Entire home·Private host

Jay’s Retreat: EV Charger-Kayaks-Bikes-Fire Pit-Private Dock-Pets Ok-Crabbing

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December 2024
January 2025

Photo gallery for Jay’s Retreat: EV Charger-Kayaks-Bikes-Fire Pit-Private Dock-Pets Ok-Crabbing

Property grounds
Smart TV, fireplace, Netflix, Hulu
Terrace/patio
Exterior
Dining

Reviews

10 out of 10

Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 693 sq m

Popular amenities

  • Parking available
    Parking available
  • Barbecue grill
    Barbecue grill
  • Pet-friendly
    Pet-friendly
  • Washer
    Washer
  • Outdoor space
    Outdoor space
  • Kitchen
    Kitchen

Explore the area

Map
Chincoteague Island, VA
  • Oyster Bay
    6 min walk
  • Maui Jack's Waterpark
    5 min drive
  • Captain Timothy Hill House
    6 min drive
  • Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)
    73 min drive

Room options

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Jay’s Retreat: EV Charger-Kayaks-Bikes-Fire Pit-Private Dock-Pets Ok-Crabbing

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.
During your stay at this holiday home, you're just a quick walk from Oyster Bay. A water park is available. The holiday home offers free WiFi and a kitchen.
  • Air-conditioned home with kitchen, washer/dryer and 1.5 bathrooms
  • Free WiFi
  • Splash around at the water park
  • Amenities include a car charging station
  • On-site recreation includes tennis courts and a playground
  • 6 minutes on foot from Oyster Bay and a 5-minute drive from Chincoteague Channel
Jay’s Retreat: EV Charger-Kayaks-Bikes-Fire Pit-Private Dock-Pets Ok-Crabbing offers its guests a water park. The family-friendly Jay’s Retreat: EV Charger-Kayaks-Bikes-Fire Pit-Private Dock-Pets Ok-Crabbing also features barbecue grills, a garden, and local meal delivery service.

Property manager

Jim & Ann O'Connor

Languages

English

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Electric car charging station on site
  • Car recommended
  • Limited on-site parking (max 4 spaces)
  • Onsite parking includes off-street options

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 1.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • Books
  • DVD player
  • Games
  • Hulu
  • Netflix
  • Smart TV with cable channels
  • Streaming services
  • Video library

Outdoor areas

  • Balcony
  • Dock
  • Firepit
  • Garden
  • Gas grill
  • Outdoor furniture

Laundry

  • Laundromat nearby
  • Washer/dryer

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming cats and dogs only
  • 2 pets total

Suitability/Accessibility

  • Smoke-free property
  • Note from host: $200 fine assessed for smoking on premises.

Services and conveniences

  • Iron/ironing board
  • Meal delivery service

Location highlights

  • In the city centre
  • Near the bay
  • Near the marina
  • Near the sea
  • On the waterfront

Things to do

  • Bicycles
  • Golf
  • Kayak
  • Tennis
  • Water park
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Hiking/biking trails nearby
  • Hunting nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Water skiing nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • At least 80% lighting from LEDs
  • At least 80% of food locally-sourced
  • Bicycles
  • Cleaning products are eco-friendly
  • Double-glazed windows
  • Electric car charging station
  • Garden
  • Local artist showcase
  • Local culture and ecosystem education
  • Locally-owned and organised tours and activities
  • No plastic coffee stirrers
  • No plastic drinking straws
  • Reusable coffee/tea filters
  • Reusable cups
  • Reusable tableware
  • Unit size: 1,000 square feet
  • Vegan dining options
  • Vegetarian dining options

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 21

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • Pets are welcome
  • Only dogs and cats are allowed
  • Maximum 2 pets
  • Service animals are exempt from fees.

Children and extra beds

  • Children are welcome.

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account, which will enable you to manage your booking.

