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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, (624 reviews)
"Great place for a quick weekend getaway"
Courtney
The price is £101
includes taxes & fees
31 Aug - 1 Sept
2. 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.
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)
"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.
4. 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.
5. Turnbridge Manor
Turnbridge ManorDenton
9.8 out of 10, Exceptional, (15 reviews)
"Really nice place and you can walk to everything.Will stay again!"
Glenn S.
The price is £449
includes taxes & fees
12 Aug - 13 Aug
6. Marblehead Farm I Swing set, Hot tub * Indoor Pickleball court
Marblehead Farm I Swing set, Hot tub * Indoor Pickleball courtRidgely
7. Little Creek Hideaway - Privacy and Perfect Family Getaway.
Little Creek Hideaway - Privacy and Perfect Family Getaway.Preston
9.8 out of 10, Exceptional, (37 reviews)
"Property was in a great location for our needs. Enjoyed breakfast with the birds."
Megan A.
8. 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, (65 reviews)
"It is beautiful. All facilities including hot tub were great. Quiet and off the beaten path. Hosts are near and very helpful with all questions. Views on river wonderful from the house or dock."
Jeannette H.
9. Riverfront Denton Estate on 7 Acres w/ Heated Pool
Riverfront Denton Estate on 7 Acres w/ Heated PoolDenton
10. 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, (54 reviews)
"Perfect location for us as we spent the thanksgiving holiday with our family in the area."
Mark B.
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. Choptank River waterfront 4 bed Farmhouse with camping on Eastern Shore Maryland
Choptank River waterfront 4 bed Farmhouse with camping on Eastern Shore MarylandGreensboro
13. Riverfront Denton Estate on 7 Acres w/ Heated Pool
Riverfront Denton Estate on 7 Acres w/ Heated PoolDenton
10.0 out of 10, Exceptional, (16 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.
14. St Michaels Inn
St Michaels InnSt. Michaels
8.2 out of 10, Very good, (1,001 reviews)
"Room was pleasant and clean and breakfast was great!"
Karen
The price is £70
includes taxes & fees
31 Aug - 1 Sept
15. Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island MarinaGrasonville
9.0 out of 10, Wonderful, (1,006 reviews)
"Me and my husband went for a one year anniversary. Staying at the hilton was wonderful relaxing, everyone was so pleasant and helpful.The restaurants nearby were great. I love the view we'll be coming back again."
Tammy
The price is £121
includes taxes & fees
24 Aug - 25 Aug
16. Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
9.4 out of 10, Exceptional, (806 reviews)
"Great location"
jeanette
The price is £137
includes taxes & fees
8 Sept - 9 Sept
17. Sandaway Suites & Beach
Sandaway Suites & BeachOxford
9.4 out of 10, Exceptional, (196 reviews)
"Great quiet getaway spot! Beautiful and the staff was amazing!"
Rob
The price is £220
includes taxes & fees
2 Sept - 3 Sept
18. Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
9.2 out of 10, Wonderful, (1,009 reviews)
"Very clean hotel,beautiful view and great staff."
Jackie
The price is £98
includes taxes & fees
8 Sept - 9 Sept
19. Inn at Perry Cabin
Inn at Perry CabinDowntown St. Michaels
9.6 out of 10, Exceptional, (395 reviews)
"maybe a little overpriced but a great place to stay in St Michaels!"
Michel
The price is £506
includes taxes & fees
26 Aug - 27 Aug
20. The Wildset
The WildsetDowntown St. Michaels
9.8 out of 10, Exceptional, (493 reviews)
"Wonderful hotel!"
Tracey
The price is £213
includes taxes & fees
1 Sept - 2 Sept
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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Top Caroline County Hotel Reviews
St Michaels Inn
10/10 Excellent
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