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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, (628 reviews)
"Great place for a quick weekend getaway"
Courtney
The price is £100
includes taxes & fees
4 Oct - 5 Oct
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)
"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!"
Amanda F.
3. 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.
4. Marblehead Farm I Swing set, Hot tub * Indoor Pickleball court
Marblehead Farm I Swing set, Hot tub * Indoor Pickleball courtRidgely
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. 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 £473
includes taxes & fees
29 Sept - 30 Sept
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."
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. 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.
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."
Mark B.
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. St Michaels Inn
St Michaels InnSt. Michaels
8.0 out of 10, Very good, (1,003 reviews)
"Great location close to downtown."
Lynn
The price is £68
includes taxes & fees
1 Oct - 2 Oct
15. Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
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."
Karen
The price is £127
includes taxes & fees
4 Oct - 5 Oct
16. Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island MarinaGrasonville
9.0 out of 10, Wonderful, (1,002 reviews)
"Nice 1 night stay"
roney
The price is £123
includes taxes & fees
5 Oct - 6 Oct
17. Sandaway Suites & Beach
Sandaway Suites & BeachOxford
9.4 out of 10, Exceptional, (211 reviews)
"Would recommend to anyone who enjoys a peaceful location, with spectacular views!"
Amber
The price is £250
includes taxes & fees
29 Sept - 30 Sept
18. The Tidewater Inn
The Tidewater InnEaston
8.8 out of 10, Excellent, (923 reviews)
"We had a wonderful stay and thoroughly enjoyed our time in Easton!"
Miriam
The price is £151
includes taxes & fees
28 Sept - 29 Sept
19. 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)
"Good hotel for the money and location."
Marc
The price is £87
includes taxes & fees
25 Oct - 26 Oct
20. Inn at Perry Cabin
Inn at Perry CabinDowntown 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."
Virgilio
The price is £427
includes taxes & fees
26 Oct - 27 Oct
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
Red Roof Inn & Suites Dover Downtown
8/10 Good
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- Flights to Annapolis
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- Blackwater National Wildlife Refuge
- Visit Downtown Cambridge
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- Spocott Windmill
- U.s. Naval Academy
- Visit Woolford
