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Great Oak Landing Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Great Oak Landing vacation rentals

A spacious living area with a dining table, sofa, and a kitchen in the background.

1. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
The price is ￥36,020
￥56,374 total
includes taxes & fees
Aug 31 - Sep 1
Newly restored apartment in the heart of Chestertown
A building with a gabled roof and a circular vent on the roof.

2. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is ￥32,018
￥50,534 total
includes taxes & fees
Aug 31 - Sep 1
BAYSIDE BUNGALOW
A sandy beach with a wooden walkway leading to a calm lake, surrounded by dense green foliage.

3. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (27 reviews)
"Everything was lovely! The dock was beautiful and the accommodations were comfortable.Thanks!"
United States
Max G.
The price is ￥36,020
￥60,267 total
includes taxes & fees
Aug 31 - Sep 1
Waterfront Retreat with Private Dock and Beach
A park with a curved wooden bridge, a tree with purple blossoms, and a grassy area.

4. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is ￥51,350
￥79,599 total
includes taxes & fees
Aug 31 - Sep 1
Wren Retweet- Country Estate in Center of C’Town
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

5. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (124 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is ￥15,849
￥25,429 total
includes taxes & fees
Sep 2 - Sep 3
First Floor Studio Apartment in Historic Chestertown

6. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is ￥29,393
￥45,219 total
includes taxes & fees
Sep 1 - Sep 2
Secluded Cottage in Middle of Chestertown
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

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

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (28 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is ￥18,859
￥46,081 total
includes taxes & fees
Aug 31 - Sep 1
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

8. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
The price is ￥25,534
￥31,736 total
includes taxes & fees
Aug 31 - Sep 1
Beachcomber Suite
A spacious living room with a leather sofa, a wooden coffee table, and a fireplace.

9. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is ￥28,016
￥58,206 total
includes taxes & fees
Sep 29 - Sep 30
Bayside Cottage steps from Rock Hall Harbor
A wooden dock with Adirondack chairs and a ladder, overlooking a calm body of water with a distant shoreline.

10. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (23 reviews)
"Excellent Property"
United States
Buu T.
The price is ￥57,632
￥102,201 total
includes taxes & fees
Aug 31 - Sep 1
Chesapeake Cottages- 2 Quaint Waterfront Retreats
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

11. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
9.8 out of 10, Exceptional, (6 reviews)
The price is ￥24,814
￥30,206 total
includes taxes & fees
Aug 31 - Sep 1
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

12. Turtle Cove Room

Turtle Cove Room
Kent County
The price is ￥22,477
￥27,893 total
includes taxes & fees
Aug 31 - Sep 1
Turtle Cove Room
A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.

13. FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
10.0 out of 10, Exceptional, (2 reviews)
"FLOHOM 14 did not disappoint!!! This was my first stay on a houseboat. Now I know why babies fall asleep when rocked. The boat is beautifully appointed & well equipped. Bring a good book. I’m already missing it!!!"
United States
Maria D.
The price is ￥40,175
￥87,776 total
includes taxes & fees
Sep 15 - Sep 16
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

14. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
The price is ￥30,257
￥46,327 total
includes taxes & fees
Sep 8 - Sep 9
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A single-story white house with a front porch, a mailbox, and a number 715 sign.

15. Watch Deer from a Farm Cottage

Watch Deer from a Farm Cottage
Bel Air
10.0 out of 10, Exceptional, (6 reviews)
"Pet friendly."
United States
Claudia L.
Watch Deer from a Farm Cottage
A dining area with a wooden table and chairs, a chandelier, a refrigerator, and a window with blinds.

16. Spacious 4-bedroom retreat house with plenty of parking

Spacious 4-bedroom retreat house with plenty of parking
Overlea
7.6 out of 10, Good, (7 reviews)
"Great visit wonderful host. "
United States
Jeton E.
The price is ￥46,426
￥100,404 total
includes taxes & fees
Aug 31 - Sep 1
Spacious 4-bedroom retreat house with plenty of parking
A living room with teal walls, a black sofa, a patterned rug, a flat-screen TV on a wooden stand, and a painting on the wall.

17. Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.6 out of 10, Good, (19 reviews)
"Nice place"
United States
christine
The price is ￥13,688
￥17,903 total
includes taxes & fees
Sep 6 - Sep 7
Charming 2-bedroom house in Aberdeen with WiFi and AC
A narrow hallway with a kitchen area on one side, featuring a microwave, oven, and cabinets. There are three black bar stools along the hallway, and a potted plant on the counter.

18. Abingdon Haven Hideaway

Abingdon Haven Hideaway
Abingdon
7.0 out of 10, Good, (2 reviews)
"We made good use of this rental, it was convenient to all our family & activities. Host is very kind & quickly helpful on request. The main problem with a basement apt is that the thermostat is usually upstairs in the main house, but host was most accommodating about temperature control. We rested well here and had a nice week."
United States
Pam L.
The price is ￥18,731
￥61,600 total
includes taxes & fees
Aug 31 - Sep 1
Abingdon Haven Hideaway
A view through a window of a wooden deck with a round table and chairs, overlooking a grassy area with trees.

19. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (12 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
The price is ￥52,349
￥64,386 total
includes taxes & fees
Sep 23 - Sep 24
Family Retreat at Lansdowne Manor
A bed with a dark headboard, a mirror, a potted plant, and a snack basket on the bedside table.

20. Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Nottingham City
10.0 out of 10, Exceptional, (1 review)
"At the end of a multi-city trip filled with mixed hotel experiences, this stay was a true breath of fresh air. Everything was spotlessly clean, beautifully organized, and exactly as pictured. What truly set it apart were the thoughtful touches throughout the space—it was clear our host anticipated our every need, which even saved us an extra trip to the store! Parking was effortless, and the location made getting into the city by car or public transit super easy. Communication with our host was...
United States
Jennifer R.
The price is ￥12,103
￥25,073 total
includes taxes & fees
Aug 31 - Sep 1
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
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

Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

8/10 Good
"Pretty quiet area. Very clean rooms. Beds were fairly comfortable."
Helio 1-night trip
Posted 4 hours ago
Hampton Inn Baltimore/White Marsh

Find out more about Great Oak Landing

Search for holiday rentals in Great Oak Landing on Expedia! You can easily find your home rentals, villas, holiday apartments in Great Oak Landing using one of the methods below:

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Frequently asked questions

Are there vacation rentals in Great Oak Landing?

Yes, we have vacation rentals close to popular sights in Great Oak Landing, or you can select a more remote option if you're looking for relaxation. Great Oak Landing is known for its restaurants.

What's the top vacation rental that Great Oak Landing has to offer?

Waterfront Oasis w/ Private Dock, Firepit, Arcade & Sunset Views: Visitors like this Great Oak Landing vacation home rental. It is located on a river and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. Make the most of the arcade game room in this rental home to help you unwind.

What can I see and do in Great Oak Landing?

Northern Chesapeake Bay and Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. Washington College and River Arts Chestertown are a couple of places you'll find in the larger area.

What are vacation rentals like in Great Oak Landing?

Vacation rentals are private accommodations you can stay in for a short or long stay in Great Oak Landing. Vacation rentals offer amenities like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a small group gathering.