42fav12

5 out of 5 stars★★★★★

Loved everything! We were very impressed with our stay and the many thoughtful details made it extra special. We were celebrating our anniversary and booked a cottage that had a view of the pool and the Chesapeake Bay. As we entered the grounds, the views and the quiet surroundings were so expansive. After a quick check in, we found our way to our room as we crossed the greens that separate our room from the Bay, the sauna area and the restaurant that was on the water. The room was so comfortable and spacious and the details like the big fluffy robes and the complimentary s’mores and was a unique touch. It was peaceful and relaxing on many levels. We went to Ticklers Restaurant and it was a great experience (it was so good, we wrote a separate review). Our evening ended with choosing between the many fire pits to roast our marshmallows, we chose one that had a local storyteller who shared interesting stories. It was a wonderful experience and we will be back.

Connector33077450358

4 out of 5 stars★★★★☆

We loved being next to the water, the fire pits with s’mores kits were a lot of fun. We really enjoyed how peaceful and quiet it is and the amenities like kayak, paddle boards, bikes, and the saltwater pool. The restaurant on site to dine by the water was also a plus! The room we had was a little small and could use a little updating but overall we enjoyed our stay.

jenniferlU190OA

5 out of 5 stars★★★★★

Great atmosphere, pretty waterfront property. Kayaks, paddle boards and a great pool. Really friendly and professional staff, who make it like your staying with friends. Fantastic drinks, the bartender knows what he's doing for sure. the food and crab are perfect. This was our 2nd time and we will be back.

ketchscott

5 out of 5 stars★★★★★

Fantastic experience exceeded our expectations, the entire property is so well managed and cared for, highly recommend for an escape to Tilghman Island. Excellent staff, spotless everywhere, housekeeping excellent.|Rooms well appointed and totally renovated just a few years ago.|We came by boat, no dock fee, 30amp service, water depth 4+feet. Decks are old but very sufficient. |Restaurant & bar do a great job, all good.|Staying here is like stepping back in time,|take a breath and enjoy!

Vacation67526717585

5 out of 5 stars★★★★★

I probably wouldn’t have left a review but then I met Isaiah who was a total gem. Throughout the day he helped with everything we needed: water, towels, ice for the cold plunge, and starting one of the fire pits. Not only did was he efficient but he was such a delight. We really enjoyed chatting with him and were so impressed by his work ethic. ||As others have mentioned the rooms leave a lot to be desired here. The service really made up for it.

Emma Broughton

5 out of 5 stars★★★★★

I worked in venue sourcing and event production for almost 10 years when I stumbled upon the Wylder Hotel in New York – it is a true gem & its sister property Wylder Tilghman Island was always a bucket list for me until last week. Just like the hotel New York, the staff & design here at Wylder Tilghman Island really makes the place shine. It’s small town lux. The front desk staff was sweet & warm for our last minute pop in. And Event Direct of Sales KD was amazing enough to chat with us. She was so responsive, knowledgeable, had an answer for every question, and zero-pressure—the ideal event partner. When we needed photo examples she sent them quickly and even more she was transparent about weather/renovation timelines (which a lot of hotels hide). Great spot for a corporate all hands/training spot or wedding venue, even greater staff.

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.

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.

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.