Welcome To Seaside Vacations & Sales
You deserve the best on your vacation, and Seaside Vacations is here to make sure that is exactly what you get - the very best - Customer Service, Premiere Properties, and special touches such as Express Check-in and Full Linens included! No matter your destination, whether it’s Chincoteague Island, Virginia or Ocean City, Maryland, we have the vacation rental for you, with all the comforts of home!

We're honored to have been awarded VRMA's 2023 Vacation Rental Company of the Year, as well as Best in Local's Choice for Best Vacation Rental Company in 2022, 2023, and 2024! We also received the VRMA Excellence Award for Community Impact in 2024, and were the FIRST vacation rental company to become Breezeway Safety Certified in Virginia AND Maryland! Check out our Chincoteague Rentals that provide an abundance of amenities and comfort no matter what size party you bring. Take an island boat tour, go fishing or crabbing, and let your taste buds rejoice with our local Chincoteague cuisine. Let us show you why Chincoteague Island has been voted ‘Best Small Beach Town”, and “Happiest Seaside Town”. You may never want to leave!

Need more city life or action-packed activities for your next vacation? Then Ocean City, MD is the destination for you and your family. Seaside Vacation provides the best selection of Ocean City Vacation Rentals, each with their own unique amenities that include; pool access, water and harbor views, boat slips, and even exercise gyms. Each vacation rental is located close to all of Ocean City’s major attractions. Take a stroll on our famous OCMD Boardwalk, catch some rays at the beach, or satisfy that retail itch with the shopping options that only Ocean City could provide.


The very best in Chincoteague Island & Ocean City Vacation Rentals

Are you all about ponies in paradise? If so, you will love comfy and cozy ‘Pony Paradise’ in the very heart of Chincoteague Island! Formerly ever-popular ‘Sunshine and Daydreams’, this Seaside Vacations’ fan-favorite is under New Ownership, and y’all are going to LOVE what they’ve done with the place! This adorable 3 Bedroom/2 Full Bath Cottage is located on Willow Street, just across from where our famous Wild Ponies are penned at the Carnival Grounds. Stroll to the Carnival weekends in July, the Historic Downtown District to shops and dining, or just skip across the street with your morning coffee to watch the ponies graze. What makes vacationing at Pony Paradise even more fun? You get to bring your favorite pup along with no additional fee (Limit 2)! Your pup will especially appreciate the Fully Fenced-in Yard - you can just open the door and they have freedom to play safely in the yard!

Pony Paradise has packed a lot of bang into your vacation buck. As you enter through the Screened Front Porch, you’re already thinking you’ll never want to leave. Just imagine curling up here with a good book and taking in that salty, sweet bay bay breeze. Watch the Ponies grazing just across the Street, and you can even enjoy your 4th of July Fireworks right from your Screened Porch!

Upon entering Pony Paradise, you’ll be warmly welcomed by serene Colors of Sand and Sea - just breathtaking. With gorgeous flooring reminiscent of a stroll on the Boardwalk and bright and beachy furnishings, you may never want to leave. There’s even a cozy Fireplace for those chilly off-season stays - one of our very favorite times on our Island. You’ll love relaxing after a fun-filled day exploring Assateague in the Living Area with Free WiFi and Flat Screen Apple Streaming TV. There’s plenty of room for all to stretch out, yet still be together. 

The Chef in your family will love the spacious Eat-in Kitchen with both a Breakfast Bar and Dining Table. Well-stocked with all you need - even a Waffle Maker - mealtime will be no chore. You can grill the Fresh Catch of the Day - which hopefully you caught - out back, while listening to the Tree Frogs sing. Dine indoors in the comfort of the AC, or wander to one of many great Restaurants nearby.  After dinner, slip out to the back Deck to take in that salty, sweet sea breeze, or gather around the fire pit in the backyard and share stories of the day’s adventures. Or maybe a game of Horseshoes for a little friendly family competition! The spacious yard has two sections, with one that is fenced-in, making it just perfect for your furbaby to get some much needed exercise. 

Pony Paradise sleeps 7 in total comfort and style. The Master Bedroom, with a Queen Bed, is dressed in beach blues and crisp whites. The Private Master Bath has a huge Vanity and Walk-in Shower. Down the Hall, Bedroom 2 has a Full Bed and is inviting with cheerful Lime and Vanilla - just like a piece of Key Lime Pie. Bedroom 3 is perfect for the kiddos with Twin Bunk Beds and sleeps 2.  A Roll-a-way Twin Bed is available for the 7th member of your family. The 2nd Full Bath with a Tub/Shower Combo is shared. And while no one likes doing laundry while on vacation, the Full Size Washer and Dryer will sure come in handy. 

