Great Oak Landing Holiday Rentals

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Holiday Rentals in Great Oak Landing

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

10.0 out of 10, Exceptional, (194)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Luxury Waterfront Executive Family Home Annapolis with All Amenities

7.6 out of 10, Good, (4)
"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

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 ! ! !

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

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (51)
"Very quaint and quiet place to stay. Very relaxing."
The price is NZ$517
includes taxes & fees
19 Oct - 20 Oct
BAYSIDE BUNGALOW

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

9.8 out of 10, Exceptional, (67)
"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

Entire Townhouse in Rock Hall

10.0 out of 10, Exceptional, (32)
"House was exactly as advertised. Quite community. Close to shopping, dining and beach! "
Entire Townhouse in Rock Hall

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

10.0 out of 10, Exceptional, (7)
"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 NZ$388
includes taxes & fees
20 Oct - 21 Oct
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

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

9.8 out of 10, Exceptional, (48)
"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

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"Excellent Property"
The price is NZ$1,138
includes taxes & fees
20 Oct - 21 Oct
Chesapeake Cottages- 2 Quaint Waterfront Retreats

The Heron's Nest at Atlantic Marina

9.8 out of 10, Exceptional, (308)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina

Charming cottage with Pool Access and WiFi in lovely Rock Hall

10.0 out of 10, Exceptional, (4)
"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

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

9.8 out of 10, Exceptional, (65)
"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

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

10.0 out of 10, Exceptional, (15)
"A very well maintained and comfy apartment that is just a short walk to the heart of Rock Hall. My family especially enjoyed the large private backyard. Rick made sure we had everything we needed."
The price is NZ$503
includes taxes & fees
20 Oct - 21 Oct
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

10.0 out of 10, Exceptional, (9)
"My kids and I absolutely loved our stay at the Outlook! So peaceful and relaxing. We spent a lot of time walking around the trails spotting deer and toads. We did a good amount of fishing on the dock, catching catfish. I hope to stay here again in the future."
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (102)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is NZ$272
includes taxes & fees
8 Oct - 9 Oct
First Floor Studio Apartment in Historic Chestertown

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

9.0 out of 10, Wonderful, (16)
"Our family of 11 stayed there for a week and absolutely loved it. Great views, large pool for the kids and a fishing dock for the fisherman in the family made it the perfect summer getaway. House is large and very clean and maintained."
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

9.8 out of 10, Exceptional, (84)
"We had a wonderful weekend. Thank you!"
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

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.

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

10.0 out of 10, Exceptional, (12)
"It was a great vacation, the house and grounds were spectacular, the amenities, pool, kayaks, were great, and host couldn’t have been more accommodating or approachable, highly recommend in the future, hope to go back"
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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Top Great Oak Landing Hotel Reviews

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 favorite 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 depends 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 NZ$272 per night. Entering your travel dates in the search wizard you might find 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?

240' Private Beachfront @Kent Island Love Point - Great for Large Groups: This holiday home rental outside of Great Oak Landing is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.