Best Dorchester County Hotels

Bicyclist's and outdoorsman's dream! Neat little rancher on two waterfront acres just 4 miles from Blackwater Wildlife Refuge and Harriet Tubman National Park. 10 minute drive from downtown, the Hyatt, and the Ironman starting point as well. Ironman and Eagleman races actually pass right by! Bright, sunny, and newly renovated, it's a great place to hang your hat after a day of hunting, fishing, bicycling, or triatholon-ing! Or just take a weekend to relax on the water!The spaceHouse is located right on route 16- one of the most popular bicycle routes on the Shore! There is a general store just a half mile away, and a great waterfront bar/restaurant down the road as well (Palm Beach Willie's and Maryland Blue). Just 10 minutes from downtown Cambridge, you're also close enough to enjoy RAR Brewing without a hassle. If you have a wedding at the Hyatt, it's a 7 minute straight shot- you literally don't have to turn!Enjoy a drink on the dock after a day of biking or kayaking. Lounge by the fire pit in the evening or enjoy the propane fire pit on the pier.Hunters- feel free to use the bow targets in the yard. Plenty of room to park a boat as well.Fishermen- catch a snakehead right out the back door! Plus the minnow trap is available and can provide a steady supply of bait.Guest accessGuests will have access to the whole house. We have three kayaks and a canoe which guests can enjoy upon signing a release. There is a hammock set up right on the water, as well as an outdoor picnic table with lights strung overhead. There are also bow targets, pull crab traps and a minnow trap for guests use on property.Other things to noteThere is a chicken coop with chickens on the property but no rooster. Feel free to enjoy some eggs from the chickens or produce from the garden.About pets:Pets allowed: dogs and cats (limit 2 total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.

Welcome to The Blue Heron, named for "Henry", the Heron that visits daily. Spacious areas for large groups to gather and also plenty of areas to spread out and relax. The house sits on just under 3 acres and is set deep back from the road, allowing you to truly enjoy nature. Many windows and sliding doors allow waterfront views. The well appointed kitchen has three separate work areas allowing lots of space to get the meals prepped. A huge crab pot and propane stand are also provided. The main house has four bedrooms and 3 full baths, also has an attached apartment just above the garage with an additional living room, kitchen, two bedrooms and full bath. All areas are included with the rental.Bedrooms:Four king bedrooms (1 in the apartment), 1 queen bedroom (in the apartment) and 1 room with 4 twin beds. All bedrooms are equipped with smart TVs. One king bedroom is on the first floor and has a full bath with shower on the same level. Living room has a pull out queen bed and family room offers a large sectional sofa for extra sleeping space.Group Areas: Huge living room has a 75" tv for movie or game nights. Dining area seats 16 for large group meals. Large screened patio just off kitchen and dining area for outdoor dining or relaxing. Large fire pit area.Outdoors:Kayaks; two tandem, two single and one canoe with paddles and life-vests are provided. Launch from shoreline, as no dock is on the property. Large fire pit and a huge waterfront yard for games. Propane grill, Rafts, beach towels. Two screened porches, one off the back of the main house and one smaller off of the apartment.About pets:Pets allowed: dogs (limit 2 total).Pets are not permitted on the furniture or bedding.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking allowed: in designated areas.About minBookingAge:Minimum age to rent: 21.About events:Events allowed: family gatherings and birthday parties.Maximum event attendees: 40.

Newly renovated house located in lower Dorchester County with fire pit and gazebo for entertaining family and friends. Property is ajoining to Blackwater national refuge which is very popular for nature watching and biking. The Blackwater river is only one mile away with great fishing and crabbing. Property is located 15 minutes from Cambridge, MD and approximately 10 minutes from the refuge visitor center and Harriet Tubman museum. About pets:Pets allowed: dogs and cats (limit 2 total).About checkOut:Check out before 10:30 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:30 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

