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Virginia Beach
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Maryland
Chesapeake Bay
Chesapeake bay, maryland, usa
972 accommodations found
About these results
Park Place - Comfy Condo Close to Beach
Kiptopeke
900 m to the coast
Sleeps 7 pers.
3 bedrooms
167 m²
Balcony
Parking
Internet
FREE cancellation
9.8
Fantastic
26 reviews
from
CA$452
per night
Best price:
Vrbo
More details
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Waterfront Paradise on the Eastern Shore of Chesapeake Bay
Chesapeake Bay
20 m to the coast
Sleeps 14 pers.
6 bedrooms
427 m²
Pool
Terrace
Parking
Internet
FREE cancellation
9.9
Fantastic
70 reviews
from
CA$1,360
per night
Best price:
Vrbo
More details
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Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!
Northumberland County
20 m to the coast
Sleeps 4 pers.
2 bedrooms
Garden
Terrace
Parking
Internet
FREE cancellation
9.4
Fantastic
62 reviews
from
CA$368
per night
Best price:
Vrbo
More details
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Spacious Home < 1 Mi to Kiptopeke State Park!
Kiptopeke
1.4 km to the coast
Sleeps 100 pers.
4 bedrooms
238 m²
Garden
Terrace
Parking
Internet
FREE cancellation
8.9
Very good
11 reviews
from
CA$528
per night
Best price:
Vrbo
More details
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Mariners Cove Waterfront - Private Dock, Pet Friendly, Wi-Fi, Off-Street Parking
Norfolk (VA)
20 m to the coast
Sleeps 12 pers.
3 bedrooms
325 m²
Balcony
Garden
Parking
Internet
FREE cancellation
7.2
Good
32 reviews
from
CA$507
per night
Best price:
Vrbo
More details
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Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!
Rappahannock River
4.8 km to the coast
Sleeps 4 pers.
2 bedrooms
120 m²
Garden
Terrace
Parking
Internet
FREE cancellation
9.6
Fantastic
125 reviews
from
CA$292
per night
Best price:
Vrbo
More details
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The Crab Shack on Carter's Creek
Rappahannock River
5.9 km to the coast
Sleeps 4 pers.
1 bedroom
78 m²
Garden
Terrace
Parking
Internet
FREE cancellation
9.9
Fantastic
80 reviews
from
CA$424
per night
Best price:
Vrbo
More details
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Romantic Waterfront Abode with Patio & Dock!
Rappahannock River
1.4 km to the coast
Sleeps 2 pers.
1 bedroom
69 m²
Balcony/Terrace
Garden
Parking
Internet
FREE cancellation
9.7
Fantastic
61 reviews
from
CA$254
per night
Best price:
Vrbo
More details
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Circa 1900 Home in the Heart of Historic Downtown Chestertown
Chestertown
Sleeps 6 pers.
4 bedrooms
Garden
Terrace
Parking
Internet
FREE cancellation
10
Fantastic
76 reviews
from
CA$459
per night
Best price:
Vrbo
More details
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Next to the park and 2 blocks to the Beach and restaurants! Right side of Duplex
Cape Charles
350 m to the coast
Sleeps 6 pers.
3 bedrooms
Garden
Terrace
Parking
Internet
FREE cancellation
9.7
Fantastic
89 reviews
from
CA$441
per night
Best price:
Vrbo
More details
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Waterfront with Private Pier and Tranquil Water views!
Gloucester County
5.7 km to the coast
Sleeps 4 pers.
2 bedrooms
120 m²
Garden
Terrace
Parking
Internet
FREE cancellation
9.9
Fantastic
74 reviews
from
CA$339
per night
Best price:
Vrbo
More details
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Waterfront Wildlife Retreat on the Patuxent River
Southern Maryland
2.3 km to the coast
Sleeps 6 pers.
3 bedrooms
148 m²
Terrace
Parking
Internet
FREE cancellation
10
Fantastic
115 reviews
from
CA$410
per night
Best price:
Vrbo
More details
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St. Paddy’s Day is coming. Treat your lassie to a weekend at the Rivah!
Rappahannock River
5.2 km to the coast
Sleeps 4 pers.
2 bedrooms
157 m²
Garden
Terrace
Parking
Internet
FREE cancellation
9.8
Fantastic
171 reviews
from
CA$374
per night
Best price:
Vrbo
More details
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Waterfront Cottage on Chesapeake Bay w Private Beach-\nbook Your Summer '26 Week!
Mathews County
350 m to the coast
Sleeps 4 pers.
2 bedrooms
111 m²
Garden
Terrace
Parking
Internet
FREE cancellation
9.9
Fantastic
151 reviews
from
CA$484
per night
Best price:
Vrbo
More details
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The Crows Nest. Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!
Cape Charles
20 m to the coast
Sleeps 4 pers.
