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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Kayaker’s Delight: Sept. Starting @ $99/Ngt * Pets OK * Free Kayaks & Bikes

Bedrooms 3
Half Baths1
Space 1,000 sq ft
Property type house
Minimum Stay 1 - 7 nights


About the property

3 Bedrooms, 1 1/2 Bath, Waterfront in Oyster Bay, Pets Considered

September Rates starting @ $99/Ngt.

With free use of 2 kayaks and 3 bikes

Pets Considered. Fees appliied

First Pet: $100/ Wk. OR $15/Night

Second Pet: $50/Wk. OR $22/Night for 2 pets

Pets are not allowed on Assateague National Park (the beach).

An old Chincoteague favorite, the Blue Hen, not only has a new name (Jay's Retreat), but it has been remolded and redecorated and is awaiting your great review. We are pleased to add this home as one of our owner managed properties.

Jay's Retreat offers 3 bedrooms, 1½ baths, waterfront home, located in Oyster Bay With budget friendly rates.

Enjoy the serenity of the private Oyster Bay community in this waterfront vacation home. Enjoy relaxing evenings on the deck while taking in the sunset. Gather with friends or family around the fire pit. HCrab from your private dock. Kayak from your dock right into Oyster Bay.

Oyster Bay and Jay's Retreat are located in the resort town of Chincoteague, Island, Virginia. Chincoteague is just a short car or bike ride to the National Seashore: Assateague Island. There you will find pristine beaches and a family atmosphere. Nature lovers are sure to appreciate the wildlife refuge with it’s hiking and bicycle trails.

Jay's Retreat will comfortably accommodate groups of at least 6. And you won’t have to board your pet: Pets welcome here (fee applies). Accommodations include a fully stocked kitchen with pots, pans, dishes, knives etc. for meal prep. Living room provides a restful atmosphere with comfortable furnishings and appointments including a flat screen TV. Three bedrooms include a master with private half-bath and queen bed, second bedroom with full size bed, and a third with 2 twin beds. Outdoor areas include a spacious screened porch complete with outdoor furnishings, grill, and dining table, along with 2 additional decks. One with a fire pit.

Like to kayak? Jay's Retreat has 2 kayaks available for your use. Enjoy!

Towel and linen rental is now available for just $50. If interested, just ask, and we will add it to your reservation.

Looking for a waterfront vacation rental that is clean and comfortable, in a quiet serene environment, close to the ocean, pet and budget friendly, then Jay's Retreat is right for you.

Pets considered. Weekly Pet fee $100 for first pet; $50 for second. Prorated for stays of less than 7 days.

*****Please note pets are not allowed on Assateague National Seashore (the beach).*****


Included: Dish soaps, laundry soap, paper towels, hand soaps, plastic storage bags, toilet paper, paper towels, tissues, basic spices

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

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

Propane grill, Crab Trap & Net

Fire pit

Community Boat Launch

Private Dock

Outside Shower

3 bedrooms: queen master, double, and 2 twins

Full bath with tub/shower

Half bath in master

Living room

Dining Area with table for 6 guests

3 Bicycles

Jay’s Retreat: discover the difference of managed!

More Details

Jim & Ann O'Connor
Member since: 2016
Premier Partner

This VRBO partner has demonstrated and is committed to fast response times, the best rates, and a great guest experience.

Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
August 15, 2018

About Jim & Ann O'Connor

We are retired PA educators who grew up in York, PA. We are both graduates of York Catholic High School. Jim did his undergrad at Indiana State University and Ann did hers at York College. Together we have 53 years of teaching experience.

Ann was first introduced to Chincoteague by her father over thirty-five years ago in this very house: Jay's Retreat. As many say, it was love at first sight. During our summer vacations there, we would dream about owning a place of our own.

After putting three sons through college, in 2008 we made the leap and purchased our first rental property on Main Street. The Main Street cottage has always received rave reviews from our renters. We enjoyed every moment we could spend there. It was our happy place.

In the summer of 2016, we became full time Islanders. Living on the Island has given us the opportunity to manage our Main Street property. And in 2017 to acquire and manage Jay’s Retreat.

Jim & Ann O'Connor purchased this house in 2017

Why Jim & Ann O'Connor chose Chincoteague Island


Pet Friendly

Beautiful Water views

Private community

Private Dock

Community Boat Launch

Bayside deck with fire pit

Kayaks provided

Bikes Provided

Towel and Linen Service offered (fee applicable)

Owner managed and maintained

What makes this house unique

You can count on receiving a clean, well-maintained rental. Furnishings have been selected to created a cozy beach cottage feel. And most importantly, the water views are amazing.

Many extras included. No need to bring paper products, laundry supplies, coffee, or tea. Fully stocked kitchen includes just about anything you need including spices.

