Beachfront Hotels Chesapeake Bay

More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers

Flexibility matters
24/7 support, so you can book with confidence

Relax with our Price Promise
Find a lower price on a hotel or package online, before your stay, and we'll refund the difference^

Check availability on Oceanfront Hotels in Chesapeake Bay

Tonight
Check prices in Chesapeake Bay for tonight, 25 Nov - 26 Nov
25 Nov - 26 Nov
Tomorrow night
Check prices in Chesapeake Bay for tomorrow night, 26 Nov - 27 Nov
26 Nov - 27 Nov
This weekend
Check prices in Chesapeake Bay for this weekend, 29 Nov - 1 Dec
29 Nov - 1 Dec
Next weekend
Check prices in Chesapeake Bay for next weekend, 6 Dec - 8 Dec
6 Dec - 8 Dec

Oceanfront Hotels in Chesapeake Bay

Best Western Plus Holiday Sands Inn & Suites

Best Western Plus Holiday Sands Inn & Suites

2.5 out of 5
1330 E Ocean View Ave, Norfolk, VA
The price is NZ$160 per night
NZ$160
includes taxes & fees
1 Dec - 2 Dec
Book a stay at this beach hotel in Norfolk. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Norfolk Beaches and Ocean View Beach are located nearby.
Free cancellation
Reserve now, pay when you stay
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is NZ$594 per night
NZ$594
includes taxes & fees
17 Dec - 18 Dec
Book a stay at this luxury hotel in St. Michaels. Enjoy free WiFi, free valet parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Chesapeake Bay Maritime Museum and St. Michaels Museum are located nearby.
Pool
Hot tub
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St, Annapolis, MD
The price is NZ$405 per night
NZ$405
includes taxes & fees
1 Dec - 2 Dec
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Ego Alley and Kunta Kinte Plaque & Alex Haley Memorial are located nearby.
Pet-friendly
Free WiFi
Free cancellation
Reserve now, pay when you stay
Comfort Suites Chincoteague Island Bayfront Resort

Comfort Suites Chincoteague Island Bayfront Resort

2.5 out of 5
4195 Main St, Chincoteague, VA
The price is NZ$180 per night
NZ$180
includes taxes & fees
22 Dec - 23 Dec
Stay at this hotel in Chincoteague. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Robert N. Reed Downtown Waterfront Park and Maui Jack's Waterpark are located nearby.
Pool
Hot tub
Free cancellation
Reserve now, pay when you stay
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd, Cambridge, MD
The price is NZ$411 per night
NZ$411
includes taxes & fees
2 Dec - 3 Dec
Stay at this 4-star beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Bay Country Shop and Dorchester County Visitors Center are located nearby.
On private beach
Pool
Free cancellation
Reserve now, pay when you stay
Hilton Garden Inn Kent Island

Hilton Garden Inn Kent Island

3 out of 5
3206 Main St, Grasonville, MD
The price is NZ$241 per night
NZ$241
includes taxes & fees
1 Dec - 2 Dec
Stay at this 3-star business-friendly hotel in Grasonville. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Chesapeake Bay Environmental Center and Queenstown Harbor Golf Links are located nearby.
Pool
Pet-friendly
Americas Best Value Inn Princess Anne

Americas Best Value Inn Princess Anne

2 out of 5
30359 Mt. Vernon Road, Princess Anne, MD
The price is NZ$133 per night
NZ$133
includes taxes & fees
3 Dec - 4 Dec
Stay at this motel in Princess Anne. Enjoy free WiFi, premium TV channels, and housekeeping. Popular attractions Hytche athletic Center and Bordeleau Winery are located nearby.
Free cancellation
Reserve now, pay when you stay
Anchor Inn

Anchor Inn

2 out of 5
3791 South Main Street, Chincoteague, VA
The price is NZ$155 per night
NZ$155
includes taxes & fees
3 Dec - 4 Dec
Book a stay at this business-friendly hotel in Chincoteague. Enjoy free WiFi, an outdoor pool, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions Robert N. Reed Downtown Waterfront Park and Maui Jack's Waterpark are located nearby.
Pool
Free WiFi
Free cancellation
Reserve now, pay when you stay
Fig Street Inn

Fig Street Inn

3.5 out of 5
711 Tazewell Avenue, Cape Charles, VA
Stay at this 3.5-star B&B in Cape Charles. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Cape Charles Museum & Welcome Center and Cape Charles Beach are located nearby.
Breakfast included
Parking included
Inn at Huntingfield Creek

Inn at Huntingfield Creek

3.5 out of 5
4928 Eastern Neck Rd, Rock Hall, MD
The price is NZ$373 per night
NZ$373
includes taxes & fees
26 Nov - 27 Nov
Stay at this 3.5-star spa B&B in Rock Hall. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Rock Hall Harbor and The Mainstay are located nearby.
Pool
Spa
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3 out of 5
6176 Tilghman Island Road, Tilghman, MD
The price is NZ$226 per night
NZ$226
includes taxes & fees
1 Dec - 2 Dec
Stay at this 3-star hotel in Tilghman. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Phillips Wharf Environmental Center and Tilghman Watermen’s Museum are located nearby.
Pool
Breakfast included
Free cancellation
Reserve now, pay when you stay
Lowes Wharf Marina Inn

Lowes Wharf Marina Inn

3 out of 5
21651 Lowes Wharf Rd, Sherwood, MD
Stay at this 3-star beach inn in Sherwood. Enjoy free WiFi, free parking, and a marina. Popular attractions Tilghman Watermen’s Museum and St. Michaels Winery are located nearby.
Don't see what you're looking for?
See all available properties in Chesapeake Bay
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Oceanfront Hotels in Chesapeake Bay

Search for hotels in Chesapeake Bay on Wotif. You can easily find your hotels in Chesapeake Bay using one of the methods below:

  • View our selection of featured hotels in Chesapeake Bay
  • Use the map to find hotels in the Chesapeake Bay neighborhood you prefer
  • Use the filters to see hotels in a specific area of Chesapeake Bay, select a specific theme, brand, or hotel class from basic (property class 1) to luxury hotels (property class 5) in Chesapeake Bay
  • Enter your travel dates to view the best deals on hotels in Chesapeake Bay - while they last

Chesapeake Bay hotels essential information

Accommodation
14,113 hotels
Lowest Price
NZ$133
Highest Price
NZ$594
Popular hotels
Best Western Plus Holiday Sands Inn & Suites, Inn at Perry Cabin, Annapolis Waterfront Hotel, Autograph Collection, Comfort Suites Chincoteague Island Bayfront Resort, Hyatt Regency Chesapeake Bay, Hilton Garden Inn Kent Island, Americas Best Value Inn Princess Anne, Anchor Inn, Fig Street Inn, Inn at Huntingfield Creek, Knapps Narrows Marina & Inn, Lowes Wharf Marina Inn

New reviews! Best hotels in Chesapeake Bay

Omni Shoreham Hotel
Wotif Verified Review
5 / 5
great location
A verified traveller stayed at Omni Shoreham Hotel
Posted 3 hours ago
Omni Shoreham Hotel

Top Cities for Oceanfront Hotels

Neighbourhoods

Nearby cities

Near an airport

Near an Attraction

Hotel themes

More accommodations

Hotel brands