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Vacation Rentals in Chestertown, MD and nearby

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All 51 Rentals in the Chestertown Area
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From
$99
Per Night
Chestertown
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
10 photos Details Reviews (4) Make Inquiry
From
$140
Per Night
Chestertown
3 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
11 photos Details Reviews (1) Make Inquiry
From
$120
Per Night
Chestertown
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
28 photos Details Reviews (2) Make Inquiry
From
$295
Per Night
Chestertown
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
12 photos Details Make Inquiry
From
$259
Per Night
Chestertown
1 Bedroom, 1 Bathroom, Sleeps 2
9 photos Details Make Inquiry

The following rentals are within 25 miles of Chestertown, Maryland.

From
$750
Per Night
Annapolis
6 Bedrooms, 5 Bathrooms, Sleeps 13
Bookings
26 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed September 27, 2014
Our large group of women in their 30's had a great time and everyone had a comfortable bed and plenty of room. Caitlyn was very responsive, friendly and accommodating from the...
5 of 5 stars Reviewed August 11, 2014
We just returned from our sailing weekend in Annapolis and had an amazing time staying at this lovely house for the weekend. The house was perfect for a larger group. The large...
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From
$275
Per Night
Baltimore
2 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
53 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed July 1, 2014
This townhouse is an end unit and private. Quiet, great location right on the water. 3 decks, had access to 2 kayaks and a paddle boat if we wanted. Plenty of room and it was...
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From
$250
Per Night
Annapolis
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
20 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed July 15, 2014
If you want a cozy place to relax this is the place. Yard was perfect for my dog to run around and I did not have to worry it was all fenced in. Love to grill so I was able to...
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From
$200
Per Night
Baltimore
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
18 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed January 13, 2014
Our family group of eight (family of four with two young kids and two sets of grandparents) had a wonderful stay at this vacation rental between Christmas and New Year's. You...
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From
$250
Per Night
Baltimore
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
11 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed May 29, 2014
My husband and I stayed with our 17 year old son; plenty of space, lovely appointments, wonderful rooftop deck. Didn't need to bring a thing for the kitchen for cooking or...
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From
$180
Per Night
Chester
4 Bedrooms, 2 Bathrooms, Sleeps 8
21 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed July 29, 2013
First I would like to say thanks, to Harry, and Scott. They were the best host, I've encountered. They have a property, they can be proud of. The house was just excellent. The...
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From
$100
Per Night
Baltimore
2 Bedrooms, 1 Bathroom, Sleeps 4
15 photos Details Reviews (3) Make Inquiry
4 of 5 stars Reviewed September 16, 2014
We stayed in Virgo during the week of the Star Spangled Banner celebration and had a very nice stay. The boat is located in Fell's point and we did not have a rental car and did...
4 of 5 stars Reviewed September 16, 2013
We rented this houseboat during our weekend trip to the races. We loved that the location was walkable to the race and right in the Fells Point Bar District at night. This is the...
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From
$150
Per Night
Baltimore
2 Bedrooms, 1 Bathroom, Sleeps 6
13 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed March 31, 2014
From check-in to check-out our weekend getaway was very smooth and we had very detailed instructions. The place was very clean and delightful. We enjoyed our stay & had a...
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From
$250
Per Night
Rock Hall
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
