Great Oak Landing Holiday Rentals

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Holiday Rentals in Great Oak Landing

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, (36)
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Fridge, microwave, oven, stovetop
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
9.8 out of 10, Exceptional, (22)
"Especially nice for summer visits."
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
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.
9.8 out of 10, Exceptional, (15)
"My friends, our wives, and kids loved our stay. Everything exceeded expectations. We especially enjoyed the backyard where we played yard games, grilled, and enjoyed the river."
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
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BAYSIDE BUNGALOW
Fridge, microwave, coffee/tea maker, toaster
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (18)
"What a delight to have found this property. Beautiful drive to get to the Eastern Shore. Rock Hall The beautiful place that’s tucked in along the Chesapeake Bay. My fiancé and I needed a much desirable getaway. The bungalow at this property was the perfect place just for us to forget about our worries back home. The owners were kind enough to message us. Let us know if the events that were happening in town but more so anything that was happening on the property they gave us just a heads up as...
The price is NZ$439
includes taxes & fees
9 Jun - 10 Jun
BAYSIDE BUNGALOW
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
10.0 out of 10, Exceptional, (19)
"Cozy & elegant ☀️ a clean bright space."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Miller's Cottage
Combined shower/bathtub, hair dryer, toilet paper
Miller's Cottage
10.0 out of 10, Exceptional, (24)
"We are from NY and had a major surgery at Johns Hopkins. Miller's Cottage was the perfect location for us to spend the week post-op prior to returning home to NY. Miller's cottage was clean, comfortable and very well equipped. There was outside seating which allowed us to enjoy the fresh air while recovering."
Miller's Cottage
The Remix Quaters
4 bedrooms, iron/ironing board, WiFi, bed sheets
The Remix Quaters
8.0 out of 10, Very good, (2)
"The home was very nice! The pictures don't do it justice. Denise went all out with her decor on the home. My guest were impressed and couldn’t stop talking about how comfortable the beds were"
The price is NZ$533
includes taxes & fees
10 Jun - 11 Jun
The Remix Quaters
200 steps to the beach!
Interior
200 steps to the beach!
10.0 out of 10, Exceptional, (76)
"House was beautifully decorated, updated, clean, and as advertised, steps from the beach!!! We had everything we needed for meal prep, including a charcoal grill. Enjoyed grilling fresh fish for dinner one night!"
200 steps to the beach!
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Balcony
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, (28)
"I organized a large (15 person) bachelorette weekend at this property in early April. It is an absolutely gorgeous house and the host had a number of thoughtful touches - like extra firewood for the firepit, coffee supplies, and a bottle of bubbly for our bride! The beds were comfortable (even the twins!), which was lucky because one bedroom on the breakdown was not really usable, so a handful of guests relocated to one of the 'kid rooms.' We found Ashleigh very responsive both before and...
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Waterfront Oasis w/ Private Dock, 3BR/2BA
Pool
Waterfront Oasis w/ Private Dock, 3BR/2BA
9.8 out of 10, Exceptional, (20)
"The kids joined us for a weekend on our sailboat, this was the perfect spot to get together after a long day on the water. My one son set a new record on the PAC Man and the other caught a beautiful bass off the dock. The river view from the sunroom is spectacular! Everyone always migrated there. Great time had by all. We will be back in the fall."
Waterfront Oasis w/ Private Dock, 3BR/2BA
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Sun-loungers, beach towels
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, (90)
"We enjoyed meeting the hosts and their llamas and emus. The home had everything we needed for our stay, and the view of the water from the house could not be better. We watch the sunsets wherever we go, and the colors were spectacular. There were plenty of things to do, and the restaurants were a short drive away. Thank you for sharing this property with others."
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Pool
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
10.0 out of 10, Exceptional, (35)
"Super clean and easy to find. I encourage anyone to rent this space"
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
The Heron's Nest at Atlantic Marina
Exterior
The Heron's Nest at Atlantic Marina
10.0 out of 10, Exceptional, (267)
"Everything is perfect over there … The paradise on earth .. Highly recommended "
The Heron's Nest at Atlantic Marina
Rambling Victorian Beach House on Maryland's Eastern Shore
Beach nearby, sun-loungers, beach towels
Rambling Victorian Beach House on Maryland's Eastern Shore
10.0 out of 10, Exceptional, (13)
"Our group of couples + kids enjoyed our getaway to the Eastern Shore. Betterton was a great home base to visit our alma mater, Washington College, in Chestertown. There, we visited the farmers market and waterfront park & playground with the kids. Back in Betterton, the house fit our group well. Plenty of bedrooms, bathrooms and space for each family. The kids & adults enjoyed spending time lounging in the third floor living room. We were pleased that the house had plenty of games, kids toys,...
Rambling Victorian Beach House on Maryland's Eastern Shore
Family-Friendly Cottage, Walk to the Beach!
Property grounds
Family-Friendly Cottage, Walk to the Beach!
10.0 out of 10, Exceptional, (14)
"Great location "
Family-Friendly Cottage, Walk to the Beach!
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Balcony
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
10.0 out of 10, Exceptional, (40)
"Beautiful property. Needs better towels and linens. Kitchen is well equipped. Living areas are spacious and comfortable"
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Very nice house with everything you need
Interior
Very nice house with everything you need
10.0 out of 10, Exceptional, (3)
"The house was exactly as stated. The only thing was the owner never got back to us until I called VRBO number because we needed instructions to get into house and owner replied in evening before day of arrival instead of replying earlier! Other than that we all enjoyed our stay!"
Very nice house with everything you need
First Floor Studio Apartment in Historic Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (59)
"This was the perfect place to rest our heads along our trip down the east coast. Very comfortable, clean and quiet. We made time to visit the beautiful town and I’m glad we did!"
The price is NZ$265
includes taxes & fees
11 Jun - 12 Jun
First Floor Studio Apartment in Historic Chestertown
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Fridge, microwave, oven, stovetop
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
10.0 out of 10, Exceptional, (3)
"Lark’s Nest was a cute little place! Very clean! The view from the patio was stunning, and if you’re a bird lover you will be in your glory! Bring your binoculars and sit on the deck and wait! House was well equipped with most everything you would need! Host was very quick to write back when asked a question! First time in this area and hopefully be back again in the future!"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
Property grounds
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
10.0 out of 10, Exceptional, (3)
"Wonderful rental home for our family with great pool and river view. Swimming every day in the pool was so much fun for everyone, kayaks, and paddle boards were great since we did not have to bring anything. Children fished every night on the dock. We played lots of games inside and out everyday and enjoyed the Nature all around to see, birds, deer, fish, frogs and small animals. Our family felt like they had their own getaway for a wonderful vacation. Thank you for everything."
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
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See all available properties in Great Oak Landing
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.

