Great Oak Landing Holiday Rentals

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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Great Oak Landing holiday rentals

Smart TV, books

Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
9.8 out of 10, Exceptional, (28 reviews)
"Extremely clean, beautifully updated, and very comfortable. Perfect location—easy to walk to shops and restaurants. Would absolutely stay again!""
United States
Maggie D.
The price is HK$2,586
HK$3,806 total
includes taxes & fees
4 Apr - 5 Apr
Newly restored apartment in the heart of Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"Every thing was great"
United States
lesia k.
The price is HK$776
HK$1,245 total
includes taxes & fees
6 Apr - 7 Apr
First Floor Studio Apartment in Historic Chestertown
Property grounds

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (22 reviews)
"Excellent Property"
United States
Buu T.
The price is HK$2,822
HK$5,209 total
includes taxes & fees
6 Apr - 7 Apr
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Dining

Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!
Abingdon
9.0 out of 10, Wonderful, (9 reviews)
"Excellent communication with host, we had everything we needed"
United States
Kelly W.
The price is HK$6,270
HK$9,488 total
includes taxes & fees
4 Apr - 5 Apr
Luxury Waterfront Home Built for Entertaining!
Dining

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 HK$1,763
HK$3,323 total
includes taxes & fees
4 Apr - 5 Apr
Grandma’s Cottage will wrap around you like a warm hug
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.6 out of 10, Good, (13 reviews)
"Met our needs. Great stay."
United States
Robert C.
The price is HK$529
HK$727 total
includes taxes & fees
5 Apr - 6 Apr
Charming 2-bedroom house in Aberdeen with WiFi and AC
TV, offices

Serenity on the Cove

Serenity on the Cove
Dundalk
9.8 out of 10, Exceptional, (9 reviews)
"Great stay - would stay again "
United States
Anonymous traveller
The price is HK$1,411
HK$6,979 total
includes taxes & fees
5 Apr - 6 Apr
Serenity on the Cove
Terrace/patio

High Tide Haven Suite

High Tide Haven Suite
Kent County
The price is HK$1,358
HK$1,565 total
includes taxes & fees
4 Apr - 5 Apr
High Tide Haven Suite
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is HK$1,411
HK$2,160 total
includes taxes & fees
4 May - 5 May
BAYSIDE BUNGALOW
Dining

Spacious 4-bedroom retreat house with plenty of parking

Spacious 4-bedroom retreat house with plenty of parking
Overlea
9.0 out of 10, Wonderful, (2 reviews)
"All good it was a great value"
United States
paul r.
The price is HK$2,273
HK$4,336 total
includes taxes & fees
5 Apr - 6 Apr
Spacious 4-bedroom retreat house with plenty of parking
Property grounds

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is HK$1,234
HK$3,302 total
includes taxes & fees
6 Apr - 7 Apr
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Smart TV

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
The price is HK$1,372
HK$2,850 total
includes taxes & fees
16 Apr - 17 Apr
Bayside Cottage steps from Rock Hall Harbor
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, (18 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is HK$972
HK$2,285 total
includes taxes & fees
9 Apr - 10 Apr
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Interior

Abingdon Haven Hideaway

Abingdon Haven Hideaway
Abingdon
7.0 out of 10, Good, (2 reviews)
"We made good use of this rental, it was convenient to all our family & activities. Host is very kind & quickly helpful on request. The main problem with a basement apt is that the thermostat is usually upstairs in the main house, but host was most accommodating about temperature control. We rested well here and had a nice week."
United States
Pam L.
The price is HK$917
HK$2,974 total
includes taxes & fees
4 Apr - 5 Apr
Abingdon Haven Hideaway
Beach

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "
United States
Debbie S.
The price is HK$1,372
HK$2,457 total
includes taxes & fees
20 Apr - 21 Apr
Waterfront Retreat with Private Dock and Beach
Room

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Nottingham City
The price is HK$903
HK$1,586 total
includes taxes & fees
14 Apr - 15 Apr
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
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

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

8/10 Good
"Limited breakfast."
Gregg 1-night trip
Posted 1 hour ago
Quality Inn & Suites Bel Air I-95 Exit 77A

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:

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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?

240' Private Beachfront @Kent Island Love Point - Great for Families: This holiday home rental outside of Great Oak Landing is located on the beach, and has a fireplace, a patio and a BBQ 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. Kick off your shoes and enjoy yourself 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.