Great Oak Landing Vacation Rentals

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Vacation Rentals in Great Oak Landing

Fridge, microwave, oven, stovetop
Small House on Gentleman’s Farm

Small House on Gentleman’s Farm

Bel Air
10.0 out of 10, Exceptional, (12)
"Great little getaway, very clean, and the bedding was so comfy! "
United States
Joan F.
$293 nightly
The price is $295
Dec 2 - Dec 3
Total with taxes and fees
Small House on Gentleman’s Farm
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
$399 nightly
The price is $460
Nov 16 - Nov 17
Total with taxes and fees
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Beach
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)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
$257 nightly
The price is $284
Nov 8 - Nov 9
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (105)
"Wonderful stay in a beautiful location convenient to everything. Host was outstanding."
United States
Randy B.
$144 nightly
The price is $159
Nov 10 - Nov 11
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Property grounds
Hobbit House one of a kind home

Hobbit House one of a kind home

Bel Air
10.0 out of 10, Exceptional, (7)
"We had a great stay! "
United States
Courtney H.
$303 nightly
The price is $305
Nov 17 - Nov 18
Total with taxes and fees
Hobbit House one of a kind home
Terrace/patio
High Tide Haven Suite

High Tide Haven Suite

Kent County
$193 nightly
The price is $200
Nov 9 - Nov 10
Total with taxes and fees
High Tide Haven Suite
Terrace/patio
Grandma’s Cottage will wrap around you like a warm hug

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

Betterton
$395 nightly
The price is $419
Nov 8 - Nov 9
Total with taxes and fees
Grandma’s Cottage will wrap around you like a warm hug
Beach
Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach

Worton
10.0 out of 10, Exceptional, (25)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
$282 nightly
The price is $311
Nov 9 - Nov 10
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
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, (1)
"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
Nov 8 - Nov 9
Total with taxes and fees
Chesapeake Bay Harbor View in a central location to events/restaurants
Marina
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

Pasadena
$404 nightly
The price is $460
Nov 10 - Nov 11
Total with taxes and fees
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
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.
$288 nightly
The price is $306
Nov 9 - Nov 10
Total with taxes and fees
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
Terrace/patio
HGTV quality, private guest suite, country getaway with hot tub & fire pit

HGTV quality, private guest suite, country getaway with hot tub & fire pit

Centreville
10.0 out of 10, Exceptional, (7)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
$420 nightly
The price is $445
Nov 17 - Nov 18
Total with taxes and fees
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Fridge, microwave, oven, stovetop
Abingdon Haven Hideaway

Abingdon Haven Hideaway

Abingdon
7.0 out of 10, Good, (2)
"This is a basement apartment and is extremely noisy. You can hear the foot traffic and conversations as if they are standing next to you. Also it appears they were having some sort of event which made it worse."
United States
Sky S.
$363 nightly
The price is $385
Nov 17 - Nov 18
Total with taxes and fees
Abingdon Haven Hideaway
Fridge, microwave, oven, stovetop
Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown

Chestertown
9.8 out of 10, Exceptional, (27)
"Extremely clean, beautifully updated, and very comfortable. Perfect location—easy to walk to shops and restaurants. Would absolutely stay again!""
United States
Maggie D.
$434 nightly
The price is $479
Nov 14 - Nov 15
Total with taxes and fees
Newly restored apartment in the heart of Chestertown
Apartment (4 Bedrooms) | Interior
Close to Hospital & White Marsh! Rosedale Townhome

Close to Hospital & White Marsh! Rosedale Townhome

3.0 star property
Nottingham
$433 nightly
The price is $500
Nov 9 - Nov 10
Total with taxes and fees
Close to Hospital & White Marsh! Rosedale Townhome
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
Nov 10 - Nov 11
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
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
Nov 9 - Nov 10
Total with taxes and fees
Close to Hospital & White Marsh! Rosedale Townhome
Interior
Chesapeake Bay Retreat W/Breathtaking Views

Chesapeake Bay Retreat W/Breathtaking Views

Rock Hall
10.0 out of 10, Exceptional, (1)
"Beautiful home situated right on the water with everything we could need. Would not hesitate to return! "
United States
josh b.
$762 nightly
The price is $801
Dec 1 - Dec 2
Total with taxes and fees
Chesapeake Bay Retreat W/Breathtaking Views
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
Baltimore
$472 nightly
The price is $545
Nov 8 - Nov 9
Total with taxes and fees
Spacious 4-bedroom retreat house with plenty of parking
6 bedrooms, iron/ironing board, WiFi, bed sheets
Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!

Abingdon
7.6 out of 10, Good, (4)
"We had such a wonderful stay! The house was spotless, comfortable, and beautifully maintained. The surrounding area was peaceful and welcoming, and perfect for a relaxing weekend. Highly recommend!"
United States
Oluwaseyi E.
$784 nightly
The price is $831
Nov 9 - Nov 10
Total with taxes and fees
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

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent
"Great breakfast, good location, clean."
william 3-night trip
Posted 3 days ago
Fairfield Inn & Suites by Marriott White Marsh

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?

Chesapeake Bay and Northern 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.