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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 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, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is £113
includes taxes & fees
9 Nov - 10 Nov
First Floor Studio Apartment in Historic Chestertown
A garden with a wooden bridge, lush greenery, and a variety of plants.

2. 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 £207
includes taxes & fees
1 Dec - 2 Dec
Secluded Cottage in Middle of Chestertown
A spacious living area with a dining table, sofa, and a kitchen in the background.

3. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 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 £251
includes taxes & fees
16 Nov - 17 Nov
Newly restored apartment in the heart of Chestertown
A building with a gabled roof and a circular vent on the roof.

4. 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 £214
includes taxes & fees
7 Nov - 8 Nov
BAYSIDE BUNGALOW
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

5. 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, (33 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is £216
includes taxes & fees
16 Nov - 17 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A covered porch with a wooden bench, potted plants, and a decorative railing.

6. 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 £326
includes taxes & fees
8 Nov - 9 Nov
Wren Retweet- Country Estate in Center of C’Town
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

7. Turtle Cove Room

Turtle Cove Room
Kent County
10.0 out of 10, Exceptional, (1 review)
"The host was very communicative. The room was clean. It was quiet and peaceful. There were blackout curtains on the windows. A very pleasant stay."
United States
Jennifer M.
The price is £144
includes taxes & fees
9 Nov - 10 Nov
Turtle Cove Room
A wooden staircase leading to a beach with a clear view of the sea.

8. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
The price is £262
includes taxes & fees
30 Nov - 1 Dec
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

9. 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 £150
includes taxes & fees
9 Nov - 10 Nov
Beachcomber Suite
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

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, (13 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 £110
includes taxes & fees
11 Nov - 12 Nov
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

11. 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 £206
includes taxes & fees
14 Nov - 15 Nov
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A modern kitchen with stainless steel appliances, white cabinetry, and a brick backsplash.

12. 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, (18 reviews)
"very wonderful home and very quite area "
United States
alan d.
The price is £231
includes taxes & fees
9 Nov - 10 Nov
B’more Restful. Comfortable Townhome -Easy access to everywhere
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, (4 reviews)
"We had a phenomenal time celebrating our engagement at Flohom! The space was spotlessly clean, super comfortable, and peaceful. The location was fantastic, and the hosting was top-notch from start to finish. We couldn't have asked for a better experience to"
United States
Charles W.
The price is £336
includes taxes & fees
8 Nov - 9 Nov
FLOHOM 14 - Luxury Houseboat with Chesapeake Bay Panoramic Views
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.

14. 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 £74
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom house in Aberdeen with WiFi and AC
A wooden dock with Adirondack chairs and a ladder, overlooking a calm body of water with a distant shoreline.

15. 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 £449
includes taxes & fees
9 Nov - 10 Nov
Chesapeake Cottages- 2 Quaint Waterfront Retreats
A single-story white house with a front porch, a mailbox, and a number '715' on the door.

16. 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 £230
includes taxes & fees
9 Nov - 10 Nov
Watch Deer from a Farm Cottage
A kitchen with wooden cabinets, a dining table, and a refrigerator.

17. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (14 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 £202
includes taxes & fees
9 Nov - 10 Nov
Family Retreat at Lansdowne Manor
A bed with a dark headboard, a mirror, a potted plant, and a snack basket on the bedside table.

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
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 £186
includes taxes & fees
11 Nov - 12 Nov
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

A modern hotel lobby with a long dining table, several chairs, and a bar area.
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood

8/10 Good

Room was spacious and super clean, beds wee comfy and staff were friendly and the breakfast was good enough. Given that I chose the hotel because it had a gym and good ratings I was really disappointed that all three treadmills were broken in different ways. The keycards to the hotel room just kept failing too. I had to get them to rescan them multiple times because they were losing magnetism….yet that rarely happens in other hotels. There is also no bar so nowhere to sit with my colleague...
United Kingdom
Ben
Reviewed March 14, 2026
Hampton Inn & Suites Edgewood/Aberdeen-South

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, apart-hotels, 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 £73 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 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.