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Featured Cottages in Great Oak Landing and around

The Heron's Nest at Atlantic Marina
Exterior
The Heron's Nest at Atlantic Marina
10.0 out of 10, Exceptional, (283)
"Great location, wonderful interactions with owners, beautiful scenery, and easy check-in"
The Heron's Nest at Atlantic Marina
House w/Water Views of Rock Creek 2BA 2BA Cottage
Smart TV
House w/Water Views of Rock Creek 2BA 2BA Cottage
10.0 out of 10, Exceptional, (22)
"Very quiet street, our stay was relaxing and just what we needed! "
House w/Water Views of Rock Creek 2BA 2BA Cottage
Be persuaded to experience this vintage cottage by the Sassa
Outdoor dining
Be persuaded to experience this vintage cottage by the Sassa
9.4 out of 10, Exceptional, (8)
"We had one of the best vacations ever. Our 9 and 7 year old grandchildren wanted to live there forever! We had a beautiful house and access to the outdoor spaces including a dock for gishing, crabbing and swimming. We were able to make smores over a great fire pit and enjoyed phenominal sunsets from a sitting area overlooking the river. Gene and Suzie, the hosts were on-site and so warm and welcoming. Our every need was met immediately. We will definitely be vacationing at Gregg Neck Cottage...
Be persuaded to experience this vintage cottage by the Sassa
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, (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
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Sun-loungers, beach towels
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, (97)
"My wife and I, and our daughter's family (including our grandkids (ages 5 and 8) spent an amazing long weekend at Spring Cove Farm. We all loved our stay so much. The house was spotlessly clean and had everything we needed and the pier/water was gorgeous with ample kayaks and paddle boards. The kids fished from the pier for hours upon hours each day, and were thrilled at the selection of toys. Our daughter and son-in-law were working remotely and the Wi-Fi and Internet worked perfectlu. Dr....
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Family-Friendly Cottage, Walk to the Beach!
Interior
Family-Friendly Cottage, Walk to the Beach!
10.0 out of 10, Exceptional, (18)
"Another amazing stay at Robin’s Rest. Highly recommend for a quiet weekend getaway "
Family-Friendly Cottage, Walk to the Beach!
Eastern Shore beach cottage get-away
Sun-loungers
Eastern Shore beach cottage get-away
10.0 out of 10, Exceptional, (132)
"This house was the cutest little place right across the street from the beach with a beautiful view. The house was clean and had all the amenities needed for our stay. We would definitely stay there again!"
Eastern Shore beach cottage get-away
Peaceful getaway convenient to local amenities including beach, boating & food
Beach towels
Peaceful getaway convenient to local amenities including beach, boating & food
9.8 out of 10, Exceptional, (109)
"We were in town for the local triathlon and had a great stay! My kids (3&4) and I were able to walk to the finish line from the location. The house was clean and large enough that we were all comfortable. If you have kids, it’s across the street from a cool boat playground. Diane was very responsive to my questions and provided plenty of towels, blankets, etc. Overall, a great stay! "
Peaceful getaway convenient to local amenities including beach, boating & food
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Property grounds
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
10.0 out of 10, Exceptional, (5)
"My friend and I wanted to meet up part way between our two cities, and when we decided on the Chesapeake Bay, Rock Hall seemed a good option, and we were right! What a great little town, and the house was just perfect for us. She brought her two little ones (6 and 2), and I was on my own. I think with just 1 bathroom, many more than that would really not be ideal. The whole stay was great, we both agreed we'd love to come back again. The only hiccup (and I am sure it will be fixed), was that...
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Waterfront and Wonderful! Welcome to the Bayburst Lodge.
Property grounds
Waterfront and Wonderful! Welcome to the Bayburst Lodge.
8.0 out of 10, Very good, (11)
"This was our second visit to Bayburst Lodge and it was even better than our first! We spent an entire week this time and it really was relaxing and quite enjoyable. We did a lot of fishing this trip. We caught huge catfish off the beach behind the house, and also did a 4 hour charter in which we caught our limit in Striped Bass. The weather was incredible and we spent a lot of time walking, shopping, and sitting on the screened porch. We tried a new restaurant called Ark and Dove this trip....
Waterfront and Wonderful! Welcome to the Bayburst Lodge.
Eastern Shore Getaway: Walk to Tolchester Marina!
House (5 Bedrooms) | Private kitchen
Eastern Shore Getaway: Walk to Tolchester Marina!
3.0 star property
Eastern Shore Getaway: Walk to Tolchester Marina!
Private cottage
Exterior
Private cottage
Private cottage
Rock Creek Cottage, Waterfront
Fridge, microwave, oven, stovetop
Rock Creek Cottage, Waterfront
10.0 out of 10, Exceptional, (1)
"Absolutely amazing place for my husband and I to relax with our midshipmen. Very clean, beautifully decorated and the view on the dock each morning was stunning! Close to restaurants (loved 3 B’s Bakery) and host was awesome! "
Rock Creek Cottage, Waterfront
Family-friendly Cottage, Walk to the Beach!
Interior
Family-friendly Cottage, Walk to the Beach!
3.0 star property
Family-friendly Cottage, Walk to the Beach!
Charming Edgemere Home w/ Deck & Grill!
Miscellaneous
Charming Edgemere Home w/ Deck & Grill!
3.0 star property
Charming Edgemere Home w/ Deck & Grill!
Waterfront Millington Vacation Rental w/ Hot Tub!
House (Multiple Bedrooms) | Private kitchen
Waterfront Millington Vacation Rental w/ Hot Tub!
3.0 star property
Waterfront Millington Vacation Rental w/ Hot Tub!
Church Creek Cottage
Exterior
Church Creek Cottage
Church Creek Cottage
Remodeled Abingdon House w/ Spacious Yard!
Interior
Remodeled Abingdon House w/ Spacious Yard!
3.0 star property
Remodeled Abingdon House w/ Spacious Yard!
Rock Hall Retreat w/ Balcony Near Park & Marina!
Terrace/patio
Rock Hall Retreat w/ Balcony Near Park & Marina!
3.0 star property
Rock Hall Retreat w/ Balcony Near Park & Marina!
Pet-friendly Home on Chester River w/ Dock!
Interior
Pet-friendly Home on Chester River w/ Dock!
3.0 star property
Pet-friendly Home on Chester River w/ Dock!
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
Beach nearby, sun-loungers
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
Property grounds
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (73)
"EasyvPeasy place."
The price is €147
includes taxes & fees
16 Nov - 17 Nov
First Floor Studio Apartment in Historic Chestertown
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
Fridge, microwave, stovetop, dishwasher
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.

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