15 photos Details Reviews (2) Make Inquiry
4 of 5 stars Reviewed September 16, 2014
My sisters and mother stayed three nights in this quaint house with great views of one of the marina's and cove area. The downstairs was perfect my mother, with a screened in...
4 of 5 stars Reviewed August 19, 2014
My family was looking for a relaxing getaway that would be an alternative to another week at the beach. We found the perfect spot at this cottage near Rock Hall. We rented with no...
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From
$170
Per Night
Baltimore
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
28 photos Details Reviews (24) Make Inquiry
5 of 5 stars Reviewed August 24, 2014
Our group of 8 converged on Baltimore for a wedding this past weekend, and the Empire House was absolutely perfect, in every way. You can park your car in the lot directly...
5 of 5 stars Reviewed August 17, 2014
We came from all the corners of the world for a wedding in Baltimore and wanted to be together. We found in the Mansion the ideal place: comfortable, elegantly appointed, and with...
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From
$200
Per Night
Baltimore
2 Bedrooms, 1 Bathroom, Sleeps 6
14 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed September 17, 2014
The only thing better than being in Baltimore for the Sailabration Blue Angels Show and massive fireworks display was being on the Scorpius for the wonderful weekend! We had...
5 of 5 stars Reviewed October 23, 2013
Loved being on the water!!! Walking distance to most of DC attractions and/or bus/Metro. Restaurant at end of pier sponsored a pet rescue night(Monday), which my 14 y.o...
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From
$200
Per Night
Baltimore
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
23 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed March 30, 2014
We truly enjoyed our stay. What a perfect place. We loved the house, the neighborhood, and the books. Very comfortable, warm, and inviting. Oren took great care to make sure we...
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From
$379
Per Night
Baltimore
5 Bedrooms, 6 Bathrooms, Sleeps 8
Bookings
21 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed July 1, 2014
This house is a no shoes house with lots of space and rooms for a big family as mine. We enjoyed the amenities, but the internet service was limited, which we did not mined. The...
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From
$800
Per Night
Annapolis
3 Bedrooms, 3 Bathrooms, Sleeps 10
31 photos Details Reviews (1) Make Inquiry
From
$400
Per Night
Annapolis
4 Bedrooms, 3 Bathrooms, Sleeps 9
Bookings
30 photos Details Reviews (2) Make Inquiry
From
$175
Per Night
Baltimore
1 Bedroom, 1 Bathroom, Sleeps 5
17 photos Details Reviews (4) Make Inquiry
4 of 5 stars Reviewed August 21, 2013
I have now rented two houseboats. Two years ago in the Boston Harbor, and now this one. They were somewhat similar; a bit aged, adequately furnished with pots, pans, utensils...
4 of 5 stars Reviewed May 28, 2013
I travel to Baltimore a lot but was unable to find a reasonable room for Preakness weekend and booked this houseboat. What a fun alternative! Great location in the Inner Harbor...
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From
$150
Per Night
Baltimore
3 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
19 photos Details Reviews (6) Make Inquiry
5 of 5 stars Reviewed August 31, 2014
We came into town early for vacation. Friends joined use mid-week for a 4 day conferance down town. The home was the perfect location. Close to grocery store, dinning too. Robert...
5 of 5 stars Reviewed July 13, 2014
Stayed here for one week while we visited the capitol and surrounding areas. Townhouse is great and we had no problems. It was hot outside and all the AC units worked well. Very...
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From
$250
Per Night
Rock Hall
3 Bedrooms, 2 Bathrooms, Sleeps 7
17 photos Details Reviews (3) Make Inquiry
From
$120
Per Night
Baltimore
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
7 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed September 19, 2014
We have stayed in Baltimore several times and this is by far the most comfortable stay we have experienced. We felt we left with new friends. The apartment is lovely and the...
5 of 5 stars Reviewed July 2, 2014
First and foremost, Sussane and Joe were the best host I have ever met! They were very nice and helpful! I couldn't ask for more accommodating hosts! The apartment is great...
