hundredroomsby Holidu
Get the appList your property

Chesapeake bay, maryland, usa

982 accommodations found

Park Place - Comfy Condo Close to Beach

0.6 mi to the beach
Sleeps 7 pers.3 bedrooms1,798 ft²
BalconyParkingInternet
FREE cancellation
9.8 · Fantastic
26 reviews
from
$331
per night
Book on Vrbo

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

4.3 mi to the beach
Sleeps 14 pers.6 bedrooms4,596 ft²
PoolTerraceParkingInternet
FREE cancellation
9.9 · Fantastic
70 reviews
from
$993
per night
Book on Vrbo
Secure dataPowered by HoliduReliable service

1140 Bay Highlands Dr

850 yd to the beach
Sleeps 18 pers.5 bedrooms
BalconyYardParkingKitchen
FREE cancellation
from
$677
per night

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

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

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

0.7 mi to the beach
Sleeps 12 pers.3 bedrooms3,498 ft²
BalconyYardParkingInternet
FREE cancellation
7.4 · Good
31 reviews
from
$359
per night
Book on Vrbo

Spacious Home < 1 Mi to Kiptopeke State Park!

1 mi to the beach
Sleeps 100 pers.4 bedrooms2,562 ft²
YardTerraceParkingInternet
FREE cancellation
8.9 · Very good
11 reviews
from
$502
per night
Book on Vrbo

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

Sleeps 6 pers.3 bedrooms1,270 ft²
YardParkingInternet
FREE cancellation
9.7 · Fantastic
42 reviews
from
$536
per night
Book on Vrbo

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

5 mi to the beach
Sleeps 8 pers.3 bedrooms13,455 ft²
BalconyYardParkingKitchen
FREE cancellation
9.6 · Fantastic
from
$116
per night

Romantic Waterfront Abode with Patio & Dock!

5.4 mi to the beach
Sleeps 2 pers.1 bedroom743 ft²
Balcony/TerraceYardParkingInternet
FREE cancellation
9.7 · Fantastic
61 reviews
from
$168
per night
Book on Vrbo

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

2.9 mi to the beach
Sleeps 4 pers.2 bedrooms1,292 ft²
YardTerraceParkingInternet
FREE cancellation
9.6 · Fantastic
124 reviews
from
$205
per night
Book on Vrbo

Waterfront Wildlife Retreat on the Patuxent River

5.1 mi to the beach
Sleeps 6 pers.3 bedrooms1,593 ft²
TerraceParkingInternet
FREE cancellation
10 · Fantastic
115 reviews
from
$290
per night
Book on Vrbo

Downtown St. Michaels | Bikes | Kayaks | Private Pier

Sleeps 6 pers.3 bedrooms2,174 ft²
YardTerraceParkingInternet
FREE cancellation
9.8 · Fantastic
34 reviews
from
$764
per night
Book on Vrbo

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

5.4 mi to the beach
Sleeps 6 pers.3 bedrooms
YardTerraceParkingInternet
FREE cancellation
9.7 · Fantastic
89 reviews
from
$324
per night
Book on Vrbo

The Crab Shack on Carter's Creek

3.2 mi to the beach
Sleeps 4 pers.1 bedroom840 ft²
YardTerraceParkingInternet
FREE cancellation
9.9 · Fantastic
80 reviews
from
$287
per night
Book on Vrbo

Love is in the air! Treat your sweetheart to a romantic weekend at Key Cottage!

2.9 mi to the beach
Sleeps 4 pers.2 bedrooms1,690 ft²
YardTerraceParkingInternet
FREE cancellation
9.8 · Fantastic
171 reviews
from
$273
per night
Book on Vrbo

The Crows Nest. Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!

5.8 mi to the beach
Sleeps 4 pers.2 bedrooms1,195 ft²
BalconyParkingInternet
FREE cancellation
9.6 · Fantastic
151 reviews
from
$308
per night
Book on Vrbo

Waterfront with Private Pier and Tranquil Water views!

