Search Holiday Rentals in Great Oak Landing

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
10 Aug - 11 Aug
Tomorrow
11 Aug - 12 Aug
Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug

Top Holiday Rentals in Great Oak Landing

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Boats docked at the marina, surrounded by a serene grassy area and wooded surroundings.

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

9.8 out of 10, Exceptional, (61)
"Awesome place!"
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
The Heron's Nest at Atlantic Marina
Situated on a grassy area, this cottage offers a peaceful retreat with a porch for relaxation or dining.

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (301)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Kitchen area with a stove, dishwasher, refrigerator, sink, and countertop with a kettle.

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (103)
"Secluded"
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Property grounds

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

9.4 out of 10, Exceptional, (89)
"What a wonderful vacation we had everything you want is there. All you have to bring is food . The trampoline will keep everyone occupied for hours. Looking forward to staying there in the future."
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Historic Downtown Garden Oasis with Private Patio
Stroll through the serene garden, surrounded by lush plants and a majestic tree.

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (37)
"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "
Historic Downtown Garden Oasis with Private Patio
Waterfront Oasis w/ Private Dock, 3BR/2BA
Guests can enjoy serene waterfront views from the dock.

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

9.4 out of 10, Exceptional, (34)
"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "
Waterfront Oasis w/ Private Dock, 3BR/2BA
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Enjoy a serene beach experience with access to the ocean via the public pier.

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

9.6 out of 10, Exceptional, (42)
"This is a jewel as it is private, peaceful with lovely setting."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Relax in this stylish living room with a large sofa, armchair, and ottoman, perfect for unwinding in comfort.

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (54)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
BAYSIDE BUNGALOW
Outdoor dining

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (43)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is £227
includes taxes & fees
11 Aug - 12 Aug
BAYSIDE BUNGALOW
Beautiful, spacious, quiet waterfront house!
Enjoy cooking in this kitchen with a central island, bar seating, and stainless steel appliances.

Beautiful, spacious, quiet waterfront house!

10.0 out of 10, Exceptional, (53)
"Wonderful stay – Kids enjoyed fishing, floating in tubes and the hot tub! Very clean property with comfortable beds."
Beautiful, spacious, quiet waterfront house!
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Enjoy a meal with a view of the ocean from this dining area with large windows.

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

10.0 out of 10, Exceptional, (6)
"Relaxing and stunning location. Beautiful bay front property with stunning views of the bay. If you are looking for a quiet and peaceful getaway that involves wildlife sightings this is the perfect spot. Well equipped and roomy rental. Very clean too. "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a granite countertop.

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.6 out of 10, Exceptional, (19)
"a great place to unwind. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Enjoy a meal with a view from the kitchen's glass doors, which lead to a patio with a deck and seating area overlooking a serene landscape.

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

10.0 out of 10, Exceptional, (54)
"Great location with a great view."
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Eastern Shore beach cottage get-away
Enjoy a serene beach experience with a gentle shoreline and peaceful surroundings.

Eastern Shore beach cottage get-away

10.0 out of 10, Exceptional, (136)
"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
Charming, updated 1930's beachfront cottage with stunning sunset views
Interior

Charming, updated 1930's beachfront cottage with stunning sunset views

10.0 out of 10, Exceptional, (1)
"Check in was a breeze. Place was clean. Simply beautiful. Most relaxing place ever. "
Charming, updated 1930's beachfront cottage with stunning sunset views
Kent Island Waterfront Cottage
Enjoy cooking in this well-equipped kitchen with a sink, microwave, oven, and refrigerator.

Kent Island Waterfront Cottage

8.8 out of 10, Excellent, (11)
"Enjoyed fishing at the pier and sitting on the porch"
Kent Island Waterfront Cottage
Luxury Waterfront Executive Family Home Annapolis with All Amenities
Relax on the patio with a view of the water, surrounded by a pergola and a charming seating area.

Luxury Waterfront Executive Family Home Annapolis with All Amenities

10.0 out of 10, Exceptional, (2)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
Luxury Waterfront Executive Family Home Annapolis with All Amenities
First Floor Studio Apartment in Historic Chestertown
Relax by the pool surrounded by a tranquil golf course view.

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (93)
"Very pretty location. Few minutes drive to town center."
The price is £121
includes taxes & fees
13 Aug - 14 Aug
First Floor Studio Apartment in Historic Chestertown
Serene Waterfront Cottage with dock and gorgeous views.
Enjoy cooking in this well-equipped kitchen with a large island and modern appliances.

Serene Waterfront Cottage with dock and gorgeous views.

9.6 out of 10, Exceptional, (38)
"Nice place with everything I could want. Would stay there again!"
Serene Waterfront Cottage with dock and gorgeous views.
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Enjoy cooking in this well-equipped kitchen with a central island and bench, featuring stainless steel appliances and ample cabinetry.

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

9.8 out of 10, Exceptional, (45)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Great Oak Landing Hotel Reviews

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

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

10/10 Excellent
"I love it"
Doryn 1-night trip
Posted 18 hours ago
Quality Inn & Suites Bel Air I-95 Exit 77A

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 Oasis w/ Private Dock, 3BR/2BA: This holiday home rental outside of Great Oak Landing is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 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.