Great Oak Landing Holiday Rentals

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Check prices for these dates

Tonight
22 Sept - 23 Sept
Tomorrow
23 Sept - 24 Sept
This weekend
26 Sept - 28 Sept
Next weekend
3 Oct - 5 Oct

Holiday Rentals in Great Oak Landing

Our top choices for Great Oak Landing holiday rentals

Luxury Waterfront Executive Family Home Annapolis with All Amenities
Outdoor dining

Luxury Waterfront Executive Family Home Annapolis with All Amenities

7.4 out of 10, Good, (3)
"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
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outdoor dining

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (193)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
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)
"This property was a great place for a family to all relax together, play games, and enjoy the water!"
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Marina

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

9.8 out of 10, Exceptional, (65)
"Perfect for the wedding I attended and great place to host a short getaway with my brother and his kids."
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
BAYSIDE BUNGALOW
Outdoor dining

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (48)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is AU$449
includes taxes & fees
23 Sept - 24 Sept
BAYSIDE BUNGALOW
The Heron's Nest at Atlantic Marina
Exterior

The Heron's Nest at Atlantic Marina

9.8 out of 10, Exceptional, (305)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Smart TV, books

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (57)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Fridge, microwave, oven, stovetop

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

10.0 out of 10, Exceptional, (6)
"This property was decorated beautifully. Roomy and functional. We enjoyed coffee on the rear deck. Neighborhood restaurants were great. We had great communication with our host. This trip far exceeded our expectations."
The price is AU$345
includes taxes & fees
24 Sept - 25 Sept
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (100)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is AU$226
includes taxes & fees
23 Sept - 24 Sept
First Floor Studio Apartment in Historic Chestertown
Entire Townhouse in Rock Hall
Fridge, microwave, oven, stovetop

Entire Townhouse in Rock Hall

10.0 out of 10, Exceptional, (31)
"Great house for us as always! It fits our needs perfectly !! Thanks for sharing !"
Entire Townhouse in Rock Hall
John’s Hopkins Downtown free parking 3 bedroom 3 bth sleeps 8 rooftop deck
Exterior

John’s Hopkins Downtown free parking 3 bedroom 3 bth sleeps 8 rooftop deck

9.4 out of 10, Exceptional, (3)
"We had a wonderful stay at Deanna’s house, everything was clean and easy to get in with self instructions. We liked that the house was also close enough to inner harbor. The owner had great communication too, thank you we’ll plan to stay again soon!! "
John’s Hopkins Downtown free parking 3 bedroom 3 bth sleeps 8 rooftop deck
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach
Indoor pool

Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach

10.0 out of 10, Exceptional, (10)
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Beach nearby, sun-loungers, beach towels

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

9.6 out of 10, Exceptional, (44)
"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
Waterfront Oasis w/ Private Dock, 3BR/2BA
Marina

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

9.4 out of 10, Exceptional, (36)
"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "
Waterfront Oasis w/ Private Dock, 3BR/2BA
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (46)
"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
Charming cottage with Pool Access and WiFi in lovely Rock Hall
Outdoor pool

Charming cottage with Pool Access and WiFi in lovely Rock Hall

10.0 out of 10, Exceptional, (3)
"Wonderful 2 night stay at this charming cottage in Rock Hall. We would definitely recommend. "
Charming cottage with Pool Access and WiFi in lovely Rock Hall
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, (57)
"We had an awesome time at the property. The pool and jacuzzi are great for the family to play together. The house has board games and toys for the little ones, plus bikes to explore the little town. We will definitely be back. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Property grounds

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"Excellent Property"
The price is AU$1,019
includes taxes & fees
23 Sept - 24 Sept
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Luxury Waterfront Home Built for Entertaining!
6 bedrooms, iron/ironing board, WiFi, bed sheets

Luxury Waterfront Home Built for Entertaining!

5.0 out of 10, (2)
"Quite lovely house with a gorgeous view over the water. It is definitely a good spot to stay with a large family or friends for a few days with plenty to do (relaxing on the dock, play games inside, not too far from Baltimore and other nice towns, etc). The host was great and very communicative as well.The only downsides were details around cleanliness and the check-out procedures. The house itself was overall fine, but there dishes left in the dishwasher that we had to put away, the bottom...
The price is AU$1,274
includes taxes & fees
23 Sept - 24 Sept
Luxury Waterfront Home Built for Entertaining!
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
Beach towels

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

9.8 out of 10, Exceptional, (64)
"Had such a great time at this cottage...would definately come back! Close to downtown activities and easy walking to water. Enjoyed our time there!"
Cottage with Harbor and Chesapeake Bay View in Rock Hall, 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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Top Great Oak Landing Hotel Reviews

Holiday Inn Express White Marsh by IHG

Holiday Inn Express White Marsh by IHG

10/10 Excellent
"Clean, quiet, comfortable "
Nalily 1-night trip
Posted 1 day ago
Holiday Inn Express White Marsh by IHG

Find out more about Great Oak Landing

Find out more about Great Oak Landing

Everything you need to know about Great Oak Landing holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Great Oak Landing holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Great Oak Landing holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Great Oak Landing holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Great Oak Landing. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Great Oak Landing holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Great Oak Landing holiday rentals we have selected for you start as low as AU$226 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Great Oak Landing rentals

At Expedia, we put the best Great Oak Landing holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Great Oak Landing rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Great Oak Landing holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Great Oak Landing. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Luxury Waterfront Executive Family Home Annapolis with All Amenities: This holiday home rental outside of Great Oak Landing offers a fireplace, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

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 Chestertown Dog 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.