Search Vacation Homes in Great Oak Landing
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 148 Vacation Homes in Great Oak Landing with updated reviews, rates, and availability.

240' Private Beachfront @Kent Island Love Point - Great for Large Groups
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
10.0 out of 10, Exceptional, (180)

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.
10.0 out of 10, Exceptional, (51)

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
10.0 out of 10, Exceptional, (46)

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.
9.8 out of 10, Exceptional, (12)

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
9.8 out of 10, Exceptional, (16)
The price is SAR 2,115
SAR 4,150 total
includes taxes & fees
1 Apr - 2 Apr

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
10.0 out of 10, Exceptional, (10)

Newly renovated single family home with attached guest suite
Newly renovated single family home with attached guest suite

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.
10.0 out of 10, Exceptional, (24)
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Great Oak Landing

240' Private Beachfront @Kent Island Love Point - Great for Large Groups
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
10.0 out of 10, Exceptional, (180)

Beautiful, spacious, quiet waterfront house!
Beautiful, spacious, quiet waterfront house!
10.0 out of 10, Exceptional, (47)

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, (33)
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.
Recent reviews of Great Oak Landing hotels
Recent reviews of Great Oak Landing hotels

Holiday Inn Express White Marsh by IHG
5/5 Excellent
"The serenity of the area and the cleanliness of the property"
A verified traveler stayed at Holiday Inn Express White Marsh by IHG
Posted 2 days ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
More Accommodation Types in Great Oak Landing
- Cottages in Great Oak Landing
- Apartments in Great Oak Landing
- Motels in Great Oak Landing
- RV Parks in Great Oak Landing
- Farmstay in Great Oak Landing
- B&B in Great Oak Landing
- Condo Rentals in Great Oak Landing
- Villas in Great Oak Landing
- Cabin Rentals in Great Oak Landing
- Lodges in Great Oak Landing
- Hotels