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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, (618 reviews)
"Clean room , staff was really friendly and lobby was very nice walking into"
craig
The price is AU$219
includes taxes & fees
18 Aug - 19 Aug
2. Charming Family Ridgely Retreat- Huge Yard, Bikes & Peaceful Porches
Charming Family Ridgely Retreat- Huge Yard, Bikes & Peaceful PorchesRidgely
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 AU$860
includes taxes & fees
10 Aug - 11 Aug
6. 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.
7. Marblehead Farm I Swing set, Hot tub * Indoor Pickleball court
Marblehead Farm I Swing set, Hot tub * Indoor Pickleball courtRidgely
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, (64 reviews)
"Wonderful setting, cabin feel with modern amenities. Really enjoyed the quiet, the pool, hot tub, and trails. "
Patrick M.
9. Riverfront Denton Estate on 7 Acres w/ Heated Pool
Riverfront Denton Estate on 7 Acres w/ Heated PoolDenton
10. 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.
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, (53 reviews)
"Perfect location for us as we spent the thanksgiving holiday with our family in the area."
Mark B.
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, (1,004 reviews)
"Room was pleasant and clean and breakfast was great!"
Karen
The price is AU$130
includes taxes & fees
17 Aug - 18 Aug
15. Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island MarinaGrasonville
9.0 out of 10, Wonderful, (1,000 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 AU$234
includes taxes & fees
30 Aug - 31 Aug
16. Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
9.4 out of 10, Exceptional, (797 reviews)
"Great location"
jeanette
The price is AU$293
includes taxes & fees
25 Aug - 26 Aug
17. Sandaway Suites & Beach
Sandaway Suites & BeachOxford
9.4 out of 10, Exceptional, (188 reviews)
"It was a beautiful stay!"
Eliza
The price is AU$338
includes taxes & fees
13 Aug - 14 Aug
18. 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 AU$982
includes taxes & fees
23 Aug - 24 Aug
19. The Wildset
The WildsetDowntown St. Michaels
9.8 out of 10, Exceptional, (488 reviews)
"Wonderful hotel!"
Tracey
The price is AU$429
includes taxes & fees
25 Aug - 26 Aug
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)
"I have stayed several times over the last few years and the place continues to be very good."
Thomas R.
The price is AU$171
includes taxes & fees
3 Aug - 4 Aug
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
Microtel Inn & Suites by Wyndham Dover
10/10 Excellent
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