Property is also known as

Spend Christmas Sea @ Jay's Retreat Rates as low as 49/ngt House
Spend Christmas Sea @ Jay's Retreat Rates as low as 49/ngt
Jay’s Waterfront Retreat inc. kayaks bikes
Jays Retreat on the Waterfront Inc. Kayaks Bikes
Jays Waterfront Retreat Fire pit kayaks bikes beach pet Friendly

Jay’s Retreat: EV Charger-Kayaks-Bikes-Fire Pit-Private Dock-Pets Ok-Crabbing Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 194 out of 200 reviews" "
Rating 8 - Good. 6 out of 200 reviews" "
Rating 6 - Okay. 0 out of 200 reviews" "
Rating 4 - Poor. 0 out of 200 reviews" "
Rating 2 - Terrible. 0 out of 200 reviews" "

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

Reviews

10/10 Excellent

ONZELLE L G.

Liked: Cleanliness
Another wonderful stay.
This was our second time staying in the home. The love and care the owners take in the property come shining through in the updates we saw throughout the house.
Stayed 11 nights in Nov 2024

8/10 Good

Christie S.

Stayed 2 nights in Oct 2024

10/10 Excellent

Lee A.

Liked: Cleanliness
Birthday Weekend in Chincoteague
We had a fabulous weekend. Loved the charming retreat and local food/sites. Much to do and absolutely stunning area. We saw many ponies on a boat ride! Our hosts at Jay's Retreat were meticulous and went out of their way to make our stay pleasant, fun, and seemless. I give then 5 stars on every metric.
Stayed 2 nights in Oct 2024

10/10 Excellent

Gavin P., Darien, CT

Liked: Cleanliness
Family Trip
We had a lovely short stay at Jay's Retreat. The location is serene and there was everything we could have asked for to make the most of the water and lovely area. A big bonus was also the EV charger. Ann and Jim were very communicative and helpful hosts. We would definitely stay there again.
Stayed 2 nights in Sep 2024

10/10 Excellent

Tom S.

Liked: Cleanliness
Late September 2024 4-night getaway
My brothers and sisters booked Jay's for four nights. Chincoteague is a place that we went to as kids and now all over 50 we wanted to go back. Jay's retreat gave us the opportunity to fish and crab from the dock, short drive to town and house amenities made for a very enjoyable long weekend. As a bonus we were able to see a NASA rocket launch at the entrance to the state park. I highly recommend Jay's Retreat and would book again. Cheers, Tom, Kathleen, Marianne & Steve
Stayed 4 nights in Sep 2024

10/10 Excellent

Sarah T.

Liked: Cleanliness
Getaway
Great stay
Stayed 4 nights in Sep 2024

10/10 Excellent

William M.

Liked: Cleanliness
Great experience
Fantastic weekend and beautiful property. Would definItely recommend to others.
Stayed 3 nights in Aug 2024

10/10 Excellent

Dawn S.

Liked: Cleanliness
Family vaca at Jays Waterfront Retreat
The property was clean, had everything we needed, great location and views. We would stay again. There was so much to do and loved the Assateaque National Seashore! We had Beach fires with s'mores, kite flying, surf fishing, sting rays, scooters, electric carts, crabbing, and amazing sunsets on Chincoteague Island!!
Stayed 4 nights in Jul 2024

10/10 Excellent

Patricia M.

Liked: Cleanliness
Great rental
Jay's Retreat had everything you could ask for to have a great time on the island.
Stayed 7 nights in Jun 2024

10/10 Excellent

Liza L.

Liked: Cleanliness
Perfect place for our group.
The property was a perfect fit for our group, from older kids to grandparents. The Property Managers were very helpful and welcoming.
Stayed 3 nights in Jun 2024

10/10 Excellent

Gareth P.

Liked: Cleanliness
family vacation at Jay's Retreat
Jay's Retreat was the perfect homebase for our family of four to explore Chincoteague and Assateague for the week. The home was very clean, convenient and comfortable. We especially enjoyed crabbing right from the dock behind the house. The neighborhood is quiet but a quick drive to all there is to do in the area. We would definitely stay again.
Stayed 5 nights in Jun 2024

10/10 Excellent

Shannon M.

Liked: Cleanliness
Beautiful location!
The hosts were very communicative. We made good use of the propane grill and ran out. The host was there with a new tank within 5 minutes. The kitchen was very well equipped with everything needed to cook and a good supply of a variety of spices. The hot water on demand was welcome for warm showers on chilly nights.
Stayed 5 nights in May 2024

10/10 Excellent

Jennifer B.

