Book Holiday Homes in Great Oak Landing

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Featured Holiday Homes in Great Oak Landing

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!
Pet-Friendly Home on Chester River w/ Dock!

Pet-Friendly Home on Chester River w/ Dock!

2 out of 5
Chestertown
With a stay at this vacation home in Chestertown, you'll be within a 5-minute drive of Kings Town Park and Historical Society of Kent County Maryland.
Pet-Friendly Home on Chester River w/ Dock!
BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

Rock Hall
The price is AU$463 per night from 13 Aug to 14 Aug
AU$463
13 Aug - 14 Aug
includes taxes & fees
Located in Rock Hall, this vacation home is within a 15-minute walk of Ferry Park and Waterman’s Museum.
BAYSIDE BUNGALOW
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Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

Amazing 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.
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Millington
Located in Millington, this vacation home is on the waterfront, within a 10-minute drive of Crumpton Auction and Crumpton Park.
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Rock Hall
Located in Rock Hall, this vacation home is on the waterfront, within a 15-minute walk of Waterman’s Museum and Rock Hall Harbor.
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Waterfront Estate w Private Pier, Game Room & Bar

Waterfront Estate w Private Pier, Game Room & Bar

Centreville
Located in Centreville, this vacation home is on a river, within a 10-minute drive of Hazel Miner Monument and Earle Landing.
Waterfront Estate w Private Pier, Game Room & Bar
Entire Townhouse in Rock Hall

Entire Townhouse in Rock Hall

Rock Hall
Located in Rock Hall, this vacation home is on the waterfront, within a 15-minute walk of Rock Hall Harbor and The Mainstay.
Entire Townhouse in Rock Hall
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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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
153 Holiday Homes
Lowest Price
AU$97
Highest Price
AU$463
Popular accommodation
Beautiful, spacious, quiet waterfront house!, Pet-Friendly Home on Chester River w/ Dock!, BAYSIDE BUNGALOW, Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets, Lark's Nest on the Chester River. Spacious, waterfront home with private dock., Waterfront w/private pier, pool, Hot Tub, kayaks and in town., Waterfront Estate w Private Pier, Game Room & Bar, Entire Townhouse in Rock Hall, Waterfront Oasis w/ Private Dock, 3BR/2BA

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$225 per night from 21 Aug to 22 Aug
AU$225
21 Aug - 22 Aug
includes taxes & fees
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
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$97 per night from 9 Sept to 10 Sept
AU$97
9 Sept - 10 Sept
includes taxes & fees
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
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

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

3 out of 5
4 Philadelphia Ct, Rosedale, MD
Fully refundableReserve now, pay when you stay
The price is AU$140 per night from 14 Aug to 15 Aug
AU$140
14 Aug - 15 Aug
includes taxes & fees
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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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$192 per night from 7 Sept to 8 Sept
AU$192
7 Sept - 8 Sept
includes taxes & fees
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
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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.