O’Connor Properties is pleased to offer Jay’s Waterside Retreat.

We provide a vacation experience designed for your convenience. Our vacation properties provide just about everything you need. Just bring food and clothing and let us take care of the rest. Here’s a sampling of what we include:

2 Kayaks
4 bicycles
Towels & Linens
Fully stocked kitchen including soaps & paper products
EV Charger: Level 2-Charging for both Tesla & Other EVs

We are committed to doing everything we can to make our rental properties a respite to escape, relax, and REJUVENATE.


★ Jay's Waterfront Retreat is part of of the owner managed properties of O'Connor Properties. We have hosted hundreds of guests in Jay's over the last 4 years and have graciously received mostly five star reviews.

* Perfect for a romantic getaway. Our waterside fire pit is the perfect place to unwind with your significant other.

* Families love crabbing and fishing from our dock and kayaking in the bay

* Fun Location to host “Girl’s Getaway”

* 3 bedrooms, 1½ bath, waterfront home, located in the private community of Oyster Bay

** Master Bedroom includes half bath with queen size bed
** Bedroom 2 features a full size bed
** Bedroom 3 features 2 twin size beds

* Comfortably accommodates groups of up to 6

* Fully stocked kitchen with pots, pans, dishes, knives, basic spices for meal prep.

* Living room: restful atmosphere with comfortable furnishings and appointments including a flat screen smart TV and DVD player. Paramount Plus, Peacock, ESPN Plus, Netflix, Hulu, & Disney+ subscriptions included in your reservation.

* Dining area with seating for 6

* Outdoor areas include a spacious screened porch complete with furnishings, gas grill, and dining table with seating for 6, along with 2 additional decks. One with a waterside fire pit.

* Community Boat launch available

* Up to 2 pets are welcome with payment of $100 non-refundable fee. ***Please note pets not allowed on beach.*****

* Located in the quaint seaside town of Chincoteague Island. Here you will find an eclectic mix of shops with many featuring the work of Eastern Shore artisans.

* Chicoteague Island provides the foodie with many different delicitable restaurant experiences.

* Short car ride from the pristine beaches of Assateague National Seashore

* Nature lovers paradise: hiking and bicycling trails run through the Assateague Refuge

* View the world famous Chincoteague Ponies in Assateague

* Kayak from your private dock to the bay with free use of the 2 kayaks.

* Towels and linens included for 6 guests.

* 4 bicycles are provided for your use.

* We provide paper products: storage bags, toilet paper, napkins, paper towels, tissues and coffee filters. Also, hand soap, bath soap, shampoo, dish soap, and laundry soap

* Ground coffee, tea, and creamer provided

* Appliances: refrigerator, dishwasher, stove, washer & dryer, drip coffee pot & Keurig, crock pot, blender

* Dishes, pots, pans, silverware, knives, basic cooking utensils and cookware, serve ware, crab pot

* Propane grill, Crab Trap & Net

* Private Dock

* Onsite parking for 4 cars

*2 very dedicated owner/managers who truly care that you have a great experience!


★ Frequently Asked Question:

* How old must you be to rent?
21 years of age

* Are the kayaks and bicycles available off-season?
Yes, they are

* Are restaurants and shops open in the off season?
Yes, there are restaurants and shops open in the off season. Days and hours of operation may
vary.

* Is the Internet reliable?
Yes, the Internet is very reliable. We provide high speed Internet with 40 mbybte download.

* Will I have access to the community boat launch?
Yes, you will have access to the community boat launch.

* Are towels and linens provided?
Yes, all reservations include towels and linens. No extra fees.

* How is the cell phone service on the island?
All cell phone providers have towers on the Island.

* How far is the cottage from downtown?
Jay’s is located 1.8 miles from the center of downtown where you will find shops and restaurants.

* Is cable TV provided?
We provide Paramount Plus, Peacock, ESPN+, Netflix, Hulu, and Disney+ subscriptions.

* Will I be able to see ponies?
Yes, the ponies are seen in Assateague throughout the year. We recommend a boat tour for pony viewing.

* Is horseback riding available? About a 15 minute drive from Chincoteague, you will find a farm that offers riding.

* Are life jackets provided?
Yes, we provide 2 adult sized life jackets.

* Can you rent bicycles and kayaks on the island?
From Easter to Thanksgiving bicycle and kayak rentals are available through local vendors.

* Do you provide Keurig pods?
No, Keurig pods are not included.

* What size bicycles are provided?
We provide 4 adult sized bicycles.

* Are children counted as part of the maximum number (6) of occupants?
Yes, they are. The house is set up to accommodate 6 people, which includes children.

* What are the checkout procedures?
*Unloading Dishwasher & putting dishes away *Washing all Dirty Dishes * Loading used towels into washer & starting machine* Taking out the trash *Returning furniture & furnishings where you found them

*Do you provide bicycle locks?
No, we do not. You will need to bring your own.

* Do you provide fishing rods?
No, we do not provide fishing rods.

* What type of grill is provided?
We provide a gas grill.

* Do you offer early check-in?
You will be contacted as soon as the house is ready for you. It may be earlier than the 4 p.m. check-in time. However, we cannot guarantee it.

*Is there a community swimming pool?
No, there is not a community swimming pool.