Great Oak Landing Holiday Rentals, Chestertown: Private House Rentals

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Our top choices for Great Oak Landing hotels

A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.

A spacious room with a large window, a seating area with a sofa and armchairs, a small table with a plant, and a display of various items including a mannequin and shelves with products.

A marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.

1. The Lodge at Great Oak Landing

Chestertown

Steve allen

฿3,647

฿4,169 total

includes taxes & fees

26 Oct - 27 Oct

A hotel lobby with a fireplace, seating area, and a television.

A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.

A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.

A hotel room with a bed, a sofa, a dining table, and a small round table.

2. Comfort Inn & Suites Chestertown

Chestertown

Roberta

฿3,313

฿3,677 total

includes taxes & fees

15 Nov - 16 Nov

A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.

A modern lobby with a bar area, seating arrangements, and a television screen.

An outdoor patio with brick walls, green chairs, and a fire pit.

A hotel room with two beds, a bathroom, and a seating area.

3. SpringHill Suites Baltimore White Marsh/Middle River

Middle River

Soma

฿3,616

฿4,177 total

includes taxes & fees

29 Oct - 30 Oct

A modern hotel lobby with a long dining table, several chairs, and a bar area.

A hotel room with a bed, a chair, a bathtub, a framed picture, and a nightstand with a lamp.

A hotel room with a kitchenette, a large mirror, a window with curtains, a desk, and a chair.

A hotel pool area with a clear pool, lounge chairs, and a seating area with tables and chairs.

4. Hampton Inn & Suites Edgewood/Aberdeen-South

Edgewood

Thomas

฿2,879

฿3,225 total

includes taxes & fees

1 Nov - 2 Nov

A modern breakfast area with labeled dispensers for yogurt, eggs, and milk, a coffee machine, and a chalkboard menu.

A large indoor swimming pool with clear pool rules and a capacity sign, surrounded by windows and a tiled floor.

A reception area with two reception desks, a blue geometric wall design, and a wooden panel accent.

A modern hotel room with a bed, a desk, a chair, a TV, and a window with a geometric curtain.

5. Holiday Inn Express White Marsh by IHG

Nottingham

Lucia

฿3,309

฿3,822 total

includes taxes & fees

22 Nov - 23 Nov

A lobby with a reception desk, seating area, and a fireplace.

A kitchenette with a microwave, refrigerator, and shelves stocked with snacks and beverages.

A hotel dining area with tables and chairs, a television mounted on the wall, and a patterned carpet.

A hotel room with a seating area featuring green and purple chairs, a small white table, and a lamp. A framed artwork is on the wall, and there is a window with curtains.

6. Fairfield Inn & Suites by Marriott White Marsh

Nottingham

Angel

฿3,702

฿4,276 total

includes taxes & fees

19 Nov - 20 Nov

A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.

A hotel reception area with a wooden reception desk, a minibar, and a wall with a textured pattern.

A modern hotel with a stone facade, a clear entrance canopy, and a prominent Hilton Inn sign.

A modern building with a stone facade, large windows, and outdoor seating area with chairs.

7. Hilton Garden Inn Bel Air

Bel Air

Jaccilynne

฿3,559

฿3,986 total

includes taxes & fees

1 Nov - 2 Nov

An outdoor patio area with seating, a fire pit, and string lights.

A swimming pool with a tiled deck, red chairs, and a view of the outdoors.

A multi-story hotel with a modern design, featuring a covered entrance and a parking area.

A breakfast bar with a 'Good Morning' sign, a 'Inspired Table' sign, and a 'Caution Hot' sign.

8. Home2 Suites by Hilton Baltimore/White Marsh

Nottingham

Rhande

฿3,452

฿3,987 total

includes taxes & fees

22 Nov - 23 Nov

A hotel room with a bed, a desk with a chair, a sofa, and a coffee table. There is a TV on the desk and a window with curtains.

A hotel lobby with a reception desk, seating area, and a large screen.

A spacious lobby with a television, multiple seating options, a coffee station, and a large pillar.

A wedding ceremony in front of a large, classical building with steps leading up to the entrance.

9. La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

Edgewood

Johanne

฿2,664

฿2,983 total

includes taxes & fees

24 Nov - 25 Nov

A hotel lobby with multiple seating areas, a coffee station, and a kitchen in the background.

A vending machine with snacks and a drink dispenser.

A hotel room with a sofa, a bed, a desk, and a lamp.

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

Edgewood

Jose

฿2,109

฿2,362 total

includes taxes & fees

27 Oct - 28 Oct

A spacious living area with a staircase, a fireplace, a sofa, and a dining area.

A dual-monitor workstation with two chairs, a desktop computer, and framed artwork on the wall.

A Country Inn & Suites hotel with a brick facade, multiple windows, and a sign indicating the entrance.