About Time: A Tranquil Eastern Shore Retreat for Families, Friends, and Multi-Generational Vacations:Welcome to About Time, a serene and idyllic escape nestled on St. John’s Creek on Taylor’s Island. About Time isn’t just a vacation property; it’s a destination that brings people together, inspiring relaxation and fun while offering a glimpse into a simpler, more authentic way of life on Maryland's Eastern Shore. Here, surrounded by pristine waterfront views, sprawling green lawns, and peaceful creeks, you’ll find the space and time to reconnect with loved ones and yourself.This unique property offers two separate houses—each equipped with its own amenities and charm—perfect for multi-generational families, groups of friends, or anyone looking to create lasting memories in a truly remarkable setting.A Step Back in Time: Experience the Eastern Shore’s Classic Charm.Taylor’s Island itself is steeped in history, reflecting Maryland’s colonial past and the long-standing traditions of communities that have thrived along these shores. About Time embodies this historic charm while offering modern conveniences, so you can enjoy all the joys of rustic living without sacrificing comfort. From the crackle of a bonfire to mornings spent fishing, the experiences here will bring you back to basics, letting you savor every moment.Located on St. John’s Creek, this quiet haven calls for unplugging, unwinding, and reconnecting with nature. It’s perfect for families wanting to escape the fast pace of daily life. The entire property is yours to explore, from the lush grassy fields to the dock extending over tranquil waters.The Perfect Setting for Unplugging:About Time is designed for those who value peace, privacy, and the great outdoors. The waters of St. John’s Creek are calm, inviting kayakers of all skill levels to explore the nearby shoreline, watch for local wildlife, or simply drift peacefully as the sun sets. Guests are welcome to use the four kayaks provided, each carefully maintained and equipped for an easy and safe paddling experience. The creek’s gentle currents make it suitable for children, teens, and adults alike.For those who love fishing, crabbing, or just watching the water, the property’s private dock offers endless opportunities. Crabbing gear and pots are available, inviting you to try your hand at one of the Eastern Shore’s most beloved traditions. Or, simply relax on the dock with a good book, taking in the soothing sights and sounds of nature all around you.The Accommodations: Cozy and Spacious for Everyone:With two houses on the property, About Time is designed to accommodate groups of all sizes. Each house has been lovingly maintained and updated to offer comfort, convenience, and a touch of modern elegance in an authentic Eastern Shore setting.The Main House: Comfort Meets Modern Amenities:The three-bedroom main house can sleep up to six people and has been updated with all the essentials for a comfortable stay. Recently renovated, the main house features a fully upgraded kitchen with granite countertops and all the tools you need to prepare delicious family meals, from fresh crab cakes to hearty breakfasts to fuel a day of adventure.The bathroom has also been renovated, now featuring modern fixtures and finishes that bring a sense of luxury to this charming rural escape. Whether you're rinsing off after a day on the water or winding down before a cozy night, you’ll appreciate the attention to detail.Each bedroom is tastefully decorated, with soft linens, comfortable bedding, and large windows that let in plenty of natural light. The spacious living area includes a cozy seating arrangement perfect for game nights, movie marathons, or simply gathering around to share stories from the day.The Bunkhouse: A Private Summer Camp Feel:The bunkhouse, which sleeps up to ten, offers a more rustic, “summer camp” vibe, ideal for larger families or groups of friends. Think of it as your own personal retreat within a retreat—separate from the main house but still close enough to feel connected to the rest of the group.Outfitted with comfortable bunk beds, the bunkhouse is a dream come true for kids and teens, though adults are sure to enjoy it just as much. Imagine the laughter and memories that will unfold here as everyone settles in for a night of storytelling, card games, and camaraderie. The bunkhouse gives families space to spread out and provides the perfect setup for creating unforgettable memories.Modern Comforts in a Rustic Setting:While About Time is all about unplugging, we understand the need for convenience, especially when it comes to creature comforts. That’s why we’ve outfitted both the main house and the bunkhouse with new, ultra-quiet ductless HVAC systems. No matter the season, you’ll stay comfortable, with powerful heating and cooling that adapts to your needs without a sound.For guests who prefer to stay connected while away, About Time is equipped with high-speed Starlink internet. Whether you need to catch up on work, stream a favorite show, or simply stay in touch with loved ones, Starlink’s reliable connectivity lets you enjoy the modern perks of WiFi without missing a beat in this beautiful setting.A New EV Charger for Eco-Friendly Travelers:We’re excited to offer an eco-friendly amenity for our guests: a brand-new EV charger for electric vehicles. Our goal is to make it easy for everyone, including electric vehicle owners, to travel to About Time with ease and convenience. Charge up right at the property and explore the Eastern Shore sustainably, without the need to search for nearby charging stations. It’s just one of the many ways we’re committed to making About Time a welcoming, accessible retreat for all.Outdoor Adventures and Activities for All AgesAbout Time is truly an adventure paradise, with an array of outdoor activities suited for all ages and interests. Spend your days kayaking on the creek, fishing off the dock, or testing your skills with crab pots provided on-site. For families with children, catching crabs or reeling in a fish can be an exciting first-time experience, one that’s sure to become a treasured memory.But the fun doesn’t stop at the water’s edge. The expansive property includes wide-open lawns and shaded areas perfect for picnics, outdoor games, and bonfires. We provide a variety of indoor and outdoor games to keep everyone entertained, from classic board games to lawn games like cornhole and horseshoes. There’s something magical about watching kids run free, laughing and playing as they explore the natural surroundings.For guests who love to hike or explore, Taylor’s Island offers some wonderful trails and scenic spots to discover. Take a walk along the creek, search for wildlife, or simply enjoy the fresh air and wide-open skies that make this area so special. The sights and sounds of the Eastern Shore—from the call of an osprey to the rustle of leaves in the breeze—are sure to leave you feeling refreshed and rejuvenated.Dining and Cooking Options: Enjoy the Flavors of the Eastern Shore:One of the best parts of a vacation at About Time is the chance to savor local flavors and try your hand at cooking fresh seafood. The fully equipped kitchen in the main house has everything you need to prepare delicious meals for the entire group, and our outdoor grill area is perfect for barbecues and fish fries.Guests can visit local markets to pick up fresh, local ingredients or even bring back the day’s catch from crabbing and fishing to cook and enjoy right here. For a unique dining experience, consider setting up a picnic by the water, or gather everyone around the fire pit for a cookout under the stars.If you’d rather explore local dining options, nearby towns offer plenty of restaurants that highlight Eastern Shore cuisine, from crab shacks and seafood eateries to charming diners and cafés. Treat yourself to Maryland crab cakes, freshly shucked oysters, and more as you sample the region’s culinary treasures.About pets:Pets allowed: dogs (limit 2 total).About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