Towel and linen service available (fee applicable)


Chincoteague Island House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 1000 sq ft
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 11:00 AM
  • Max. occupancy: 6
  • Max. adults: 6
  • Min. age of primary renter: 21
  • Children welcome
  • Parties/events not allowed
  • Pets considered ...
  • Non smoking only ...
  • Check-Out Procedures: Failure to abide by check-out procedures will result in the assessment of an additional fee.
Location Type:
  • Near The Ocean
  • Waterfront ...
  • Away From It All
  • Budget
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning
  • Clothes Dryer ...
  • Hair Dryer
  • Heating
  • Internet ...
  • Iron & Board
  • Living Room ...
  • Parking ...
  • Washing Machine ...
  • Wireless Internet
  • Coffee Maker
  • Dishes & Utensils ...
  • Dishwasher ...
  • Kitchen ...
  • Microwave
  • Oven
  • Pantry Items ...
  • Refrigerator ...
  • Stove
  • Toaster
  • Dining
  • Dining Area
  • seating for 6 people
  • 1 Bathroom
  • 1 Half Bath
  • Bathroom 1 - toilet , combination tub/shower
    Bathroom in Master - toilet
  • You can add towel rental to your reservation.
  • 3 Bedrooms, Sleeps 6
  • Master - 1 queen , 1/2 Bath
    Bedroom 2 - 1 double
    Bedroom 3 - 2 twin/ single
  • Towel and linen rental is just $50. Let us know and we’ll add it to your reservation.
  • Books
  • DVD Player
  • Games
  • Television
  • Video Library
  • Bicycles ...
  • Deck / Patio ...
  • Golf ...
  • Kayak / Canoe ...
  • Lawn / Garden
  • Outdoor Grill ...
  • Tennis ...
  • 3 bicycles
  • autumn foliage
  • bay/sound
  • churches
  • cinemas
  • festivals
  • library
  • live theater
  • marina
  • museums
  • restaurants
  • water parks
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • eco tourism
  • photography
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • hiking
  • hunting
  • jet skiing
  • paragliding
  • pier fishing
  • sailing
  • sound/bay fishing
  • surf fishing
  • surfing
  • swimming
  • water skiing
Towel & Linen Rental: $50 Let us know and we will add it to your reservation.


Exceptional! 5/5 -
(48 traveler reviews)

97% Complete
2% Complete
0% Complete
0% Complete
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Kayaker’s Delight: Sept. Starting @ $99/Ngt * Pets OK * Free Kayaks & Bikes
average rating of 4.9791665 based on 48 reviews

We enjoyed our week at Jay’s Retreat. The house was everything that was described.

  • 5 of 5

Beautifully decorated! Kitchen well stocked. Comfortable beds. Enjoyed crabbing off the dock and relaxing on the screened in porch. Nice neighborhood. Bikes and kayaks were available. Close to everything. Short ride to Assateague Beach. Owners were quick to respond to our questions. Would recommend this beach house to others.

  • Submitted: Aug 13, 2018
  • Stayed: August 2018
  • Source: HomeAway
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Great vacation!

  • 5 of 5

The house was more of a home then we expected, very cozy, and relaxing. Everything we needed was right there there was a crab trap there was bicycles there was kayaks a picnic table for outside dinners and a gas fire pit on the deck for late-night family gatherings. Would greatly recommend this home also we wanted to do some exploring and mr. O'Connor recommended a trolley tour that was fun and he was also the guide. We learned a lot of history about Chincoteague. Hope to come back again next year.

  • Submitted: Aug 7, 2018
  • Stayed: July 2018
  • Source: HomeAway
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Fantastic home in a spectacular place

  • 5 of 5

This house is a gem - comfortably sleeps 6 people. Spacious, bright, great location on Chincoteague Island, close to stores, restaurants and the beach. I highly recommend this property to anyone interested in a great vacation on Chincoteague.

  • Submitted: Jul 29, 2018
  • Stayed: July 2018
  • Source: HomeAway
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Gilbertsville, Pennsylvania

Amazing week at Jay's Retreat!

  • 5 of 5

We had a great week and loved the location of this home. Being right on the water was a real treat. We loved using the kayaks available and floating on tubes in the canal. We spent all of our time while at the home either down by the dock, on the screened in porch or on the deck with the fire pit! If you love great outdoor space - this is an amazing find. Definitely would recommend this home for a small group.

  • Submitted: Jul 23, 2018
  • Stayed: July 2018
  • Source: VRBO, from HomeAway
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Perfect Family Get Away

  • 5 of 5

We stayed at Jay's Retreat in June for a week with our family of 5. The house was clean, cozy, and had everything we needed. We've stayed in Chincoteague for several years at a hotel. Jay's Retreat was our first house rental on the Island and the location was perfect for us. The screened porch was great for a relaxing breakfast and escaping the rain, while still being outside. The views are really lovely. Our older kids especially enjoyed the kayaks and crab pot. They checked the trap every few hours! We would definitely stay again and may be returning as soon as the fall. The owners are friendly and responsive and gave us lots of tips and information about Chincoteague and the surrounding area that helped make our stay even more enjoyable.

  • Submitted: Jul 9, 2018
  • Stayed: June 2018
  • Source: VRBO, from HomeAway
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Springfield, MO

Chincoteague Island Vacation

  • 4 of 5

We just returned from our week's stay in this 3-bedroom house on the North side of Chincoteague Island. We were happy to find it clean, decorated nicely and well-stocked upon our arrival. The kitchen has everything you need to cook full meals, and we also used the grill on the deck. We spent a lot of time on the screened-in porch especially early in the morning as the sun was rising over the bay. We used the provided kayaks daily in the neighborhood canals and out on the bay - a very nice extra! We enjoyed the quiet location away from the main street of Chincoteague.

  • Submitted: Jul 6, 2018
  • Stayed: June 2018
  • Source: VRBO, from HomeAway
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Car: recommended


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Refundable damage deposit $200
Cleaning fee $95
Pet Fee $100

Owner's Cancellation Policy

  • Canceled bookings will not receive a refund

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