hundredroomsby Holidu
Get the appList your property

Chesapeake bay, virginia, usa

1,061 accommodations found

Park Place - Comfy Condo Close to Beach

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

Adorable Chesapeake Bay Beach Cottage B Just 1 Block from the Sand!

Sleeps 6 pers.3 bedrooms1,798 ft²
ParkingInternet
9.3
Fantastic
15 reviews
from
$399
per night
Free cancellation
Book on Vrbo
Secure dataPowered by HoliduReliable service

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

4.3 mi to the beach
Sleeps 14 pers.6 bedrooms4,596 ft²
PoolTerraceParkingInternet
9.9
Fantastic
70 reviews
from
$1,021
per night
Free cancellation
Book on Vrbo

❤️The Safe House❤️Downtown Newport News!

8.3 mi to the beach
Sleeps 4 pers.1 bedroom947 ft²
ParkingKitchenInternet
9.3
Fantastic
9 reviews
from
$108
per night
Free cancellation

The 1850 House

Sleeps 7 pers.4 bedrooms6,060 ft²
ParkingKitchenInternet
from
$255
per night
Free cancellation

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

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

❤️Breakfast @ Tiffany's❤️Downtown Newport News!

8.3 mi to the beach
Sleeps 4 pers.1 bedroom947 ft²
ParkingKitchenInternet
8.5
Very good
4 reviews
from
$154
per night
Free cancellation

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

5 mi to the beach
Sleeps 8 pers.3 bedrooms13,455 ft²
BalconyYardParkingKitchen
9.6
Fantastic
from
$153
per night
Free cancellation

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
7.2
Good
32 reviews
from
$401
per night
Free cancellation
Book on Vrbo

❤️The Speakeasy❤️Downtown Newport News!

8.4 mi to the beach
Sleeps 4 pers.1 bedroom947 ft²
ParkingKitchenInternet
8.7
Very good
12 reviews
from
$109
per night
Free cancellation

Modern Beachfront Cottage with Endless Bay Views

6.5 mi to the beach
Sleeps 6 pers.2 bedrooms667 ft²
YardTerraceParkingInternet
9.9
Fantastic
56 reviews
from
$369
per night
Free cancellation
Book on Vrbo

The Crab Shack on Carter's Creek

3.2 mi to the beach
Sleeps 4 pers.1 bedroom840 ft²
YardTerraceParkingInternet
9.9
Fantastic
80 reviews
from
$315
per night
Free cancellation
Book on Vrbo

Gwynn's Island Cottage w/ Private Beach-Summer Weeks Open!

6.2 mi to the beach
Sleeps 4 pers.2 bedrooms1,195 ft²
YardTerraceParkingInternet
9.9
Fantastic
152 reviews
from
$334
per night
Free cancellation
Book on Vrbo

Romantic Waterfront Abode with Patio & Dock!

5.4 mi to the beach
Sleeps 2 pers.1 bedroom743 ft²
Balcony/TerraceYardParkingInternet
9.7
Fantastic
61 reviews
from
$205
per night
Free cancellation
Book on Vrbo

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Sleeps 6 pers.4 bedrooms
YardTerraceParkingInternet
10
Fantastic
77 reviews
from
$348
per night
Free cancellation
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
9.9
Fantastic
74 reviews
from
$272
per night
Free cancellation
Book on Vrbo

Sailor's Sunrise Cottage - Chesapeake Bay

1.9 mi to the beach
Sleeps 6 pers.3 bedrooms797 ft²
Hot tubYardParkingInternet
9.5
Fantastic
51 reviews
from
$283
per night
Free cancellation
Book on Vrbo

Waterfront Cottage in Beautiful Hoopers Island

Sleeps 5 pers.2 bedrooms570 ft²
YardTerraceParkingInternet
9.8
Fantastic
79 reviews
from
$258
per night
Free cancellation
Book on Vrbo

Nancy’s Touch, A Waterfront Paradise!

350 yd to the beach
Sleeps 6 pers.3 bedrooms
YardTerraceParkingInternet
10
Fantastic
125 reviews
from
$484
per night
Free cancellation
Book on Vrbo

\"Gull Cottage\" 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
9.7
Fantastic
66 reviews
from
$175
per night
Free cancellation
Book on Vrbo

Bay Front Small Contemporary

2 mi to the beach
Sleeps 4 pers.2 bedrooms646 ft²
TerraceParkingInternet
9.7
Fantastic
82 reviews
from
$301
per night
Free cancellation
Book on Vrbo

Peaceful getaway convenient to local amenities including beach, boating & food

5.9 mi to the beach
Sleeps 4 pers.2 bedrooms1,195 ft²
YardParkingInternet
9.6
Fantastic
85 reviews
from
$242
per night
Free cancellation
Book on Vrbo

Waterfront Property, kayaks, private dock, near town

Sleeps 6 pers.3 bedrooms2,992 ft²
BalconyYardParkingInternet
9.9
Fantastic
70 reviews
from
$715
per night
Free cancellation
Book on Vrbo

Welcome to \"The Happy Soul\"

Sleeps 6 pers.3 bedrooms1,798 ft²
TerraceParkingInternet
10
Fantastic
56 reviews
from
$220
per night
Free cancellation
Book on Vrbo

St. Paddy’s Day is coming. Treat your lassie to a weekend at the Rivah!

2.9 mi to the beach
Sleeps 4 pers.2 bedrooms1,690 ft²
YardTerraceParkingInternet
9.8
Fantastic
171 reviews
from
$279
per night
Free cancellation
Book on Vrbo

Charming Waterfront Home on Sought After Piankatank!

Sleeps 6 pers.3 bedrooms
YardTerraceParkingInternet
9.9
Fantastic
55 reviews
from
$290
per night
Free cancellation
Book on Vrbo

Stay in the landmark Lighthouse!

6.1 mi to the beach
Sleeps 6 pers.3 bedrooms2,293 ft²
YardTerraceParkingInternet
9.9
Fantastic
73 reviews
from
$471
per night
Free cancellation
Book on Vrbo

Thelma’s Dawn Getaway! A true No Drama Zone

7.7 mi to the beach
Sleeps 4 pers.1 bedroom291 ft²
YardTerraceParkingInternet
9.9
Fantastic
86 reviews
from
$258
per night
Free cancellation
Book on Vrbo

All the comforts of home!

0.7 mi to the beach
Sleeps 7 pers.3 bedrooms1,894 ft²
BalconyParkingInternet
9.8
Fantastic
56 reviews
from
$263
per night
Free cancellation
Book on Vrbo

Beachfront Getaway, Mermaid Suite, 🐶 💙

0.6 mi to the beach
Sleeps 6 pers.3 bedrooms2,067 ft²
YardTerraceParkingInternet
One more unit available
9.9
Fantastic
101 reviews
from
$516
per night
Free cancellation
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