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Wylder Hotel - Tilghman Island

★★★★ 21551 Chesapeake House Drive, Saint Michaels, US

8.7 guest rating· 222 reviews

About this hotel

Waterfront Charm and History

Experience the rebirth of a historic 1898 boarding house where watermen once ruled and crabs were a staple. The Wylder Hotel Tilghman Island pays homage to the hardworking fishermen of the past with a touch of irreverence, offering a welcoming vibe that instantly makes you feel at home.

Exciting Amenities

Indulge in the delights of Tickler’s Crab Shack & Restaurant and Bar Mumbo, or take advantage of the private marina with 25 boat slips. For adventure seekers, charter fishing trips and a variety of fun activities await. Whether you're an overnight guest or a local, there's something for everyone at this waterfront gem.

Eastern Shore Paradise

Escape to Tilghman Island, just a short drive from major cities like Baltimore, Washington D.C., and Philadelphia. Immerse yourself in the relaxed yet vibrant Eastern Shore lifestyle, filled with sailing, kayaking, and the freshest seafood. Book your stay now and discover the magic of Tilghman Island!

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Rooms & rates

Waterfront Suite

Sleeps 3 · 36 m² · King bed

  • Desk
  • Laptop-friendly workspace
  • Air conditioning
  • Bathrobe
  • Private bathroom

Double Cabin

Sleeps 3 · 18 m² · Twin bed, Double bed

  • Air conditioning
  • Single-room air conditioning for guest accommodation
  • Bathrobe
  • Private bathroom
  • Shower

Partial Waterview Queen

Sleeps 2 · 20 m² · Queen bed

  • Air conditioning
  • Single-room air conditioning for guest accommodation
  • Bathrobe
  • Private bathroom
  • Shower

Waterman's Galley

Sleeps 2 · 20 m² · Double bed

  • Air conditioning
  • Single-room air conditioning for guest accommodation
  • Bathrobe
  • Private bathroom
  • TV

Widow's Walk Suite

Sleeps 2 · 37 m² · Extra-large double bed (Super-king size)

  • Air conditioning
  • Single-room air conditioning for guest accommodation
  • Bathrobe
  • Private bathroom
  • TV

Waterfront King Suite

Sleeps 2 · 37 m² · Extra-large double bed (Super-king size)

  • Air conditioning
  • Single-room air conditioning for guest accommodation
  • Bathrobe
  • Private bathroom
  • Shower

Widows Walk Suite

Sleeps 3 · 36 m² · King bed

  • Air conditioning
  • Bathrobe
  • Private bathroom
  • Free WiFi
  • Hair dryer

Partial Waterview Full

Sleeps 2 · 15 m² · Double bed

  • Air conditioning
  • Single-room air conditioning for guest accommodation
  • Bathrobe
  • Private bathroom
  • TV

Bungalow King

Sleeps 3 · 28 m² · Extra-large double bed (Super-king size)

  • Air conditioning
  • Single-room air conditioning for guest accommodation
  • Bathrobe
  • Private bathroom
  • TV

Bungalow 2 Queens

Sleeps 4 · 28 m² · 2× Queen bed

  • Air conditioning
  • Single-room air conditioning for guest accommodation
  • Bathrobe
  • Private bathroom
  • TV

Amenities

  • Free WiFi
  • Fence around pool
  • Heated pool
  • Outdoor pool
  • Outdoor pool - seasonal
  • Pool with view
  • Salt-water pool
  • Swimming pool
  • Sauna
  • Free Parking
  • Accessible parking
  • Breakfast takeaway containers
  • Restaurant
  • Bar
Show all 59 amenities
  • Air conditioning
  • Pets allowed
  • Beach
  • Beachfront
  • Private beach area
  • Sun loungers or beach chairs
  • Non-smoking rooms
  • Non-smoking throughout
  • Family rooms
  • Board games/puzzles
  • Canoeing
  • Cashless payment available
  • CCTV in common areas
  • CCTV outside property
  • Cleaning standards that are effective against Coronavirus
  • Concierge service
  • Cycling
  • Daily housekeeping
  • Face masks for guests available
  • Fire extinguishers
  • First aid kit available
  • Fishing
  • Garden
  • Guest rooms disinfected between stays
  • Guests can opt-out any cleaning services during stay
  • Hand sanitizer in guest room and key areas
  • Happy hour
  • Heating
  • Invoice provided
  • Key access
  • Kid meals
  • Laundry washed per local authority guidelines
  • Meeting/banquet facilities
  • Outdoor fireplace
  • Outdoor furniture
  • Picnic area
  • Sanitized tableware & silverware
  • Shallow end
  • Shared stationery like menus, pens are removed
  • Smoke alarms
  • Special diet menus - on request
  • Staff adhere to local safety protocols
  • Sun terrace
  • Water sport facilities on site
  • Wine/champagne

Location

© OpenStreetMap contributors

21551 Chesapeake House Drive, Saint Michaels, US

Check-in
from 04:00 PM to 08:00 PM
Check-out
until 11:00 AM

What guests say8.7222 reviews

+ Great location+ Friendly staff+ Lovely views+ Cozy atmosphereLimited food serviceSmall room sizeCold food at buffet
Cleanliness8.8
Service9.3
Location9.3
Room Quality7.8
Amenities8.8
Value for Money8.3

Unwind, relax, and recharge on a little slice of heaven on earth

10.0

From the moment we arrived, we were greeted with exceptional hospitality by Ramon and Lauren! We needed a bit more room than the unit we originally booked and were graciously upgraded the next night to accommodate our needs by Ramon.. Ramon offered help with our luggage and checked in throughout our long weekend stay; always with a smile, while Lauren solved our television issue promptly. The grounds are very well maintained offering a serene place to relax and recharge. Everything from the bikes available to ride and explore, the sauna and cold plunge, relaxing poolside, and enjoying our morning coffee outside on the waterfront was exactly what our souls needed. We will definitely be back to stay!

T262PRmichelleg · 2026-07-27

Anniversary Quick Getaway

10.0

This place was exactly what we needed to celebrate our anniversary while traveling with our toddler. The value for money felt very reasonable given everything included. There were plenty of activities for the whole family—our toddler had a blast with the pool, kayaking, and canoeing! Our room was clean, quiet, and relaxing. What set the experience apart was the staff. They were so kind and accommodated an early check-in and late check-out for us. They even gifted us a bottle of wine to celebrate our anniversary! Thank you Ramon and team. We will be returning!

sgK8062XZ · 2026-07-27

Nice stay by the water

8.0

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.

Connector33077450358 · 2026-07-25

A Great Escape!!

10.0

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!

ketchscott · ANNAPOLIS, MARYLAND · 2026-07-20

Great stay

10.0

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.

jenniferlU190OA · 2026-07-20

Thanks Isaiah!

10.0

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.

Vacation67526717585 · 2026-07-17

Good to know

The resort fee includes the following:

-Wifi

-Parking

-Paddleboards, Kayaks, Canoes

-Heated Saltwater Pool

Parking

Free private parking is possible on site (reservation is not needed).

Internet

WiFi is available in all areas and is free of charge.

Children and extra bed policy

Children of any age are allowed.

You haven't added any cots.

You haven't added any extra beds.

Pets

Pets are allowed. Charges may be applicable.

Groups

When booking more than 9 rooms, different policies and additional supplements may apply.