Welcome to our charming 2-bedroom farm stay in the heart of Fishing Creek! Nestled in a picturesque setting, this cozy accommodation offers the perfect escape for your next vacation.As you step inside, you'll be greeted by a fully stocked kitchen, complete with a stove, oven, refrigerator, and all the essential appliances you need to whip up delicious meals. Enjoy your culinary creations at the dining table, or step outside and fire up the grill for an alfresco dining experience.When it's time to unwind, you can curl up on the comfortable living room furniture and enjoy the smart TV, or explore the selection of books, games, and DVDs. The free WiFi and in-unit washer and dryer make it easy to stay connected and refreshed during your stay.Just a short 10-minute drive away, you'll find the stunning Blackwater National Wildlife Refuge, where you can immerse yourself in nature and spot an abundance of wildlife. Back at the property, take in the serene water views from the porch, relax on the beach loungers, or gather around the fire pit for a cozy evening under the stars. Two dogs welcome but must be leashed when outside.With its thoughtful amenities, charming atmosphere, and convenient location, this farm stay is the perfect home base for your Fishing Creek adventure. We can't wait to host you!Please note: The pet fee is PER PET. If you have two pets staying please let us know, and we will send a payment request for the second pet.About pets:Pets allowed: dogs less than 50 lbs per pet (limit 2 pets total).Guest must clean up after pets. Scoop the poop!.About checkOut:Check out before 10:30 AM.About children:Children allowed: ages 0-17.About customRules:Owners must clean up their dogs' poop! Unattended dogs must be crated..Septic system! Only flush toilet paper.,Before checking out, please wash dishes. If you used the crab trap, please leave it on the dock..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.Additional event fee. Contact host for pricing..

