Fairlee Holiday Rentals, Chestertown: Private House Rentals

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Our top choices for Fairlee hotels

A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.

A Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.

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

A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

1. Comfort Inn & Suites Chestertown

Chestertown

Amy

฿3,270

฿3,629 total

includes taxes & fees

8 Nov - 9 Nov

A hotel room with a sofa, two beds, a painting, and a lamp.

A multi-story brick building with a covered entrance and a parking lot.

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

A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.

2. Red Roof Inn & Suites Chestertown

Chestertown

Kate

฿2,413

฿2,678 total

includes taxes & fees

8 Nov - 9 Nov

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

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.

3. The Lodge at Great Oak Landing

Chestertown

Sandra

฿3,620

฿4,138 total

includes taxes & fees

21 Oct - 22 Oct

A two-story house with a covered porch, a staircase, and a garden area.

A bedroom with a bed, a ceiling fan, a door, a chair, and a wall with three framed pictures.

A dining room with a long wooden table set for six, surrounded by chairs. There are framed pictures on the walls, a window with a view of trees, and a sofa in the background.

A garden with a lawn and a table with chairs under a canopy.

4. Haven Point Inn and Gallery

Rock Hall

Joe

฿4,495

฿4,990 total

includes taxes & fees

20 Oct - 21 Oct

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

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

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

A hotel with a modern facade, a covered entrance, and a red car parked outside.

5. SpringHill Suites Baltimore White Marsh/Middle River

Middle River

Rashawna

฿3,589

฿4,146 total

includes taxes & fees

22 Oct - 23 Oct

A boat deck with a white bench and a view of a calm lake and distant trees.

A large white barn with a star on the side, surrounded by a field of sunflowers, and a large house with a green roof in the background.

A sunflower field with a white barn and a large house in the background.

A modern living room with a large sofa, a small armchair, a coffee table, and a fireplace.

6. Inn at Huntingfield Creek

Rock Hall

Christine

฿4,696

฿5,213 total

includes taxes & fees

16 Nov - 17 Nov

A row of motel rooms with stone walls and red doors.

A two-story building with a brick facade, large windows, and a sloped roof.

A living room with two patterned armchairs, a wooden coffee table, and a standing fan.

A hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.

7. Driftwood Inn

Chestertown

Kathy

฿2,128

฿2,362 total

includes taxes & fees

18 Oct - 19 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 pool area with a clear pool, lounge chairs, and a seating area with tables and chairs.

A hotel reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.

8. Hampton Inn & Suites Edgewood/Aberdeen-South

Edgewood

Thomas

฿2,858

฿3,201 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 snack and beverage vending area with a sign for the Express Shop.

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

9. Holiday Inn Express White Marsh by IHG

Nottingham

Kevin

฿3,532

฿4,079 total

includes taxes & fees

1 Nov - 2 Nov

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

An outdoor event area with round tables and a view of the water.

10. Hyatt Place Kent Narrows & Marina

Grasonville

Joseph

฿5,113

฿5,675 total

includes taxes & fees

25 Oct - 26 Oct

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

A hotel room with a large bed, a wooden headboard, a desk with a chair, 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.

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

11. Fairfield Inn & Suites by Marriott White Marsh

Nottingham

Angel

฿3,891

฿4,494 total

includes taxes & fees

16 Nov - 17 Nov

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

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.

A modern lounge area with a green sofa, red ottomans, a wooden bench, and a wooden table.

12. Home2 Suites by Hilton Baltimore/White Marsh

Nottingham

Rhande

฿3,408

฿3,936 total

includes taxes & fees

1 Nov - 2 Nov

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

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

A lobby with a beige carpet, a reception desk, and two beige armchairs.

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

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

Edgewood

Jose

฿2,063

฿2,310 total

includes taxes & fees

29 Oct - 30 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 hotel room with two beds, a desk with a television, a chair, and a window with curtains.

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

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

Bel Air

Vanessa

฿2,986

฿3,345 total

includes taxes & fees

2 Nov - 3 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.

15. Hilton Garden Inn Bel Air

Bel Air

Jaccilynne

฿3,545

฿3,971 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.

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

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

A hotel dining area with a buffet setup, multiple dining tables, chairs, and a ceiling fan.

16. Homewood Suites by Hilton Bel Air

Bel Air

Jennifer

฿3,390

฿3,797 total

includes taxes & fees

15 Nov - 16 Nov

A hotel room with a bed, a chair, a nightstand, a lamp, and a painting on the wall.

An outdoor patio area with picnic tables and a Samuel Adams branded umbrella.

A restaurant with a counter, seating area, and a clock on the wall.

17. Best Western Kent Narrows Inn

Grasonville

Wesley

฿3,012

฿3,344 total

includes taxes & fees

9 Nov - 10 Nov

A hotel room with a kitchenette, a desk, a chair, a sofa, and a bathroom visible through an open door.

A hotel room with a large bed, a desk, a sofa, and a patterned carpet.

A hotel room with a kitchenette, a sofa, a coffee table, and a patterned rug.

A buffet setup with multiple self-service food dispensers.

18. Holiday Inn Belcamp - Aberdeen Area by IHG

Belcamp

Jenny

฿2,949

฿3,303 total

includes taxes & fees

11 Nov - 12 Nov

Two Adirondack chairs facing a calm body of water with a clear sky above.

A hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.

A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

A reception desk with a modern design, a digital display, and a check-in counter.

19. Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

Marc

฿3,318

฿3,683 total

includes taxes & fees

15 Nov - 16 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 with a prominent sign, multiple parking spaces, and a covered entrance.

