Search Caroline County Hotels
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
Our top choices for Caroline County hotels
1. Best Western Denton Inn
Best Western Denton InnDenton
8.6 out of 10, Excellent, (632 reviews)
The price is CA $169
CA $187 total
includes taxes & fees
Oct 12 - Oct 13
2. Relaxation Haven on the Shore near Choptank River
Relaxation Haven on the Shore near Choptank RiverGreensboro
9.4 out of 10, Exceptional, (10 reviews)
3. Marblehead Farm I Swing set, Hot tub * Indoor Pickleball court
Marblehead Farm I Swing set, Hot tub * Indoor Pickleball courtRidgely
10.0 out of 10, Exceptional, (1 review)
"Beautiful place. We stayed during Ironman 2026 and were there long enough to sleep. Wish we could have enjoyed just hanging out in this peaceful country home for a full day."
Chad S.
4. 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)
5. Turnbridge Manor
Turnbridge ManorDenton
9.8 out of 10, Exceptional, (18 reviews)
"Really nice place and you can walk to everything.Will stay again!"
Glenn S.
The price is CA $512
CA $879 total
includes taxes & fees
Oct 13 - Oct 14
6. Spacious Ridgely Home- Huge Yard, Bikes & Peaceful Porches near tourist hubs
Spacious Ridgely Home- Huge Yard, Bikes & Peaceful Porches near tourist hubsRidgely
10.0 out of 10, Exceptional, (1 review)
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, (70 reviews)
"Had a great stay. Excellent property, beautiful location, perfect fenced yard for our dogs and lovely hosts. 100% recommend."
Kirsty D.
8. Choptank River waterfront 4 bed Farmhouse with camping on Eastern Shore Maryland
Choptank River waterfront 4 bed Farmhouse with camping on Eastern Shore MarylandGreensboro
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."
Kathryn B.
9. Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD
Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MDDenton
10.0 out of 10, Exceptional, (15 reviews)
"The house was perfect, welcoming and comfortable, will be coming back again"
Dallas S.
10. On 7 Acres! Riverfront Estate w/ Views in Denton
On 7 Acres! Riverfront Estate w/ Views in DentonDenton
11. 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)
"Great Lake house. Fully stocked. Clean. Great for a family. Would stay again."
Wes H.
12. 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 FarmGreensboro
9.8 out of 10, Exceptional, (50 reviews)
"Hosts were great. The house and location made for a memorable getaway. Would recommend."
Brice P.
13. Eastern Shore Waterfront Retreat. Easy Access to Easton and St Michaels.
Eastern Shore Waterfront Retreat. Easy Access to Easton and St Michaels.Denton
14. On 7 Acres! Riverfront Estate w/ Views in Denton
On 7 Acres! Riverfront Estate w/ Views in DentonDenton
10.0 out of 10, Exceptional, (18 reviews)
"My family enjoyed our stay the amenities were outstanding. The property was gorgeous and we would love to come back next year! "
Dan S.
15. St Michaels Inn
St Michaels InnSt. Michaels
8.0 out of 10, Very good, (1,001 reviews)
"Great location close to downtown."
Lynn
The price is CA $122
CA $134 total
includes taxes & fees
Nov 2 - Nov 3
16. Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
9.4 out of 10, Exceptional, (841 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."
Karen
The price is CA $216
CA $240 total
includes taxes & fees
Oct 18 - Oct 19
17. Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
9.2 out of 10, Wonderful, (1,000 reviews)
"Good hotel for the money and location."
Marc
The price is CA $141
CA $156 total
includes taxes & fees
Nov 8 - Nov 9
18. The Tidewater Inn
The Tidewater InnEaston
8.8 out of 10, Excellent, (925 reviews)
"We had a wonderful stay and thoroughly enjoyed our time in Easton!"
Miriam
The price is CA $234
CA $258 total
includes taxes & fees
Nov 2 - Nov 3
19. Sandaway Suites & Beach
Sandaway Suites & BeachOxford
9.4 out of 10, Exceptional, (214 reviews)
"Would recommend to anyone who enjoys a peaceful location, with spectacular views!"