Friendly dogs welcome with NO ADDITIONAL FEE. Max 2 Dogs with pre-approval. Dogs MUST be current on Flea/Tick Preventative and Immunizations. No Cats.

Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors.

Relax in comfort and style with Free WiFi and Flat Screen Streaming TV

Located on Willow just across from the Pony Pens and Carnival Grounds!

Plenty of parking - walk to Carnival and Pony Penning Festivities.

You can watch 4th of July Fireworks from your Front Porch!

Riptide was hanging out just across the street during this photo shoot!

Mealtime will be a bay breeze in the Well-Stocked Kitchen.

No need to eat out everyday - unless you want to!

Dine in the comfort of Central AC or grab a bite at the Breakfast Bar before hitting the Beach.

Slip out to the Deck to relax and take in that salty, sweet sea breeze.

Pony Paradise has a huge Yard, with half of it fully enclosed!

Master Bedroom has a comfy King Bed and lovely Yard Views.

Bedroom 2 has a Queen Bed and cheerful colors.

Bedroom 3 has Twin Bunkbeds and sleeps 2.

Looking across to the Pony Pens at the Carnival Grounds.

Pony Paradise is a breath of fresh air in THE best Location!

Gather around the fire pit while recapping your day on Chincoteague

Beach equipment and bikes available to use!

Gaze at the Ponies - you can chat with them from your Front Porch!

You never know who you'll see hanging out just across the street!

Pony Paradise

Chincoteague

United States

Virginia

Bedroom 1

Bedroom 2

Roll-a-way Twin Bed

Seaside Vacations, LLC Terms & Conditions

As of the date set forth on the rental agreement and for good and valuable consideration, the receipt and sufficiency of which is hereby acknowledged, the parties hereto agree as follows:

1.    Seaside Vacations is the rental agent of the Owner of the Property and is fully authorized to enter into this Agreement on behalf of the Owner. The Property shall be provided to Guest in a reasonably furnished and clean condition, and all necessary appliances are included in the Property. The Property is not equipped with linens, towels, soap, paper products, and similar household wares. Pillows, blankets, cookware, flatware, dishes and glasses will be provided within the Property. Other items not expressly listed herein will not be provided. Guest may contact Agent to make separate rental arrangements for use of excluded items (e.g. sheets, pillowcases, towels, high chairs, cribs).

2.    Maximum Occupancy. The maximum number of occupants (including Guest and any adult and minor invitee of Guest) is limited to the number of persons as shown for the property. All signers of this Agreement represent and warrant the following: (1) that the principal Guest executing this Agreement is over the age of 25, and all co-guests executing this Agreement are over the age of 18; and (2) that no “house parties” or other large gathering shall occur on the Property. These representations and warranties are material to this Agreement and Agent’s decision to rent the Property to Guest.

3.    Term of this Agreement. The term of this Agreement commences at the noted check in time on the Check-In Date at the Property address; and ends at the noted check out time on the Check-Out Date. Early Check-Ins are not available. Guest will be charged one hundred dollars per hour if the Property is not vacated by Check-Out time. All keys for the Property must be left upon vacating in the designated spot in the Property, as described in the Check-In instructions. There is a $25.00 charge to Guest for lost, missing or unreturned keys.

4.    Processing Fee. There is a non-refundable processing fee for the reservation included in your charges for the rental of the Property (the “Processing Fee”).

5.    Rental Rate and Fees.

a.    Initial Deposit. Upon the initial reservation made by Guest, Guest shall have made an initial reservation payment/deposit of thirty-five percent (35%) of the total rent due hereunder, which such deposit shall be applied toward the entire rent due hereunder. Deposits may be held by Agent in an interest bearing account, however, any and all accrued interest may be retained by Agent or Owner. This Agreement shall not become binding until and unless the initial deposit is paid.

b.    Balance Due. The rent balance after payment of deposit and all other unpaid charges shall be paid in full at least thirty (30) days in advance of the Check-In Date. Payments shall be made by check, credit card or cash. Checks shall be made payable to Seaside Vacations, LLC, and shall be delivered to Agent on or before the aforementioned payment date. Failure to make payment as required hereunder may result in termination by Agent and Owner of this Agreement, and in that event, the provisions below governing cancellation shall apply.

c.     Additional Fees. Unless otherwise stated in writing, Guest is responsible for the payment of any and all additional fees arising under this Agreement and for any and all applicable registration, pool or amenity fees that are charged independently at the Property. Guest may refer to the Property-specific information emailed to Guest (which information is incorporated herein) along with confirmation of Guest's reservation confirmation for more information concerning these fees, and when they are due and payable.

