Book Holiday Homes in Great Oak Landing

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Featured Holiday Homes in Great Oak Landing

Pet-Friendly Home on Chester River w/ Dock!

Pet-Friendly Home on Chester River w/ Dock!

2 out of 5
Chestertown
When you stay at this vacation home in Chestertown, you'll be within a 5-minute drive of Washington College.
Pet-Friendly Home on Chester River w/ Dock!
Waterfront family resort Lodge with private pier, game room and bar

Waterfront family resort Lodge with private pier, game room and 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 family resort Lodge with private pier, game room and bar
A waterfront gem with dock, kayaks great water views.  Sleeps up to 12.

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

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.
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
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Waterfront w/upper sundeck and private pier located near Rock Hall,  sleeps 18.

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

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/upper sundeck and private pier located near Rock Hall, sleeps 18.
Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Rock Hall
Located in Rock Hall, this vacation home is on the waterfront, within a 10-minute drive of Eastern Neck National Wildlife Refuge and The Mainstay.
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!

Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!

Rock Hall
With a stay at this vacation home in Rock Hall, you'll be within a 15-minute walk of Rock Hall Harbor and Waterman’s Museum.
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11

Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11

Rock Hall
With a stay at this vacation home, you'll be centrally located in Rock Hall, just a 3-minute walk from Waterman’s Museum and 10 minutes by foot from Rock Hall ...
Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11
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
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.
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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
112 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Pet-Friendly Home on Chester River w/ Dock!, Waterfront family resort Lodge with private pier, game room and bar, A waterfront gem with dock, kayaks great water views. Sleeps up to 12., Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18., Waterfront Paradise on the Eastern Shore of Chesapeake Bay , Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!, Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11, RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING , Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

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^Subject to availability and chosen travel dates.