A gym with treadmills, elliptical machines, and a weight machine.

11. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Bel Air

Anne

฿3,008

฿3,369 total

includes taxes & fees

1 Nov - 2 Nov

A spacious living room with a fireplace, a stone accent wall, and a television mounted above it.

A hotel room with a bed, a desk, a chair, a sofa, and a painting on the wall.

A living room with a fireplace, a television, and a stone accent wall.

A hotel room with a bed, a couch, a painting, and a window with curtains.

12. Red Roof Inn & Suites Chestertown

Chestertown

Kate

฿2,431

฿2,698 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a large bed, a sofa, a TV, and a wall-mounted artwork.

A pool area with chairs and a changing room.

A modern lounge area with sofas, armchairs, and tables.

An outdoor patio area with a sectional sofa, lounge chairs, and a round table.

13. SpringHill Suites by Marriott Edgewood/Aberdeen

Bel Air

Nita

฿3,559

฿3,986 total

includes taxes & fees

1 Nov - 2 Nov

A modern lobby with a curved sofa, red armchairs, a fireplace, and a dining area with green chairs.

A hotel room with a dining area, a TV, a dresser, and a tray table.

An outdoor patio with round tables and chairs, a barbecue grill, and umbrellas providing shade.

An indoor swimming pool with lounge chairs and a hot tub, surrounded by large windows.

14. Homewood Suites by Hilton Bel Air

Bel Air

Jennifer

฿3,415

฿3,825 total

includes taxes & fees

1 Nov - 2 Nov

A buffet area with multiple self-service stations, including trays of omelets and other prepared foods.

A coffee station with two coffee machines, a coffee press, and various coffee accessories on a wooden counter.

A modern office with a desk, two chairs, a computer, and a lamp. Large windows provide a view of the outdoors.

An aerial view of a sports complex with multiple soccer fields, parking areas, and buildings.

15. Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Edgewood

Robert

฿2,802

฿3,139 total

includes taxes & fees

23 Nov - 24 Nov

An outdoor patio area with wicker furniture, a fire pit, and umbrellas.

A restaurant interior with multiple tables and booths, wooden flooring, and artwork on the walls.

A modern reception area with a wooden reception desk, a digital screen, and a wall-mounted decorative piece.

A modern living room with a stone accent wall, a flat-screen TV, and a dining area with wooden furniture.

16. Fairfield Inn & Suites by Marriott Aberdeen

Aberdeen

Robert

฿3,737

฿4,185 total

includes taxes & fees

1 Nov - 2 Nov

A spacious lobby with a high ceiling, a stone fireplace, and a seating area with orange sofas and chairs.

A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a coffee maker.

An outdoor patio with a round table, chairs, a stone fireplace, and a grill.

A hotel room with a living area, a bed, a desk, a television, a fireplace, and a kitchenette.

17. Residence Inn by Marriott Baltimore White Marsh

Nottingham

Mary

฿4,025

฿4,649 total

includes taxes & fees

8 Nov - 9 Nov

An indoor swimming pool with clear water, a changing room, and exercise equipment.

A hotel entrance with a covered walkway, brick facade, and multiple windows.

A living room with a fireplace, a television mounted above it, and a coffee table with decorative items.

A spacious lobby with a fireplace, comfortable seating, and large windows.

18. Hilton Garden Inn Baltimore/White Marsh

Nottingham

Glyne

฿3,299

฿3,810 total

includes taxes & fees

20 Nov - 21 Nov

A Hampton Inn with a 'Welcome' sign under a covered entrance, surrounded by greenery.

A patio area with a fire pit, outdoor seating, and umbrellas providing shade.

A hotel room with a desk, chair, television, and a painting on the wall.

A hotel dining area with a long wooden table, multiple chairs, and a buffet counter.

19. Hampton Inn Baltimore/White Marsh

Nottingham

Olusola Sanusi

฿3,433

฿3,965 total

includes taxes & fees

1 Nov - 2 Nov

A hotel entrance with a clear sign reading "LA QUINTA".

A modern hotel lobby with a reception desk, two computer workstations, a seating area, and a decorative vase on a table.

A hotel lobby with seating areas, a TV on the wall, and patterned curtains.

A vending area with two beverage dispensers, a wall-mounted display of personal care items, and shelves stocked with snacks and beverages.

20. City Express by Marriott Aberdeen

Aberdeen

robin

฿3,208

฿3,592 total

includes taxes & fees

26 Oct - 27 Oct

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Top Great Oak Landing Hotel Reviews

Holiday Inn Express White Marsh by IHG

10/10 Excellent

"Wonderful stay thanks!"

