Great Oak Landing Holiday Rentals

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Check prices for these dates

Tonight
10 Jan - 11 Jan
Tomorrow
11 Jan - 12 Jan
Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan

Our top choices for Great Oak Landing holiday rentals

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 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 HK$1,239
HK$3,882 total
includes taxes & fees
12 Jan - 13 Jan
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 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is HK$772
HK$1,238 total
includes taxes & fees
12 Jan - 13 Jan
First Floor Studio Apartment in Historic Chestertown
Exterior
Spacious Private 2BR Suite in Abingdon with Separate Entrance

Holiday Home in Bel Air South

Spacious Private 2BR Suite in Abingdon with Separate Entrance
2.0 star property
The price is HK$642
HK$1,011 total
includes taxes & fees
1 Feb - 2 Feb
Spacious Private 2BR Suite in Abingdon with Separate Entrance
Dining
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 HK$1,754
HK$3,264 total
includes taxes & fees
17 Jan - 18 Jan
Grandma’s Cottage will wrap around you like a warm hug
Property grounds
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

Houseboat in Pasadena

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
The price is HK$1,228
HK$3,310 total
includes taxes & fees
20 Jan - 21 Jan
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Beach
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Apartment in Rock Hall

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (17 reviews)
"Clean, comfortable and convenient! "
United States
Jill J.
The price is HK$918
HK$2,211 total
includes taxes & fees
12 Jan - 13 Jan
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Interior
Hobbit House one of a kind home

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 HK$828
HK$2,303 total
includes taxes & fees
14 Jan - 15 Jan
Hobbit House one of a kind home
Fridge, microwave, dishwasher, coffee/tea maker
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Holiday Home in Centreville

HGTV quality, private guest suite, country getaway with hot tub & fire pit
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 HK$1,536
HK$3,496 total
includes taxes & fees
12 Jan - 13 Jan
HGTV quality, private guest suite, country getaway with hot tub & fire pit
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 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is HK$1,364
HK$2,452 total
includes taxes & fees
12 Jan - 13 Jan
Waterfront Retreat with Private Dock and Beach
Terrace/patio
High Tide Haven Suite

Holiday Home in Kent County

High Tide Haven Suite
The price is HK$1,350
HK$1,573 total
includes taxes & fees
12 Jan - 13 Jan
High Tide Haven Suite
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 HK$1,481
HK$4,161 total
includes taxes & fees
12 Jan - 13 Jan
Close to Hospital & White Marsh! Rosedale Townhome
Interior
Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Holiday Home in Bel Air

Modern and Cozy Home in Bel Air with a Home Office and Fireplace
10.0 out of 10, Exceptional, (5 reviews)
"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
Dining
Spacious 4-bedroom retreat house with plenty of parking

Holiday Home in Overlea

Spacious 4-bedroom retreat house with plenty of parking
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 HK$2,260
HK$4,312 total
includes taxes & fees
12 Jan - 13 Jan
Spacious 4-bedroom retreat house with plenty of parking
Property grounds
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Cottage in Pasadena

Chesapeake Cottages- 2 Quaint Waterfront Retreats
9.6 out of 10, Exceptional, (22 reviews)
"Excellent Property"
United States
Buu T.
The price is HK$2,806
HK$5,180 total
includes taxes & fees
12 Jan - 13 Jan
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Dining
Luxury Waterfront Home Built for Entertaining!

Holiday Home in Abingdon

Luxury Waterfront Home Built for Entertaining!
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 HK$3,858
HK$6,478 total
includes taxes & fees
12 Jan - 13 Jan
Luxury Waterfront Home Built for Entertaining!
TV
Close to Hospital & White Marsh! Rosedale Townhome

Holiday Home in Nottingham

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 HK$1,325
HK$4,174 total
includes taxes & fees
12 Jan - 13 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

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Profesional staff. Verry clean room. Nice break fast."
Anwar 1-night trip
Posted 2 days ago
Hampton Inn & Suites Edgewood/Aberdeen-South

Find out more about Great Oak Landing

Search for holiday rentals in Great Oak Landing on Expedia! You can easily find your home rentals, villas, holiday apartments in Great Oak Landing using one of the methods below:

  • View our selection of featured holiday rentals in Great Oak Landing
  • Use the map to find apartments and other holiday homes in the Great Oak Landing neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Great Oak Landing while they last

Look no further and take a look at our great range of rental properties in Great Oak Landing!

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.