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Top cities in Caroline County

Denton
Federalsburg

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Find vacation rentals that suit your style
Our top choices for Caroline County condo rentals




1. Station House East: Upscale Loft in the Historic District Cambridge, MD
Station House East: Upscale Loft in the Historic District Cambridge, MDDowntown Cambridge
9.6 out of 10, Exceptional, (14 reviews)
9.6/10
Exceptional
(14 reviews)
"Overall our stay here was excellent. The king bed was comfortable and the location perfect for us. We enjoyed walking around downtown."
"Overall our stay here was excellent. The king bed was comfortable and the location perfect for us. We enjoyed walking around downtown."Janette W.




2. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
The Drinking Gourd: Stunning Penthouse in Historic Downtown CambridgeDowntown Cambridge
9.8 out of 10, Exceptional, (15 reviews)
9.8/10
Exceptional
(15 reviews)
"Great stay! Gorgeous apartment!"
"Great stay! Gorgeous apartment!"Kristen S.
The price is AED 661
AED 661
AED 1,386 total
includes taxes & fees
1 Dec - 2 Dec




3. Walk to Parks & Marina! Waterfront Cambridge Condo
Walk to Parks & Marina! Waterfront Cambridge CondoCambridge
8.0 out of 10, Very good, (1 review)
8.0/10
Very good
(1 review)
"Great location in close proximity to the water and much of what Camrbridge has to offer. Host was a great communicator and check in/out was very simple and smooth. Only issues worth calling out was the lack of lighting in certain areas Couch in living room is extremely firm and there is insufficient lighting in several places."
"Great location in close proximity to the water and much of what Camrbridge has to offer. Host was a great communicator and check in/out was very simple and smooth. Only issues worth calling out was the lack of lighting in certain areas Couch in living room is extremely firm and there is insufficient lighting in several places."Nezam D.




4. Walkable Condo w/ Drawbridge Views in Cambridge
Walkable Condo w/ Drawbridge Views in CambridgeCambridge




5. Welcome to a Cozy Waterfront Condo in Charming Cambridge, MD
Welcome to a Cozy Waterfront Condo in Charming Cambridge, MDCambridge




6. Tred Avon Tidehouse 2BR Downtown Oxford Retreat
Tred Avon Tidehouse 2BR Downtown Oxford RetreatOxford
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.
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 reviews in Caroline County




Best Western Denton Inn
Best Western Denton InnDenton
10/10 Excellent
Knowledgable & helpful reception staff, breakfast attendant was very helpful, a clean hotel and a happy place to stay.
Knowledgable & helpful reception staff, breakfast attendant was very helpful, a clean hotel and a happy place to stay.
rich




Bally's Dover Casino Resort
Bally's Dover Casino ResortDover
10/10 Excellent
There was ONLY ONE option of places to eat... we stayed on a Tue so i understand it's not a busy day but that was disappointing
There was ONLY ONE option of places to eat... we stayed on a Tue so i understand it's not a busy day but that was disappointing
Kimberly




Holiday Inn Express Hotel & Suites Harrington-Dover area, DE by IHG
Holiday Inn Express Hotel & Suites Harrington-Dover area, DE by IHGHarrington
10/10 Excellent
I checked in very late (past 10:00pm) and was in no mood to deal with humanity in general. I walked in and the receptionist immediately noted my exhaustion and had everything squared away for me in under five minutes! Mood greatly improved, I asked if they had room service because I was starving. I was informed that it was too late for food to be ordered there but she provided me with four different options of local restaurants that were still open and delivered directly to the hotel. Very...
I checked in very late (past 10:00pm) and was in no mood to deal with humanity in general. I walked in and the receptionist immediately noted my exhaustion and had everything squared away for me in under five minutes! Mood greatly improved, I asked if they had room service because I was starving. I was informed that it was too late for food to be ordered there but she provided me with four different options of local restaurants that were still open and delivered directly to the hotel. Very...
Anonymous traveler




Microtel Inn & Suites by Wyndham Milford
Microtel Inn & Suites by Wyndham MilfordMilford
10/10 Excellent
We needed a quick hotel book because my car broke down in a road trip. This was a great choice! The room was large and comfortable, even had an extra sink in the room with a microwave and small fridge. The breakfast in the morning was real nice andbthey had a snack bar that was reasonably priced.
They were very courteous and allowed me to leave my car a couple nights after we departed, so that when we returned after reaching our destination, it was safe and ready to be towed.
We needed a quick hotel book because my car broke down in a road trip. This was a great choice! The room was large and comfortable, even had an extra sink in the room with a microwave and small fridge. The breakfast in the morning was real nice andbthey had a snack bar that was reasonably priced.
They were very courteous and allowed me to leave my car a couple nights after we departed, so that when we returned after reaching our destination, it was safe and ready to be towed.
LeAnna




Fairfield Inn & Suites by Marriott Easton
Fairfield Inn & Suites by Marriott EastonEaston
10/10 Excellent
The Fairfield Inn on US50 has become our go-to mid-range hotel in Easton. We have stayed here several times in recent years, and once again had a great experience during this Christmas stay. The facilities are clean and in good condition. The staff is friendly, welcoming, and accommodating. When I booked our stay this time through a third-party, I got a little confused about room options, and took the only king-bed room that I saw. The manager didnt know I had any concerns, and when the staff...
The Fairfield Inn on US50 has become our go-to mid-range hotel in Easton. We have stayed here several times in recent years, and once again had a great experience during this Christmas stay. The facilities are clean and in good condition. The staff is friendly, welcoming, and accommodating. When I booked our stay this time through a third-party, I got a little confused about room options, and took the only king-bed room that I saw. The manager didnt know I had any concerns, and when the staff...
Richard




Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
10/10 Excellent
The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...
The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...
Christina




Microtel Inn & Suites by Wyndham Dover
Microtel Inn & Suites by Wyndham DoverDover
10/10 Excellent
The hotel is very CLEAN
The hotel is very CLEAN
Amira




Hampton Inn Milford
Hampton Inn MilfordMilford
10/10 Excellent
Overall, this hotel exceeded my expectations, and I’d happily stay here again. Highly recommended for both business and leisure travelers!
Overall, this hotel exceeded my expectations, and I’d happily stay here again. Highly recommended for both business and leisure travelers!
Laura




Knapps Narrows Marina & Inn
Knapps Narrows Marina & InnSherwood
10/10 Excellent
We had a wonderful two night stay at the hotel. The marina is beautiful with nightly rentals if needed. Our first stay and we will return. Great staff very helful. If you are looking for a peacefull,tranquil location you will like it.
We had a wonderful two night stay at the hotel. The marina is beautiful with nightly rentals if needed. Our first stay and we will return. Great staff very helful. If you are looking for a peacefull,tranquil location you will like it.
Stan and Joan




Best Western Plus Easton Inn & Suites
Best Western Plus Easton Inn & SuitesEaston
10/10 Excellent
Everything was good with checkin ,check out, and the room. The only complaint I can voice is with the breakfast service attendant. She was not very warm or inviting, did not speak to guest. She did have everything out and the area clean, but at the end of breakfast time, she removed all plates and bowls first so no one could get anything else to eat. We were late eating on our 3rd morning, but were in time to get our food before she started putting away. But then put chairs on the tables so...
Everything was good with checkin ,check out, and the room. The only complaint I can voice is with the breakfast service attendant. She was not very warm or inviting, did not speak to guest. She did have everything out and the area clean, but at the end of breakfast time, she removed all plates and bowls first so no one could get anything else to eat. We were late eating on our 3rd morning, but were in time to get our food before she started putting away. But then put chairs on the tables so...
Nancy




Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island MarinaGrasonville
10/10 Excellent
I had a very nice stay, the room had a very nice view of the Bay.
I had a very nice stay, the room had a very nice view of the Bay.
Kathie




Hampton Inn Easton
Hampton Inn EastonEaston
10/10 Excellent
Nice location about 20 minutes from St Michaels. Hotel seemed to be newly renovated. Our room was clean with the exception of a leftover hand towel that was sitting on the desk. Other than that everything was fantastic.
Nice location about 20 minutes from St Michaels. Hotel seemed to be newly renovated. Our room was clean with the exception of a leftover hand towel that was sitting on the desk. Other than that everything was fantastic.
Anonymous traveler




Inn at Huntingfield Creek
Inn at Huntingfield CreekRock Hall
10/10 Excellent
Quaint property - very laid-back. Exactly what we were looking for.
Quaint property - very laid-back. Exactly what we were looking for.
George




Fairfield Inn & Suites by Marriott Dover
Fairfield Inn & Suites by Marriott DoverDover
10/10 Excellent
Very nice hotel.
Very nice hotel.
Kimberly




Comfort Inn & Suites Chestertown
Comfort Inn & Suites ChestertownChestertown
10/10 Excellent
Inside the building it was clean, quiet and nice. In the back parking lot, it was very dirty. The grounds surrounding the lot was littered with trash and debris. One person looked to be sleeping in his car. I did appreciate the very bright lighting in that lot. A small clean up of the back lot would make a big difference in first impressions!!
Inside the building it was clean, quiet and nice. In the back parking lot, it was very dirty. The grounds surrounding the lot was littered with trash and debris. One person looked to be sleeping in his car. I did appreciate the very bright lighting in that lot. A small clean up of the back lot would make a big difference in first impressions!!
Laura




Holiday Inn Express Easton by IHG
Holiday Inn Express Easton by IHGEaston
10/10 Excellent
We had a group of friends getting together for a fun weekend away. Had a great experience here, Alexia at the front desk was very helpful and friendly for all of our requests and was very accommodating. Had a good time and great breakfast that was included the next morning. Will definitely stay here for our 2nd annual get together next year.
We had a group of friends getting together for a fun weekend away. Had a great experience here, Alexia at the front desk was very helpful and friendly for all of our requests and was very accommodating. Had a good time and great breakfast that was included the next morning. Will definitely stay here for our 2nd annual get together next year.
Belinda




Microtel Inn & Suites By Wyndham Georgetown Delaware Beaches
Microtel Inn & Suites By Wyndham Georgetown Delaware BeachesGeorgetown
10/10 Excellent
My children and I loved our stay! Very clean rooms, comfortable beds and friendly staff made this hotel stay among one of the best we've experienced. The free breakfast had something for everyone and was an added bonus. Beautifully decorated room added a flare. Will be coming back for repeat stays in the near future without hesitation!!
My children and I loved our stay! Very clean rooms, comfortable beds and friendly staff made this hotel stay among one of the best we've experienced. The free breakfast had something for everyone and was an added bonus. Beautifully decorated room added a flare. Will be coming back for repeat stays in the near future without hesitation!!
Stachein



