Holiday Homes in Chester

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Featured Holiday Homes in Chester

"We had a great stay! The property has everything we needed and host was easy to communicate with "

includes taxes & fees

19 Oct - 20 Oct

"Nice and peaceful stay for a quick local getaway. "

includes taxes & fees

21 Oct - 22 Oct

"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"

includes taxes & fees

27 Oct - 28 Oct

"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "

includes taxes & fees

17 Oct - 18 Oct

"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"

includes taxes & fees

22 Oct - 23 Oct

"Very quaint and quiet place to stay. Very relaxing."

includes taxes & fees

19 Oct - 20 Oct

"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"

includes taxes & fees

21 Oct - 22 Oct

includes taxes & fees

18 Oct - 19 Oct

"Very clean - well equipped - perfect for our relaxing weekend."

includes taxes & fees

19 Oct - 20 Oct

"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."

includes taxes & fees

11 Nov - 12 Nov

"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"

includes taxes & fees

21 Oct - 22 Oct

"Great house in cute neighborhood. Thanks for a very comfortable stay!"

includes taxes & fees

11 Nov - 12 Nov

"Check in was super easy and he was very nice and accommodating. Location was easy enough to find and his instructions were very clear. Thank you! "

includes taxes & fees

20 Oct - 21 Oct

"Very comfortable bedrooms and sitting area. Perfect location for the event we were attending. Very clean. Friendly host. "

includes taxes & fees

19 Oct - 20 Oct

Beach nearby, sun-loungers, beach towels

"Absolutely beautiful and spacious home perfectly located in North Beach. Very peaceful area and close to the beach, restaurants and shopping. We really enjoyed our stay and hope to visit again in the future. "

includes taxes & fees

21 Oct - 22 Oct

"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "

includes taxes & fees

4 Nov - 5 Nov

"The property is lovely and the home is truly beautiful and comfortable. I highly recommend staying here; beautiful, peaceful--perfect."

includes taxes & fees

3 Nov - 4 Nov

4 bedrooms, desk, iron/ironing board, travel cot

"Our family gathered for a special celebration and loved the home! It was roomy and had everything we needed for our stay. The location was perfect for getting around."

includes taxes & fees

21 Oct - 22 Oct

"The water that comes out of the house tastes bad."

includes taxes & fees

29 Oct - 30 Oct

"Very clean, had everything we needed for our stay!"

includes taxes & fees

30 Oct - 31 Oct

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Top Chester Hotel Reviews

Sonesta ES Suites Annapolis

10/10 Excellent

"Our night at your hotel was just fine! Room was clean. Supply toiletries, towels for the bath and kitchen were as expected, neat and plentiful. There was a creak in the bathroom door, but that is a nitpick. Coffee maker was easy to operate. Breakfast was as expected, with some delay when coffee carafe and food service trays were empty. I would go back."