What are the top rated Short Term Stays in Chesapeake Bay?

There are a lot of options in Chesapeake Bay. If you plan on staying in the Chesapeake Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the top Short Term Stays in Chesapeake Bay: <a href="/property/ultraclean-family-waterfront-home-annapolis-area-200-top-reviews/HA-321432131" class="class="static-page-link"">Ultraclean Family Waterfront Home Annapolis Area - 200+ Top Reviews!</a> <a href="/property/renovated-apt-in-historic-dist-w-2-parking-spots/HA-3211355581" class="class="static-page-link"">Renovated Apt In Historic Dist w 2 Parking Spots</a> <a href="/property/overlook-on-dun-s-cove-luxury-waterfront-hideaway-minutes-from-st-michaels/HA-1214500814" class="class="static-page-link"">Overlook on Dun&#39;s Cove - Luxury waterfront hideaway minutes from St. Michaels</a> <a href="/property/annapolis-eastport-private-beautiful-apt-1-mile-walk-to-downtown/HA-321775994" class="class="static-page-link"">Annapolis/Eastport Private Beautiful Apt- &lt; 1 Mile Walk To Downtown</a> <a href="/property/stunning-new-construction-in-historic-cape-charles-3-1-2-blocks-to-the-beach/HA-3211999565" class="class="static-page-link"">Stunning New Construction in Historic Cape Charles 3 1/2 Blocks to the Beach</a> <a href="/property/beautiful-waterfront-cottage-near-downtown-norfolk-a-peaceful-secluded-paradise/HA-3211163766" class="class="static-page-link"">Beautiful Waterfront Cottage near Downtown Norfolk- A Peaceful Secluded Paradise</a> <a href="/property/sea-la-vie-steps-to-the-beach-without-a-crowd/HA-321572528" class="class="static-page-link"">Sea La Vie - steps to the beach without a crowd</a> <a href="/property/hurry-reserve-your-stay-for-nsummer-fall-of-2025nstr-22-30/HA-3211294816" class="class="static-page-link"">Hurry, reserve your stay for nSummer &amp; Fall of 2025nSTR #22-30</a> <a href="/property/waterfront-paradise-with-pool-hot-tub-plus-4-king-beds-4-full-baths/HA-3212745552" class="class="static-page-link"">Waterfront Paradise with Pool &amp; Hot Tub plus 4 King Beds &amp; 4 Full baths</a> <a href="/property/southern-comfort-on-the-bay/HA-321305827" class="class="static-page-link"">Southern Comfort on the Bay</a>

How much is rent for a furnished short-term stay in Chesapeake Bay?

At Bestfamilyescapes short-term furnished accommodation in or near Chesapeake Bay ranges from $54 to $2,650 per night.

How many holiday rentals near Chesapeake Bay are available?

We have 1414 places to stay near Chesapeake Bay. Check out the complete list of holiday rentals in Chesapeake Bay to find what works for your next trip.

Can we get a self-catering short-term stay in Chesapeake Bay?

Yes, there are 1414 self-catering short-term rental homes in Chesapeake Bay that have hot tubs & other amenities The most popular self-catering top-rated rental homes are: PERFECT LOCATION in the heart of history Candlewood Suites Annapolis by IHG ROOST Baltimore GREAT HOUSE ON LITTLE BAY WITH PIER

What are the best luxury short-term stays for families near Chesapeake Bay?

There are more than 1414 luxury temporary places to stay near Chesapeake Bay, with other amenities available according to 2025 data from Bestfamilyescapes.

Chesapeake Bay Short-Term Rentals

PERFECT LOCATION in the heart of history

From US $376

10.0 (214 Reviews)

House

PERFECT LOCATION in the heart of history

Air Conditioner
Parking
TV

Chesapeake Bay Short-Term Vacation Rentals

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