Key West Cottages in Chincoteague — A Family-Friendly Getaway
Taking a family vacation with three young boys can feel more like a challenge than a getaway. So, when my wife suggested we visit Virginia and stay at the Key West Cottages in Chincoteague Island, I had my doubts. But I’ve learned to trust her research, which is usually more thorough than a detective on a high-profile case.
The drive from Pennsylvania was just over four hours, a manageable trip even with the whole crew. I had visions of National Lampoon’s Vacation playing in my head, but I’m happy to report our reality was much smoother.
The journey was a breeze, and we were left with a fantastic family experience that created lasting memories. As a writer, and with my nine-year-old son also developing a love for it, we decided to document our trip. This is our official review of the Key West Cottages and the adventures we had.
My wife packed a notebook, and my oldest son took on the role of chief journalist, jotting down a recap of our activities each day. This review is a collaboration, a father-son project to share our story.
Disclaimer: This article on Key West Cottages in Chincoteague Island reflects our personal experience and opinions. We were not asked by Key West Cottages to write this, and we paid full price for our stay. It was not provided in exchange for a review of any kind.
Table of contents
Key Takeaways
- Immaculate Property: The cottages and grounds are exceptionally clean and well-maintained, feeling brand new.
- Family-Friendly Amenities: The resort features a zero-entry, two-tier pool perfect for all ages, a private bay-side beach with firepits, and complimentary bicycles for exploring.
- Prime Location: Key West Cottages is within walking or biking distance of top-rated restaurants, food trucks, and local attractions, yet it offers a peaceful waterfront setting.
- Must-Try Foodie Scene: Don’t miss the local culinary delights. Island Creamery was named one of the best ice cream shops in America, and Sandy Pony Donuts offers incredible donuts and acai bowls.
- Access to Nature: The location is a perfect base for exploring the Chincoteague National Wildlife Refuge and seeing the famous wild ponies on Assateague Island.
The Full Key West Cottages Experience
The first thing you will notice at Key West Cottages is that everything looks brand new and pristine. The entire property, from the landscaping to the cottage interiors, is spotless and beautifully maintained. If you want to see more photos or learn about their policies, you can click here to visit their official website.
Being an entrepreneur, my curiosity got the best of me. I started asking the staff about the history of the property and discovered they had only been open for a few months before our arrival. This explained the immaculate condition, but their commitment to service is what truly makes the place shine.
Cottage Options
Key West Cottages offers several layouts to accommodate different group sizes, from couples to families of five. Options typically include Waterfront King, Poolside King, and Poolside Queen cottages, each designed with a clean, coastal aesthetic.
Our family of five stayed in a poolside cottage, which was around 600 square feet. While that may sound compact, the smart layout made it feel cozy and comfortable, not cramped. There was plenty of room to move around without tripping over each other.
The interiors were impressive. Each cottage is equipped with modern comforts like multiple flat-screen TVs, a kitchenette with a refrigerator, microwave, and stovetop, and beautifully finished bathrooms. The climate control was also perfect, keeping us cool and comfortable.
Every cottage also features a furnished porch. It’s the perfect spot to enjoy your morning coffee while looking out over Chincoteague Bay or watching the kids splash in the pool.
Amenities
The amenities at Key West Cottages are a huge part of the appeal. As a fitness professional, I would have loved to see a small gym on-site for a convenient workout. However, the available options provide more than enough for a fantastic vacation. For those who want to stay active, you can easily get a great workout during vacation by using the complimentary bikes or going for a run with incredible scenery.
Here are the key amenities that make this place special:
- Outdoor Pool: This was the highlight for our kids. The zero-entry design is perfect for little ones, and the two-tier layout lets toddlers splash safely in a one-foot-deep area while older kids enjoy the six-foot deep end. They provide pool toys, floats, and towels, so you don’t have to pack your own.
- Private Beach Area: On the bay side of the property, there’s a sandy beach area with chairs and firepits. It’s an amazing spot to watch the sunset over the water without having to drive anywhere. The firepits are free to use and perfect for a cool evening.
- Complimentary Bicycles: You can borrow beach cruisers for adults and kids to explore the island at your own pace. This is a huge perk, as bike rentals can add up quickly. It’s the best way to get around Maddox Boulevard and see the sights.
- Fishing and Crabbing Pier: If you have a Virginia Saltwater Fishing License, you can fish and crab right off the property’s pier. You can get a license just a few blocks away at retailers like Sea Hawk Sports Center.
- Community Grills: Down by the beach area, there are several high-quality gas grills available for guests. We saw many families grilling up burgers and hot dogs for an easy and delicious dinner.
Things to Do
Chincoteague Island is packed with activities, and Key West Cottages is the perfect home base. We didn’t get to everything on our list, but here are some of the top attractions you can plan for your trip.
- Nature and Wildlife: Your top priority should be the Chincoteague National Wildlife Refuge. It costs about $25 for a 7-day vehicle pass. Inside the refuge, you can visit the famous Assateague Beach to see the wild ponies and climb the historic Assateague Lighthouse for incredible views.
