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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, (626 reviews)
"Great place for a quick weekend getaway"
Courtney
The price is CA $170
CA $188 total
includes taxes & fees
Aug 31 - Sep 1
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. 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 CA $495
CA $850 total
includes taxes & fees
Aug 27 - Aug 28
6. 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.
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. 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. 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.
10. 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)
"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.
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. Riverfront Denton Estate on 7 Acres w/ Heated Pool
Riverfront Denton Estate on 7 Acres w/ Heated PoolDenton
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, (18 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, (1,012 reviews)
"Room was pleasant and clean and breakfast was great!"
Karen
The price is CA $110
CA $121 total
includes taxes & fees
Aug 31 - Sep 1
15. Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island MarinaGrasonville
9.0 out of 10, Wonderful, (1,009 reviews)
"Nice 1 night stay"
roney
The price is CA $202
CA $224 total
includes taxes & fees
Aug 30 - Aug 31
16. Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
9.4 out of 10, Exceptional, (818 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 CA $230
CA $255 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, (1,009 reviews)
"Very clean hotel,beautiful view and great staff."
Jackie
The price is CA $175
CA $194 total
includes taxes & fees
Sep 1 - Sep 2
18. Sandaway Suites & Beach
Sandaway Suites & BeachOxford
9.4 out of 10, Exceptional, (202 reviews)
"Nice and relaxing place in a quaint town Amber was very welcoming and friendly!"
Sandra
The price is CA $371
CA $409 total
includes taxes & fees
Aug 26 - Aug 27
19. Inn at Perry Cabin
Inn at Perry CabinDowntown St. Michaels
9.6 out of 10, Exceptional, (397 reviews)
"Amazing experience highly recommend"
Andrew
The price is CA $585
CA $644 total
includes taxes & fees
Sep 7 - Sep 8
20. The Tidewater Inn
The Tidewater InnEaston
8.8 out of 10, Excellent, (913 reviews)
"The Tidewater Inn was the best"
Diana
The price is CA $224
CA $247 total
includes taxes & fees
Aug 24 - Aug 25
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
Tru by Hilton Georgetown
10/10 Excellent
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