2 bedrooms
111 m²
Balcony
Parking
Internet
FREE cancellation
9.6
Fantastic
152 reviews
from
CA$443
per night
Best price:
Vrbo
More details
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Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
St. Michaels
Sleeps 6 pers.
3 bedrooms
118 m²
Garden
Parking
Internet
FREE cancellation
9.7
Fantastic
43 reviews
from
CA$861
per night
Best price:
Vrbo
More details
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All the comforts of home!
Kiptopeke
1 km to the coast
Sleeps 7 pers.
3 bedrooms
176 m²
Balcony
Parking
Internet
FREE cancellation
9.8
Fantastic
56 reviews
from
CA$353
per night
Best price:
Vrbo
More details
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2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free
Annapolis
1.8 km to the coast
Sleeps 7 pers.
3 bedrooms
78 m²
Garden
Terrace
Internet
FREE cancellation
9.9
Fantastic
36 reviews
from
CA$660
per night
Best price:
Vrbo
More details
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Waterfront Property, kayaks, private dock, near town
Easton region
Sleeps 6 pers.
3 bedrooms
278 m²
Balcony
Garden
Parking
Internet
FREE cancellation
9.9
Fantastic
70 reviews
from
CA$972
per night
Best price:
Vrbo
More details
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2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free
Annapolis
3 km to the coast
Sleeps 8 pers.
4 bedrooms
120 m²
Terrace
Parking
Internet
FREE cancellation
9.8
Fantastic
53 reviews
from
CA$961
per night
Best price:
Vrbo
More details
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Waterfront Cottage in Beautiful Hoopers Island
Chesapeake Bay
0 m to the coast
Sleeps 5 pers.
2 bedrooms
53 m²
Garden
Terrace
Parking
Internet
FREE cancellation
9.8
Fantastic
79 reviews
from
CA$350
per night
Best price:
Vrbo
More details
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Recently Renovated Annapolis Home - Conveniently Located
Annapolis
4.3 km to the coast
Sleeps 8 pers.
4 bedrooms
Garden
Terrace
Parking
Internet
FREE cancellation
10
Fantastic
68 reviews
from
CA$807
per night
Best price:
Vrbo
More details
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Modern Beachfront Cottage with Endless Bay Views
Chesapeake Bay
80 m to the coast
Sleeps 6 pers.
2 bedrooms
62 m²
Garden
Terrace
Parking
Internet
FREE cancellation
9.9
Fantastic
56 reviews
from
CA$564
per night
Best price:
Vrbo
More details
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Nancy’s Touch, A Waterfront Paradise!
Chesapeake Bay
1.6 km to the coast
Sleeps 6 pers.
3 bedrooms
Garden
Terrace
Parking
Internet
FREE cancellation
10
Fantastic
124 reviews
from
CA$658
per night
Best price:
Vrbo
More details
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Cozy Cottage - quaint and comfy - 5 blocks to the beach, 1 block to Mason Ave.
Cape Charles
300 m to the coast
Sleeps 7 pers.
3 bedrooms
Garden
Terrace
Parking
Internet
FREE cancellation
10
Fantastic
86 reviews
from
CA$357
per night
Best price:
Vrbo
More details
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Bay Front Small Contemporary
Northumberland County
40 m to the coast
Sleeps 4 pers.
2 bedrooms
60 m²
Terrace
Parking
Internet
FREE cancellation
9.7
Fantastic
82 reviews
from
CA$410
per night
Best price:
Vrbo
More details
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Cozy cottage on the Chesapeake Bay
Chesapeake Bay
150 m to the coast
Sleeps 6 pers.
3 bedrooms
92 m²
Garden
Terrace
Parking
Internet
FREE cancellation
9.7
Fantastic
49 reviews
from
CA$280
per night
Best price:
Vrbo
More details
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Bay View Studio Apartment
Annapolis
1.5 km to the coast
Sleeps 4 pers.
2 bedrooms
92 m²
Hot tub
Garden
Terrace
Parking
FREE cancellation
10
Fantastic
53 reviews
from
CA$430
per night
Best price:
Vrbo
More details
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Historic Chapel Views, Steps to Usna Gate 1 with Private Patio and Off-Site Parking
Annapolis
2.9 km to the coast
Sleeps 7 pers.
3 bedrooms
224 m²
Terrace
Internet
FREE cancellation
9.8
Fantastic
53 reviews
from
CA$919
per night
Best price:
Vrbo
More details
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\"Heron's Nest\" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip Included
Chesapeake Bay
300 m to the coast
Sleeps 4 pers.
1 bedroom
34 m²
Garden
Terrace
Parking
Internet
One more unit available
FREE cancellation
9.7
Fantastic
66 reviews
from
CA$234
per night
Best price:
Vrbo
More details
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