O'Connor Properties is pleased to offer our newest vacation property: Pearl in the Pines


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


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

★ Pearl in the Pines is part of of the owner managed properties of O'Connor Properties. We have hosted hundreds of guests in our rental houses over the last 7 years and have graciously received mostly five star reviews.

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

* Fun place to host “Girl's Getaway”

* Families love crabbing and fishing at the community boat launch area and kayaking in the bay

* 3 bedrooms, 2 bath, limited water-view home, located in the private community of Oyster Bay

** Primary Bedroom with queen size bed with Smart TV
** Bedroom 2 features a full size bed with small bathroom & shower
** Bedroom 3 features 2 twin size beds with Smart TV

* Comfortably accommodates groups of up to 6

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

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

* Dining area with seating for 6

* Outdoor areas include a spacious screened porch complete with furnishings, charcoal grill, and dining table with seating for 6. Top the evening off with star watching on the patio while roasting marshmallows over the fire-pit.

* Community Boat launch available: a good place to launch the 2 kayaks included in your reservation

* Pets welcome with payment of applicable fee: $100 wk. for first pet: $50 for second
Prorated for stays less than a week. ***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 delectable 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

* Nature lovers are sure to appreciate the wildlife refuge with it’s hiking and bicycle trails.

* Kayak from the community dock to the bay

* Towels and linens provided

* 2 kayaks, 2 paddles, 2 life-vests included

* 4 adult sized bicycles are provided for your use. Bring your own helmet.

* 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

* Charcoal grill

* Crab trap & net

* Community Boat launch

* Corn Hole Game

* Onsite parking for 3 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.

*Is the weekly pet fee prorated for shorter stays?
Yes, the pet fee prorated for stays less than a week: $15/ngt for first pet; an additional $7/ngt for the second. We will add pet fee for shorter stays.

* Are towels and linens provided?
Yes, all reservations include towels and linens.
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* How is the cell phone service?
All cell phone providers have towers on the Island.

* How far is the cottage located from downtown?
Pearl is located about 1.8 miles from the center of downtown.

* Is cable TV provided?
We provide 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.

* Do you provide firewood?
We try to provide a bit of firewood for each guest. Firewood can be purchased at the local grocery store.

* 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 pods for the Keurig?
No, we do not. We provide ground coffee for the drip coffee maker.

* Do you provide bicycle helmets?
No, we do not provide bicycle helmets.

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

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

* What are the checkout procedures?
*Unloading Dishwasher *Washing all Dirty Dishes * Stripping Sheets off beds used * Taking out the trash *Returning furniture & furnishings where you found them *Bagging soiled towels

* 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.

* Do you provide charcoal?
No, we do not. It’s available at the local grocery store for purchase.

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

* Is there a community pool for guest use?
No, there is not a community pool.
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