Liked: Cleanliness
Quiet and beautiful
We had a fantastic time! The house was lovely with all amenities you’d need. The island was great! It was overcast and cold but we still had a great time. Definitely recommend Chincoteagues island adventure with captain Randy! He’s fantastic! Thank you for everything!
Stayed 4 nights in May 2024

10/10 Excellent

Mike P., State College PA USA

Liked: Cleanliness
Peaceful, relaxing place!
The house was perfect for our Chincoteague visit. Well stocked kitchen, excellent outdoor seating and just clean and comfortable all around. The bikes and kayaks were important to us too as was the peaceful neighborhood with lots of trees and bird life. Would definitely stay here again.
Stayed 6 nights in Apr 2024

10/10 Excellent

laurie p.

Liked: Cleanliness
Women's get away!
we were all so pleased with the features of this home. Large screen porch, canal deck with gas fireplace, cozy decor. Small sq footage but cozy for friends gathering! The pictures are accurate.
Stayed 3 nights in Apr 2024

10/10 Excellent

Karen M.

Liked: Cleanliness
Delightful
We were impressed with the attention to details. Everything we needed was supplied, beds were comfortable, location was great. We loved having the kyacks to use. The bikes were not in very good condition and one of them got a flat while riding because the tire was dry rotten. But, we made the best of riding them and were grateful for having them. I would recommend this place to others and would stay here again.
Stayed 3 nights in Apr 2024

10/10 Excellent

Patrick R.

Liked: Cleanliness
Peaceful waterfront location
We enjoyed our stay and wouldn't hesitate to recommend it to others. The location was great and we enjoyed sitting on the screened in porch and enjoying the view.
Stayed 2 nights in Apr 2024

10/10 Excellent

Jan R.

Liked: Cleanliness
Relaxing Getaway
Enjoyed our stay here. The house was very clean and had a beach vibe. Close to the beach and quiet neighborhood.
Stayed 4 nights in Apr 2024

10/10 Excellent

Micaela O.

Liked: Cleanliness
Our little stay at Jay’s
My daughters and I were looking for a fun place to escape for a few days for April vacation, and my daughter’s and my birthdays. We absolutely found the perfect place. Jay’s was clean, in a wonderful location, had amazing view, amazing amenities, and the girls are already talking about when they want to go back. We were able to cook a lot of our meals in the great and well-stocked kitchen, which was key. We used the bikes and the kayaks, and Chincoteague is an amazing town to visit. We were even greeted with a personal message and a little something sweet for our birthdays. We will definitely be back.
Stayed 3 nights in Apr 2024

10/10 Excellent

Terry H.

Liked: Cleanliness
Short stay - wish it were longer!
This house was perfect for us - had everything we needed and more. Would love to come back one day.
Stayed 2 nights in Mar 2024

10/10 Excellent

Margaret H.

Liked: Cleanliness
Great location and very clean, happy house
We loved the well stocked kitchen, bikes, and beautiful views!
Stayed 3 nights in Mar 2024

8/10 Good

Mellissa K.

Liked: Cleanliness
Peaceful Retreat
We had a wonderful time at Jay’s Retreat. It was quiet, peaceful, and refreshing. We wish we could have stayed longer.
Stayed 2 nights in Jan 2024

10/10 Excellent

Michael G.

Liked: Cleanliness
great spot
quiet, beautiful, clean. very relaxing
Stayed 3 nights in Dec 2023

10/10 Excellent

Sandy L.

Liked: Cleanliness
Serenity on the water
I brought my family to see the Ponies of Chincoteague. We found the home and location to be calm and charming. A highlight was taking the kayaks out, turning to the right, right again after a short distance to the bay and seeing the oyster beds up close. Everything was perfect!
Stayed 3 nights in Nov 2023

10/10 Excellent

Jeannie A., US

Liked: Cleanliness
Loved it!
Trees and water are my jam!! The location was absolutely gorgeous. The house was cozy and comfortable. The decks were fantastic places to hang out. The kitchen counter was veeerrry long. The place was well stocked with everything. I appreciated the story behind the house. Such a peaceful retreat, I look forward to returning next year.
Stayed 4 nights in Nov 2023