Search Vacation Homes in Great Oak Landing

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

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.0 out of 10, Wonderful, (2)
"no kettle no cutting board"
Pet-Friendly Home on Chester River w/ Dock!

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

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

9.8 out of 10, Exceptional, (50)
" We ( a group of 16 women) enjoyed having our annual retreat at Nauti or Knot. We stayed for a weekend and the accommodations could not have been better! The bedrooms and bathrooms were wonderful. The living room was able to sit 16 comfortably and the dining room table was big enough for all of us to have dinner together. This is an excellent house!! Our only complaint and it’s minor is that the freezer door was really hard to open."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Baseball Lovers Paradise!

9.4 out of 10, Exceptional, (6)
"Difficult getting in touch with and not timely responses with host. The house was clean….but the bedspreads and throw pillows need washing. They smell and are very dirty. There were no wash clothes to shower with. The house was not dirty itself. Bathrooms, bedrooms, and kitchen were clean. The location was great for our needs and very close to Ripken. Directions and address to the location need to be better communicated. Overall, I would stay there again and we do travel there a lot. I would...
Baseball Lovers Paradise!

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

10.0 out of 10, Exceptional, (24)
"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Waterfront Oasis w/ Private Dock, 3BR/2BA

9.6 out of 10, Exceptional, (29)
"We stayed here over the weekend and had a great time. The home is located about twenty mins from lots of great restaurants and things to do for kids! The arcade machine was a huge hit with my kids. The view of the river was amazing. We sat in the house and watched the sunset and sunrise every day. The host was also very responsive. "
Waterfront Oasis w/ Private Dock, 3BR/2BA

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

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

10.0 out of 10, Exceptional, (18)
"We had an annual girls trip at this property last weekend and it was perfect and as described! The local food recommendations were on point and the house was clean and well stocked with all we needed. Thank you for opening your home to us!"
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!

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

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

9.4 out of 10, Exceptional, (87)
"This was our 1st time in Maryland. We wanted a place on the water and that was able sleeps 8 adults and 5 children ages 5-16 comfortably. This home was perfect! The home was situated on the lake with a dock. It had 5 bedrooms (4 bedrooms with king size beds) and a sleeper in the living room area. Plenty of beach towels, fishing rods, access to canoe and kayak. Easy communication with owner and hassle free check-in. We would return and recommend this home to anyone looking for a relaxing...
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (36)
"We had a great time at the house with friends from our apartment building and neighborhood for the long Thanksgiving weekend. Debbie and Bob had everything we needed to cook with, the porch overlooking the Bay was amazing, and the living room, TV room and dining room were all used frequently. We also played games, and had a nice fire in the portable fire pit outside. Weather got coooold but the house was always warm and cozy. It was a really fun stay. The bedrooms were great, too. They've taken...
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Stay in the landmark Lighthouse!

10.0 out of 10, Exceptional, (96)
"We stayed at the light house for three nights in celebration of the new year, 2025. It was a work vacation involving winter covering of our sailboats as well as celebrating the new year. We thoroughly enjoyed our time together and will come here again."
Stay in the landmark Lighthouse!

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

10.0 out of 10, Exceptional, (62)
"Bigger, nicer and newer than it looks in the pics; a pleasant surprise. Great location, we’d go again. "
Waterfront Paradise on the Eastern Shore of Chesapeake Bay

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

Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View

8.8 out of 10, Excellent, (11)
"The location is spectacular with expansive views of the Chesapeake Bay and the Bay Bridge. The house itself is immaculate and had lots of space for our family. I would imagine it's even better in the summer when the pool is available.One caution: the playhouse is really cool but not a place to let younger kids play unsupervised."
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View

Amazing Waterfront Home on the Bush River

10.0 out of 10, Exceptional, (20)
"We had a wonderful stay at Ted’s property. The basement was cold as they hadn’t figured out to adjust the thermostat yet, so we didn’t spend any time down there. We also encountered challenges with the hot water heater, but overall it was a lovely stay. "
Amazing Waterfront Home on the Bush River

CHeerful 3-bedroom waterfront home

10.0 out of 10, Exceptional, (32)
"We had a wonderful stay at this 3 bedroom house and would recommend this location 100%. The owner had great communication and responded very quickly on all questions. Very clean and the location was perfect. House was very clean and perfect for our family trip. This house will not disappoint! "
CHeerful 3-bedroom waterfront home

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!

Quiet Bird River Bungalow and Nature Retreat Pet Friendly

10.0 out of 10, Exceptional, (10)
"This was the perfect escape from the city. I was in town for medical appointments and after a long day away, it was nice to come back to a cozy place. The yard was full of beautiful flowers and fun little surprises (we saw frogs, turtles, birds and a groundhog!). The house came fully equipped for anything you might need. Will was very responsive and communicated well. We will definitely put this cute vintage house on the list for our next visit to Maryland."
Quiet Bird River Bungalow and Nature Retreat Pet Friendly

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

10.0 out of 10, Exceptional, (5)
"The house and property were wonderful. Right on the river with all you need. Fantastic stay, great communication, would love to return again!"
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
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

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

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

9.8 out of 10, Exceptional, (50)
" We ( a group of 16 women) enjoyed having our annual retreat at Nauti or Knot. We stayed for a weekend and the accommodations could not have been better! The bedrooms and bathrooms were wonderful. The living room was able to sit 16 comfortably and the dining room table was big enough for all of us to have dinner together. This is an excellent house!! Our only complaint and it’s minor is that the freezer door was really hard to open."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

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
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.