Chester Guest Houses | Find the Top Guest Houses in Chester

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Our top choices for Chester guest houses

1. The Tilghman Island Inn

Tilghman

Pamela

includes taxes & fees

16 Sept - 17 Sept

2. West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis

Homewood

Jordan B.

includes taxes & fees

9 Sept - 10 Sept

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Top Chester Hotel Reviews

Historic Inns of Annapolis

8/10 Good

"Fantastic location. Clean room with comfortable beds and powerful AC. Liked the history of the building. We were able to consistently get parking on the street near the hotel, which was great. The only real con was that we discovered upon reaching our room that we didn't have an exterior window--our two "windows" looked over the covered event area, which had pretty lights but was nonetheless an interior hallway, so no outside view. There were also a couple hiccups with the bathroom, one being that the glass shelf was falling down, and the other being that we were consistently given two towels even though we had four people on the reservation. But overall we were happy with our stay and appreciated being in a historic building in such a great location."

Sonesta ES Suites Annapolis

8/10 Good

"Ver nice older hotel but well maintained. Spacious rooms and good breakfast. My only complaint is that you can tell they also keep long term tenants as there were cats roaming around (which didn’t bother me but might others) and bikes/trash outside some of the rooms and plants in windows. A normal nightly rental hotel would not allow this id think so it made the atmosphere seem a lil run down even if the room was decent."