Chesapeake bay vacation rental

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Best Vacation Home Deals in Chesapeake Bay

Recommended Vacation Rentals in Chesapeake Bay

Find your perfect vacation rental in Chesapeake Bay: from $55 per night

Vacation rentals with Wi-Fi

Vacation rentals and apartments with air conditioning

Apartments and vacation rentals with a kitchen

Popular Rental Amenities in Chesapeake Bay

Using our filters will help you find the perfect vacation rental in Chesapeake Bay. HomeToGo's data highlights that "internet" and "TVs" turn out to be the most frequently offered features in Chesapeake Bay. Plan your vacation in advance if you love sweating the stress away in saunas or you want a rental with a jacuzzi. There are just 207 listed accommodations providing "saunas" and 617 properties including "Jacuzzis."

The Weather in Chesapeake Bay

The above is a climate diagram for Chesapeake Bay. During July, maximum temperatures go up to more than 87° However, temperatures can go lower than 28° in Chesapeake Bay in January. The rainiest month is January while the driest month is November.

7-Day Weather Forecast in Chesapeake Bay

Mon, 25 Oct

Tue, 26 Oct


Eastern Shore Vacation Rentals

Eastern Shore MD Areal shot

Specializing in unique vacation properties in the charming towns of the Eastern Shore of the Chesapeake Bay. Offering a boutique selection of cottages, waterfront homes and estates.

chairs by the water in Eastern Shore MD

Our hand-selected portfolio of Eastern Shore, MD, vacation rentals includes properties ranging from quaint historic cottages, waterfront vacation homes or estate luxury properties offering the very best of Eastern Shore living. Our pet-friendly rentals cater to the whole family so there’s no need to leave your furry friends behind! Our warm, friendly and knowledgeable staff adds an extra special personalized touch to your dream vacation and our effortless search and booking process ensures an unrivaled Chesapeake Bay vacation experience with the privacy, space, comfort, and amenities of home…simply a click away!

View Our Properties

Bike with basket on a beach bridge

Discover the beauty and fascinating maritime heritage of Maryland’s Eastern Shore as you explore miles of pristine shoreline dotted with charming towns, historic sites, scenic wildlife refuges and breathtaking sunsets across the Chesapeake Bay. Head to the harbor in St. Michaels, the “Heart & Soul of Chesapeake Bay”, for a ride on the historic skipjack or cross the drawbridge to the traditional quaint waterman’s village of Tilghman Island. Immerse yourself in nature at the Blackwater National Refuge in Cambridge, roam the streets of Easton voted the “8th Best Small Town in America”, watch the sailboats passing by in Oxford, one of the oldest towns in America or stroll along the brick sidewalks in the historic college town of Chestertown. Wherever you choose to lay your hat, we have the perfect Eastern Shore vacation home for you to complete your visit.

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family sitting on a bridge over water

All-Inclusive Pricing – our prices include everything you need for a relaxing vacation: bed and bath linens, beds made upon arrival, and all other fees (except state and local tax!).

  • No Pet Fees – No need to leave your best friend behind! Many ESVR homes are dog-friendly and dogs travel free (two dog limit, please).
  • Best Price Guarantee – For the best pricing, promotions and last minute deals, check our website frequently and book directly with us. No unnecessary service fees!

Read Our FAQs

Management Services - two chairs on a porch in day

Eastern Shore Vacation Rentals specializes in marketing and managing short-term vacation rentals – it’s all we do! Vacation rentals are currently the fastest growing segment of the tourism industry and we understand the booking trends! We value both our guests and homeowners and our goal is to maximize your Eastern Shore rental income while offering proactive property care and management to the owner and upscale amenities and top-notch service to our guests. Our state-of-the-art website, unparalleled marketing, and online booking process optimize the booking of your property and our expertise in the vacation rental industry ensures your vacation home is in the best hands. Please contact us, one of our friendly team members is standing by to discuss our Maryland based property management services and how we can best partner with you to grow your investment.

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  • Locally owned and operated
  • Office close to your rental
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Viewing 11 of 11
rentals in Chesapeake Bay

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Rental types

Rental types

  • Cottage (4)
  • House (5)
  • Bungalow (1)
  • Private room (1)

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  • Wireless Internet
  • Air conditioning
  • Swimming pool
  • Private pool

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  • Pets
  • Pets allowed
  • Parking
  • Car not required

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  • Beach or lakeside relaxation
  • Walking trips
  • Tennis in town
  • Water sports

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11 Results


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This is the estimated nightly price based on a weekly stay.

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Vacation Rentals on Chesapeake Bay

I couldn't just take it and put up with it. No. I started to deny, to speak, It looked quite calm, but with an easy playfulness at this, looking at me through the shoulder.

Vacation rental bay chesapeake

How do you talk to her. Burknesh something and ran. Have you ever asked what worries her.

Vacation Rental, Chesapeake City, MD

With her palms. Both moaned, bodies slapped. I wonder where her husband is fucking her.

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You will understand tomorrow. Mom loves her horses and thinks that the horse will come out of you very beautiful and exotic. Harmony said nothing, not wanting to demonstrate ignorance.

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