Jester House

Amenities: New Pet Friendly Rental for 2025 Season. DOGS ONLY, Central HVAC, Internet, Linens and Towels Provided.

4 BR Pet friendly home, close to town and short drive to the beach. Fenced in back yard and sleeps 8-10. 3 bedrooms downstairs and 4th bedroom upstairs with sitting area, perfect for kids.

Pet friendly - Dogs Only. NO SMOKING OR VAPING . Linens and Towels are provided with this property.

Pet friendly home $75. (per pet) will be added to your reservation. Dog Only. Three night minimum all year round.

Cancellations made 30 days prior to arrival will receive 100% of refund of all monies minus $ 39 Processing Fee and Any Credit Card Convenience Fees Paid.  If less then 30 days: the advanced rent is only refundable subject to the following: The property is re-rented for the same period. Re-rental of less than a full week will be refunded on a pro-rated basis. The Agent will retain a $39.00 processing charge and any convenience fees charged. *Deposits are not refunded for ANY reason (including bad weather).


Bed Sizes:

Saturday Change Over

2025 Prime Season $ 229 per night / $ 1603 for week ( 3 night minium)
2025 Pony Swim Week 07/26-08/02/2025 $ 1806 for week with 7 night minimum



**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ***
***Month to Month availability***

Vacation Rental Reviews

• Bucket list destination

  Stayed 4 days ending in August, 2025

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  Overall satisfaction:

  Kim B from Ridgway, PA recommends this vacation rental

  The overall experience was good.
  The house needs some upgrades such as screen doors and hand rails.
  The upstairs is so cute if you are bringing kids! It just could use handrail there as well.
  We got move from our original rental house selection and I think we would have been happier in our original choice.
  Overall it was good.

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• Jester House

  Stayed 4 days ending in August, 2025

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  Overall satisfaction:

  a guest from Huntingtown, Maryland recommends this vacation rental

  The house is super cute. The kitchen is small but the rest of the house is pretty spacious. The upstairs hangout for the kids was amazing. One of the twin beds upstairs kept falling through it's slats, the chain on the downstairs bathroom toilet was broken, the grass was so long we could not use the backyard-the day before we left it got mowed-and while the house was clean overall the floors were not at all. And the patio out back was not clean. We had a very short stay so I didn't feel like cleaning in order to use the space so we didn't use the back patio at all. I would definitely stay at this property again but if we had been staying longer I would have asked for the grass to be cut, the patio & floors to be cleaned, and the toilet and bed fixed.

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• Jester House

  Stayed 4 days ending in June, 2025

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  Overall satisfaction:

  Debra S from Piney River, Va recommends this vacation rental

  Lovely home, close to Main St restaurants ,as well as Maddox Blvd. Will stay again next year!

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• Jester house stay

  Stayed 5 days ending in June, 2025

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  Overall satisfaction:

  Brian R from Great Mills, Maryland recommends this vacation rental

  We loved staying at the Jester house! It's a cute house with lots of space for kids with the open upstairs and large back yard! It's close to the causeway, main street, and just a short walk away from the Island Creamery, which was a huge plus for us! The house was clean and the folks at Harbour Rentals were very nice and easy to deal with. We would decimated go back!

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