Holiday Rentals in Great Oak Landing

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Check prices for these dates

Tonight
20 Feb - 21 Feb
Tomorrow
21 Feb - 22 Feb
This weekend
21 Feb - 23 Feb
Next weekend
28 Feb - 2 Mar

Holiday Rentals in Great Oak Landing

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

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

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Guest Lodge | Private Pool | Outdoor Dining | Game Room
Exterior

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Guest Lodge | Private Pool | Outdoor Dining | Game Room
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
Baseball Lovers Paradise!
Dining

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!
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Interior

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

10.0 out of 10, Exceptional, (32)
"Beautiful home, beautiful property! My family meets up annually and the house fit us perfectly. Plenty of room to spread out and congregate together. The home also provides so much to do with all the amenities! Thanks for the memories "
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Interior

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.
Beautiful Chesapeake Bay Views -pet friendly
Outdoor dining

Beautiful Chesapeake Bay Views -pet friendly

9.6 out of 10, Exceptional, (114)
"The home accomodated"
Beautiful Chesapeake Bay Views -pet friendly
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (78)
"Very clean, excellent communications,"
The price is €155
includes taxes & fees
4 Mar - 5 Mar
First Floor Studio Apartment in Historic Chestertown
BAYSIDE BUNGALOW
Exterior detail

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 €262
includes taxes & fees
5 Mar - 6 Mar
BAYSIDE BUNGALOW
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Lake

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 ! ! !
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.

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 CHeerful 2 with Private Pier
Fridge, microwave, oven, stovetop

Waterfront CHeerful 2 with Private Pier

10.0 out of 10, Exceptional, (8)
"Quiet location on the water, well laid out. Very clean and very easy to work with. "
Waterfront CHeerful 2 with Private Pier
Eastern Shore beach cottage get-away
Sun-loungers

Eastern Shore beach cottage get-away

10.0 out of 10, Exceptional, (133)
"Perfect location for watching the sunsets as the house is located right across the street from the beach. Also, an easy bike ride to restaurants and shops on Main St. The house is clean and comfortable. Highly recommend to other guests!"
Eastern Shore beach cottage get-away
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, (18)
"Good location."
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
Stay in the landmark Lighthouse!
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!
Pet-Friendly Home on Chester River w/ Dock!
Interior

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (4)
"An absolute stunning view from the four season enclosed porch. This beautiful home is well equiped and a perfect location for Fall and Winter hunting trips near Chestertown/Kennedyville. Plenty of rooms/bathrooms/beds. Highly recommend!!!"
Pet-Friendly Home on Chester River w/ Dock!
Cozy 2 bedroom apartment w/ free parking
Fridge, microwave, stovetop, dishwasher

Cozy 2 bedroom apartment w/ free parking

8.8 out of 10, Excellent, (5)
"Very good communication, address was listed wrong on website but the host helped a lot, it wasn't his fault. It's in the basement, and it's really nice, but it's in the basement lol"
The price is €373
includes taxes & fees
21 Feb - 22 Feb
Cozy 2 bedroom apartment w/ free parking
Luxury Waterfront Executive Family Home Annapolis with All Amenities
Outdoor dining

Luxury Waterfront Executive Family Home Annapolis with All Amenities

Luxury Waterfront Executive Family Home Annapolis with All Amenities
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
Outdoor dining

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
Waterfront Home & Dock,Remodel Kitchen,Eastern shore, Betterton,Chestertown MD.
Miscellaneous

Waterfront Home & Dock,Remodel Kitchen,Eastern shore, Betterton,Chestertown MD.

9.8 out of 10, Exceptional, (87)
"The house and location on Still Pond Maryland was great!! House was clean and tiddy. Caught perch, catfish and bass off their dock!! Area is beautiful and quiet! "
Waterfront Home & Dock,Remodel Kitchen,Eastern shore, Betterton,Chestertown MD.
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 types of properties in Great Oak Landing you may be interested in

Quality Inn & Suites Bel Air I-95 Exit 77A
Desk, free WiFi, bed sheets, alarm clocks

Quality Inn & Suites Bel Air I-95 Exit 77A

2.5 star property
7.2 out of 10, Good, (1002)
"LIKE ALL"
The price is €56
includes taxes & fees
25 Feb - 26 Feb
Quality Inn & Suites Bel Air I-95 Exit 77A
Hilton Garden Inn Baltimore/White Marsh
Exterior

Hilton Garden Inn Baltimore/White Marsh

3.0 star property
8.0 out of 10, Very good, (1003)
"Na"
The price is €112
includes taxes & fees
9 Mar - 10 Mar
Hilton Garden Inn Baltimore/White Marsh
Best Western Plus Hotel & Conference Center
Lobby

Best Western Plus Hotel & Conference Center

2.5 star property
7.6 out of 10, Good, (1001)
"Quiet and clean. Needs an upgrade."
The price is €110
includes taxes & fees
24 Feb - 25 Feb
Best Western Plus Hotel & Conference Center
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.

Frequently asked questions

Are there holiday rentals in Great Oak Landing?

Yes, there are holiday rentals close to the most popular sights in Great Oak Landing, or you can select a more secluded option if you're looking for a relaxing stay. Great Oak Landing is known for its restaurants.

What are some of the best holiday rentals that Great Oak Landing has to offer?

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.: This holiday home rental outside of Great Oak Landing is located on the waterfront, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of an arcade/games room in this rental home to help you unwind.

What can I see and do in Great Oak Landing?

While exploring the area, visit family-friendly sights like Crumpton Auction, or get outside and enjoy nature at Ferry Park. Washington College and River Arts Chestertown are a couple of places you'll find in the wider area.

What are holiday rentals like in Great Oak Landing?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Great Oak Landing. Holiday rentals feature amenities such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family trip.