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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 bed, 1 private bathroom
26–31 Jul
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4.96 out of 5 average rating, 291 reviews
Guest favourite
Home in Chester
Crab Alley | Waterfront Home + Hot Tub + Game Room
4.88 out of 5 average rating, 24 reviews, 4 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Home in Chester
Island Blue Getaway
5.0 out of 5 average rating, 14 reviews, 3 bedrooms, 5 beds, 2 bathrooms
16–21 Jul
Top guest favourite
Home in Chester
The Fitz Inn
4.96 out of 5 average rating, 80 reviews, 1 bedroom, 2 beds, 1 bathroom
24–29 Aug
Top guest favourite
Home in Stevensville
Cheerful & Spacious Shore Life Beauty!
4.91 out of 5 average rating, 112 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Jul
Superhost
Home in Chester
Waterfront Hot Tub, Fire Pit & Views
4.89 out of 5 average rating, 19 reviews, 2 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Guest favourite
Home in Chester
Kent Island Escape
4.97 out of 5 average rating, 37 reviews, 2 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
Home in Chester
Farmhouse by the Sea *Pool Pass*
4 bedrooms, 4 beds, 2.5 bathrooms
18–23 Jul
Top guest favourite
Guest house in Stevensville
Private | Near BayBridge | Wedding Venue Proximity
5.0 out of 5 average rating, 61 reviews, 2 beds, 1 bathroom
26–31 Jul
Top guest favourite
Home in Chester
200+ Feet of Waterfront on 3 Acres
4.96 out of 5 average rating, 26 reviews, 4 bedrooms, 5 beds, 2 bathrooms
11–16 Aug
Guest favourite
Home in Stevensville
Cozy home with Screened Porch, Min from Weddings
4.98 out of 5 average rating, 85 reviews, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Jul
Top guest favourite
Home in Stevensville
Kent Island Waterfront Home with Amazing Sunsets
4.99 out of 5 average rating, 143 reviews, 3 bedrooms, 6 beds, 2 bathrooms
3–8 Aug
Home in Chester
Kent Island 4 BR 2.5B Near Water
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Jul
Top guest favourite
Home in Stevensville
Screened Porch | Near Bay Bridge & USNA | Big Yard
4.98 out of 5 average rating, 50 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
26–31 Jul
Top guest favourite
Guest house in Stevensville
Private Guesthouse | 7-acres | Near wedding venues
5.0 out of 5 average rating, 17 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
4.97 out of 5 average rating, 463 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Jul
Guest favourite
Flat in Stevensville
Kent Island Getaway
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Jul
Top guest favourite
Flat in Saint Michaels
Blue Crab Lodge
4.97 out of 5 average rating, 151 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in Shady Side
Canary Pointe-A popular getaway for 2!
4.99 out of 5 average rating, 268 reviews, 1 bedroom, 2 beds, 1 bathroom
21–26 Aug