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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, (627 reviews)
"Great place for a quick weekend getaway"
Courtney
The price is ￥18,855
￥20,929 total
includes taxes & fees
Sep 13 - Sep 14
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, (17 reviews)
"Really nice place and you can walk to everything.Will stay again!"
Glenn S.
The price is ￥57,161
￥96,777 total
includes taxes & fees
Sep 8 - Sep 9
7. 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.
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, (66 reviews)
"Had a great stay. Excellent property, beautiful location, perfect fenced yard for our dogs and lovely hosts. 100% recommend."
Kirsty D.
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. Riverfront Denton Estate on 7 Acres w/ Heated Pool
Riverfront Denton Estate on 7 Acres w/ Heated PoolDenton
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, (55 reviews)
"Perfect location for us as we spent the thanksgiving holiday with our family in the area."
Mark B.
12. 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.
13. St Michaels Inn
St Michaels InnSt. Michaels
8.0 out of 10, Very Good, (1,003 reviews)
"We decided to stay overnight last minute, this property was clean, and the bed was comfortable."
Jennifer
The price is ￥14,080
￥15,488 total
includes taxes & fees
Sep 7 - Sep 8
14. Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island MarinaGrasonville
9.0 out of 10, Wonderful, (1,000 reviews)
"Nice 1 night stay"
roney
The price is ￥23,306
￥25,870 total
includes taxes & fees
Oct 4 - Oct 5
15. Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
9.4 out of 10, Exceptional, (825 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 ￥24,135
￥26,790 total
includes taxes & fees
Oct 4 - Oct 5
16. Sandaway Suites & Beach
Sandaway Suites & BeachOxford
9.6 out of 10, Exceptional, (204 reviews)
"Nice and relaxing place in a quaint town Amber was very welcoming and friendly!"
Sandra
The price is ￥43,060
￥47,365 total
includes taxes & fees
Sep 8 - Sep 9
17. Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
9.2 out of 10, Wonderful, (1,000 reviews)
"My third stay. Hotel is clean, staff are friendly and helpful and the location is great."
Emily
The price is ￥20,347
￥22,584 total
includes taxes & fees
Sep 7 - Sep 8
18. Inn at Perry Cabin
Inn at Perry CabinDowntown St. Michaels
9.6 out of 10, Exceptional, (399 reviews)
"Amazing experience highly recommend"
Andrew
The price is ￥96,646
￥106,311 total
includes taxes & fees
Sep 7 - Sep 8
19. The Tidewater Inn
The Tidewater InnEaston
8.8 out of 10, Excellent, (914 reviews)
"The Tidewater Inn was the best"
Diana
The price is ￥27,908
￥30,698 total
includes taxes & fees
Sep 8 - Sep 9
20. The Wildset
The WildsetDowntown St. Michaels
9.8 out of 10, Exceptional, (510 reviews)
"Stayed before and will stay again. Love it because of location, staff and food."
Paula
The price is ￥37,948
￥45,713 total
includes taxes & fees
Sep 23 - Sep 24
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
St Michaels Inn
10/10 Excellent
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