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

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

Edgewood

Jenri

฿2,669

฿2,990 total

includes taxes & fees

9 Nov - 10 Nov

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Top Fairlee Hotel Reviews

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"The staff was awesome. Very professional and helpful. Our room was cleaned and well maintained. The food was great and the spa service was awesome as well."

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."

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent

"Just like always a nice quiet place to stay"

SpringHill Suites Baltimore White Marsh/Middle River

8/10 Good

"The staff answered any and all questions, were friendly and helpful. The room was spacious and clean. Breakfast was available buffet style and the coffee was hot. There were plenty of parking spaces, so parking was not a problem. There were other food options right across the street."

WoodSpring Suites Baltimore White Marsh - Nottingham

8/10 Good

"The room was clean and comfortable"

Hyatt Place Kent Narrows & Marina

10/10 Excellent

"We stay here frequently. The best hotel in a great location."

Country Inn & Suites by Radisson, Baltimore North, MD

8/10 Good

"Our stay was quite un eventful and very restful with the following exception; I had checked the wrong date on the arrival and called Expedia to correct it which they said they would do, then beyond that my brother in law passed away and we had to leave a day early, which the hotel was very understanding and only charged for the nights we stayed. BUT Expedia has not refunded any of the excessive charges for either of the two nights involved. They sent a letter saying the hotel would not accept refunding the two nights, which is completely not true as I have a copy of the bill from the hotel and it only covers the two nights we actually spent. At this time I can never trust Expedia again to book anything!"

Hampton Inn Baltimore/White Marsh

8/10 Good

"good"

More cheap stays in Fairlee

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

2112a Emmorton Park Road Edgewood MD

฿2,063

฿2,310 total

29 Oct - 30 Oct

includes taxes & fees

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

฿2,413

฿2,678 total

8 Nov - 9 Nov

includes taxes & fees

7.2/10 Good! (510 reviews)

Hampton Inn & Suites Edgewood/Aberdeen-South

2110 Emmorton Park Rd Edgewood MD

฿2,858

฿3,201 total

1 Nov - 2 Nov

includes taxes & fees

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

฿3,012

฿3,344 total

9 Nov - 10 Nov

includes taxes & fees

Hampton Inn Baltimore/White Marsh

8225 Town Center Drive Baltimore MD

฿3,408

฿3,936 total

28 Oct - 29 Oct

includes taxes & fees

SpringHill Suites Baltimore White Marsh/Middle River

6110 Greenleigh Avenue Middle River MD

฿3,589

฿4,146 total

22 Oct - 23 Oct

includes taxes & fees

9/10 Wonderful! (959 reviews)

Frequently asked questions

Where is the best place to stay in Fairlee?

Hampton Inn Baltimore/White Marsh, located 18.6 mi (29.9 km) from the heart of Fairlee, is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Hampton Inn & Suites Edgewood/Aberdeen-South and La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A. See all available top hotels, or vacation rentals in Fairlee.

If I need to cancel my hotel reservation in Fairlee, will I receive a refund?

Yes! The majority of hotel reservations are refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of check in. If you booked a non-refundable reservation, you might still have the option to cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Fairlee.

What is staying in Fairlee like?

Those travelling to Fairlee will definitely enjoy the sights to see and things to do. There are 347 hotels and other accommodation options in the surrounding area. Find out more about Fairlee.

What should I see while I'm in Fairlee?

Places to visit in the wider area include Chestertown Historic District, Historical Society of Kent County Maryland and Rock Hall Harbor. You'll also find Rolphs Wharf Marina and Betterton Beach in the area. Take a look at what more there is to see and do in Expedia's Fairlee guide.

What's the seasonal weather like in Fairlee?

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 Fairlee is 1232 mm.

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Find hotels in Fairlee, MD from ฿2,310

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Fairlee

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Fairlee hotels

1. Comfort Inn & Suites Chestertown

2. Red Roof Inn & Suites Chestertown

3. The Lodge at Great Oak Landing

4. Haven Point Inn and Gallery

5. SpringHill Suites Baltimore White Marsh/Middle River

6. Inn at Huntingfield Creek

7. Driftwood Inn

8. Hampton Inn & Suites Edgewood/Aberdeen-South

9. Holiday Inn Express White Marsh by IHG

10. Hyatt Place Kent Narrows & Marina

11. Fairfield Inn & Suites by Marriott White Marsh

12. Home2 Suites by Hilton Baltimore/White Marsh

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

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

15. Hilton Garden Inn Bel Air

16. Homewood Suites by Hilton Bel Air

17. Best Western Kent Narrows Inn

18. Holiday Inn Belcamp - Aberdeen Area by IHG

19. Holiday Inn Express Annapolis East-Kent Island by IHG

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

Top Fairlee Hotel Reviews

The Inn at Chesapeake Bay Beach Club

Red Roof Inn & Suites Chestertown

Hampton Inn & Suites Edgewood/Aberdeen-South

SpringHill Suites Baltimore White Marsh/Middle River

WoodSpring Suites Baltimore White Marsh - Nottingham

Hyatt Place Kent Narrows & Marina

Country Inn & Suites by Radisson, Baltimore North, MD

Hampton Inn Baltimore/White Marsh

More cheap stays in Fairlee

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

Red Roof Inn & Suites Chestertown

Hampton Inn & Suites Edgewood/Aberdeen-South

Best Western Kent Narrows Inn

Hampton Inn Baltimore/White Marsh

SpringHill Suites Baltimore White Marsh/Middle River

Frequently asked questions

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