319 Chestnut Street (8)

In-town Lewes with lots of space to spread out. The owners have thought of everything to make your vacation a comfortable stay. With plenty of room to spread out take advantage of the living space for game night or a movie after the beach.

One bedroom is located on the 1st floor. The remaining bedrooms are on the second floor.

All guests must supply their own sheets, towels and beach towels or OPT in for our linen rental package.

Pets are not permitted at this property.

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.

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.

Lewes Lic# R2300318

Vacation Rental Reviews

• Great house

  Stayed 4 days ending in October, 2025

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  a guest from Narberth, PA recommends this vacation rental

  Very roomy, light filled, near the town, great places to walk.

  • Manager Responded on 10/16/2025

    Thank you Mary, It's wonderful to know that you enjoyed the open, light-filled design of the space. We strive to offer a setting that feels both expansive and inviting. We're also glad you found the location favorable, particularly the easy access to town and the nearby walking paths. We hope to see you again soon! Lewes Rental Team

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• Pleasant stay in downtown Lewes

  Stayed 7 days ending in August, 2025

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  Chris E from Columbia, MD recommends this vacation rental

  The house was nice and was a very short walk to downtown Lewes. The beach was a short drive, but is walkable for older kids and adults. Cape Henlopen and the Cape May - Lewes Ferry are just a few minutes away.

  • Manager Responded on 8/6/2025

    Thank you for sharing your experience! We’re glad you enjoyed the convenient location with easy access to downtown Lewes and nearby attractions like Cape Henlopen and the ferry. It’s great to hear the beach was walkable for your group as well. We hope to welcome you back soon! Lewes Rental Team

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• Another Year at the Big Blue House

  Stayed 7 days ending in July, 2025

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  a guest from West Chester, PA recommends this vacation rental

  Another great stay at 319 Chestnut Street. Property is well maintained and clean - tons of space. Walkable to just about everything in Lewes and two parking spots out back. Quiet and peaceful! Could see some recently replaced boards on the deck out back we enjoy sitting on. Lots of mosquitos, but we just come prepared.

  • Manager Responded on 7/13/2025

    Denise,Thank you for returning to 319 Chestnut Street and for sharing such a detailed and thoughtful review! We're so glad to hear you enjoyed the space, the peaceful surroundings, and the convenience of being close to everything in Lewes. We’re also happy you noticed the updates to the deck — it's one of our favorite spots too. Thanks for the heads-up about the mosquitos; we’re looking into additional ways to help minimize them for future guests. We truly appreciate your review. Lewes Rental Team

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• Terrific beach escape

  Stayed 7 days ending in September, 2024

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  Amanda B from Wilmington, DE recommends this vacation rental

  Great stay!

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• Big Blue House!

  Stayed 7 days ending in July, 2024

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  a guest from West Chester, PA recommends this vacation rental

  The big blue house was a wonderful vacation home. The house was accurately described, clean, and provided all the amenities you could need in Lewes. The owners take good care in making sure the house is not humid, clean, stocked with what you need, and is decorated wonderfully. We hope to return!

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• The Wonderful Blue House

  Stayed 7 days ending in July, 2024

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  Paul & Vivian C from Silver Spring, MD recommends this vacation rental

  Beautiful house and garden! We’ve been staying here for a long time and it is always a pleasure to be here. Most everything in the house was in fine shape, except for a few minor things which I’m sure they will take care of.

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• Fantastic family home

  Stayed 7 days ending in July, 2023

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  Lisa M from Washington, DC recommends this vacation rental

  Our family had a fabulous stay at 319 Chestnut Street and hope to be back next year!

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• We

  Stayed 7 days ending in July, 2023

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  Debbie D from Haverford, PA recommends this vacation rental

  The house was great and everything worked out perfectly.

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• Awesome Summer Family Vacay

  Stayed 7 days ending in August, 2022

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  April B from Silver Spring, MD recommends this vacation rental

  Keep coming back year after year. Very comfortable family home.

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• The Blue House for the Past 9 Years

  Stayed 7 days ending in July, 2022

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  Paul & Vivian C from Silver Spring, MD recommends this vacation rental

  Always a pleasure to stay in this house. The owners did a beautiful job with the exterior painting (and now a yellow door!). Our family loves coming with us to the Blue House.

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• Great location but not **** and span

  Stayed 3 days ending in April, 2022

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  Elizabeth M from Silver Spring, MD recommends this vacation rental

  We have rented homes from Gallo for years and while the properties are nice and well-located and the company is easy to work with, the cleaning provided before arrival is rudimentary. At this property, the sink was filthy, the kitchen garbage can had crusty gunk all over it, the countertops were full of crumbs, and the floors hadn't been properly swept. We spent an hour wiping and vacuuming upon arrival--not pleasant, especially after paying a $125 cleaning fee.

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