hundredroomsby Holidu
List your property

Chesapeake bay, maryland, usa

1,011 accommodations found

Park Place - Comfy Condo Close to Beach

0.6 mi to the coast
Sleeps 7 pers.
3 bedrooms
1,798 ft²
BalconyParkingInternet
FREE cancellation
9.8 · Fantastic
26 reviews
from
$330
per night
Book on Vrbo

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

20 yd to the coast
Sleeps 14 pers.
6 bedrooms
4,596 ft²
PoolTerraceParkingInternet
FREE cancellation
9.9 · Fantastic
69 reviews
from
$942
per night
Book on Vrbo
Secure dataPowered by HoliduReliable service

Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!

20 yd to the coast
Sleeps 4 pers.
2 bedrooms
YardTerraceParkingInternet
FREE cancellation
9.4 · Fantastic
61 reviews
from
$272
per night
Book on Vrbo

Mariners Cove Waterfront - Private Dock, Pet Friendly, Wi-Fi, Off-Street Parking

20 yd to the coast
Sleeps 12 pers.
3 bedrooms
3,498 ft²
BalconyYardParkingInternet
FREE cancellation
7.4 · Good
29 reviews
from
$379
per night
Book on Vrbo

Spacious Home < 1 Mi to Kiptopeke State Park!

0.9 mi to the coast
Sleeps 100 pers.
4 bedrooms
2,562 ft²
YardTerraceParkingInternet
8.9 · Very good
11 reviews
from
$590
per night
Book on Vrbo

Cozy Mother-in-Law Suite

550 yd to the coast
Sleeps 2 pers.
1 bedroom
248 ft²
YardTerraceParkingInternet
FREE cancellation
8.9 · Very good
51 reviews
from
$85
per night
Book on Vrbo

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Sleeps 6 pers.
3 bedrooms
1,270 ft²
YardParkingInternet
FREE cancellation
9.7 · Fantastic
41 reviews
from
$496
per night
Book on Vrbo

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Sleeps 6 pers.
4 bedrooms
YardTerraceParkingInternet
FREE cancellation
10 · Fantastic
72 reviews
from
$335
per night
Book on Vrbo

New! Residential Retreat. Located minutes to the Oceanview beach and Naval base.

0.9 mi to the coast
Sleeps 6 pers.
3 bedrooms
1,733 ft²
YardTerraceParkingInternet
FREE cancellation
9.5 · Fantastic
47 reviews
from
$170
per night
Book on Vrbo

Waterfront Wildlife Retreat on the Patuxent River

1.4 mi to the coast
Sleeps 6 pers.
3 bedrooms
1,593 ft²
TerraceParkingInternet
FREE cancellation
10 · Fantastic
112 reviews
from
$282
per night
Book on Vrbo

Romantic Waterfront Abode with Patio & Dock!

0.9 mi to the coast
Sleeps 2 pers.
1 bedroom
743 ft²
Balcony/TerraceYardParkingInternet
FREE cancellation
9.7 · Fantastic
57 reviews
from
$152
per night
Book on Vrbo

The Crab Shack on Carter's Creek

3.7 mi to the coast
Sleeps 4 pers.
1 bedroom
840 ft²
YardTerraceParkingInternet
FREE cancellation
9.9 · Fantastic
80 reviews
from
$237
per night
Book on Vrbo

Autumn in Irvington - it’s so inviting and gorgeous. And it’s waiting for you!

3.2 mi to the coast
Sleeps 4 pers.
2 bedrooms
1,690 ft²
YardTerraceParkingInternet
FREE cancellation
9.9 · Fantastic
167 reviews
from
$242
per night
Book on Vrbo

Buckroe Bungalow · #Buckroe Bungalow ~Escape to the Beach 2mins Away!

350 yd to the coast
Sleeps 8 pers.
3 bedrooms
13,455 ft²
BalconyYardParkingKitchen
FREE cancellation
9.6 · Fantastic
from
$111
per night

Your Annapolis Waterfront retreat - ready for a December or January Annapolis getaway! Midnight M...

