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Great Oak Landing Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Great Oak Landing vacation rentals

Property grounds

1. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (120 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is AED 364
AED 583 total
includes taxes & fees
20 Aug - 21 Aug
First Floor Studio Apartment in Historic Chestertown
Exterior detail

2. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (62 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is AED 661
AED 1,062 total
includes taxes & fees
14 Sep - 15 Sep
BAYSIDE BUNGALOW
Smart TV, books

3. 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 AED 826
AED 1,297 total
includes taxes & fees
19 Aug - 20 Aug
Newly restored apartment in the heart of Chestertown
Beach nearby

4. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is AED 826
AED 1,390 total
includes taxes & fees
30 Aug - 31 Aug
Waterfront Retreat with Private Dock and Beach
Property grounds

5. 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 AED 1,178
AED 1,838 total
includes taxes & fees
17 Aug - 18 Aug
Wren Retweet- Country Estate in Center of C’Town
Beach

6. 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)
"What a great apartment and location for a getaway. Had everything we needed and so convenient! I will absolutely stay here again."
United States
Charlotte M.
The price is AED 455
AED 1,086 total
includes taxes & fees
23 Aug - 24 Aug
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
TV, fireplace

7. 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 AED 674
AED 1,037 total
includes taxes & fees
19 Aug - 20 Aug
Secluded Cottage in Middle of Chestertown
Property grounds

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 AED 586
AED 728 total
includes taxes & fees
24 Aug - 25 Aug
Beachcomber Suite
Smart TV

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 AED 746
AED 1,460 total
includes taxes & fees
24 Aug - 25 Aug
Bayside Cottage steps from Rock Hall Harbor
Terrace/patio

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

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful location, nicely decorated. The host thought of everything you may need including a free snack basket, washer/dryer with detergent and dryer sheets, BBQ grill with utensils, board games and cards, kayaks and life vests, hot tub, firetable etc."
United States
Andy W.
The price is AED 749
AED 907 total
includes taxes & fees
31 Aug - 1 Sep
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
1 bedroom, WiFi, bed sheets

11. Turtle Cove Room

Turtle Cove Room
Kent County
The price is AED 516
AED 640 total
includes taxes & fees
17 Aug - 18 Aug
Turtle Cove Room
Property grounds

12. 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 AED 1,322
AED 2,441 total
includes taxes & fees
17 Aug - 18 Aug
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Property grounds

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, (1 review)
"My wife and I had a great time staying in this houseboat. It was our first time ever trying a houseboat and it did not disappoint us at all. The house was very clean and the host provides fully stocked kitchen cabinets, toiletries, towels, etc...We spent most of our time on the rooftop patio, soaking in the sun, and relaxing by the fire pit playing games. The bed was very comfortable as well. It was a great weekend, at a great house that has the benefit of being in a gated marina which was an...
United States
Justin M.
The price is AED 868
AED 1,944 total
includes taxes & fees
24 Aug - 25 Aug
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Exterior

14. 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.
The price is AED 519
AED 1,233 total
includes taxes & fees
30 Aug - 31 Aug
Watch Deer from a Farm Cottage
TV

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

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.4 out of 10, Good, (18 reviews)
"Nice place"
United States
christine
The price is AED 288
AED 383 total
includes taxes & fees
27 Aug - 28 Aug
Charming 2-bedroom house in Aberdeen with WiFi and AC
Interior

16. 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 AED 430
AED 1,405 total
includes taxes & fees
27 Aug - 28 Aug
Abingdon Haven Hideaway
Interior

17. 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 AED 1,223
AED 1,482 total
includes taxes & fees
2 Sep - 3 Sep
Family Retreat at Lansdowne Manor
1 bedroom, in-room safe, desk, iron/ironing board

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

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Nottingham City
The price is AED 264
AED 560 total
includes taxes & fees
18 Aug - 19 Aug
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

SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River

10/10 Excellent
"This is my fourth stay at the Springhill Suites. It’s always very clean, quiet, caters to a very professional crowd, and the staff is awesome. I had one problem, the hotel charged my card twice for incidentals and I had to wait to get $400 returned on my card for 7-10 days. That was an extreme inconvenience but other than that, the stay was great!"
Katrice 4-night trip
Posted 1 hour ago
SpringHill Suites Baltimore White Marsh/Middle River

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.