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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, (639 reviews)
"Very nice! Staff extremely helpful. Breakfast very plain & towels are like sandpaper."
Lorna
The price is AED 401
AED 445 total
includes taxes & fees
13 Dec - 14 Dec
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, (2 reviews)
"We really enjoyed our stay at Marblehead Farms. The property is clean, inviting, and has fun amenities for families and couples. We enjoyed the firepit and pickleball court, and our brothers kids who joined us for a day enjoyed the trampoline and game room. Very nice place to stay in the Eastern shore"
david m.
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 AED 1,469
AED 2,305 total
includes taxes & fees
1 Dec - 2 Dec
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 AED 826
AED 1,281 total
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, (1,002 reviews)
"Convenient to St Michael’s and inexpensive."
John
The price is AED 289
AED 318 total
includes taxes & fees
3 Dec - 4 Dec
17. Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
9.4 out of 10, Exceptional, (860 reviews)
"Great place to stay"
Michael
The price is AED 493
AED 547 total
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 AED 1,686
AED 1,855 total
includes taxes & fees
7 Dec - 8 Dec
19. The Tidewater Inn
The Tidewater InnEaston
8.8 out of 10, Excellent, (939 reviews)
"We had a wonderful stay and thoroughly enjoyed our time in Easton!"
Miriam
The price is AED 565
AED 622 total
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, (1,001 reviews)
"Staff was very friendly."
Michelle
The price is AED 349
AED 387 total
includes taxes & fees
13 Dec - 14 Dec
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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