Other types of properties in Great Oak Landing you may be interested in

The Lodge at Great Oak Landing
Private beach nearby, sun-loungers, beach volleyball, beach bar
The Lodge at Great Oak Landing
3.0 star property
7.6 out of 10, Good, (4)
"The place is beautiful. The rooms are little small and could use updating. When I turned the air on the windows rattled so loud. I had to keep it on low to avoid the noise. No microwave in the room and be prepared for the slamming door at 6am. Other than those things we really enjoyed our time. "
The price is NZ$243
includes taxes & fees
11 Jun - 12 Jun
The Lodge at Great Oak Landing
Best Western Plus Hotel & Conference Center
Lobby
Best Western Plus Hotel & Conference Center
2.5 star property
7.6 out of 10, Good, (1009)
"Good value for your money. Staff very accommodating. Have pool & a small patio. Did not use shuttle, had a car club next doir but heard nothing. Mcdonalds to walk to. Room has fridge & microwave. Breakfast was great with plenty if options & staff(seveka)? Wss so nice & friendly& aleays accomodating, very pleasant. It was a good stay. "
The price is NZ$186
includes taxes & fees
7 Jul - 8 Jul
Best Western Plus Hotel & Conference Center
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Lobby
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
2.5 star property
7.4 out of 10, Good, (1014)
"It was easy check in the room was clean and it was quiet "
The price is NZ$156
includes taxes & fees
4 Jul - 5 Jul
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Great Oak Landing holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Great Oak Landing. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Great Oak Landing. Seeing all the best attractions is bound to make you fall in love with Great Oak Landing. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Great Oak Landing short-term rentals, that won’t be hard to do.

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?

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock : This holiday home rental outside of Great Oak Landing is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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 Miami Beach. 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.

Recent reviews of Great Oak Landing properties
Expedia verified reviews

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

5/5 Excellent
"Came in out of a storm. Very nice and accommodating Room and facility very nice and comfortable"
A verified traveller from Burbank stayed at Hampton Inn & Suites Edgewood/Aberdeen-South
Posted 2 days ago
Hampton Inn & Suites Edgewood/Aberdeen-South