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Top cities in Caroline County
Denton
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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, (638 reviews)
"Very nice! Staff extremely helpful. Breakfast very plain & towels are like sandpaper."
Lorna
The price is €114
includes taxes & fees
12 Nov - 13 Nov
2. 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.
3. 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.
4. 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, (72 reviews)
"The house was wonderful for our family of 5. Everything was clean and Allison kept in touch despite being out of the area. Lots of wildlife to see and very peaceful. Thanks for an amazing stay! We'll be back."
Wesley L.
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."
Megan A.
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, (2 reviews)
"This is a great house for a family gathering! Grandparents, parents, and adult kids all appreciated the space. Thank you!"
Kate C.
7. Turnbridge Manor
Turnbridge ManorDenton
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful home. Plenty of space inside with great outdoor spaces. Very clean and easy to contact host. Family friendly-would highly recommend!"
Jessica H.
The price is €527
includes taxes & fees
19 Nov - 20 Nov
8. On 407 Acres! Rural Gem w/ Game Room in Goldsboro
On 407 Acres! Rural Gem w/ Game Room in GoldsboroGoldsboro
9. 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.
10. 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.
The price is €309
includes taxes & fees
1 Dec - 2 Dec
11. On 7 Acres! Riverfront Estate w/ Views in Denton
On 7 Acres! Riverfront Estate w/ Views in DentonDenton
12. Eastern Shore Waterfront Retreat. Easy Access to Easton and St Michaels.
Eastern Shore Waterfront Retreat. Easy Access to Easton and St Michaels.Denton
13. 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, (57 reviews)
"Perfect location for us as we spent the thanksgiving holiday with our family in the area."
Mark B.
14. Incredible Riverside House in a Gated Community on the Choptank River, on an 18-Acre Farm
Incredible Riverside House in a Gated Community on the Choptank River, on an 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.
15. 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)
"We are a family of 6 adults and 6 children, ranging in age from 2 to 10 years old. The house is spacious and at no point did it feel crowded. The kids loved the large pool. We also enjoyed the beautiful view of the Choptank River, where there was quite the fishing competition between the kids. The communication from our host Sarah was prompt and pleasant.Overall, my family had a great time!"
Stacey D.
16. St Michaels Inn
St Michaels InnSt. Michaels
8.0 out of 10, Very good, (1,006 reviews)
"Staff was very pleasant. Room was clean and a very nice Breakfast included."
Dean
The price is €76
includes taxes & fees
1 Dec - 2 Dec
17. Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
9.4 out of 10, Exceptional, (858 reviews)
"Great place to stay"
Michael
The price is €134
includes taxes & fees
15 Nov - 16 Nov
18. Inn at Perry Cabin
Inn at Perry CabinDowntown St. Michaels
9.6 out of 10, Exceptional, (407 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."
Virgilio
The price is €430
includes taxes & fees
9 Dec - 10 Dec
19. The Tidewater Inn
The Tidewater InnEaston
8.8 out of 10, Excellent, (938 reviews)
"We had a wonderful stay and thoroughly enjoyed our time in Easton!"
Miriam
The price is €177
includes taxes & fees
22 Nov - 23 Nov
20. Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
9.2 out of 10, Wonderful, (1,002 reviews)
"A wonderful stay! Already planning a trip for next year!"
Michelle
The price is €101
includes taxes & fees
15 Nov - 16 Nov
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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Showing deals for:20 Nov - 22 Nov
8.6 out of 10, Excellent, (638 reviews)
The price is €304
for 2 nights, 1 room
€152 per night
includes taxes & fees
Top Caroline County Hotel Reviews
Holiday Inn Express Hotel & Suites Harrington-Dover area, DE by IHG
Holiday Inn Express Hotel & Suites Harrington-Dover area, DE by IHGHarrington
8/10 Good
Big room, very spacious, excellent wifi.
Breakfast involved huge amounts of plastic and polystyrene and pre-packaged food. The smell of sugar and fat was quite over-whelming, but I found some fresh fruit and eggs which was adequate for me.
Monique
