Apartment holiday rentals in Queen Anne&#x27;s County

Apartment in Stevensville

4.98 out of 5 average rating, 273 reviews

Boutique by the Bay

MicheleRating, 5 stars5 months ago

Enjoyed our stay and appreciated all of the details like creamer in the refrigerator this morning. Tastefully appointed and very comfortable - exactly as pictured. We were in the area for a wedding and Diane was flexible and communicated throughout the reservation/stay. We would love to go back and stay longer.

4.97 out of 5 average rating, 228 reviews

Private cozy cottage - center of Chestertown .

JenniferRating, 5 stars2 weeks ago

We enjoyed everything about our stay here! Beautifully decorated. Lots of great and thoughtful amenities. The large gardens and grounds are so pretty and our dogs enjoyed exploring everywhere. Great location with easy walking to all the restaurants and shops but still private and secluded. Everyone was friendly and welcoming. I would definitely stay here again and recommend to anyone.

4.9 out of 5 average rating, 78 reviews

1-br apt in downtown Chestertown (Unit 1)

SusanRating, 5 stars1 month ago

We found this beautiful place when we needed a dog-friendy rental for our large dog while visiting our son at college. The rental is in a fanatic location, a very short walk to the waterfront and downtown Chestertown and its great shops and restaurants. The rental was immaculate and very comfortable. It had everything we needed. The backyard was more private than we thought and our dog enjoyed playing fetch in the back. The bedding was comfortable and relaxing. The host was very responsive and helpful. Great experience! Thank you!

4.98 out of 5 average rating, 87 reviews

Bright, new apartment in the heart of Chestertown

KendraRating, 5 stars1 month ago

Everything about this airbnb was wonderful for our dtay in Chestertown! You can not beat the location- right across the street was a wonderful bakery and we were just a few minutes walk away from numerous restaurants, the farmers market, and the park. We felt very comfortable and even with 2 small kids the appartment was spacious and easy to maintain during our stay. I am hoping we can stay there the next time we are in Chestertown- it was a great apartment and Julie was a great host!

5 out of 5 average rating, 11 reviews

Apartment in Rock Hall

DragonflyPeake Studio

JoniRating, 5 stars7 months ago

We were charmed by the comfortable design of Kimberly’s place. Great a/c, fully functional kitchen, lots of extras (water, snacks, oil, seasonings, coffee, tea, creamers, etc). Spacious for the two of us, this is a small apartment, with kitchen, LR with table, bedroom and bathroom. Everything is like new. We initially had some problems with the WiFi, but Kimberly and her husband kept working on it until we found a solution. Excellent communication! Close bike ride to town, beach, restaurants in walking distance, beautiful spot.

4.97 out of 5 average rating, 262 reviews

Apartment in Chester

Cozy Waterfront Apartment Chester, MD

BrettRating, 5 stars3 months ago

We needed a quiet and private space to relax. Jordan’s space was all of this. We stayed here for a month and hardly ever heard Jordan and her family. Jordan was quick to respond if we had any questions. The bed was very comfortable and the views of the water were nice.

5 out of 5 average rating, 10 reviews

114 High Street First Floor Unit Chestertown

KeithRating, 5 stars1 week ago

I have stayed at this property before and it is always a great experience. Katie is a wonderful, responsive, host. The welcome basket and handwritten note are thoughtful details. I very much look forward to my next opportunity to stay in Katie’s house again.

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What guests are saying

DragonflyPeake Studio

5 out of 5 average rating, 11 reviews7 months ago

We were charmed by the comfortable design of Kimberly’s place. Great a/c, fully functional kitchen, lots of extras (water, snacks, oil, seasonings, coffee, tea, creamers, etc). Spacious for the two of us, this is a small apartment, with kitchen, LR with table, bedroom and bathroom. Everything is like new. We initially had some problems with the WiFi, but Kimberly and her husband kept working on it until we found a solution. Excellent communication! Close bike ride to town, beach, restaurants in walking distance, beautiful spot.

Apartment in Rock Hall

What guests are saying

⋘ Lakeside Apartment ⋙| Private+Cozy Setting |

4.76 out of 5 average rating, 63 reviews5 days ago

What a wonderful place for a peaceful, lakeside getaway. Upon entering the space i immediately wanted to move in! So cozy and spacious with great natural light. I loved watching the sun set beyond the lake. Kevin was a gracious and responsive host. I felt very welcome and cared for. Highly recommend!

Apartment in Wye Mills

What guests are saying

Private cozy cottage - center of Chestertown .

4.97 out of 5 average rating, 228 reviews2 weeks ago

We enjoyed everything about our stay here! Beautifully decorated. Lots of great and thoughtful amenities. The large gardens and grounds are so pretty and our dogs enjoyed exploring everywhere. Great location with easy walking to all the restaurants and shops but still private and secluded. Everyone was friendly and welcoming. I would definitely stay here again and recommend to anyone.

Apartment in Chestertown

What guests are saying

1-br apt in downtown Chestertown (Unit 1)

4.9 out of 5 average rating, 78 reviews1 month ago

We found this beautiful place when we needed a dog-friendy rental for our large dog while visiting our son at college. The rental is in a fanatic location, a very short walk to the waterfront and downtown Chestertown and its great shops and restaurants. The rental was immaculate and very comfortable. It had everything we needed. The backyard was more private than we thought and our dog enjoyed playing fetch in the back. The bedding was comfortable and relaxing. The host was very responsive and helpful. Great experience! Thank you!

