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Search results; Over 1,000 homes in Chester

Top guest favourite
Flat in Chester
Cozy Waterfront Apartment Chester, MD
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 297 reviews
Home in Chester
NEW I Waterfront, HotTub, Dock, Fire Pit, GameRoom
4 bedrooms, 4 king beds, 3.5 bathrooms
30 Aug – 4 Sept
New place to stay
Guest favourite
Home in Chester
Crab Alley | Waterfront Home + Hot Tub + Game Room
4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
4.89 out of 5 average rating, 27 reviews
Top guest favourite
Home in Chester
The Fitz Inn
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
4.96 out of 5 average rating, 82 reviews
Top guest favourite
Home in Stevensville
Cheerful & Spacious Shore Life Beauty!
2 bedrooms, 2 beds, 1 bathroom
17–22 Aug
4.91 out of 5 average rating, 115 reviews
Superhost
Home in Chester
Waterfront Hot Tub, Fire Pit & Views
2 bedrooms, 4 beds, 2 bathrooms
3–8 Sept
4.91 out of 5 average rating, 22 reviews
Guest favourite
Home in Chester
Kent Island Escape
2 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
4.98 out of 5 average rating, 42 reviews
Guest favourite
Home in Stevensville
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
4 bedrooms, 7 beds, 2.5 bathrooms
18–23 Aug
4.92 out of 5 average rating, 359 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 469 reviews
Top guest favourite
Home in Chester
Island Blue Getaway
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Room in Stevensville
Rustic & Elegant Private Bed & Bath
1 bed, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 306 reviews
Home in Chester
Kent Island 4 BR 2.5B Near Water
4 bedrooms, 5 beds, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Stevensville
Cozy home with Screened Porch, Min from Weddings
3 bedrooms, 4 beds, 2 bathrooms
17–22 Aug
4.98 out of 5 average rating, 86 reviews
Guest favourite
Home in Chester
200+ Feet of Waterfront on 3 Acres
4 bedrooms, 5 beds, 2 bathrooms
20–25 Aug
4.96 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Stevensville
Heron Roost
2 bedrooms, 2 beds, 1 bathroom
24–29 Oct
5.0 out of 5 average rating, 93 reviews
Home in Chester
Eclectic Farmhouse by the Sea. Kent Island.
4 bedrooms, 4 beds, 2.5 bathrooms
19–24 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Stevensville
Private & Peaceful | Water Views, Big Deck, Games
3 bedrooms, 5 beds, 3 bathrooms
17–22 Aug
New place to stay
Top guest favourite
Guest house in Stevensville
Private Guesthouse | 7-acres | Near wedding venues
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 24 reviews