We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Looking to vacation in the Chesapeake Bay area.

Altoona...
1 post
1 review
Save Topic
Looking to vacation in the Chesapeake Bay area.

We normally vacation in the OBX area every year but are looking to change it up. We have never been to the Chesapeake Bay area and were thinking that it would be a nice change. But we have no clue what community/city would be a good place to start our rental search.

We have two small children and dogs and we like to rent waterfront houses. Could somebody point me in the right direction? Thank you so much in advance!

3 replies to this topic
Baltimore, Maryland
Destination Expert
for North Conway
Level Contributor
12,223 posts
58 reviews
Save Reply
1. Re: Looking to vacation in the Chesapeake Bay area.

You don't know where to start because the bay doesn't have any beach resorts. Bad year to switch with NJ getting wiped out. Suggest either cape cod North or cape may South but stay on the ocean.

gettysburg, pa
Destination Expert
for Gettysburg
Level Contributor
1,010 posts
55 reviews
Save Reply
2. Re: Looking to vacation in the Chesapeake Bay area.

The Chesapeake Bay offers more of a boating and fishing vacation. Is that what you are looking for? If so, you may want to think about the Kent Island area, Rock Hall, or Oxford. You may also like the Lewes, DE area, which is on the Delaware Bay.

If you are looking for a beach vacation, you would probably be better off with Ocean City, Bethany Beach DE, or Chincoteague, VA. The Chincoteague area might have everything that you are looking for and the forum is very friendly. They'll have lots of ideas for you! :)

Rehoboth Beach...
Destination Expert
for Myrtle Beach
Level Contributor
3,374 posts
29 reviews
Save Reply
3. Re: Looking to vacation in the Chesapeake Bay area.

The Chesapeake Bay is huge. At the northern tip (closest to you), North East and Havre de Grace are worth a look with unique shops, restaurants, and scenery. For renting a cottage waterfront or waterview, you could try nearby Charlestown, MD.

"Eastern Shore" towns of interest include St. Michaels, Tilghman Island, historic Easton & Oxford, and Crisifield at the southern tip.

Staying on the bay, as aster143 points out, is not a typical "beach" vacation, more for boaters and fishermen. You can swim in the bay, and the water is often warmer than the ocean, but access with easy ingress/egress and sand beaches are few and far between. However, the water can get quite choppy on windy days (or near boat traffic, and sea lice can be a problem in hot weather.

People swim along the sandy shoreline in Charlestown and the nearby campgrounds (which you can enter on a day pass), and some marinas also offer daily admission to their sandy, roped off swimming beaches.

The aforementioned Lewes (DE) beach, on the DE bay, is a better choice for swimming and broad sandy beaches. Very safe for young children. There are houses/cottages you can rent both beachfront (beyond the seagrass) and within a short walk. The town is also charming, and right next door to Rehoboth with plenty to see/do. We love it there.

Reply to: Looking to vacation in the Chesapeake Bay area.
Get notified by e-mail when a reply is posted