Apartment in Chestertown

What guests are saying

Cozy Waterfront Apartment Chester, MD

4.97 out of 5 average rating, 262 reviews3 months ago

We needed a quiet and private space to relax. Jordan’s space was all of this. We stayed here for a month and hardly ever heard Jordan and her family. Jordan was quick to respond if we had any questions. The bed was very comfortable and the views of the water were nice.

Apartment in Chester

What guests are saying

Bright, new apartment in the heart of Chestertown

4.98 out of 5 average rating, 87 reviews1 month ago

Everything about this airbnb was wonderful for our dtay in Chestertown! You can not beat the location- right across the street was a wonderful bakery and we were just a few minutes walk away from numerous restaurants, the farmers market, and the park. We felt very comfortable and even with 2 small kids the appartment was spacious and easy to maintain during our stay. I am hoping we can stay there the next time we are in Chestertown- it was a great apartment and Julie was a great host!

Apartment in Chestertown

What guests are saying

114 High Street First Floor Unit Chestertown

5 out of 5 average rating, 10 reviews1 week ago

I have stayed at this property before and it is always a great experience. Katie is a wonderful, responsive, host. The welcome basket and handwritten note are thoughtful details. I very much look forward to my next opportunity to stay in Katie’s house again.

Apartment in Chestertown

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Popular amenities for Queen Anne's County apartment rentals

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Weekly apartment rentals

4.98 out of 5 average rating, 104 reviews

RIVER WATCH

Eric Rating, 5 stars2 months ago

Comfortable beds, spacious layout, great shower and great scenery

4.76 out of 5 average rating, 63 reviews

Apartment in Wye Mills

⋘ Lakeside Apartment ⋙| Private+Cozy Setting |

TalleRating, 5 stars5 days ago

What a wonderful place for a peaceful, lakeside getaway. Upon entering the space i immediately wanted to move in! So cozy and spacious with great natural light. I loved watching the sun set beyond the lake. Kevin was a gracious and responsive host. I felt very welcome and cared for. Highly recommend!

4.97 out of 5 average rating, 228 reviews

Private cozy cottage - center of Chestertown .

JenniferRating, 5 stars2 weeks ago

We enjoyed everything about our stay here! Beautifully decorated. Lots of great and thoughtful amenities. The large gardens and grounds are so pretty and our dogs enjoyed exploring everywhere. Great location with easy walking to all the restaurants and shops but still private and secluded. Everyone was friendly and welcoming. I would definitely stay here again and recommend to anyone.

4.9 out of 5 average rating, 78 reviews

1-br apt in downtown Chestertown (Unit 1)

SusanRating, 5 stars1 month ago

We found this beautiful place when we needed a dog-friendy rental for our large dog while visiting our son at college. The rental is in a fanatic location, a very short walk to the waterfront and downtown Chestertown and its great shops and restaurants. The rental was immaculate and very comfortable. It had everything we needed. The backyard was more private than we thought and our dog enjoyed playing fetch in the back. The bedding was comfortable and relaxing. The host was very responsive and helpful. Great experience! Thank you!

4.9 out of 5 average rating, 29 reviews

Apartment in Centreville

⋘ Private Wye BranchManorApartment ⋙Private entree

MattRating, 5 stars2 months ago

Clean, peaceful and exactly as described.

4.97 out of 5 average rating, 262 reviews

Apartment in Chester

Cozy Waterfront Apartment Chester, MD

BrettRating, 5 stars3 months ago

We needed a quiet and private space to relax. Jordan’s space was all of this. We stayed here for a month and hardly ever heard Jordan and her family. Jordan was quick to respond if we had any questions. The bed was very comfortable and the views of the water were nice.

5 out of 5 average rating, 9 reviews

114 High Street Upper Floors Unit Chestertown

ZuleymaRating, 5 stars5 months ago

Katie was an amazing host and communicator! We loved the space and it was exactly as it was shown. The location was unbeatable. Would love to stay here again!

4.98 out of 5 average rating, 87 reviews

Bright, new apartment in the heart of Chestertown

KendraRating, 5 stars1 month ago

Everything about this airbnb was wonderful for our dtay in Chestertown! You can not beat the location- right across the street was a wonderful bakery and we were just a few minutes walk away from numerous restaurants, the farmers market, and the park. We felt very comfortable and even with 2 small kids the appartment was spacious and easy to maintain during our stay. I am hoping we can stay there the next time we are in Chestertown- it was a great apartment and Julie was a great host!

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Private apartment rentals

4.76 out of 5 average rating, 63 reviews

Apartment in Wye Mills

⋘ Lakeside Apartment ⋙| Private+Cozy Setting |

TalleRating, 5 stars5 days ago

What a wonderful place for a peaceful, lakeside getaway. Upon entering the space i immediately wanted to move in! So cozy and spacious with great natural light. I loved watching the sun set beyond the lake. Kevin was a gracious and responsive host. I felt very welcome and cared for. Highly recommend!

5 out of 5 average rating, 9 reviews

114 High Street Upper Floors Unit Chestertown

ZuleymaRating, 5 stars5 months ago

Katie was an amazing host and communicator! We loved the space and it was exactly as it was shown. The location was unbeatable. Would love to stay here again!