6.    Cancellation Policy. Guest may cancel this Agreement only in accordance with the terms and conditions of this provision. Any cancellations (whether timely or untimely as specified below) must be delivered to Agent in writing either by electronic mail 4073 Main Street, Chincoteague, VA 23336 or by facsimile 757-336-6006 and shall not be effective otherwise. For the purposes of this Agreement, the term “cancellation” includes any transfer at the Guest’s request (if approved by Seaside Vacations) from the rental of the Property to another vacation property. Agent shall, in the event of a cancellation, take reasonable steps to re- rent the Property in order to mitigate any loss.

a.    If, in the event of either a timely or untimely cancellation, Agent is able to re-rent the Property for the same dates of occupancy and for at least the same amount of rent, Guest will be entitled to a refund of all amounts paid under this Agreement, less a liquidated damage amount of sixteen percent (16%) of the total rental amount (as compensation to Agent and Owner for time and expense associated with efforts to re-rent the Property, which Guest agrees is proportionate to what actual costs may be), and less the Processing Fee (which Guest agrees has been earned by Agent for services already rendered).

b.    If, in the event of either a timely or untimely cancellation, Agent is able to re-rent the Property for the same dates of stay, but only for a lesser amount (or for a shorter duration), then Guest will be entitled to a refund of all amounts paid under this Agreement, less a liquidated damage amount of sixteen percent (16%) of the total rental amount (as compensation to Agent and Owner for time and expense associated with efforts to re-rent the Property, which Guest agrees is proportionate to what actual costs may be), less the Processing Fee (which Guest agrees has been earned by Agent for services already rendered), and less the difference between the amount paid or to be paid under the original booking and the amount of rent revenue actually earned from the re- booking.

c.     If Guest cancels thirty (30) days or more in advance of the scheduled Check-In date, and Agent is unable to re-rent the Property for the same dates of stay, Guest will forfeit all paid deposits up to thirty-five percent (35%) of the total rental amount, plus the Processing Fee, and any other amounts collected from the Guest will be returned to the Guest.

d.    If Guest cancels less than thirty (30) days in advance of the scheduled Check-In date, and Agent is unable to re-rent the Property for the same dates of stay, Guest will be responsible for the full rental amount due under this Agreement, plus the Processing Fee, and Guest shall forfeit any and all monies already paid or deposited for the rental.

Guest is in agreement with the stated cancellation policy:

7.    Accidental Damage:  As a part of your stay, you have purchased a Vacation Rental Damage Protection plan designed to cover unintentional damages to the rental unit interior that occur during your stay provided they are disclosed to management prior to check-out. The plan will pay a maximum benefit of $1500.00. Any damages that exceed $1500.00 or are not covered under the plan will be charged to the credit card on file. If, during your stay at one of our rental properties, an insured person causes any damage to real or personal property of the unit as a result of inadvertent acts or omissions, the Insurer will reimburse the Insured for the cost of repair or replacement of such property up to a maximum benefit of $1500.00. Please contact Seaside Vacations directly if you do not wish to participate in this assignment. In the event you do not wish to purchase this plan, a $1,500.00 security deposit is required.

8.    Vacation Rental Insurance - CSA Vacation Rental Insurance has been offered with your reservation. Vacation Rental Insurance reimburses for pre-paid, non-refundable expenses due to certain unforeseeable circumstances that may jeopardize your vacation and force you to incur unplanned expenses. We strongly recommend you purchase this valuable protection. View a Description of Coverage/Policy at www.vacationrentalinsurance.com/330cert

9.    Changing/Transferring Reservations. Any change or transfer of a reservation requested by Guest within the same property is subject to the Property owner approval. Any requested change by Guest from one property to another property are subject to our cancellation terms and conditions set forth in Section 7 above.

