Wake up to a free continental breakfast at this Prince Frederick hotel, just minutes from Calvert Historical Society Park and King Memorial Park. Enjoy free WiFi and convenient parking during your Maryland getaway.
Set on the bay, this Tilghman hotel offers waterfront relaxation with complimentary breakfast and free parking. Explore by kayak or bicycle with onsite rentals, or unwind at the marina. Each room includes convenient refrigerators and microwaves for added comfort.
Splash into vacation mode at this Prince Frederick hotel offering a refreshing indoor pool and free breakfast. Near calvART Gallery and local dining options, guests rave about the helpful staff, fitness center, and convenient parking.
Wake up to a complimentary breakfast at this Maryland hotel before exploring nearby R&J's PlayPark or calvART Gallery. Unwind in the indoor pool and hot tub after using the fitness center. Rooms feature convenient sofa beds and refrigerators.
This waterfront inn on Tilghman Island features a seasonal outdoor pool and welcoming restaurant with bar. Near local marinas, it offers free breakfast, WiFi, and parking. Guests can relax on the terrace or stroll through the garden while experiencing exceptional staff service.
Escape to this luxurious B&B offering free breakfast, WiFi, and parking near Upper Yough River. Unwind in the hot tub after exploring local attractions on complimentary bikes, then relax on the terrace amid the estate's peaceful atmosphere.
Wake up refreshed in clean, comfortable rooms at this Upper Marlboro motel. Free WiFi and parking make exploration easy, with Lake Presidential Golf Club and Darnall's Chance House Museum just minutes away. The helpful 24-hour staff ensures a smooth stay.
Relax in clean, quiet rooms after exploring nearby restaurants or bowling onsite. This Waldorf hotel offers thoughtful amenities including free breakfast, WiFi and parking, plus a fitness center. Helpful staff and peaceful atmosphere earn consistent praise from travelers.
Escape to this quiet retreat with hiking trails and a garden terrace. Just minutes from Saint Michaels Village and Classic Motor Museum, this hotel offers free breakfast, WiFi and parking. Guests consistently praise the helpful staff and clean accommodations.
Soak in the charm of this waterfront getaway near Higgins Yacht Yard and Marina. Enjoy complimentary breakfast before exploring Muskrat Park. After sightseeing, unwind with drinks at the bar or grab a bite at the on-site café.
Tucked in Waldorf near Waldorf Marketplace, this hotel features The Bistro for breakfast and dinner plus a welcoming bar/lounge. Every room includes helpful refrigerators and microwaves, with free parking and friendly staff to enhance your stay.
Set along Maryland's Eastern Shore, this luxurious retreat features a marina, golf course, and serene spa treatments. Enjoy cocktails at the poolside bar before savoring locally-inspired cuisine at Stars restaurant. The helpful staff ensures a peaceful waterfront getaway.
Just 10 minutes from U.S. Naval Academy, this quiet hotel offers free WiFi and parking for easy exploration. After a day of nearby kayaking or hiking trails, unwind in the 24-hour fitness center. Travelers consistently praise the helpful staff and convenient location.
Located in Waldorf with easy access to Waldorf Marketplace and St. Charles Towne Center, this hotel welcomes you with an indoor pool and 24-hour fitness center. Enjoy free breakfast, WiFi, and parking while the helpful staff ensures a comfortable stay.
A serene escape with 24-hour fitness center and seasonal outdoor pool near Annapolis Harbor Center. Close to shopping and restaurants with highway convenience, these suites offer free breakfast and WiFi for both business and leisure travelers.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
When the beach is calling your name, you might want to head down to Breezy Point Beach, located 5.2 mi (8.3 km) from central Chesapeake Beach. Enjoy the sunset by the shore at Brownies Beach.
Why not give yourself a treat with a trip to Chesapeake Beach Water Park, just one of the family attractions in central Chesapeake Beach. If you have fun at Chesapeake Beach Water Park, you'll love Chesapeake Beach Railway Museum, just a short walk away.
Imagine strolling along Rod n Reel Charter Fishing for some great waterfront pics when in the heart of Chesapeake Beach.
If you carry on walking you'll get to Brownies Beach for some more water views.
The center of Chesapeake Beach is home to cultural attractions like Chesapeake Beach Railway Museum, so you might want to stop by during your stay. If you want to experience more of the culture Chesapeake Beach has to offer, head to Rod n Reel Charter Fishing, Chesapeake Beach Water Park, and Bayside History Museum.
Bruce Gabrielson's Surf Art Gallery and Museum is 3.4 mi (5.5 km) from central Chesapeake Beach, why not stop by during your stay. If you want to experience more of the culture Chesapeake Beach has to offer, head to Breezy Point Beach, Chesapeake Beach Railway Museum, and Rod n Reel Charter Fishing.
