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Painted Pony Cottage by Seaside Vacations & Sales

Photo gallery for Painted Pony Cottage by Seaside Vacations & Sales

A covered porch with a rocking chair and a chair with a cushion. - Painted Pony Cottage by Seaside Vacations & Sales (Chincoteague Island)
A living room with a blue sofa, a floral sofa, a wooden staircase, and a TV on a stand. - Painted Pony Cottage by Seaside Vacations & Sales (Chincoteague Island)
A living room with a floral sofa, a blue sofa, and a wooden door leading outside. - Painted Pony Cottage by Seaside Vacations & Sales (Chincoteague Island)
A two-story house with a porch, a screened-in area, and a white picket fence. - Painted Pony Cottage by Seaside Vacations & Sales (Chincoteague Island)
A white house with a window and a metal ladder leaning against it. - Painted Pony Cottage by Seaside Vacations & Sales (Chincoteague Island)
Take advantage of a water park, a garden and laundry facilities at Painted Pony Cottage by Seaside Vacations & Sales. Guests can connect to in-room WiFi.

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Air-conditioning
  • Outdoor space

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About this property

Painted Pony Cottage by Seaside Vacations & Sales

  • 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.

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About the area

Chincoteague is home to this holiday home. Museum of Chincoteague and Captain Timothy Hill House are cultural highlights, and some of the area's attractions include Maui Jack's Waterpark and Wallops Flight Facility. Discover the area's water adventures with power boating, fishing and swimming nearby, or enjoy the great outdoors with cycling. Visit our Chincoteague travel guide
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Map
Chincoteague Island, VA

What's nearby

  • A lake with a dock extending into it, surrounded by houses and greenery.
    Chincoteague Channel
    6 min walk - 0.6 km
  • beach near Downtown Chincoteague
    6 min walk - 0.6 km
  • Robert N. Reed Downtown Waterfront Park
    15 min walk - 1.3 km
  • beach near Down the Marsh
    2 min drive - 1.4 km
  • beach near Snotty Ridge
    2 min drive - 1.4 km

Getting around

  • Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)
    58 min drive

Restaurants

  • Island Creamery
    3 min drive
  • McDonald's
    6 min drive
  • Ropewalk
    12 min walk
  • Captain Zack's Seafood
    3 min drive
  • Asian Express
    5 min drive

Frequently asked questions

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

Yes, pets are allowed at this property.

What time is check-in at Painted Pony Cottage by Seaside Vacations & Sales?

Check-in begins at 4:00 PM.

What time is check-out at Painted Pony Cottage by Seaside Vacations & Sales?

Checkout is at 10:00 AM.

Where is Painted Pony Cottage by Seaside Vacations & Sales located?

Situated in Chincoteague, this holiday home is within a 15-minute walk of Chincoteague Channel and Robert N. Reed Downtown Waterfront Park. Chincoteague National Wildlife Refuge and Maui Jack's Waterpark are also within 3 miles (5 km).

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Reviews

Painted Pony Cottage by Seaside Vacations & Sales Reviews

9.6

Exceptional

9.4

Cleanliness

9.4

Location
Rating 10 - Excellent. 10 out of 13 reviews
Rating 8 - Good. 3 out of 13 reviews
Rating 6 - Okay. 0 out of 13 reviews
Rating 4 - Poor. 0 out of 13 reviews
Rating 2 - Terrible. 0 out of 13 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cottage With Charm

Well maintained pet-friendly cottage provided an excellent location to explore the town and National Park.
Stayed 4 nights in Apr 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy

Comfortable clean house

Nice place. Very comfortable and a good location close to town. We really enjoyed ourselves.
Stayed 3 nights in Oct 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Chincoteague

Perfect! Loved the screened porch and fenced yard for the dog.
Stayed 4 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Adorable home

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.
Stayed 4 nights in Aug 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice place

We had a nice stay. It was just me, my wife and our dog there were no issues. If you are gong with a family note that the only way to the bathroom is through the master bedroom. And the bed in the master is only a full size. Other than that the place was very clean and equipped with all the necessities. Property management was excellent and checking with us making sure that all was well. Close to everything you need.
Stayed 6 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Painted Pony Plus

Pet friendly property was great for three adults and our dog. Walking distance to fairgrounds and Main Street. Although it wasn’t a problem for us, there was no dishwasher or ironing board as listed among the amenities. And only coffee machine was drip coffee maker. No kuerig.
Stayed 7 nights in Jun 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely!
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great communications around check-in, check-out, and navigating the property. Host was super-responsive. The extra amenities were helpful and exceeded my expectations. (e.g., bicycles for the family, beach chairs, grill with charcoal chimney, etc.)
Stayed 4 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Painted pony cottage was great!

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!
Stayed 6 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is THE house to be with families with younger kids or fur babies. Our poodles LOVED this house, the doggy door was an unexpected surprise, we didn’t even realize it was there in the listing. There wasn’t a single moment we were hot in that house. The air conditioning is efficient and quiet!(The floors needed a sweeping when we got there but we took care of that really quick) other than that the house was exactly what we needed! You can’t beat the location we had the best week ever. Thank you for the best stay! We will be back to rent again!
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 8 nights in Oct 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 5 nights in Jun 2024