Amber
The price is CA $427
CA $469 total
includes taxes & fees
Oct 20 - Oct 21
20. Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island MarinaGrasonville
9.0 out of 10, Wonderful, (1,001 reviews)
The price is CA $197
CA $219 total
includes taxes & fees
Oct 19 - Oct 20
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.
Top Caroline County Hotel Reviews
Bally's Dover Casino Resort
10/10 Excellent
Explore a world of travel with Expedia
- Downtown Cambridge Hotels
- Walk to Park & River
- Easton Hotels
- Queenstown Waterfront
- Sherwood Forest Hotels
- Hotels with Waterslides in Cambridge
- Preston Hotels
- Cambridge Hotels
- Grasonville Hotels
- Selby-On-The-Bay Hotels
- Hotels near Harriet Tubman Underground Railroad National Historical Park
- Highland Beach Hotels
- Maryland Hotels
- North Beach Hotels
- Minutes from Downtown St. Michaels
- Luxury Hotels in Cambridge
- Chesapeake Bay Large Beautiful Waterfront Estate! "Belle Aire Landing"
- Hotels near Blackwater National Wildlife Refuge
- Oxford Hotels
- New! Gorgeous Waterfront Estate with Saltwater pool
- Hyatt Hotels in St. Michaels
- Spacious 7
- Hotels with an Indoor Pool in Kent Narrows
- Vacation Homes in Pomona
- Ridgely Hotels
- Centreville Hotels
- Parole Hotels
- Marriott Hotels & Resorts in St. Michaels
- Salisbury Hotels
- Queenstown Hotels
- Chalets in Centreville
- Wades Point Inn
- Motels in Secretary
- Apartments in Oxford
- Cass
- Hotels with Waterslides in Downtown Cambridge
- Ironman & Eagleman
- Motels in Royal Oak
- Hilton Hotels in Eastern Shore
- Hotels near Baltimore Washington Intl. Thurgood Marshall
- Stevensville Hotels
- Edgewater Hotels
- Cabin Rentals in Newcomb
- Adults Only Resorts & in Eastern Shore
- Denton Hotels
- 5 Star Hotels in Secretary
- Casino Hotels in Cambridge
- Kent Island Resort
- Cabin Rentals in Goldsboro
- Hotels near Avalon Theatre
- Pet-Friendly Hotels in Cambridge
- Family Retreat at Lansdowne Manor
- The Colonial Farmhouse with Private Boat Rental
- Minutes from Downtown St. Michaels
- St. Michaels Hotels
- Ocean City Hotels
- Cabin Rentals in Federalsburg
- Chesapeake Beach Hotels
- Cabin Rentals in Eastern Shore
- Robert Morris Inn
- Cottages in Linkwood
- Baltimore Hotels
- Marriott Hotels & Resorts in Cambridge
- Arundel on the Bay Hotels
- Houseboats in Queenstown
- 4 Star Hotels in Algonquin
- B&B in Preston
- Oceanfront Hotels in Eastern Shore
- B&B in Royal Oak
- Annapolis Hotels
- Motels in Eastern Shore
- Flights from Vancouver (YVR) to Baltimore (BWI)
- Flights from Winnipeg (YWG) to Baltimore (BWI)
- Flights from Preston
- Flights from Cincinnati (CVG) to Easton (ESN)
- Flights from Church Hill
- Flights from Allentown (ABE) to Easton (ESN)
- Flights to Baltimore
- Flights to Maryland
- Flights from Calgary (YYC) to Baltimore (BWI)
- Flights to Eastern Shore
- Flights from Washington (DCA) to Easton (ESN)
- Flights to St. Michaels
- Flights to Cambridge
- Flights from Toronto (YYZ) to Baltimore (BWI)
- Flights from Toronto (YYZ) to Cambridge (CGE)
- Flights from Los Angeles (LAX) to Easton (ESN)
- Flights from Buffalo (BUF) to Baltimore (BWI)
