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Great Oak Landing Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Great Oak Landing holiday rentals

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

1. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (130 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is NZ$283
includes taxes & fees
13 Oct - 14 Oct
First Floor Studio Apartment in Historic Chestertown
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

2. 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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is NZ$507
includes taxes & fees
13 Oct - 14 Oct
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

3. 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 NZ$488
includes taxes & fees
15 Oct - 16 Oct
Secluded Cottage in Middle of Chestertown
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

4. Turtle Cove Room

Turtle Cove Room
Kent County
The price is NZ$352
includes taxes & fees
19 Oct - 20 Oct
Turtle Cove Room
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

5. 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 NZ$376
includes taxes & fees
19 Oct - 20 Oct
Beachcomber Suite
A building with a gabled roof and a circular vent on the roof.

6. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is NZ$558
includes taxes & fees
13 Oct - 14 Oct
BAYSIDE BUNGALOW
A spacious living area with a dining table, sofa, and a kitchen in the background.

7. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (33 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
The price is NZ$616
includes taxes & fees
21 Oct - 22 Oct
Newly restored apartment in the heart of Chestertown
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

8. 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, (11 reviews)
"The host was incredibly friendly and communicative. The place was a lot bigger than I expected, and it was beautiful to sit out by the fire pit and look at the river nearby. And, she left us snacks and smores for the stay! A nice quiet spot to spend a night."
United States
Matthew
The price is NZ$274
includes taxes & fees
2 Nov - 3 Nov
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
A hallway with wooden flooring, a door on the right, and a window at the end.

9. 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 NZ$846
includes taxes & fees
28 Oct - 29 Oct
Wren Retweet- Country Estate in Center of C’Town
A deck with outdoor furniture, a potted plant, and a house in the background.

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

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is NZ$548
includes taxes & fees
19 Oct - 20 Oct
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A modern kitchen with white cabinetry, stainless steel appliances, and a marble countertop.

11. Private 2 story waterfront entire home w/ dedicated pier located on Sue Creek!

Private 2 story waterfront entire home w/ dedicated pier located on Sue Creek!
Essex
The price is NZ$981
includes taxes & fees
16 Oct - 17 Oct
Private 2 story waterfront entire home w/ dedicated pier located on Sue Creek!
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.

12. 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 NZ$172
includes taxes & fees
13 Oct - 14 Oct
Charming 2-bedroom house in Aberdeen with WiFi and AC
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 NZ$800
includes taxes & fees
18 Oct - 19 Oct
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
A modern kitchen with stainless steel appliances, white cabinetry, and a brick backsplash.

14. B’more Restful. Comfortable Townhome -Easy access to everywhere

B’more Restful. Comfortable Townhome -Easy access to everywhere
Dundalk
10.0 out of 10, Exceptional, (15 reviews)
"very wonderful home and very quite area "
United States
alan d.
The price is NZ$617
includes taxes & fees
13 Oct - 14 Oct
B’more Restful. Comfortable Townhome -Easy access to everywhere
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.

15. 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 NZ$670
includes taxes & fees
13 Oct - 14 Oct
Abingdon Haven Hideaway
A bed with a dark headboard, a mirror, a potted plant, and a snack basket on the bedside table.

16. 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 NZ$360
includes taxes & fees
27 Oct - 28 Oct
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
A single-story white house with a red door, a front porch, and a brick pathway leading to the entrance.

17. Watch Deer from a Farm Cottage

Watch Deer from a Farm Cottage
Bel Air
10.0 out of 10, Exceptional, (7 reviews)
"Pet friendly."
United States
Claudia L.
The price is NZ$632
includes taxes & fees
3 Nov - 4 Nov
Watch Deer from a Farm Cottage
A modern kitchen with stainless steel appliances, white cabinetry, and a large window providing a view of greenery.

18. Welcome to the secluded waterfront oasis

Welcome to the secluded waterfront oasis
Millington
8.0 out of 10, Very good, (3 reviews)
"We really enjoyed our stay here! The house was clean, cozy, and had everything we needed. The host was so nice and easy to communicate with, which made everything really easy. We felt right at home and would definitely stay here again!"
United States
Destiny H.
The price is NZ$690
includes taxes & fees
13 Oct - 14 Oct
Welcome to the secluded waterfront oasis
A wooden dock with Adirondack chairs and a ladder, overlooking a calm body of water with a distant shoreline.

19. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (24 reviews)
"Excellent Property"
United States
Buu T.
The price is NZ$1,131
includes taxes & fees
13 Oct - 14 Oct
Chesapeake Cottages- 2 Quaint Waterfront Retreats
A kitchen with wooden cabinets, a dining table, and a refrigerator.

20. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (13 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 NZ$507
includes taxes & fees
13 Oct - 14 Oct
Family Retreat at Lansdowne Manor
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

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

10/10 Excellent
"The room was clean, staff was helpful for the most part with a few exceptions, wasn’t able to get breakfast because the lady snatched everything up quickly even after seeing me wait for someone to finish making their waffles,and wasn’t many options for breakfast anyways"
Kashay 7-night trip
Posted 2 hours ago
Quality Inn & Suites Bel Air I-95 Exit 77A

Find out more about Great Oak Landing

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?

240' Private Beachfront @Kent Island Love Point - Great for Families: 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?

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 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.