10.  Property Condition. The Property is rented “as is” and as described above. Owner and Agent make no representations or warranties as to the condition of the Property, other than that it shall be provided in a reasonably neat and clean condition, reasonable wear and tear excepted, and in a condition that is fit for its intended use.

11.  Internet Access. Many properties are equipped with internet access. Property owners contract with a service provider of their choice. Seaside Vacations shall not be held responsible for service interruption or internet speeds. Properties with internet access are indicated on the property listing sheet and subject to third party management and repair. If internet access is not expressly disclosed on the listing sheet for the Property, then no internet access shall be provided.

12.  Condition of Property Upon Check-Out. Guest is responsible for leaving the Property in good order, clean and broom swept, prior to Check-Out. Guest shall ensure that all doors and windows are locked and that the Air Conditioning is set to 78 degrees and all lights are turned off upon Check-Out. Additionally, Guest is responsible for the following:

a.    Return furniture to original locations. b. Wash and put away all dishes including those in dishwasher and clean all utensils. c. Remove all food and trash from home. d. Place trash in sealed plastic bags in proper receptacle(s). e. Appliances, counters and other surfaces must be wiped clean. f. Carpets and floors are to be broom cleaned of excessive debris.

13.  Failure to complete the above will result in extra charges for which Guest hereby accepts liability.

14.  Termination of Property Rental by Seaside Vacations. Seaside Vacations may refuse to rent, not allow check-in, or terminate occupancy of Guest and enter the Property, if, in Seaside Vacations sole discretion, the occupancy by Guest or any co-guest may be detrimental to the Property. Guest shall forfeit all payments made under this Agreement in the event that occupancy is not allowed or terminated as a result of rental regulation violation or if the reservation was obtained under false pretenses.

15.  Pets. No pets are allowed at the Property without the prior written consent of the Property Owner. If the Property Owner permits pets, Guest shall pay a non-refundable pet fee of $100/pet per stay, plus tax. Guest shall be charged an additional cleaning fee for any and all pet related damage or cleanup of pet debris at the Property.

16.  Method of Payment. All payments due under this Agreement are payable by cash, check, e-check, or credit card in U.S. funds. Seaside Vacations, LLC accepts MasterCard, Visa and Discover cards.

17.  Trash Removal. Guest shall bag all trash and place it in containers for weekly trash removal. Trash must be sealed and bagged in plastic trash bags and left in designated area in supplied containers. Trash not sealed and placed in plastic bags or in designated areas will result in additional trash removal/cleanup charges to Guest.

18.  Subletting Prohibited. Subleasing of the Property is strictly prohibited and shall be immediate grounds for termination of this Agreement and Guest shall forfeit all payments made and due under this Agreement.

19.  Compliance with the Town of Ocean City’s Noise Control Ordinance and other Laws. Guest and all co-guests staying in Ocean City, MD properties shall comply with all applicable State, Federal, and local laws, including, but not limited to, the Town of Ocean City Noise Control Ordinance. That ordinance makes it unlawful to cause or permit noise levels which exceed those established by the Department of Health and Mental Hygiene of the State of Maryland (COMAR 10.20.01). Additionally, if any penalty or charge is incurred by Owner of the Property or Seaside Vacations, based on any violation of ordinance or other law (including, but not limited to, the Town of Ocean City’s Noise Control Ordinance), Guest's credit card on file with Seaside Vacations shall be charged for the penalty or charge, and Guest expressly authorizes such charge(s).

20.  Default. In the event of a default of this Agreement by Guest, Guest forfeits all payments made under this Agreement, and Guest shall otherwise be liable for any and all losses incurred by Agent or Owner as a result of Guest’s default(s) (including without limitation reasonable attorney’s fees incurred by Agent and/or Owner as a result of Guest’s default(s)). Further, in the event of a default by Guest, Agent may immediately terminate occupancy and take lawful steps to remove Guest and Guest’s personal belongings from the Property.

21.  Parking. Parking is limited to the spaces designated at the Property. Excess vehicles at the Property are subject to removal at tenant's expense.

22.  Fireworks. Fireworks at the Property are strictly prohibited.

23.  Mechanical and Appliance Failure. Seaside Vacations will use its best efforts to have mechanical (water, septic, electrical and plumbing) and appliance failures corrected as soon as possible, but does not control the scheduling of outside service contractors. NO REFUNDS will be issued under this Agreement for any appliance or mechanical failures or breakdowns. Agent may enter the Property to arrange, inspect and/or facilitate or make repairs during the Term of this Agreement. Tenant will be charged for unnecessary maintenance and service calls or repairs caused by abuse beyond normal wear and tear.

