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Vacation rentals in Chester, MD and nearby

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All 40 Rentals in the Chester Area
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From
$202
Per Night
Chester
4 Bedrooms, 2 Bathrooms, Sleeps 8
21 photos Details Reviews (2) Make Enquiry
From
$421
Per Night
Chester
4 Bedrooms, 5 Bathrooms, Sleeps 10
37 photos Details Make Enquiry

The following rentals are within 25 kilometres of Chester, Kent Island, Maryland.

From
$281
Per Night
Rock Hall, MD
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
15 photos Details Reviews (2) Make Enquiry
From
$898
Per Night
Annapolis, MD
3 Bedrooms, 3 Bathrooms, Sleeps 10
31 photos Details Reviews (1) Make Enquiry
From
$842
Per Night
Annapolis, MD
6 Bedrooms, 5 Bathrooms, Sleeps 13
Bookings
26 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 27 September 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 11 August 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
$281
Per Night
Annapolis, MD
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
20 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 15 July 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
$281
Per Night
Rock Hall, MD
3 Bedrooms, 2 Bathrooms, Sleeps 7
17 photos Details Reviews (3) Make Enquiry
From
$421
Per Night
St. Michaels, MD
4 Bedrooms, 3 Bathrooms, Sleeps 10
22 photos Details Reviews (1) Make Enquiry
From
$505
Per Night
St. Michaels, MD
3 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
13 photos Details Reviews (5) Make Enquiry
5 of 5 stars Reviewed 9 September 2014
The home was absolutely beautiful. Right around the corner from the town. Perfect location! We had been to St. Michaels 3 times before this trip and now we finally found our...
5 of 5 stars Reviewed 19 August 2014
Very comfortable, well furnished and equipped house with both modern and historical features. We took advantage of the great location to walk to tourist sites, restaurants and...
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From
$449
Per Night
Annapolis, MD
4 Bedrooms, 3 Bathrooms, Sleeps 9
Bookings
30 photos Details Reviews (2) Make Enquiry
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From
$190
Per Night
Annapolis, MD
3 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
4 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 29 June 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 12 November 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
$202
Per Night
Rock Hall, MD
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
12 photos Details Make Enquiry
From
$449
Per Night
Annapolis, MD
2 Bedrooms, 2 Bathrooms, Sleeps 10
Booking
23 photos Details Make Enquiry
From
$197
Per Night
Annapolis, MD
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
14 photos Details Make Enquiry
From
$168
Per Night
Annapolis, MD
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
18 photos Details Make Enquiry
From
$449
Per Night
Annapolis, MD
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
7 photos Details Make Enquiry
From
$281
Per Night
Annapolis, MD
3 Bedrooms, 1 Bathroom, Sleeps 7
20 photos Details Make Enquiry
From
$780
Per Night
Annapolis, MD
5 Bedrooms, 3 Bathrooms, Sleeps 20
25 photos Details Make Enquiry
From
$1,684
Per Night
Annapolis, MD
4 Bedrooms, 4 Bathrooms, Sleeps 10
Bookings
15 photos Details Make Enquiry
From
$852
Per Night
St. Michaels, MD
6 Bedrooms, 6 Bathrooms, Sleeps 12
Bookings
38 photos Details Make Enquiry
From
$786
Per Night
Annapolis, MD
5 Bedrooms, 6 Bathrooms, Sleeps 12
Booking
6 photos Details Make Enquiry
From
$314
Per Night
Annapolis, MD
4 Bedrooms, 4 Bathrooms, Sleeps 8
3 photos Details Make Enquiry
From
$561
Per Night
Annapolis, MD
1 Bedroom, 2 Bathrooms, Sleeps 4
11 photos Details Make Enquiry
From
$337
Per Night
Annapolis, MD
1 Bedroom, 1 Bathroom, Sleeps 2
9 photos Details Make Enquiry
From
$404
Per Night
St. Michaels, MD
7 Bedrooms, 4 Bathrooms, Sleeps 11
12 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 27 September 2014
Friends and family stayed at the home to watch my nephew get married on 9/20/14. I must say, the house was as much of the event as the wedding celebration. We went from 6 of us...
5 of 5 stars Reviewed 23 July 2014
Our daughter was married at the Tidewater Inn in Easton. We rented this lovely, large home the week before the wedding to have a place for the bride to relax while we spent time...
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From
$747
Per Night
Bozman, MD
4 Bedrooms, 3 Bathrooms, Sleeps 13
7 photos Details Reviews (8) Make Enquiry
From
$421
Per Night
Bozman, MD
2 Bedrooms, 1 Bathroom, Sleeps 6
9 photos Details Reviews (1) Make Enquiry
From
$281
Per Night
Claiborne, MD
3 Bedrooms, 5 Bathrooms, Sleeps 8
11 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 10 October 2014
Very new, very clean, very spacious, very comfortable. The family thoroughly enjoyed our stay here with plenty of room to spread out, a huge kitchen, meals on the deck and...
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From
$168
Per Night
St. Michaels, MD
2 Bedrooms, 2 Bathrooms, Sleeps 5
20 photos Details Reviews (12) Make Enquiry
5 of 5 stars Reviewed 22 August 2014
The pictures of this house do not lie. It is that nice. We parked our car and didn't need again until we left. Close to everything. Walk to the water , sit on the bench and...
5 of 5 stars Reviewed 20 July 2014
We fully enjoyed our relaxing stay in the sleepy little town of St. Michaels, and would definitely return when given the chance. The location is perfect - within a one block walk...
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From
$213
Per Night
St. Michaels, MD
2 Bedrooms, 2 Bathrooms, Sleeps 4
7 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 18 August 2014
Location location location! Walk to perhaps the cutest town ever! Friendly people ,dog loving community, sail boats, restaurants and such a lovely little town.. Perfection found!
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From
$281
Per Night
Annapolis, MD
3 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details Make Enquiry
From
$505
Per Night
Grasonville, MD
4 Bedrooms, 4 Bathrooms, Sleeps 10
12 photos Details Make Enquiry
From
$449
Per Night
Annapolis, MD
4 Bedrooms, 5 Bathrooms, Sleeps 8
13 photos Details Make Enquiry
From
$1,283
Per Night
St. Michaels, MD
6 Bedrooms, 6 Bathrooms, Sleeps 12
16 photos Details Make Enquiry
From
$314
Per Night
St. Michaels, MD
3 Bedrooms, 4 Bathrooms, Sleeps 6
9 photos Details Make Enquiry
From
$6,176
Per Week
St. Michaels, MD
5 Bedrooms, 5 Bathrooms, Sleeps 10
16 photos Details Make Enquiry
From
$1,605
Per Night
St. Michaels, MD
6 Bedrooms, 8 Bathrooms, Sleeps 12
16 photos Details Make Enquiry
From
$5,895
Per Week
St. Michaels, MD
5 Bedrooms, 5 Bathrooms, Sleeps 10
16 photos Details Make Enquiry
From
$802
Per Night
St. Michaels, MD
5 Bedrooms, 5 Bathrooms, Sleeps 8
10 photos Details Make Enquiry
From
$674
Per Night
Annapolis, MD
3 Bedrooms, 5 Bathrooms, Sleeps 10
5 photos Details Make Enquiry
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Suitability

  • Wheelchair access (5)
  • Elder access (11)
  • Suitable for children (20)
  • Pet friendly (14)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (34)
  • Internet (33)
  • Other outdoor space (33)
  • Washer/Dryer (32)
  • Grill (31)
  • View all amenities
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