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent

"Everyone seemed to care and were nice"

WoodSpring Suites Baltimore White Marsh - Nottingham

8/10 Good

"WiFi was not working"

Red Roof Inn & Suites Chestertown

8/10 Good

"The place was a little better than average, I'd stay here again. The room smelled musty as if it used to be a smoking room, but not completely unbearable. The desk help was not friendly but not rude either...kind of robotic. Easy parking, roomy room. Decent shower."

More cheap stays in Great Oak Landing

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

2112a Emmorton Park Road Edgewood MD

฿2,109

฿2,362 total

27 Oct - 28 Oct

includes taxes & fees

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

฿2,431

฿2,698 total

1 Nov - 2 Nov

includes taxes & fees

7.2/10 Good! (511 reviews)

Hampton Inn & Suites Edgewood/Aberdeen-South

2110 Emmorton Park Rd Edgewood MD

฿2,879

฿3,225 total

1 Nov - 2 Nov

includes taxes & fees

9.4/10 Exceptional! (1,001 reviews)

WoodSpring Suites Baltimore White Marsh - Nottingham

4985 Mercantile Road Baltimore MD

฿2,836

฿3,276 total

25 Oct - 26 Oct

includes taxes & fees

Hampton Inn Baltimore/White Marsh

8225 Town Center Drive Baltimore MD

฿3,433

฿3,965 total

1 Nov - 2 Nov

includes taxes & fees

Best Western Plus Hotel & Conference Center

5625 O'Donnell Street Baltimore MD

฿3,604

฿4,234 total

4 Nov - 5 Nov

includes taxes & fees

Frequently asked questions

Where is the best place to stay in Great Oak Landing?

The Lodge at Great Oak Landing is one of the top choices for your stay based on our traveller data. This lodge offers a golf course and 2 restaurants. Other good choices for your visit to the area are La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh and Best Western Plus Hotel & Conference Center. See all available top hotels, or vacation rentals in Great Oak Landing.

If I need to cancel my hotel reservation in Great Oak Landing, will I receive a refund?

Yes! You'll find that most hotel reservations are fully refundable if you cancel before the hotel's cancellation deadline, which is usually within 24-48 hours of check in. If your reservation is non-refundable, it might still be possible to cancel it and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Great Oak Landing.

What's the best LGBTQ-friendly place to stay in Great Oak Landing?

The Lodge at Great Oak Landing is a top LGBTQ-friendly lodge, and features a golf course and free WiFi. See all available hotels listed as LGBTQ-friendly in Great Oak Landing.

How is it to stay in Great Oak Landing?

Visitors can enjoy all that Great Oak Landing has to offer, including its restaurants. Tourists to the city can also enjoy its welcoming locals. There are 351 hotels and other accommodation options in the surrounding area. Find out more about Great Oak Landing.

What is there to see in Great Oak Landing?

The picturesque setting of Northern Chesapeake Bay and Chesapeake Bay exemplify the area's natural beauty. You'll also find Historical Society of Kent County Maryland and Chestertown Historic District in the area. Take a look at what more there is to see and do in Expedia's Great Oak Landing guide.

What's the weather like in Great Oak Landing?

The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Great Oak Landing is 1223 mm.

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Find hotels in Great Oak Landing, MD from ฿2,362

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Great Oak Landing

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Great Oak Landing hotels

1. The Lodge at Great Oak Landing

2. Comfort Inn & Suites Chestertown

3. SpringHill Suites Baltimore White Marsh/Middle River

4. Hampton Inn & Suites Edgewood/Aberdeen-South

5. Holiday Inn Express White Marsh by IHG

6. Fairfield Inn & Suites by Marriott White Marsh

7. Hilton Garden Inn Bel Air

8. Home2 Suites by Hilton Baltimore/White Marsh

9. La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

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

11. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

12. Red Roof Inn & Suites Chestertown

13. SpringHill Suites by Marriott Edgewood/Aberdeen

14. Homewood Suites by Hilton Bel Air

15. Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

16. Fairfield Inn & Suites by Marriott Aberdeen

17. Residence Inn by Marriott Baltimore White Marsh

18. Hilton Garden Inn Baltimore/White Marsh

19. Hampton Inn Baltimore/White Marsh

20. City Express by Marriott Aberdeen

Top Great Oak Landing Hotel Reviews

Holiday Inn Express White Marsh by IHG

Hampton Inn & Suites Edgewood/Aberdeen-South

WoodSpring Suites Baltimore White Marsh - Nottingham

Red Roof Inn & Suites Chestertown

More cheap stays in Great Oak Landing

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

Red Roof Inn & Suites Chestertown

Hampton Inn & Suites Edgewood/Aberdeen-South

WoodSpring Suites Baltimore White Marsh - Nottingham

Hampton Inn Baltimore/White Marsh

Best Western Plus Hotel & Conference Center

Frequently asked questions

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