Book Holiday Homes in Great Oak Landing

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Featured Holiday Homes in Great Oak Landing

Charming Waterfront house with expansive views of the Chesapeake Bay and Sunsets

Charming Waterfront house with expansive views of the Chesapeake Bay and Sunsets

Rock Hall
With a stay at this vacation home in Rock Hall, you'll be within a 15-minute drive of The Mainstay and Waterman’s Museum.
Charming Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16

Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16

Rock Hall
Located in Rock Hall, this vacation home is on the waterfront, within a 10-minute drive of The Mainstay and Waterman’s Museum.
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
Waterfront Oasis w/ Private Dock, 3BR/2BA

Waterfront Oasis w/ Private Dock, 3BR/2BA

Middle River
Located in Middle River, this vacation home is on the waterfront, within a 15-minute drive of Gunpowder Falls State Park and Freestate Gun Range.
Waterfront Oasis w/ Private Dock, 3BR/2BA
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Beautiful, spacious, quiet waterfront house!

Beautiful, spacious, quiet waterfront house!

Middle River
With a stay at this vacation home in Middle River (Bowleys Quarters), you'll be a 4-minute drive from Miami Beach and 7 minutes from Freestate Gun Range.
Beautiful, spacious, quiet waterfront house!
Amazing Waterfront Home on the Bush River

Amazing Waterfront Home on the Bush River

Edgewood
When you stay at this vacation home in Edgewood, you'll be on the waterfront and 9 minutes by car from CopperPlex.
Amazing Waterfront Home on the Bush River
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING

RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING

Rock Hall
A stay at this vacation home places you in the heart of Rock Hall, within a 5-minute drive of The Mainstay and Waterman’s Museum.
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
Kent Island Luxury Waterfront

Kent Island Luxury Waterfront

Stevensville
Located in Stevensville, this vacation home is on the waterfront, within a 10-minute drive of Love Point State Park and Paul Reed Smith Guitars.
Kent Island Luxury Waterfront
BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

Rock Hall
The price is AU$421 per night from 5 Dec to 6 Dec
AU$421
includes taxes & fees
5 Dec - 6 Dec
Located in Rock Hall, this vacation home is within a 15-minute walk of Ferry Park and Waterman’s Museum.
BAYSIDE BUNGALOW
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Betterton
When you stay at this vacation home in Betterton, you'll be on the waterfront and 7 minutes by foot from Betterton Beach.
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
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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.

Great Oak Landing Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Great Oak Landing vacation homes are the perfect way for you to wing it.

Holiday houses in Great Oak Landing let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Great Oak Landing in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Great Oak Landing adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Great Oak Landing with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Great Oak Landing vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Great Oak Landing Holiday Homes essential information

Accommodation
116 Holiday Homes
Lowest Price
AU$87
Highest Price
AU$421
Popular accommodation
Charming Waterfront house with expansive views of the Chesapeake Bay and Sunsets, Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16, Waterfront Oasis w/ Private Dock, 3BR/2BA, Beautiful, spacious, quiet waterfront house!, Amazing Waterfront Home on the Bush River, RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING , Kent Island Luxury Waterfront, BAYSIDE BUNGALOW, Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Top trending hotels in Great Oak Landing

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
22170 Great Oak Landing Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is AU$171 per night from 5 Dec to 6 Dec
AU$171
includes taxes & fees
5 Dec - 6 Dec
With a stay at The Lodge at Great Oak Landing in Chestertown, you'll be 8.8 mi (14.2 km) from Washington College and 9.6 mi (15.5 km) from Garfield Center for ...
The Lodge at Great Oak Landing
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 out of 5
5625 O'Donnell Street, Baltimore, MD
Fully refundableReserve now, pay when you stay
The price is AU$177 per night from 1 Dec to 2 Dec
AU$177
includes taxes & fees
1 Dec - 2 Dec
With a stay at Best Western Plus Hotel & Conference Center in Baltimore (Medford), you'll be within a 10-minute drive of Baltimore Cruise Terminal and Baltimore ...
Best Western Plus Hotel & Conference Center
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

2.5 out of 5
4 Philadelphia Ct, Rosedale, MD
Fully refundableReserve now, pay when you stay
The price is AU$139 per night from 24 Nov to 25 Nov
AU$139
includes taxes & fees
24 Nov - 25 Nov
When you stay at La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh in Rosedale, you'll be in the business district, within a 15-minute drive of Baltimore ...
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
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Quality Inn & Suites Bel Air I-95 Exit 77A

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

2.5 out of 5
2112a Emmorton Park Road, Edgewood, MD
Fully refundableReserve now, pay when you stay
The price is AU$87 per night from 24 Nov to 25 Nov
AU$87
includes taxes & fees
24 Nov - 25 Nov
Located in Edgewood, Quality Inn & Suites Bel Air I-95 Exit 77A is within a 10-minute drive of CopperPlex and Cedar Lane Regional Park.
Quality Inn & Suites Bel Air I-95 Exit 77A
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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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^Subject to availability and chosen travel dates.