A river with a green embankment and a boat.

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Top Cities in Caroline County

A calm lake surrounded by tall trees and dense reeds.
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Denton

Denton
A forest with tall trees and a sunset in the background.
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Ridgely

Ridgely

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2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

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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

Best Western Denton Inn
2.5 star property
Denton
8.6 out of 10, Excellent, (628 reviews)
"Great place for a quick weekend getaway"
United States
Courtney
The price is NZ$233
includes taxes & fees
6 Oct - 7 Oct
Best Western Denton Inn
A modern kitchen with granite countertops, stainless steel appliances, and a dishwasher.

2. Relaxation Haven on the Shore near Choptank River

Relaxation Haven on the Shore near Choptank River
Greensboro
9.4 out of 10, Exceptional, (10 reviews)
"We were here for an Iron Man event and had such a beautiful stay. Helen is such a wonderful host and we would absolutely stay here again!"
United States
Amanda F.
Relaxation Haven on the Shore near Choptank River
A kitchen counter with a basket of snacks, a cookbook, and kitchen utensils.

3. Spacious Ridgely Home- Huge Yard, Bikes & Peaceful Porches near tourist hubs

Spacious Ridgely Home- Huge Yard, Bikes & Peaceful Porches near tourist hubs
Ridgely
10.0 out of 10, Exceptional, (1 review)
"Such a cute house in a cute little town surrounded by corn fields! We ate fresh foods the whole time we were there! The neighbor even brought us fresh veggies right from his garden! The house was well stocked with all the necessities (toilet paper, towels, blankets, etc). We wanted for nothing!!I will caution you if you have issues with mobility as it is an older house with some quirks. My elderly in-laws stayed with us and I was worried that they would fall down the step into the bathroom in...
United States
MEREDITH M.
Spacious Ridgely Home- Huge Yard, Bikes & Peaceful Porches near tourist hubs
A spacious living area with a high ceiling, wooden flooring, a central island with seating, and a kitchen with wooden cabinets and appliances.

4. Marblehead Farm I Swing set, Hot tub * Indoor Pickleball court

Marblehead Farm I Swing set, Hot tub * Indoor Pickleball court
Ridgely
Marblehead Farm I Swing set, Hot tub * Indoor Pickleball court
A living room with a brick fireplace, two armchairs, a red sofa, and large windows.

5. Little Creek Hideaway - Privacy and Perfect Family Getaway.

Little Creek Hideaway - Privacy and Perfect Family Getaway.
Preston
9.8 out of 10, Exceptional, (38 reviews)
"Property was in a great location for our needs. Enjoyed breakfast with the birds."
United States
Megan A.
Little Creek Hideaway - Privacy and Perfect Family Getaway.
A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

6. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is NZ$1,069
includes taxes & fees
28 Sept - 29 Sept
Turnbridge Manor
A two-story house with a covered patio and a swimming pool.

7. Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*
Greensboro
10.0 out of 10, Exceptional, (69 reviews)
"Had a great stay. Excellent property, beautiful location, perfect fenced yard for our dogs and lovely hosts. 100% recommend."
United States
Kirsty D.
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*
A house with a flag in front, surrounded by a well-maintained lawn and trees.

8. Choptank River waterfront 4 bed Farmhouse with camping on Eastern Shore Maryland

Choptank River waterfront 4 bed Farmhouse with camping on Eastern Shore Maryland
Greensboro
10.0 out of 10, Exceptional, (1 review)
"Beautiful, huge property with very clean and well-equipped home. We brought our kayaks and paddled in the river two days. The campground on the property is absolutely perfect for anyone wanting to camp by the river and just use the house for showering and air conditioning. It’s also just a short drive to Denton for a nice restaurant. Highly recommend this lovely farmhouse."
United States
Kathryn B.
Choptank River waterfront 4 bed Farmhouse with camping on Eastern Shore Maryland
A two-story house with a porch, two windows, and a door.

9. Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD
Denton
10.0 out of 10, Exceptional, (15 reviews)
"The house was perfect, welcoming and comfortable, will be coming back again"
United States
Dallas S.
Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

10. On 7 Acres! Riverfront Estate w/ Views in Denton

On 7 Acres! Riverfront Estate w/ Views in Denton
3.0 star property
Denton
On 7 Acres! Riverfront Estate w/ Views in Denton
A covered patio with wicker furniture, a table, and chairs, surrounded by potted plants and a grill.

11. Amazing River House Waterfront Condo on the Choptank River on 18 Acre Farm

Amazing River House Waterfront Condo on the Choptank River on 18 Acre Farm
Greensboro
9.8 out of 10, Exceptional, (50 reviews)
"Hosts were great. The house and location made for a memorable getaway. Would recommend."
United States
Brice P.
Amazing River House Waterfront Condo on the Choptank River on 18 Acre Farm
A spacious living area with a high ceiling, wooden staircase, and a fireplace.

12. Stylish Home on the Choptank River (with Tidal Beach)

Stylish Home on the Choptank River (with Tidal Beach)
Preston
10.0 out of 10, Exceptional, (55 reviews)
"Perfect location for us as we spent the thanksgiving holiday with our family in the area."
United States
Mark B.
Stylish Home on the Choptank River (with Tidal Beach)
A bedroom with a large bed, a window with curtains, and a view of a lake.

13. Eastern Shore Waterfront Retreat. Easy Access to Easton and St Michaels.

Eastern Shore Waterfront Retreat. Easy Access to Easton and St Michaels.
Denton
Eastern Shore Waterfront Retreat. Easy Access to Easton and St Michaels.
A two-story building with a covered entrance and an American flag.

14. St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.0 out of 10, Very good, (1,004 reviews)
"Great location close to downtown."
United States
Lynn
The price is NZ$173
includes taxes & fees
27 Oct - 28 Oct
St Michaels Inn
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

15. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (836 reviews)
"Beautiful location on a marina, very friendly and helpful staff, well-stocked breakfast, and great views made this a wonderful stay for our family."
United States
Karen
The price is NZ$298
includes taxes & fees
13 Oct - 14 Oct
Hyatt Place Kent Narrows & Marina
A patio with outdoor seating, overlooking a marina with boats.

16. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,002 reviews)
"Nice 1 night stay"
United States
roney
The price is NZ$253
includes taxes & fees
27 Oct - 28 Oct
Hilton Garden Inn Kent Island Marina
A lakeside view with sailboats, grassy areas, and white Adirondack chairs.

17. Sandaway Suites & Beach

Sandaway Suites & Beach
3.0 star property
Oxford
9.4 out of 10, Exceptional, (211 reviews)
"Would recommend to anyone who enjoys a peaceful location, with spectacular views!"
United States
Amber
The price is NZ$586
includes taxes & fees
29 Sept - 30 Sept
Sandaway Suites & Beach
A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.

18. The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (923 reviews)
"We had a wonderful stay and thoroughly enjoyed our time in Easton!"
United States
Miriam
The price is NZ$317
includes taxes & fees
14 Oct - 15 Oct
The Tidewater Inn
Two Adirondack chairs facing a calm body of water with a clear sky above.

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

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,002 reviews)
"Good hotel for the money and location."
United States
Marc
The price is NZ$202
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
A room with a view of a wooden deck and a gazebo by the water.

20. Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (404 reviews)
"Fantastic place; one of those that you don’t want to leave the property until the very sad time to go. Lovely staff, all of them, amazing food."
United States
Virgilio
The price is NZ$996
includes taxes & fees
26 Oct - 27 Oct
Inn at Perry Cabin
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 Caroline County Hotel Reviews

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"My room was nice, clean and cozy"
jerria 2-night trip
Posted less than an hour ago
Hyatt Regency Chesapeake Bay

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