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From
$200
Per Night
Baltimore
5 Bedrooms, 5 Bathrooms, Sleeps 6
Bookings
7 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed August 12, 2014
Marta and Kelly's house was a godsend! It was PERFECT and may have been the single best planning decision we made for our wedding weekend. I rented it for my immediate family...
5 of 5 stars Reviewed August 3, 2014
Nice old home with lots of character, we could tell that there is a lot of love put in the house. It was only a 10 minute walk from Johns Hopkins, which was why we were there...
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From
$169
Per Night
Annapolis
3 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
4 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed June 29, 2014
We really enjoyed our stay at your condo. It was roomy and felt like home. It is in a very nice condo community which was very quiet. It was nice being able to cook and see into...
5 of 5 stars Reviewed November 12, 2013
My family of four stayed there for the weekend. We were there to watch the Navy-Hawaii football game. We could not find any hotel rooms in/around Annapolis that could host a...
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From
$400
Per Night
Annapolis
2 Bedrooms, 2 Bathrooms, Sleeps 10
Booking
23 photos Details Make Inquiry
From
$700
Per Night
Annapolis
5 Bedrooms, 6 Bathrooms, Sleeps 12
Booking
6 photos Details Make Inquiry
From
$400
Per Night
Annapolis
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
7 photos Details Make Inquiry
From
$695
Per Night
Annapolis
5 Bedrooms, 3 Bathrooms, Sleeps 20
25 photos Details Make Inquiry
From
$250
Per Night
Annapolis
3 Bedrooms, 1 Bathroom, Sleeps 7
20 photos Details Make Inquiry
From
$315
Per Night
Ridgely
5 Bedrooms, 4 Bathrooms, Sleeps 13
35 photos Details Make Inquiry
From
$250
Per Night
Annapolis
3 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details Make Inquiry
From
$400
Per Night
Annapolis
4 Bedrooms, 4 Bathrooms, Sleeps 8
13 photos Details Make Inquiry
From
$375
Per Night
Chester
4 Bedrooms, 4 Bathrooms, Sleeps 10
37 photos Details Make Inquiry
From
$450
Per Night
Grasonville
4 Bedrooms, 4 Bathrooms, Sleeps 10
12 photos Details Make Inquiry
From
$180
Per Night
Rock Hall
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
12 photos Details Make Inquiry
From
$325
Per Night
Baltimore
3 Bedrooms, 2 Bathrooms, Sleeps 8
5 photos Details Make Inquiry
From
$600
Per Night
Annapolis
3 Bedrooms, 4 Bathrooms, Sleeps 10
5 photos Details Make Inquiry
From
$325
Per Night
Baltimore
3 Bedrooms, 2 Bathrooms, Sleeps 9
22 photos Details Make Inquiry
From
$275
Per Night
Baltimore
2 Bedrooms, 1 Bathroom, Sleeps 4
6 photos Details Make Inquiry
From
$120
Per Night
Baltimore
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
4 photos Details Make Inquiry
From
$150
Per Night
Annapolis
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
18 photos Details Make Inquiry
From
$175
Per Night
Annapolis
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
14 photos Details Make Inquiry
From
$1,500
Per Night
Annapolis
4 Bedrooms, 4 Bathrooms, Sleeps 10
Bookings
15 photos Details Make Inquiry
From
$280
Per Night
Annapolis
4 Bedrooms, 4 Bathrooms, Sleeps 8
3 photos Details Make Inquiry
From
$480
Per Night
Baltimore
3 Bedrooms, 3 Bathrooms, Sleeps 6
8 photos Details Make Inquiry
From
$300
Per Night
Annapolis
1 Bedroom, 1 Bathroom, Sleeps 2
9 photos Details Make Inquiry
From
$500
Per Night
Annapolis
1 Bedroom, 2 Bathrooms, Sleeps 4
11 photos Details Make Inquiry
From
$140
Per Night
Baltimore
2 Bedrooms, 1 Bathroom, Sleeps 4
6 photos Details Make Inquiry
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Book Online(43)
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Suitability

  • Wheelchair access (5)
  • Elder access (18)
  • Suitable for children (26)
  • Pet friendly (16)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (37)
  • Internet (35)
  • Other outdoor space (32)
  • Grill (27)
  • Washer/Dryer (26)
  • View all amenities
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Book Online(43)

Suitability

  • Wheelchair access (5)
  • Elder access (18)
  • Suitable for children (26)
  • Pet friendly (16)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (37)
  • Internet (35)
  • Other outdoor space (32)
  • Grill (27)
  • Washer/Dryer (26)
  • View all amenities