24.  Community Rules and Regulations. All community rules and regulations applicable to the Property are hereby incorporated by reference herein. Any breach or violation of any community rule or regulation shall constitute a default under this Agreement as set forth in Section 19 hereof.

25.  No Responsibility for Items Lost, Stolen, or Left Behind at Property. Neither Seaside Vacations nor Property Owner are responsible for any articles lost, stolen or left behind at the Property by Guest or Guest’s invitees. Upon request, Seaside Vacations will attempt to locate and return forgotten articles subject to a $25.00 service charge. Unclaimed personal belongings left in the Property may be retained or disposed of by Agent and Owner as they deem appropriate in their freely exercised discretion.

26.  Water Safety:  All tenants agree and acknowledge that:

(a) NO DIVING is permitted off any dock because the water level at high tide is too shallow to safely dive from any part of the dock;

(b) that the surface of the bay contains SHARP OBJECTS and that the renter or any invitee of the renter enters the waters of the Chincoteague Bay surrounding the Property at their own risk;

(c) that any kayak or other flotation object that may be stored on or under the property are EXCLUDED from the rental and shall NOT be utilized by the Renter for any reason or for any purpose.

27.  Property For Sale. In the event that the Property is listed for sale during the Term of this Agreement, the Property may be shown to prospective purchasers upon prior notice at a mutually agreeable time.

28.  Unforeseen Circumstances. If the Property becomes unavailable or uninhabitable for any reason whatsoever, Guest may be transferred to a reasonably comparable location accommodating the same number of persons and within the same price range. Guest hereby acknowledges that such relocation to a different Property shall not constitute a default of this Agreement by Agent or Owner, and that Guest shall continue to be bound by the terms of this Agreement with regard to the replacement property selected by Agent (so long as replacement property is reasonably comparable).

29.  Indemnification and Hold Harmless. Guest(s) hereby indemnifies fully and holds Agent and Owner harmless (and their respective owners, officers, representatives, and employees), from and against any claims, losses, causes of action, demands, judgments, expenses, of any kind, at law or at equity, and attorney’s fees, asserted against Guest, Agent, and or Owner (and their respective owners, officers, representatives, and employees) by any other person, and related to or arising from Guest’s occupancy.

30.  Release/Exculpatory Clause. Guest, for itself and his/her/its invitees, hereby waives, discharges, and releases, any claims, losses, causes of action, demands, judgments, expenses, of any kind, at law or at equity, and attorney’s fees, known or unknown, arising from the negligent conduct of Agent or Owner (or their respective employees, officers, agents, owners, or representatives) or arising from conditions on or in the Property which are the result of Agent’s or Owner’s negligence. This exculpatory clause/release does not apply to any intentionally wrongful or grossly negligent conduct of Owner or Agent (or their respective employees, officers, agents, owners, or representatives).

31.  Agency Disclosure. Guest understands, acknowledges, and agrees that Seaside Vacations, LLC is a known and disclosed agent of the Property Owner for all purposes related the rental and this Agreement, and (as a known and disclosed agent), Seaside Vacations, LLC shall have no liability to Guest, arising from this Agreement or occupancy of the Property.

32.  Miscellaneous Provisions.

a. Governing Law/Venue. This Agreement shall be interpreted, construed and governed in accordance with the laws of the State of the property address, either Virginia or Maryland as applicable. Any dispute(s) arising from this Agreement, the Closing, or any of the related documents shall be litigated in the Courts of Accomack County, Virginia or Worcester County, Maryland according to the properties physical address.

b. Waiver of Jury Trial. The parties hereto hereby release and waive any and all rights provided by law to a trial by jury in any court or other legal proceeding initiated to enforce the terms of this Agreement, or connected in any other manner with this Agreement.

c. Assignment. This Agreement is not assignable or transferable by Guest.

Pony Paradise

About The Property

Sleeping Arrangements

Amenities

Reviews

Location

Chincoteague Island, VA 23336

About The Host

The very best in Chincoteague Island & Ocean City Vacation Rentals

Seaside Vacations LLC

Safety & Inspections

Additional Details

Cancellation Policy