Painted Pony Cottage by Seaside Vacations & Sales

Top rated by guests
This Charming Cottage even welcomes your Family Dog.
Painted Pony Cottage has a spacious Kitchen well-stocked with all you need.
All of the quintessential Island Charm you love about Chincoteague.
Bright, Colorful touches throughout make this a fun-filled family vacation.
Welcome to Painted Pony Cottage on Chincoteague Island.
review stars
9.4Outstanding
(10 Ratings)
"This was a wonderful little house for my husband and my dogs. Check in was east. House had everything we needed. It was clean and as described. "
Angela S.
Don't miss out! Price and availability may change
9.4 / 10
Outstanding(10 Ratings)

House in Chincoteague Island, VA

6 guests · 3 bedrooms · 1 bath

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Well priced for this locationPriced under area average

About this house rental

Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe Painted Pony Cottage, but the word Charming is the first to come to mind. This quintessential Chincoteague Cottage simply oozes it. The perfect blend of Yesteryear and Modern Amenities, there's no better home base for making Chincoteague Island Vacation Memories. 

As you pull up to this whimsical Cottage, the White Picket Fence and Sea Glass Blue Door are so welcoming. You can already feel yourself relaxing. Just the thought of sipping Sweet Tea on that Screened Porch - you can hardly wait. Located in the heart of Chincoteague Island on Willow Street, you are tucked away in a quiet location, yet close to everywhere you want to be. Walk to the Carnival Grounds in July to enjoy our famous Firemen's Carnival, and visit the ponies penned up just a short walk from the Cottage. 

There is ample parking for 3 Cars just behind the house, off of Willow Street. As you enter Painted Pony Cottage, fond memories of Grandma's house may come back to you - it just feels so comfy and full of love. The spacious Kitchen has Warm Knotty Pine Cabinets and lots of Countertop space. The Chef in the family will be pleased with how well-stocked it is. Dine indoors at the colorful Kitchen Table, or Al Fresco at the Picnic Table in the backyard - a great place to enjoy some of our Fresh Local Crabs! 

As you wander to the Living Area, you'll fall madly in love with the Rustic Hardwood Floors throughout the Cottage. Relax after a fun-filled day at the Beach in the AC, and enjoy the Free WiFi and Flat Screen Streaming TV. Colors of Sunshine and Blue Sea are so bright and cheerful - it's just a great room to spend time in. Just off the Living Area lining the front of the Cottage is a fabulous Screened Porch with relaxing Rockers and Gliders - a wonderful place to gather in the evening and share stories of the day's adventures. Watch the kids play safely in the Fenced-in Front Yard, which Fido will appreciate, as well!

Painted Pony Cottage sleeps 6 more than comfortably in 3 Bedrooms, with a Full Sleeper in the Living Area. The Master Bedroom is on the 1st Floor and is also the only access to the Full Bathroom. Adorned in Nautical Navy and White, it is bright and cheerful, and has a comfy Full Bed. The shared Full Bath has a Tub/Shower Combo, and although you access it through the Bedroom, it is quite convenient for all. Fun painted pony decor greets you, keeping this awesome theme going throughout the Cottage. Watch your head as you follow the Winding Wood Stairs upstairs to Bedrooms 2 and 3. There are 2 Twins in Bedroom 2, and another Twin in Bedroom 3. This is an awesome place for the kids, who will feel like they have their own private hideaway. 

Painted Pony Cottage - The perfect place to Relax and Reconnect with those who matter most in this life........

Seaside Vacations does not allow group rentals to guests under age 25.  Therefore, online bookings for group rentals will not be honored. Friendly dogs welcome with $100 Pet Fee. Dogs MUST be current on Flea/Tick Preventative and Immunizations. No Cats.

Amenities at Painted Pony Cottage by Seaside Vacations & Sales

Non-smoking
Pets allowed
Family friendly

Map of Chincoteague Island, VA


Ratings and reviews

9.4 / 10
Outstanding(10 Ratings)
10 / 10Outstanding·Oct 2025
This was a wonderful little house for my husband and my dogs. Check in was east. House had everything we needed. It was clean and as described.
10 / 10Outstanding·Sep 2025
Property was welcoming to poochies, as well! Loved the fenced in yard for extra security when letting our girl out to do her business! Comfortable space and well-equipped!
10 / 10Outstanding·Jul 2025
Loved everything about this place! It was good walking distance to the carnival and a short drive to Maddox. It was clean and tidy with a unique floor plan that you can only get from an old house!
10 / 10Outstanding·Sep 2024
Our family adored the house. We will be coming back every year. It has a nice big kitchen and cute bedrooms. If you’re tall, duck, as you go through doors because it is a bit of a miniature house. That adds to its charm though. Very well equipped.

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Painted Pony Cottage by Seaside Vacations & Sales. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Painted Pony Cottage by Seaside Vacations & Sales pet friendly?

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Painted Pony Cottage by Seaside Vacations & Sales?

We found 3 amenities for this rental. This includes non-smoking, pets allowed, and family friendly.