3 mi to the coast
Sleeps 4 pers.
1 bedroom
700 ft²
YardParkingInternet
FREE cancellation
10 · Fantastic
83 reviews
from
$324
per night
Book on Vrbo

Downtown St. Michaels | Bikes | Kayaks | Private Pier

Sleeps 6 pers.
3 bedrooms
2,174 ft²
YardTerraceParkingInternet
FREE cancellation
9.8 · Fantastic
33 reviews
from
$720
per night
Book on Vrbo

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

4.3 mi to the coast
Sleeps 3 pers.
1 bedroom
484 ft²
BalconyParkingInternet
FREE cancellation
9.7 · Fantastic
76 reviews
from
$144
per night
Book on Vrbo

Waterfront Property, kayaks, private dock, near town

Sleeps 6 pers.
3 bedrooms
2,992 ft²
BalconyYardParkingInternet
FREE cancellation
9.9 · Fantastic
67 reviews
from
$677
per night
Book on Vrbo

Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!

3 mi to the coast
Sleeps 4 pers.
2 bedrooms
1,292 ft²
YardTerraceParkingInternet
FREE cancellation
9.6 · Fantastic
123 reviews
from
$199
per night
Book on Vrbo

Nancy’s Touch, A Waterfront Paradise!

1 mi to the coast
Sleeps 6 pers.
3 bedrooms
YardTerraceParkingInternet
FREE cancellation
10 · Fantastic
121 reviews
from
$434
per night
Book on Vrbo

Sweet Bamboo Beach Cottage

550 yd to the coast
Sleeps 6 pers.
3 bedrooms
958 ft²
YardTerraceParkingInternet
FREE cancellation
9.8 · Fantastic
69 reviews
from
$221
per night
Book on Vrbo

Cozy 2br home w/ parking in downtown Annapolis

2 mi to the coast
Sleeps 6 pers.
2 bedrooms
904 ft²
YardTerraceParkingInternet
FREE cancellation
9.9 · Fantastic
65 reviews
from
$389
per night
Book on Vrbo

Waterfront with Private Pier and Tranquil Water views!

3.5 mi to the coast
Sleeps 4 pers.
2 bedrooms
1,292 ft²
YardTerraceParkingInternet
FREE cancellation
9.9 · Fantastic
73 reviews
from
$249
per night
Book on Vrbo

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

3.4 mi to the coast
Sleeps 7 pers.
4 bedrooms
YardTerraceParkingInternet
FREE cancellation
10 · Fantastic
79 reviews
from
$437
per night
Book on Vrbo

Next to the park and 2 blocks to the Beach and restaurants! Right side of Duplex

400 yd to the coast
Sleeps 6 pers.
3 bedrooms
YardTerraceParkingInternet
FREE cancellation
9.8 · Fantastic
85 reviews
from
$297
per night
Book on Vrbo

Beachfront Getaway, Mermaid Suite, 🐶 💙

70 yd to the coast
Sleeps 6 pers.
3 bedrooms
2,067 ft²
YardTerraceParkingInternet
One more unit available
FREE cancellation
9.9 · Fantastic
99 reviews
from
$366
per night
Book on Vrbo

Recently Renovated Annapolis Home - Conveniently Located

2.7 mi to the coast
Sleeps 8 pers.
4 bedrooms
YardTerraceParkingInternet
FREE cancellation
10 · Fantastic
64 reviews
from
$499
per night
Book on Vrbo

All the comforts of home!

0.6 mi to the coast
Sleeps 7 pers.
3 bedrooms
1,894 ft²
BalconyParkingInternet
FREE cancellation
9.8 · Fantastic
55 reviews
from
$259
per night
Book on Vrbo

Million $ Views No Extra Charge! Hot Tub! Pool! Beach! Resort-Like Amenities!

40 yd to the coast
Sleeps 6 pers.
3 bedrooms
818 ft²
PoolHot tubBalconyYard
FREE cancellation
9.9 · Fantastic
57 reviews
from
$241
per night
Book on Vrbo

Bay View Studio Apartment

0.9 mi to the coast
Sleeps 4 pers.
1 bedroom
990 ft²
Hot tubYardTerraceParking
FREE cancellation
10 · Fantastic
47 reviews
from
$267
per night
Book on Vrbo

Loading…

hundredroomsby Holidu
Holidu
CareersAbout usMagazine
Contact
Help for guestsHelp for hostsPressAffiliate Partnerships
Hosting
For hostsFor agencies (30+ properties)
App
Download the app
© 2025 hundredrooms is a Holidu GmbH company
·Imprint·GTC·Privacy policy·Content policy·Whistleblower system