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Compare 116 Vacation Homes in Great Oak Landing with updated reviews, rates, and availability.

Charming Waterfront house with expansive views of the Chesapeake Bay and Sunsets
10.0 out of 10, Exceptional, (1)
"What a wonderful home, spacious just beautiful! But the view of the bay was everyone’s favorite, we spent 98% of the time outside only inside for eating and sleeping. The grandkids didn’t pick up and electronic device the entire time, they played basketball, fished, cornhole, counting boats. The only time a TV was turned on was to watch Big Blue Madness and the Kentucky/Vandy game (we’re from Kentucky). But if you like TV there is one in every room! This home is very well stocked with everything...
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
10.0 out of 10, Exceptional, (48)
"The house was beautiful. The location was perfect. The owner was very responsive. 5 couples stayed in the house and we would all love to return. Thank you for everything!!"
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
Waterfront Oasis w/ Private Dock, 3BR/2BA
9.8 out of 10, Exceptional, (26)
"The house is spacious (more than the photos may lead you to believe), with numerous gathering centers inside and out. My guests enjoyed the dock at sunset and the fire pit by the water. The patio under the house had a charcoal grill and ample space for tables and chairs. Though our weekend had perfect weather, the covered patio made the place "weatherproof" had it rained. There is tons of parking, and a beautiful view over the water. The Host was readily available via VRBO messaging, Usually...
Waterfront Oasis w/ Private Dock, 3BR/2BA
Beautiful, spacious, quiet waterfront house!
10.0 out of 10, Exceptional, (45)
"Good"
Beautiful, spacious, quiet waterfront house!
Amazing Waterfront Home on the Bush River
10.0 out of 10, Exceptional, (18)
"Wonderful place to stay!"
Amazing Waterfront Home on the Bush River
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
7.4 out of 10, Good, (3)
"About a 10 minute walk to main street, 15-20 to the Marinas. The house is cute, has a nice common room, and the bed was comfy."
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
Kent Island Luxury Waterfront
10.0 out of 10, Exceptional, (5)
"Such a beautiful property. . Wonderful experience. Love to come back again. House is way better than we expected. Gorgeous views and had an amazing experience of moonrise abd sunrise"
Kent Island Luxury Waterfront
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (33)
"The bay cottage's porch was a perfect spot to enjoy a bottle of wine and snacks provided by the thoughtful hosts. Clever decor , furnishings, and sauna made our stay special and warm. Had crab dinner viewing sunset over the bay at dockside suggested by hosts. we hope to return. "
The price is AED 643
AED 997 total
includes taxes & fees
17 Dec - 18 Dec
BAYSIDE BUNGALOW
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
9.6 out of 10, Exceptional, (35)
"This house had the most amazing views and was clean and tidy. It was perfect for us and the dogs. The yard was clean and mowed and provided plenty of room for frisbee play which is part of my german shepherd's job. The kitchen was very adequate for our needs! As expected, the upstairs bedrooms were "historic" and the staircase was steep also "historic". The showers were perfect. We had a great visit and would love to come back here!"
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Very nice house with everything you need
9.8 out of 10, Exceptional, (7)
"This location was within a reasonable distance from our activities of checking our colleg students into their new housing. Free parking for 2 vehicles. Sleeping arrangements worked for our party of 3 parents and 3 students. Adequate kitchen ammenities to cook a nice meal. Quiet neighborhood. Would stay here again. "
Very nice house with everything you need
Waterfront family resort Lodge with private pier, game room and bar
9.8 out of 10, Exceptional, (23)
"The property was excellent for a large group. We was there for a Sailing Regatta on the lake in front of the house. The perfect house for groups."
Waterfront family resort Lodge with private pier, game room and bar
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
10.0 out of 10, Exceptional, (15)
"My family enjoyed this house so much. The place is perfect for a relaxing gateway with so much peace and nature. Will definitely be back!"
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
200 steps to the beach!
10.0 out of 10, Exceptional, (85)
"I enjoyed my stay. I've stayed in the house before."
200 steps to the beach!
Circa 1900 Home in the Heart of Historic Downtown Chestertown
10.0 out of 10, Exceptional, (64)
"We enjoyed everything about the property."
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
10.0 out of 10, Exceptional, (14)
"Rock Hall is the perfect little bay town and this property captures that same appeal. Spacious home with great outdoor space. Lovely neighborhood for walks and bike rides. Everything in home worked perfectly. We are certain to return. "
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
Charming Edgemere Home w/ Deck & Grill!
10.0 out of 10, Exceptional, (2)
"Excellent property. Very comfortable. Owner was awesome. Would definitely book here again"
Charming Edgemere Home w/ Deck & Grill!
Waterfront Millington Vacation Rental w/ Hot Tub!
Waterfront Millington Vacation Rental w/ Hot Tub!
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
9.2 out of 10, Wonderful, (5)
"The owners were very flexible with us and understanding when it came to a booking mistake on my end. The house is lovely and the property is absolutely gorgeous. The deck was picture perfect. Highly recommend for a getaway on the eastern shore!"
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
Rock Hall Retreat w/ Balcony Near Park & Marina!
2.0 star property
10.0 out of 10, Exceptional, (1)
Rock Hall Retreat w/ Balcony Near Park & Marina!
A Spacious Haven For Ultimate Comfort 3 Bedroom Home by RedAwning
3.0 star property
A Spacious Haven For Ultimate Comfort 3 Bedroom Home by RedAwning
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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Other property types in Great Oak Landing

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (44)
"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (73)
"EasyvPeasy place."
The price is AED 360
AED 557 total
includes taxes & fees
20 Nov - 21 Nov
First Floor Studio Apartment in Historic Chestertown
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
10.0 out of 10, Exceptional, (48)
"The house was beautiful. The location was perfect. The owner was very responsive. 5 couples stayed in the house and we would all love to return. Thank you for everything!!"
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
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.