Great Oak Landing Holiday Rentals

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Our top choices for Great Oak Landing holiday rentals

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 AU$241
includes taxes & fees
14 Jan - 15 Jan
First Floor Studio Apartment in Historic Chestertown
10.0 out of 10, Exceptional, (25 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is AU$467
includes taxes & fees
14 Jan - 15 Jan
Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (17 reviews)
"Clean, comfortable and convenient! "
United States
Jill J.
The price is AU$428
includes taxes & fees
14 Jan - 15 Jan
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
3.0 star property
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 AU$742
includes taxes & fees
11 Feb - 12 Feb
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Holiday Home in Bel Air

Hobbit House one of a kind home
10.0 out of 10, Exceptional, (8 reviews)
"We had a great stay! "
United States
Courtney H.
The price is AU$439
includes taxes & fees
15 Jan - 16 Jan
Hobbit House one of a kind home
2.0 star property
The price is AU$197
includes taxes & fees
1 Feb - 2 Feb
Spacious Private 2BR Suite in Abingdon with Separate Entrance
2.0 star property
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 AU$820
includes taxes & fees
26 Jan - 27 Jan
Spacious 4-bedroom retreat house with plenty of parking
9.6 out of 10, Exceptional, (22 reviews)
"Excellent Property"
United States
Buu T.
The price is AU$976
includes taxes & fees
26 Jan - 27 Jan
Chesapeake Cottages- 2 Quaint Waterfront Retreats
10.0 out of 10, Exceptional, (8 reviews)
"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 AU$652
includes taxes & fees
26 Jan - 27 Jan
HGTV quality, private guest suite, country getaway with hot tub & fire pit
The price is AU$620
includes taxes & fees
20 Jan - 21 Jan
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

Holiday Home in Kent County

High Tide Haven Suite
The price is AU$304
includes taxes & fees
25 Jan - 26 Jan
High Tide Haven Suite
The price is AU$615
includes taxes & fees
17 Jan - 18 Jan
Grandma’s Cottage will wrap around you like a warm hug
8.8 out of 10, Excellent, (8 reviews)
"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.
The price is AU$1,212
includes taxes & fees
14 Jan - 15 Jan
Luxury Waterfront Home Built for Entertaining!
3.0 star property
The price is AU$796
includes taxes & fees
19 Jan - 20 Jan
Close to Hospital & White Marsh! Rosedale Townhome
2.0 star property
2.0 out of 10, (1 review)
"House was poorly maintained. Bathrooms, dishes, kitchen, floors, refrigerator were dirty. Lac of furniture, etc. We left the 2nd day from an 8 day stay and Vrbo CS and Envolve did nothing to at least reimburse the remaining of the stay, regardless the emails and picture sent. Never again. "
United States
Christopher T.
The price is AU$793
includes taxes & fees
26 Jan - 27 Jan
Close to Hospital & White Marsh! Rosedale Townhome
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

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 favourite 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 depend 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 AU$241 per night. Entering your travel dates in the search wizard might find you 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?

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !: This holiday home rental outside of Great Oak Landing 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 that you can cook with friends or family. You can relax into your holiday 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 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.