Find & Book the Best Hotels in Caroline County for 2026

Top Cities in Caroline County

A calm lake surrounded by tall trees and dense reeds.

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Our top choices for Caroline County hotels

A swimming pool with a metal ladder, lounge chairs, and a small building in the background.

1. Best Western Denton Inn

Denton

Courtney

NT$4,359 total

includes taxes & fees

Aug 31 - Sep 1

A hallway with wooden flooring, a chandelier, a mirror, and a bookshelf.

2. Riverfront Denton Estate on 7 Acres w/ Heated Pool

Denton

A two-story building with a covered entrance and an American flag.

3. St Michaels Inn

St. Michaels

Karen

NT$3,123 total

includes taxes & fees

Aug 31 - Sep 1

A patio with outdoor seating, overlooking a marina with boats.

4. Hilton Garden Inn Kent Island Marina

Grasonville

roney

NT$5,191 total

includes taxes & fees

Aug 30 - Aug 31

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

5. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

NT$5,906 total

includes taxes & fees

Sep 8 - Sep 9

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

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

Grasonville

Jackie

NT$4,491 total

includes taxes & fees

Sep 1 - Sep 2

A grassy area with white Adirondack chairs and a view of sailboats on the water.

7. Sandaway Suites & Beach

Oxford

Sandra

NT$9,461 total

includes taxes & fees

Aug 26 - Aug 27

A room with a view of a wooden deck and a gazebo by the water.

8. Inn at Perry Cabin

Downtown St. Michaels

Andrew

NT$14,910 total

includes taxes & fees

Sep 7 - Sep 8

A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.

9. The Tidewater Inn

Easton

Diana

NT$6,273 total

includes taxes & fees

Aug 24 - Aug 25

A two-story house with a porch, a front door, and a small garden area.

10. The Wildset

Downtown St. Michaels

Paula

NT$9,172 total

includes taxes & fees

Sep 8 - Sep 9

A swimming pool with a mural, lounge chairs, and a hot tub.

11. Best Western Kent Narrows Inn

Grasonville

chanel

NT$4,500 total

includes taxes & fees

Aug 30 - Aug 31

A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.

12. Best Western Plus Easton Inn & Suites

Easton

Margaret

NT$4,871 total

includes taxes & fees

Aug 24 - Aug 25

A hotel room with a sofa, armchairs, a TV, a bed, and a large window.

13. Quality Inn Grasonville near Kent Island

Grasonville

Faezeh

NT$3,563 total

includes taxes & fees

Sep 14 - Sep 15

A modern building with large windows, a brick facade, and a well-maintained lawn with flower beds.

14. Quality Inn

Easton

Karen

NT$3,962 total

includes taxes & fees

Aug 26 - Aug 27

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.

15. The Oaks Waterfront

Easton

Jeffrey

NT$15,423 total

includes taxes & fees

Aug 26 - Aug 27

A buffet with labeled food stations including omelets and cheese.

16. Holiday Inn Express Easton by IHG

Easton

Alicia

NT$5,572 total

includes taxes & fees

Aug 24 - Aug 25

A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.

17. Fairfield Inn & Suites by Marriott Easton

Easton

Stephanie

NT$4,736 total

includes taxes & fees

Aug 30 - Aug 31

A two-story house with a swimming pool, outdoor seating, and a covered patio area.

18. George Brooks House B&B

St. Michaels

Erin

NT$7,412 total

includes taxes & fees

Aug 24 - Aug 25

A modern hotel dining area with a long table, four chairs, and three pendant lights.

19. Hampton Inn Easton

Easton

Jason

NT$5,535 total

includes taxes & fees

Aug 31 - Sep 1

A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.

20. Parsonage Inn

Downtown St. Michaels

Paul

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Top Caroline County Hotel Reviews

Tru by Hilton Georgetown

10/10 Excellent

"Check in was easy. Snacks were plentiful. The facility is very clean. The pillows are oh-so-soft!!!! Breakfast had plenty of choices. I suggest adding non-pork meat as an alternative, but I enjoyed my breakfast regardless. I’d definitely recommend Tru!!!!"

Microtel Inn & Suites By Wyndham Georgetown Delaware Beaches

8/10 Good

"The room was very clean. A light above our kitchen area in the suite did not work so it was a little inconvenient. Our bathtub was chipped and stained. The outdoor pool was dirty and not well maintained. However every one of the staff members was very friendly and helpful"

Best Western Kent Narrows Inn

10/10 Excellent

"The hotel staff was very accommodating, updating our room choice once we had to add our daughter to the trip. After we checked in, our TV wasn’t working. Someone came to the room right away to problem solve. Once he couldn’t figure it out, he sent us to another room. We will surely stay there again."

Hyatt Regency Chesapeake Bay

10/10 Excellent

"Excellent well-maintained rooms with new ceiling fan. Summer amenities are geared to families and include mini golf, multiple pools indoors & outdoors, day spa, convenience shop with coffee , pool tables (although not as well maintained as other areas of the property), walking paths, and a regulationgolf course. Families can be quite boisterous; we will opt for calmer winter months in future."

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Our top choices for Caroline County hotels

1. Best Western Denton Inn

2. Riverfront Denton Estate on 7 Acres w/ Heated Pool

3. St Michaels Inn

4. Hilton Garden Inn Kent Island Marina

5. Hyatt Place Kent Narrows & Marina

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

7. Sandaway Suites & Beach

8. Inn at Perry Cabin

9. The Tidewater Inn

10. The Wildset

11. Best Western Kent Narrows Inn

12. Best Western Plus Easton Inn & Suites

13. Quality Inn Grasonville near Kent Island

14. Quality Inn

15. The Oaks Waterfront

16. Holiday Inn Express Easton by IHG

17. Fairfield Inn & Suites by Marriott Easton

18. George Brooks House B&B

19. Hampton Inn Easton

20. Parsonage Inn

Top Caroline County Hotel Reviews

Tru by Hilton Georgetown

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