18 Best Hotels on Chesapeake Bay (2026)

Hotels on Chesapeake Bay: Enjoy Rates Starting at $121 per Night

Inn at Perry Cabin
Hotel
308 Watkins Lane, Saint Michaels, MD 21663, USA
• View on map
  • Oceanfront
    Oceanfront
  • Spa
    Spa
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
9 Baths431.53 ft²
9.2

Exceptional

57 reviews

$1317
Average price / night
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Historic Inns of Annapolis
Hotel
58 State Circle, Annapolis, MD 21401, USA
• View on map
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
  • Pet Friendly
    Pet Friendly
  • Kitchen
    Kitchen
16 Baths251.61 ft²
8.2

Exceptional

579 reviews

$356
Average price / night
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Sandaway Suites & Beach
Hotel
• View on map
  • Private Beach
    Private Beach
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
  • Highly Rated
    Highly Rated
  • Ocean View
5 Baths374.05 ft²
9.2

Exceptional

108 reviews

$331
Average price / night
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Wades Point Inn on the Bay
Bed & Breakfast
• View on map
  • Balcony/Terrace
    Balcony/Terrace
  • Parking
    Parking
  • Air Conditioner
    Air Conditioner
  • Internet
    Internet
  • Highly Rated
    Highly Rated
  • Group Friendly
24 Baths
10

Exceptional

89 reviews

$289
Average price / night
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Inn at Warner Hall
Bed & Breakfast
4750 Warner Hall Road, Gloucester, VA 23061, USA
• View on map
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
  • View
    View
  • Breakfast
    Breakfast
12 Baths348.36 ft²
9.8

Exceptional

13 reviews

$305
Average price / night
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Wylder Hotel - Tilghman Island
Hotel
21551 Chesapeake House Drive, Saint Michaels, MD 21671, USA
• View on map
  • Private Beach
    Private Beach
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
9 Baths264.31 ft²
8.7

Exceptional

114 reviews

$283
Average price / night
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Inn at Osprey Point
Hotel
• View on map
  • Oceanfront
    Oceanfront
  • Spa
    Spa
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
  • Highly Rated
    Highly Rated
  • Free Cancellation
14 Baths322.92 ft²
9.5

Exceptional

89 reviews

$188
Average price / night
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The Hermitage Inn and Taphouse
Hotel
203 Virginia Avenue, Petersburg, WV 26847, USA
• View on map
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
  • Kitchen
    Kitchen
  • Parking
    Parking
7 Baths204.51 ft²
8.7

Exceptional

43 reviews

$121
Average price / night
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The Charlotte Hotel & Restaurant
Hotel
• View on map
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
  • Parking
    Parking
  • Air Conditioner
    Air Conditioner
1 Baths330.99 ft²
8.6

Exceptional

82 reviews

$157
Average price / night
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Hornsby House Inn
Bed & Breakfast
• View on map
  • Balcony/Terrace
    Balcony/Terrace
  • View
    View
  • Breakfast
    Breakfast
  • Parking
    Parking
  • Highly Rated
    Highly Rated
  • Family Friendly
7 Baths276.79 ft²
9.7

Exceptional

55 reviews

$206
Average price / night
Check Availability
Annapolis Waterfront Hotel, Autograph Collection
Hotel
80 Compromise Street, Annapolis, MD 21401, USA
• View on map
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
  • Breakfast
    Breakfast
  • Pet Friendly
    Pet Friendly
13 Baths255.85 ft²
8.1

Exceptional

124 reviews

$332
Average price / night
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The Inn at Chesapeake Bay Beach Club
Hotel
180 Pier One Road, Stevensville, MD 21666, USA
• View on map
  • Oceanfront
    Oceanfront
  • Spa
    Spa
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
  • Highly Rated
    Highly Rated
  • Ocean View
16 Baths426.64 ft²
8.8

Exceptional

108 reviews

$229
Average price / night
Check Availability
Graduate by Hilton Annapolis
Hotel
126 West Street, Annapolis, MD 21401, USA
• View on map
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
  • Pet Friendly
    Pet Friendly
  • Parking
    Parking
1 Baths4051.15 ft²
8.3

Exceptional

601 reviews

$410
Average price / night
Check Availability
Hummingbird Inn
Bed & Breakfast
14 North Aurora Street, Easton, MD 21601, USA
• View on map
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
  • View
    View
6 Baths376.74 ft²
9.9

Exceptional

34 reviews

$367
Average price / night
Check Availability
Inn at Huntingfield Creek
Bed & Breakfast
4928 Eastern Neck Rd, Rock Hall, 21661, USA
• View on map
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
  • Ocean View
    Ocean View
12 Baths618.03 ft²
9.4

Exceptional

38 reviews

$308
Average price / night
Check Availability
The Oaks Waterfront Hotel
Hotel
25876 Royal Oaks Road , Saint Michaels, MD 21662, USA
• View on map
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
  • Ocean View
    Ocean View
14 Baths398.26 ft²
9.5

Exceptional

24 reviews

$210
Average price / night
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Swanendele Inn
Bed & Breakfast
• View on map
  • Private Beach
    Private Beach
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
  • Highly Rated
    Highly Rated
  • Free Cancellation
7 Baths445.93 ft²
9.6

Exceptional

56 reviews

$320
Average price / night
Check Availability
The Tidewater Inn
Hotel
• View on map
  • Spa
    Spa
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
  • View
    View
  • Price Dropped
    Price Dropped
  • Free Cancellation
5 Baths204.51 ft²
8

Exceptional

129 reviews

$179
Average price / night
Check Availability

Compare the 18 Best Hotels on Chesapeake Bay (2026) – Addresses, Prices, Stars, Rating, and Review Count

Hotel Name Address Price ($)Star Rating Review Count Book
Inn at Perry Cabin308 Watkins Lane, Saint Michaels, MD 21663, USA131759.257
Historic Inns of Annapolis58 State Circle, Annapolis, MD 21401, USA35638.2579
Inn at Warner Hall4750 Warner Hall Road, Gloucester, VA 23061, USA30559.813
Wylder Hotel - Tilghman Island21551 Chesapeake House Drive, Saint Michaels, MD 21671, USA28348.7114
The Hermitage Inn and Taphouse203 Virginia Avenue, Petersburg, WV 26847, USA12108.743
Annapolis Waterfront Hotel, Autograph Collection80 Compromise Street, Annapolis, MD 21401, USA33248.1124
The Inn at Chesapeake Bay Beach Club180 Pier One Road, Stevensville, MD 21666, USA22948.8108
Graduate by Hilton Annapolis126 West Street, Annapolis, MD 21401, USA41048.3601
Hummingbird Inn14 North Aurora Street, Easton, MD 21601, USA36749.934
Inn at Huntingfield Creek4928 Eastern Neck Rd, Rock Hall, 21661, USA30849.438
The Oaks Waterfront Hotel25876 Royal Oaks Road , Saint Michaels, MD 21662, USA21009.524

Note: The prices for each 18 Best Hotels on Chesapeake Bay (2026) do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here>) to get the latest prices.

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