8.7 mi to the beach
Sleeps 4 pers.2 bedrooms1,292 ft²
YardTerraceParkingInternet
FREE cancellation
9.9 · Fantastic
74 reviews
from
$250
per night
Book on Vrbo

Cozy Cottage 3 beds 2 baths W/ Outdoor grill!

Sleeps 6 pers.1 bedroom1,098 ft²
BalconyYardParkingInternet
FREE cancellation
9.7 · Fantastic
71 reviews
from
$230
per night
Book on Vrbo

Bay View Studio Apartment

700 yd to the beach
Sleeps 4 pers.1 bedroom990 ft²
Hot tubYardTerraceParking
FREE cancellation
10 · Fantastic
52 reviews
from
$317
per night
Book on Vrbo

Bay Front Small Contemporary

2 mi to the beach
Sleeps 4 pers.2 bedrooms646 ft²
TerraceParkingInternet
FREE cancellation
9.7 · Fantastic
82 reviews
from
$278
per night
Book on Vrbo

Nancy’s Touch, A Waterfront Paradise!

350 yd to the beach
Sleeps 6 pers.3 bedrooms
YardTerraceParkingInternet
FREE cancellation
10 · Fantastic
124 reviews
from
$488
per night
Book on Vrbo

Waterfront Cottage in Beautiful Hoopers Island

Sleeps 5 pers.2 bedrooms570 ft²
YardTerraceParkingInternet
FREE cancellation
9.8 · Fantastic
78 reviews
from
$260
per night
Book on Vrbo

Stay in the landmark Lighthouse!

6.1 mi to the beach
Sleeps 6 pers.3 bedrooms2,293 ft²
YardTerraceParkingInternet
FREE cancellation
9.9 · Fantastic
73 reviews
from
$412
per night
Book on Vrbo

Sweet Victorian Beach Cottage

5.2 mi to the beach
Sleeps 6 pers.3 bedrooms1,690 ft²
YardTerraceParkingInternet
FREE cancellation
9.7 · Fantastic
46 reviews
from
$323
per night
Book on Vrbo

\"Heron's Nest\" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip Included

1.9 mi to the beach
Sleeps 4 pers.1 bedroom366 ft²
YardTerraceParkingInternet
One more unit available
FREE cancellation
9.7 · Fantastic
66 reviews
from
$170
per night
Book on Vrbo

Waterfront Cottage on Chesapeake Bay w Private Beach-\nbook Your Summer '26 Week!

6.2 mi to the beach
Sleeps 4 pers.2 bedrooms1,195 ft²
YardTerraceParkingInternet
FREE cancellation
9.9 · Fantastic
151 reviews
from
$304
per night
Book on Vrbo

Modern Beachfront Cottage with Endless Bay Views

6.5 mi to the beach
Sleeps 6 pers.2 bedrooms667 ft²
YardTerraceParkingInternet
FREE cancellation
9.9 · Fantastic
55 reviews
from
$416
per night
Book on Vrbo

Historic home on Smith Island w/ dock!

Sleeps 6 pers.3 bedrooms1,195 ft²
YardTerraceParkingInternet
FREE cancellation
9.5 · Fantastic
45 reviews
from
$203
per night
Book on Vrbo

Sailor's Sunrise Cottage - Chesapeake Bay

1.9 mi to the beach
Sleeps 6 pers.3 bedrooms797 ft²
Hot tubParkingInternet
FREE cancellation
9.5 · Fantastic
51 reviews
from
$10,629
per night
Book on Vrbo

Waterfront Property, kayaks, private dock, near town

Sleeps 6 pers.3 bedrooms2,992 ft²
BalconyYardParkingInternet
FREE cancellation
9.9 · Fantastic
70 reviews
from
$705
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
© 2026 hundredrooms is a Holidu GmbH company
·Imprint·GTC·Privacy policy·Content policy·Whistleblower system