Search Vacation Homes in Great Oak Landing

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Compare 126 Vacation Homes in Great Oak Landing with updated reviews, rates, and availability.

Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
Property grounds
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
10.0 out of 10, Exceptional, 2 reviews
"Beautiful property, both inside and out, which was comfortable for two families with numerous children. Hosts were kind enough to make amenities beyond the usual available, including yard games, fishing rods, fire pit, and bicycles. We were VERY comfortable throughout our stay and were appreciative of everything this charming house had to offer. Three out of the four bedrooms had enough space for a crib, and the last still had a queen size bed that fit perfectly in the space with room to move...
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Interior
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, 15 reviews
"My friends, our wives, and kids loved our stay. Everything exceeded expectations. We especially enjoyed the backyard where we played yard games, grilled, and enjoyed the river."
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool | Outdoor pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, 52 reviews
"My family of 4 stayed here. So many things to do outside-truly a good time. So many games and accessories to have an easy good time. Would definitely stay at this place again."
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
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BAYSIDE BUNGALOW
Fridge, microwave, coffee/tea maker, toaster
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, 18 reviews
"This is a excellent cottage for a short getaway. As the listing states, the cottage is small so only big enough for 1-2 people. There is a nice refrigerator and microwave to heat things up but no facilities for cooking. Paul and Chris are very friendly and helpful. Their dog Vinny is also friendly. We came for a triathlon and the porch was a covered so we could keep our bikes there. The sauna was also great to use after our triathlon."
The price is $175
$272 total
includes taxes & fees
Jun 9 - Jun 10
BAYSIDE BUNGALOW
Entire Townhouse in Rock Hall
Fridge, microwave, oven, stovetop
Entire Townhouse in Rock Hall
10.0 out of 10, Exceptional, 15 reviews
"We have stayed in this neighborhood before on a previous visit, we enjoyed how quiet and friendly the neighborhood is. We will definitely visit again. The house is very, very clean, cozy, and well stocked with all the supplies you could possibly need. We enjoyed sitting out in the evenings and watching the stars!!! Thanks for making our visit complete!!!"
Entire Townhouse in Rock Hall
Miller's Cottage
Combined shower/tub, hair dryer, toilet paper
Miller's Cottage
10.0 out of 10, Exceptional, 24 reviews
"We are from NY and had a major surgery at Johns Hopkins. Miller's Cottage was the perfect location for us to spend the week post-op prior to returning home to NY. Miller's cottage was clean, comfortable and very well equipped. There was outside seating which allowed us to enjoy the fresh air while recovering."
Miller's Cottage
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
Property grounds
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
9.8 out of 10, Exceptional, 80 reviews
"House was fine. Odd they did not provide sheets. Was difficult for folks who came from far away. But the house was lovely and we enjoyed our time there!!"
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
The Remix Quaters
4 bedrooms, iron/ironing board, WiFi, bed sheets
The Remix Quaters
8.0 out of 10, Very Good, 2 reviews
"The home was very nice! The pictures don't do it justice. Denise went all out with her decor on the home. My guest were impressed and couldn’t stop talking about how comfortable the beds were"
The price is $200
$330 total
includes taxes & fees
Jun 10 - Jun 11
The Remix Quaters
New Townhouse - 2 Car Garage by CCBC & Franklin Sq
Fridge, microwave, oven, stovetop
New Townhouse - 2 Car Garage by CCBC & Franklin Sq
10.0 out of 10, Exceptional, 18 reviews
"Very nice place, great location, safe neighborhood, great communication with host. Would recommended!"
New Townhouse - 2 Car Garage by CCBC & Franklin Sq
Rambling Victorian Beach House on Maryland's Eastern Shore
Beach nearby, sun loungers, beach towels
Rambling Victorian Beach House on Maryland's Eastern Shore
10.0 out of 10, Exceptional, 13 reviews
"Our group of couples + kids enjoyed our getaway to the Eastern Shore. Betterton was a great home base to visit our alma mater, Washington College, in Chestertown. There, we visited the farmers market and waterfront park & playground with the kids. Back in Betterton, the house fit our group well. Plenty of bedrooms, bathrooms and space for each family. The kids & adults enjoyed spending time lounging in the third floor living room. We were pleased that the house had plenty of games, kids toys,...
Rambling Victorian Beach House on Maryland's Eastern Shore
Waterfront Oasis w/ Private Dock, 3BR/2BA
Pool
Waterfront Oasis w/ Private Dock, 3BR/2BA
9.8 out of 10, Exceptional, 20 reviews
"The kids joined us for a weekend on our sailboat, this was the perfect spot to get together after a long day on the water. My one son set a new record on the PAC Man and the other caught a beautiful bass off the dock. The river view from the sunroom is spectacular! Everyone always migrated there. Great time had by all. We will be back in the fall."
