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Our top choices for Caroline County hotels
1. Best Western Denton Inn
Best Western Denton InnDenton
8.6 out of 10, Excellent, (632 reviews)
"Great place for a quick weekend getaway"
Courtney
The price is CA $169
CA $187 total
includes taxes & fees
Oct 13 - Oct 14
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)
"Even though it is the only option in Greensboro, the host went out of here way to help us feel welcomed."
Brandon M.
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)
"Property was in a great location for our needs. Enjoyed breakfast with the birds."
Megan A.
5. Turnbridge Manor
Turnbridge ManorDenton
9.8 out of 10, Exceptional, (18 reviews)
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)
"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...
MEREDITH M.
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)
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)
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)
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 3 - Nov 4
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)
The price is CA $235
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)
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
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