Find Romantic Hotels in Chestertown, MD
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18 Sep - 20 SepOur top choices for Chestertown romantic hotels
1. Cozy Fells Point Gem / In The Heart of Fells Point
Cozy Fells Point Gem / In The Heart of Fells PointFells Point
Tammy
AED 191
AED 798 total
includes taxes & fees
13 Sep - 14 Sep
2. 5-bedroom vacation home 5 minutes from historic Charlestown
5-bedroom vacation home 5 minutes from historic CharlestownPerryville
Teresa M.
AED 975
AED 1,980 total
includes taxes & fees
8 Sep - 9 Sep
3. Chesapeake Cottages- 2 Quaint Waterfront Retreats
Chesapeake Cottages- 2 Quaint Waterfront RetreatsPasadena
Buu T.
AED 1,322
AED 2,345 total
includes taxes & fees
8 Sep - 9 Sep
4. Cozy 2br home w/ parking in downtown Annapolis
Cozy 2br home w/ parking in downtown AnnapolisHistoric District
Nancy N.
AED 826
AED 1,629 total
includes taxes & fees
9 Sep - 10 Sep
5. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!Stevensville
barbara s.
AED 2,755
AED 4,865 total
includes taxes & fees
8 Sep - 9 Sep
6. Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!Stevensville
David R.
AED 2,938
AED 5,096 total
includes taxes & fees
8 Sep - 9 Sep
Top Chestertown Hotel Reviews
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
10/10 Excellent
"Affordable"
Best Western Plus Hotel & Conference Center
10/10 Excellent
"Great breakfast. Pool and hot tub were great. Close to 95 and convenient to downtown Baltimore."
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."
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