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Oceanfront Hotels in Chesapeake Bay

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Featured Chesapeake Bay Oceanfront Hotels

Inn at Perry Cabin
Inn at Perry Cabin
5 out of 5
308 Watkins Ln, St. Michaels, MD
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. ...
9.4/10 Exceptional! (344 reviews)
"A true 5-star experience from the moment we pulled up. Highly recommend a sail with Captain Sean, participating in the 5pm toast, and staying for longer than the one night that we did! We’ll be back!"

Reviewed on Apr 27, 2025

Inn at Perry Cabin
Comfort Suites Chincoteague Island Bayfront Resort
Comfort Suites Chincoteague Island Bayfront Resort
2.5 out of 5
4195 Main St, Chincoteague, VA
Fully refundableReserve now, pay when you stay
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 ...
9.4/10 Exceptional! (1,000 reviews)
"Extremely friendly staff, excellent location. Enjoyed sitting on the Adirondack chairs facing the water. Great experience, would definitely stay here again!"

Reviewed on Apr 26, 2025

Comfort Suites Chincoteague Island Bayfront Resort
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina
3 out of 5
3206 Main St, Grasonville, MD
Stay at this 3-star business-friendly hotel in Grasonville. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff ...
9/10 Wonderful! (913 reviews)
"Service and friendliness of staff was awesome. Water pressure in shower was low and bathroom sink did not drain well. From 9:30 am until 10:30 there were no carts available to help with luggage. Overall was great."

Reviewed on Apr 27, 2025

Hilton Garden Inn Kent Island Marina
Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection
4 out of 5
80 Compromise St, Annapolis, MD
Fully refundableReserve now, pay when you stay
Stay at this 4-star eco-certified hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (813 reviews)
"Good"

Reviewed on Mar 23, 2025

Annapolis Waterfront Hotel, Autograph Collection
Hyatt Regency Chesapeake Bay
Hyatt Regency Chesapeake Bay
4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
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. ...
8.6/10 Excellent! (1,000 reviews)
"Beautiful property and love movie night."

Reviewed on Apr 20, 2025

Hyatt Regency 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
Fully refundableReserve now, pay when you stay
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. ...
7.8/10 Good! (999 reviews)
Blessed
"IWe enjoyed our stay and yes everything was nice, the room was clean and staff gave a great service, they were kind and breakfast was awesome and we want to return in the month of July."

Reviewed on Apr 22, 2025

Best Western Plus Holiday Sands Inn & Suites
Americas Best Value Inn Princess Anne
Americas Best Value Inn Princess Anne
2 out of 5
30359 Mt. Vernon Road, Princess Anne, MD
Fully refundableReserve now, pay when you stay
Stay at this motel in Princess Anne. Enjoy free WiFi, premium TV channels, and housekeeping. Popular attractions Manokin Park and Hytche athletic Center are ...
6.2/10 (44 reviews)
Great two nights stay!!!
"My two-nights stay was relaxing and peaceful. The bed was very comfortable, and the TV had lots of channels to choose from. The heater was somewhat noisy, but my room was nice and warm. Overall, nice stay."

Reviewed on Feb 10, 2025

Americas Best Value Inn Princess Anne
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.

Hotels with Pools in Chesapeake Bay

Washington Plaza Hotel
Washington Plaza Hotel
4 out of 5
10 Thomas Circle NW, Washington, DC
Book a stay at this business-friendly hotel in Washington. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the breakfast and the ...
8.6/10 Excellent! (4,240 reviews)
"Great stay. No issues."

Reviewed on Apr 30, 2025

Washington Plaza Hotel
Capitol Skyline Hotel
Capitol Skyline Hotel
3.5 out of 5
10 I Street S.W, Washington, DC
Stay at this 3.5-star business-friendly hotel in Washington. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Popular attractions National Mall and ...
7.8/10 Good! (1,000 reviews)
"Its clos3e"

Reviewed on Jul 4, 2021

Capitol Skyline Hotel
Hilton Vacation Club The Historic Powhatan Williamsburg
Hilton Vacation Club The Historic Powhatan Williamsburg
3.5 out of 5
3601 Ironbound Rd, Williamsburg, VA
Stay at this 3.5-star golf resort in Williamsburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the restaurant in ...
8.8/10 Excellent! (2,719 reviews)
"If you're looking for a home away from home on your vacation, look no further. This place was amazing. Enormous, clean, relaxing. Definitely check it out."

Reviewed on Apr 28, 2025

Hilton Vacation Club The Historic Powhatan Williamsburg
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.

Spa Hotels in Chesapeake Bay

The Founders Inn and Spa, Tapestry Collection by Hilton
The Founders Inn and Spa, Tapestry Collection by Hilton
4 out of 5
5641 Indian River Rd, Virginia Beach, VA
Book a stay at this spa hotel in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
The Founders Inn and Spa, Tapestry Collection by Hilton
The Watergate Hotel
The Watergate Hotel
5 out of 5
2650 Virginia Ave NW, Washington, DC
Book a stay at this spa hotel in Washington. Enjoy free WiFi, a full-service spa, and 3 bars/lounges. Our guests praise the bar and the helpful staff in our ...
The Watergate Hotel
Archer Hotel Old Town Alexandria
Archer Hotel Old Town Alexandria
4.5 out of 5
1600 King Street, Alexandria, VA
Stay at this 4.5-star luxury hotel in Alexandria. Enjoy free WiFi, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
Archer Hotel Old Town Alexandria
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.

Ocean View Hotels in Chesapeake Bay

Hear that? The soothing sounds of the sea? Of course you can because you booked a stay in a Chesapeake Bay with an ocean view. Gaze out your hotel window, admire that sea of endless blue, and listen for the sound of the waves gently lapping the shore. Sounds pretty nice, doesn’t it? Well, you could experience it all during your next trip when you book a hotel overlooking the ocean.

See the sea easily

Whether you’re here with the fam or sailing solo, when you head to Chesapeake Bay’s coast you have one thing in mind: beach day, all day. When you stay in one of the Chesapeake Bay ocean view hotels you’ll have your sights set on the shore morning, noon, and night. Because let’s face it, things are just cooler closer to the coast. You have that easy, sea breezy vibe and you’ll find yourself tuning into island time.

The coast is clear

When you want that postcard-worthy view from your room, then a beachfront resort is where it’s at. You can sort our ocean view hotels by:

  • Hotwire Hot Rate: That ocean view won’t cost you a ton of clams. You’ll find out the hotel name after you book, but you can rest assured the view is going to be great!

  • Price: No need to drain your bank account for a hotel with a million-dollar view. Our rooms start at $89.

  • Amenities: Hotels in Chesapeake Bay with an indoor pool? Maybe you want a kitchenette to make it homier? Search our inventory for a sea of fabulous options.

When nothing but an ocean view will do on your next trip to Chesapeake Bay then look no further than Hotwire. We can get you a sweet deal on your Chesapeake Bay hotel, which means you’ll have more cash left over to make your vacay more than a lovely view.