Waterfront Oasis w/ Private Dock, 3BR/2BA
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Fridge, microwave, oven, stovetop
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
10.0 out of 10, Exceptional, 3 reviews
"Lark’s Nest was a cute little place! Very clean! The view from the patio was stunning, and if you’re a bird lover you will be in your glory! Bring your binoculars and sit on the deck and wait! House was well equipped with most everything you would need! Host was very quick to write back when asked a question! First time in this area and hopefully be back again in the future!"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
Property grounds
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
10.0 out of 10, Exceptional, 3 reviews
"Wonderful rental home for our family with great pool and river view. Swimming every day in the pool was so much fun for everyone, kayaks, and paddle boards were great since we did not have to bring anything. Children fished every night on the dock. We played lots of games inside and out everyday and enjoyed the Nature all around to see, birds, deer, fish, frogs and small animals. Our family felt like they had their own getaway for a wonderful vacation. Thank you for everything."
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
Private pier by Kurtz Beach pet-friendly Dock of the Bay
Property grounds
Private pier by Kurtz Beach pet-friendly Dock of the Bay
10.0 out of 10, Exceptional, 12 reviews
"Very comfortable. The view was fantastic. All that we had hoped for. Definitely going to try to make it back."
Private pier by Kurtz Beach pet-friendly Dock of the Bay
House near Patapsco River
Beach
House near Patapsco River
9.4 out of 10, Exceptional, 11 reviews
"Stayed 3 nights in the house, mainly to host the bridal party for day of wedding events and it was a close location for rehearsal dinner and wedding venue. Other than some odd construction on house, it definitely met our needs. We never cooked in the house so I can't say anything as for cooking accessories or servingware but it had a great coffee station. And the master suite upstairs had a great view of the bay. The host was extremely responsive and great to work with."
House near Patapsco River
200 steps to the beach!
Interior
200 steps to the beach!
10.0 out of 10, Exceptional, 76 reviews
"House was beautifully decorated, updated, clean, and as advertised, steps from the beach!!! We had everything we needed for meal prep, including a charcoal grill. Enjoyed grilling fresh fish for dinner one night!"
200 steps to the beach!
Tesla House-Gorgeous Smart House
Property grounds
Tesla House-Gorgeous Smart House
10.0 out of 10, Exceptional, 12 reviews
"The home was right across the street from the fall. The house was full of space and really comfortable. I definitely plan on booking again in the near future."
Tesla House-Gorgeous Smart House
Small House on Gentleman’s Farm
Fridge, microwave, oven, stovetop
Small House on Gentleman’s Farm
10.0 out of 10, Exceptional, 5 reviews
"Very quiet neighborhood. Host was very friendly. House was as described. Everything was clean. Will do it again for next graduation."
The price is $94
$278 total
includes taxes & fees
Jun 9 - Jun 10
Small House on Gentleman’s Farm
Quiet Bird River Bungalow and Nature Retreat Pet Friendly
Exterior
Quiet Bird River Bungalow and Nature Retreat Pet Friendly
10.0 out of 10, Exceptional, 8 reviews
"We had a great time. Was worried about how the window A/C units would work but they were perfect"
Quiet Bird River Bungalow and Nature Retreat Pet Friendly
Want to get away? Staying with us. Very relaxing.
Property grounds
Want to get away? Staying with us. Very relaxing.
9.0 out of 10, Wonderful, 8 reviews
"Nice property in convenient area. Water view is spectacular."
Want to get away? Staying with us. Very relaxing.
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See all available properties in Great Oak Landing
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.

Other property types in Great Oak Landing

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach nearby, sun loungers
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, 36 reviews
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Fridge, microwave, oven, stovetop
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
9.8 out of 10, Exceptional, 22 reviews
"Especially nice for summer visits."
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Interior
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, 15 reviews
"My friends, our wives, and kids loved our stay. Everything exceeded expectations. We especially enjoyed the backyard where we played yard games, grilled, and enjoyed the river."
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
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 Vacation Homes information

Number of reviews
352
Accommodation
126 Vacation Homes
Lowest Price
$94
Highest Price
$200

Recent reviews of Great Oak Landing hotels
Expedia verified reviews

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

5/5 Excellent
"The room was clean and very comfortable. The breakfast was great as was all the staff. I would highly recommend this hotel!!"
A verified traveler from Weston stayed at La Quinta Inn & Suites by Wyndham Aberdeen-APG
Posted 22 hours ago
La Quinta Inn & Suites by Wyndham Aberdeen-APG