If you can't wait to get to the beach, you might enjoy a trip to Brownies Beach located 1 mi (1.7 km) from central Chesapeake Beach. Enjoy the sunset by the shore at Breezy Point Beach.
Fishing charters depart daily from the marina, where captains share tales of record catches in Chesapeake Bay's fertile waters. The Railway Museum occupies the former train station, chronicling how this once-thriving resort town lured city dwellers to its shores. After exploring history, cool off at the Water Park where slides and fountains provide relief from summer heat. Rod n' Reel offers fresh seafood with bay views that explain why locals never tire of the scenery. Breezy Point Beach provides a quieter alternative for sunbathing and shell collecting. For nature enthusiasts, the Rail Trail winds through wetlands where herons pose like statues in the shallows. Bruce Gabrielson's Surf Art Gallery showcases maritime culture through a creative lens.
We had a wonderful two night stay at the hotel. The marina is beautiful with nightly rentals if needed. Our first stay and we will return. Great staff very helful. If you are looking for a peacefull,tranquil location you will like it.
We had a great time at the Wylder Inn on Tilghman Island (20-21 May). This is a great spot for a quick getaway, and there are many things to do on site and in the area if you want to stay longer.
The staff was welcoming and responsive from our arrival to departure when our key was collected from our car so we didn't have to get out in the rain.
The Continental Breakfast had a variety of items to start the day right and the fire pits provided a relaxing venue at the end of the day.
We look...
Huge resort in a small, well kept town!
Our room was right on the bay and was clean and nice. The beds and pillows were super comfortable.
There is not a place for breakfast but if you go a little further south on the main road, there is a shopping center with a McDonalds (and a CVS and some other things)... We were in a hurry to get home so did not try any of the breakfast places that the desk clerk recommended.
The staff guy that checked us in was SUPER nice and helpful!
We needed overnight accommodations before heading out for a day of sailing on the bay and Hidden Harbour popped up as the closest venue geographically and we're glad it did. The accommodations are new, with quality and fixtures and bathrooms that you wouldn't mind taking home with you. The price seemed fair and as we watched the full moon rising from our deck we wished that we were spending a week.
This is an elegant old hotel with lovely gardens and a great view of the bay. Restaurant was very nice with fantastic views and excellent food. Best crab cakes ever! The main part of the hotel is original with low ceilings and uneven floors, and has several nice sitting rooms, nooks and alcoves. Reminds me of some European hotels I have visited.
I took a solo trip and picked the perfect spot. This family owned inn is great for a family trip, a romantic getaway, or for a quiet escape by yourself. The owners are such a welcoming family and made me feel very like VIP. I will be going back and recommend Sandaway to anyone looking for that getaway in the Eastern Shore. Thank you Gibson Family for a wonderful experience!
This was my first time at this brand of hotel so I didn’t have any expectations. I was surprised in a good way. The room was well appointed for a short stay and very clean. The kitchen was fully stocked. The gym was small but had everything I needed for a couple of workouts. There was also a very well stocked breakfast in the morning. I have special food needs and I found plenty to eat. The entire staff was pleasant and helpful. I had never been there before but will definitely go back.
We didn't have any plans for Spring Break, but the weather was fantastic and we decided to go to St. Michaels to go kayaking. Found the Parsonage online and got a great suite for ourselves and our son at the last minute. Way comfortable and LOVED how close to everything in town it was. Enjoyed relaxing evenings watching movies from the DVD collection. Great parking for our truck.
Holly and Jay were friendly hosts. The farmhouse was clean and comfortable. The breakfast was very yummy. We only stayed one night, but next time we will definitely spend more time there. If you are down near calvert cliffs/flag ponds, the farmhouse was only about 10 minutes to flag ponds.
We really loved everything, but Guinness the dog topped everything. There was a miscommunication about dinner reseservations but it worked out. Would have appreciated more whole food at breakfast. Neither of these would keep me away. In fact, we would love to see the property in the spring.
Great price! Large clean rooms! Awesome pool, breakfast not so great but since it was such an amazing stay we didn’t mind going out for breakfast. We would stay again
We collected as a family on December 28 and stayed for five days. The rooms were comfortable and very clean.
The staff went beyond the norm to make our stay great.
Can I book a refundable accommodation in Chesapeake Beach?
If you need the flexibility to change your plans to Chesapeake Beach, most hotels provide refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
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If you want to find a good alternative to a hotel, look over our selection of 8 vacation homes.
What will the weather in Chesapeake Beach be like during my visit?
The warmest months in Chesapeake Beach are usually July and August with an average temp of 75°F. January and February are the chilliest months when the average temp is 40°F. The rainiest months are July and August.
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