Great Oak Landing Holiday Rentals

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Our top choices for Great Oak Landing holiday rentals

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)
"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 NZ$863
includes taxes & fees
12 Jan - 13 Jan
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is NZ$275
includes taxes & fees
12 Jan - 13 Jan
First Floor Studio Apartment in Historic Chestertown

Spacious Private 2BR Suite in Abingdon with Separate Entrance

Spacious Private 2BR Suite in Abingdon with Separate Entrance
2.0 star property
Bel Air South
The price is NZ$225
includes taxes & fees
1 Feb - 2 Feb
Spacious Private 2BR Suite in Abingdon with Separate Entrance

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 NZ$722
includes taxes & fees
22 Jan - 23 Jan
Grandma’s Cottage will wrap around you like a warm hug

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is NZ$731
includes taxes & fees
20 Jan - 21 Jan
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

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)
"Clean, comfortable and convenient! "
United States
Jill J.
The price is NZ$493
includes taxes & fees
10 Jan - 11 Jan
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Hobbit House one of a kind home

Hobbit House one of a kind home
Bel Air
10.0 out of 10, Exceptional, (8)
"We had a great stay! "
United States
Courtney H.
The price is NZ$499
includes taxes & fees
11 Jan - 12 Jan
Hobbit House one of a kind home

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, (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 NZ$764
includes taxes & fees
13 Jan - 14 Jan
HGTV quality, private guest suite, country getaway with hot tub & fire pit

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.
The price is NZ$528
includes taxes & fees
9 Feb - 10 Feb
Waterfront Retreat with Private Dock and Beach

High Tide Haven Suite

High Tide Haven Suite
Kent County
The price is NZ$346
includes taxes & fees
22 Jan - 23 Jan
High Tide Haven Suite

Close to Hospital & White Marsh! Rosedale Townhome

Close to Hospital & White Marsh! Rosedale Townhome
3.0 star property
Nottingham
The price is NZ$925
includes taxes & fees
18 Jan - 19 Jan
Close to Hospital & White Marsh! Rosedale Townhome

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)
"The house was even better than I anticipated! It was very clean, quiet and comfy. The beds were amazing and we got the best nights sleep! Location was perfect for Ripken Experience. The owner was very helpful and quick to respond to my messages. "
United States
Alexandra C.
Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Spacious 4-bedroom retreat house with plenty of parking

Spacious 4-bedroom retreat house with plenty of parking
2.0 star property
Overlea
10.0 out of 10, Exceptional, (1)
"Property was comfortable. TV streaming isnt a preferred way to watch, "
United States
Joseph M. G.
The price is NZ$956
includes taxes & fees
12 Jan - 13 Jan
Spacious 4-bedroom retreat house with plenty of parking

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.
The price is NZ$1,125
includes taxes & fees
12 Jan - 13 Jan
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!
Abingdon
8.8 out of 10, Excellent, (8)
"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 NZ$1,418
includes taxes & fees
10 Jan - 11 Jan
Luxury Waterfront Home Built for Entertaining!

Close to Hospital & White Marsh! Rosedale Townhome

Close to Hospital & White Marsh! Rosedale Townhome
2.0 star property
Nottingham
2.0 out of 10, (1)
"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 NZ$920
includes taxes & fees
11 Jan - 12 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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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 favorite 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 depends 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 NZ$275 per night. Entering your travel dates in the search wizard 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 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.