- Family Fun: For a day of thrills, check out Maui Jack’s Waterpark, which is just a short drive away. For something more low-key, the Iron Pony Adventure Park offers climbing and zip-lining courses suitable for various ages.
- History and Culture: Learn about the island’s unique history at the Museum of Chincoteague Island. You can also visit the Captain Timothy Hill House, which is one of the oldest homes on the island.
- Local Experiences: Take a boat tour to see dolphins and get a closer look at the ponies. Don’t forget to explore the local coffee shops, each offering unique brews of coffee, or visit the weekend Farmer’s Market for local goods.
Our Most Memorable Key West Cottages Takeaways
We built so many incredible memories during our vacation at Key West Cottages. These are the moments that really stood out for our family.
The Pool
Our kids are now officially begging for a pool at home, and we have the Key West Cottages pool to thank for that. The cleanliness was exceptional, with staff cleaning the pool and deck every single morning. They even have an outdoor shower for a quick rinse.
The best part was that the pool never felt overcrowded. There was always plenty of space for the kids to play with the provided slide and toys without us worrying about them bothering other guests. The lounge chairs and tables were also comfortable, making it a relaxing spot for parents to supervise.
The Beach
Our beach of choice was Assateague Beach, which is inside the National Seashore. You have to drive there and pay the entrance fee, but it is absolutely worth it. A 7-day pass is a great value if you plan to go multiple times.
Related Article: Workouts at the Beach to Keep You Fit During Your Vacation
My oldest son and I tried body surfing, and he was instantly hooked. After that first day, he asked to go back every single day to catch waves with me. My four-year-old twins had a blast letting the smaller waves chase them up the sand. It was simple, classic beach fun.
Pro Tip: When viewing the wild ponies, always maintain a distance of at least 40 feet (about one bus length). The National Park Service enforces this rule for both your safety and the horses’ well-being. Never feed the ponies, as it can be harmful to their health.
Boat Tour
We were worried our four-year-old twins wouldn’t last on a boat tour, but they absolutely loved it. We booked a private cruise through Daisey’s Island Cruises, which I highly recommend. A private tour allows you to customize the trip to your family’s interests.
Our captain was incredibly knowledgeable, taking us to see the wild horses from the water, pointing out historic landmarks, and finding pods of dolphins. We even spotted a bald eagle. Daisey’s offers a popular “Pony & Dolphin Tour” that lasts about two hours and is a fantastic way to see the best of the island from a different perspective.
The Food
The food scene on Chincoteague Island is a highlight. The area around Key West Cottages, especially along Maddox Boulevard, is filled with incredible restaurants, food trucks, and treat shops. It’s a true test of willpower if you’re trying not to overindulge.
We had an excellent sit-down meal at Ropewalk, which has a great atmosphere and delicious seafood. However, most of our meals came from walk-up spots with outdoor seating, which is perfect for families with active kids.
My wife loved the acai bowls from Sandy Pony Donuts. It might seem strange to get a health bowl from a donut shop, but they are fantastic. And their donuts? Absolutely incredible. We tried other donut shops, and nothing compared. Their signature hot, made-to-order donuts are a must-try.
Now, for the main event, ice cream. We were told to try the two local legends: Mr. Whippy for soft-serve and Island Creamery for homemade, hard-packed ice cream.
We also discovered BYOC (Build Your Own Cookie), a food truck that serves ice cream over a warm, freshly baked cookie. While all were delicious, Island Creamery was the undisputed champion.
There’s a reason “The Best Ice Cream Place in America” was a title given to them in July 2023. The quality is simply on another level. The line can get long, especially after dinner, but it moves quickly and is well worth the wait.
Book a Trip to Key West Cottages
Whether you’re planning a family vacation or a quiet getaway, Key West Cottages gets my highest recommendation. I was able to manage my businesses remotely without any issues, and when it was time to unplug, adventure was right outside our door.
The combination of a pristine, comfortable property and a prime location makes for an unforgettable experience. You won’t regret your stay at Key West Cottages in Chincoteague Island, VA.
FAQs About Key West Cottages
What is the best time of year to visit Key West Cottages in Chincoteague?
The peak season is from late spring to early fall (May through September) when the weather is warm and all attractions are open. For a quieter experience with fewer crowds, consider visiting in the shoulder seasons of April or October.
Are the Key West Cottages pet-friendly?
Based on their policies, pets are not permitted at Key West Cottages to ensure the comfort and safety of all guests, with the exception of certified service animals.
How close are the cottages to the beach?
Key West Cottages has its own small, private beach area on the bay side. The main ocean beach, Assateague Beach, is about a 10-minute drive away, located within the Chincoteague National Wildlife Refuge.
Do the Key West Cottages have full kitchens?
The cottages are equipped with kitchenettes that include a mini-refrigerator, microwave, and stovetop, which is perfect for preparing simple meals and snacks. They do not have conventional ovens.
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