Amanda Yip

5 out of 5 stars★★★★★

We had a wonderful Fourth of July weekend stay at the Wylder Hotel on Tilghman Island. If you’re traveling with a dog, this place is truly a paradise. The property is exceptionally dog-friendly, and it was clear that many guests were repeat visitors who return year after year—a testament to how special the experience is. We took advantage of many of the amenities during our stay, including kayaking, paddle boarding, the oyster shucking class, biking around the island, the sauna, and the sunset boat cruise (which was well worth the additional fee). The pool was lovely and a great place to relax, though there could have been a few more lounge chairs given the holiday weekend crowds. The location is excellent—peaceful and scenic while still being an easy drive to St. Michaels for shopping, dining, and exploring. Our room appeared recently updated, was comfortable and functional, and the air conditioning performed impressively well during the 100-degree temperatures. It’s the perfect kind of room when you’re spending most of your time enjoying the property and surrounding area and simply need a comfortable place to recharge at the end of the day. My only critique is that the indoor communal space closed around 10:15 p.m. on Sunday evening while guests were still watching the World Cup match and playing games. Since it’s the primary indoor gathering space on the property, it would have been nice if it could have remained open a bit later, especially during a holiday weekend. I understand there may be staffing or operational considerations, but extended evening access would have made an already great stay even better. Overall, a fantastic, dog-friendly getaway with plenty to do, a relaxed atmosphere, and lots of reasons to return.

Chewie Dipnrip

3 out of 5 stars★★★☆☆

We stayed at The Wylder for a few nights over my wife’s birthday, and overall it was a pleasant, low-key getaway right on the Chesapeake. The property has a quiet, cute vibe that felt relaxing when we checked in on Thursday. The check-in process was smooth, and the staff were all genuinely friendly and accommodating — we were even able to get a small refrigerator delivered quickly for our dog’s food. The location is a big plus, especially if you enjoy being on the water. We had a great time taking advantage of the free kayaks and paddleboards on Friday; it was honestly the highlight of the trip and something we’d definitely do again. That said, there are a few areas that could use some attention. Our partial-view queen room felt a bit small and dated, and the bathroom could really use additional towel hooks. The single, miniature towel bar was not large enough for hand towels, bath towels, and beach towels. Dinner at the on-site restaurant (Tickler’s) was convenient, but the seafood was just mediocre, which was a bit of a letdown since restaurant options nearby are limited unless you drive into St. Michaels. The only real frustration came on Friday when a large group of families checked in. The atmosphere shifted noticeably and began feeling more chaotic than relaxing, especially at the price point (nearly $500 per night). The saltwater pool and food and beverage service had initially provided an elevated experience; however, once the larger groups arrived, the pool became dominated by children, creating an atmosphere that felt more like a community pool than a luxury, boutique resort. We completely understand that families are there to enjoy their vacation as well, but we also heard children running up and down the hallways well after 10:00 p.m. and again close to midnight. It didn’t seem that quiet hours were being respected or reinforced, which made it difficult to enjoy the peaceful atmosphere we had experienced earlier in the stay. Better management of large groups or designated family-friendly areas could help preserve the relaxing, upscale environment that makes the property so appealing. All in all, we enjoyed our stay and appreciated the waterfront access and friendly service. With a few updates to the rooms and better control over large groups, this could be an even stronger option for a romantic or relaxing Chesapeake escape.

Wildly Native Team

5 out of 5 stars★★★★★

Working alongside Wylder Hotel Tilghman Island is always an exceptional experience—and that’s something we don’t say lightly. As a floral design team that works across a wide range of venues, we pay close attention to how a space operates behind the scenes and Wylder consistently stands out. The staff is not only professional, but genuinely thoughtful and kind—qualities that make an enormous difference on event days where timing, communication, and care all matter. From polishing the forks and making sure the glassware is spotless to ensuring the exact table set up is correct for their event we have seen the incredible care that goes into each set up. From a vendor perspective, they are true partners. Their team understands what it takes to execute a seamless event and supports every detail with intention. As hosts, they create an environment where both clients and vendors feel taken care of, which ultimately elevates the entire experience for everyone involved. And beyond operations—the setting, the food, the atmosphere—it all aligns beautifully. It’s a space that allows our work to shine while also enhancing the overall guest experience. The guests always are smiling and enjoying the laid back atmosphere that truly sets things apart from other locations. A variety of activities to choose from without feeling overwhelming is also something that I often see with the guests. We value Wylder highly within our business and always look forward to returning. It’s a venue we trust, recommend, and genuinely enjoy working in. — Wildly Native Flower Farm

Mary Kemberling

5 out of 5 stars★★★★★

Cozy, old tyme feel. Place was clean, adequate, and very friendly staff. Unfortunately we were only there over night – wedding near by. Sunday brunch was fantastic. Loved the hotel location on the water.

Melody Hunt

4 out of 5 stars★★★★☆

Loved our experience at Wylder TI. The customer service was great with a champagne welcome from Lauren. After checking in we were able to eat some amazing food, grab a delicious cocktail, and play cards on the wrap around deck. The sauna and fire pit were a must. The only thing missing was a fridge in our rooms!