18 Chesapeake Street

THE CUTEST BEACH HOUSE IN DEWEY...STEPS TO OCEAN! 18 Chesapeake Street is located in the Rehoboth-By-The-Sea section of Dewey Beach. Mere steps to the beach - you don't have to cross a street! Gorgeous landscaping, ocean view from roof top deck, backyard oasis, relaxing screened porch, decorated with style, panache and care - NOT YOUR AVERAGE BEACH HOUSE! Fire pit in back yard, hammock, outdoor shower with dressing area, upper deck dining, awesome fun bunk room for the kids, walking distance to Rehoboth and Dewey dining, shops and fun! All bedrooms have ceiling fans for your comfort! Home can accommodate 1 Dog with pet fee! (Please inquire if you have an additional dog.) Two parking spaces and 2 Dewey Beach permits supplied. Gas grill, fully equipped kitchen, spa-like bathrooms and wireless internet! Available off season weeks and weekends and full weeks in season.
The property must be occupied for the entire rental period by the Guest signing the Lodging Agreement (Responsible Guest), and all occupants of the Property shall be supervised by the Responsible Guest. The Responsible Guest must be at least 25 years of age. If the party is made up of unrelated individuals (a group rental where the Responsible Guest is NOT the legal guardian/parent of any other guests), ALL guests occupying the property must be at least 25 years of age.
Guests pay a $165.00 cleaning fee for stays under 7 nights. Sheets/towels/paper products are not included, linens are available for rent.
Guests must choose to purchase a $70 Vacation Rental Damage Insurance policy covering $3,000.00 in accidental damage or pay a refundable security deposit of $2,000.00. Policies of a lesser amount are not acceptable.
We accept Mastercard, Visa, American Express and Discover Credit Cards and eChecks for your initial deposit. We also accept personal checks for final payments. Final payments are due 30 days prior to your check-in date. NOTE: Any payments within 30 days of arrival require to be in certified funds or by credit card. You will be provided a link to a Guest Portal where you can securely make your payments online.
VRBO BOOKINGS: This property is hosted by the management company noted as owner on this site. After booking the property you will be charged a booking fee by VRBO. ALL other fees and the rental amount will be charged by the management company and paid to the management company. Once you have booked on VRBO, you will be contacted by a representative from the management company via phone or email and you will be sent a Lodging Agreement that must be signed to confirm your reservation. Apart from damage protection, all fees associated with the booking are displayed in the VRBO booking. Unless indicated otherwise, Linens/Towels and paper products are NOT INCLUDED. Guests may rent Linens/Towels through the hosting company or bring their own.

Vacation Rental Reviews

• My summer vacation

  Stayed 7 days ending in June, 2026

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  Pat C from Vienna, VA recommends this vacation rental

  Great house! Loved the porch and outdoor space!

  • Manager Responded on 6/24/2026

    Thank you for the review and hope you had a great vacation! Let us know if there is anything we can improve on.

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• 18 Chesapeake Street

  Stayed 7 days ending in June, 2024

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  Kimberly S from Clifton, VA recommends this vacation rental

  Cute house close to the beach. Fantastic screened porch, outside space and sun deck. House has a fun surfer beach vibe, kitchen was fully stocked with everything we needed, bathrooms are nicely updated. My only complaint is the furniture is not all that comfortable.

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• Dewey dream

  Stayed 3 days ending in August, 2023

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  a guest from North Potomac, MD recommends this vacation rental

  18 Chesapeake is the perfect dog friendly, beach block vacation spot! We had a wonderful time and will be back!

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• 18 Chesapeake Street 2023 Review

  Stayed 7 days ending in June, 2023

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  Cathy C from Glenmont, NY recommends this vacation rental

  Amazing, fun, happy, relaxing, beautiful, comfortable,

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• Dewey Beach House

  Stayed 7 days ending in June, 2023

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  Terrence G from Coopersburg, PA recommends this vacation rental

  We had a great week at 18 Chesapeake. Great location! Great outdoor living spaces. Furniture inside living areas a bit dated. We plan to rent again next year

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• Retro Dream Beach House

  Stayed 7 days ending in May, 2022

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  a guest from North Potomac, MD recommends this vacation rental

  We had a wonderful stay and can't wait to return. The house is beautiful and in the perfect location - steps to the ocean and close to all activities. The retro style of the beach house is something I love! Plenty of gathering places for family and friends.

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