor dining
BAYSIDE BUNGALOW

Vacation Home in Rock Hall

BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ￥31,224
￥47,164 total
includes taxes & fees
Jan 1 - Jan 2, 2026
BAYSIDE BUNGALOW
Apartment (4 Bedrooms) | Interior
Close to Hospital & White Marsh! Rosedale Townhome

Apartment in Nottingham

Close to Hospital & White Marsh! Rosedale Townhome
3.0 star property
The price is ￥29,663
￥83,339 total
includes taxes & fees
Dec 30 - Dec 31
Close to Hospital & White Marsh! Rosedale Townhome
Terrace/patio
Close to Hospital & White Marsh! Rosedale Townhome

Vacation Home in Nottingham

Close to Hospital & White Marsh! Rosedale Townhome
2.0 star property
The price is ￥26,540
￥81,802 total
includes taxes & fees
Dec 30 - Dec 31
Close to Hospital & White Marsh! Rosedale Townhome
Property grounds
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Cottage in Pasadena

Chesapeake Cottages- 2 Quaint Waterfront Retreats
9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
The price is ￥56,203
￥103,760 total
includes taxes & fees
Dec 25 - Dec 26
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Microwave, stovetop, dishwasher
Spacious 4-bedroom retreat house with plenty of parking

Vacation Home in Overlea

Spacious 4-bedroom retreat house with plenty of parking
2.0 star property
The price is ￥59,169
￥101,159 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Spacious 4-bedroom retreat house with plenty of parking
6 bedrooms, iron/ironing board, travel crib, WiFi
Luxury Waterfront Home Built for Entertaining!

Vacation Home in Abingdon

Luxury Waterfront Home Built for Entertaining!
8.8 out of 10, Excellent, (8)
"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.
The price is ￥77,279
￥129,742 total
includes taxes & fees
Dec 28 - Dec 29
Luxury Waterfront Home Built for Entertaining!
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

SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River

10/10 Excellent
"The room was clean and the staff were professional and pleasant."
Eshe 1-night trip
Posted 2 days ago
SpringHill Suites Baltimore White Marsh/Middle River

Find out more about Great Oak Landing

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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.