Delightful waterfront vacation cottage. Pet friendly with fee. Sleeps 4 people and has a pack and play and high chair for a young child. Enjoy sunset views from the screened in porch and sunrises from the shared dock. Enjoy fishing, crabbing, and boating off of the property's shared fishing pier. Bring your own boat and park it out back at the shared dock. Purchased and updated in 2022. New furniture and bedding. Full amenities and fiber optic WiFi included in price. First floor of the house is the main living space which includes kitchen, dining area, living room, and a full bathroom with large walk-in shower. Gas grill available. Two adirondack chairs and charming bistro adorn the front porch. Bring your own boat, kayak, or wave-runner and tie up at the shared dock. Smart TV and DVD player are available for your viewing pleasure. Excellent opportunity for duck, goose, turkey, and sika deer (the smallest member of the elk family) hunting in Dorchester County (off property). We are located 10 minutes from the Blackwater National Wildlife Refuge. Please visit their website for hunting information. Our home is on the Honga River at the mouth the Chesapeake Bay. We are located on historic Upper Hoopers Island in Fishing Creek, MD. Pet friendly with pet fee. Unattended dogs must be crated when left alone. One large dog crate is included with the pet fee of $150 per stay. Please note, all dogs must be leashed when outside and they must stay on the property. Please note: The pet fee is PER PET. If you have two pets staying please let us know, and we will send a payment request for the second pet. Sorry, no smoking and you must be 25 years or older to rent this home.About pets:Pets allowed: dogs less than 50 lbs per pet (limit 2 pets total).About checkOut:Check out before 10:30 AM.About children:Children allowed: ages 0-17.About customRules:Owners must clean up their dogs' poop! Unattended dogs must be crated..Before checking out: 1. Wash dishes. 2. Please leave crab trap on the dock.,Septic system! Only flush toilet paper..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

Water view cozy remolded 118 year old home with a large, screened porch, gas log fireplace for winter stays, Blackwater Wildlife Refuge park nearby. Harriet Tubman Underground Railroad Museum. Free boat ramps at upper and lower island.About pets:Pets allowed: dogs less than 50 lbs per pet (limit 2 pets total).About checkOut:Check out before 12:00 PM.About children:Children allowed: ages 0-17.About checkIn:Check in after 11:00 AM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:Events allowed: family gatherings.Maximum event attendees: 8.

5+ acres, private pool, wide water, sandy beach, dock, boats, firepit & bikes Beautiful, newer custom 3-story home w/ wrap-around porches, 7 bedrooms & 5 baths & can accommodate up to 18 guests*. The 3rd floor is a haven for kids with a game room, two bdrms & a bath.Close to town, yet your own, secluded compound for extended family & friends.Gorgeous upscale neighborhood just 10 mins from Cambridge & Easton MD.A perfect retreat with massive entertaining areas.Family retreat perfection!"Saddle Beach", our fabulous, newer waterfront owner’s home is on 500 feet of private Chesapeake waterfront.It’s a grand vacation home with idyllic wrap around porches, your own private pool, dock, beach and pond. It's just 10 minutes from the renowned Hyatt Chesapeake Bay Spa and Resort, countless restaurants and quaint shops and, if it suits you, less than an hour from Ocean beaches. 'Saddle Beach' is on Dorchester County's exclusive McKeil Point neighborhood on the Little Choptank river, just off the Chesapeake Bay. The property has a mile-wide view and a 200' dock. The home is exceptionally furnished, with 4200sf of living area with another 1200sf of open and screened porches. 6 bedrooms and a sleeper den with sofa-bed and bath with walk-in shower. A large eat-in kitchen, two full size refrigerators, massive open entertaining area with 3 living rooms and a study. The 3rd floor is designed for kids with a recreation area, wide dormers, a full bath, and two bedrooms with 8 beds. An in-ground pool is off the porch & the home has beautiful millwork and exotic, reclaimed hand-cut wide-plank walnut floors. A lovely tidal pond is just off the living room.The Property: The perfect Family Retreat!Gorgeous wrap around porches include a screened outdoor eating area overlooking the pool. The compound was designed as an owners' dream, and includes a pool, ample decks for entertainment, a gorgeous beach, private natural setting, and walkways to the adjacent marsh. Towering pines, aromatic cedars, and marsh grasses dot the landscape. There is a rustic tidal pond next to the house providing rest for swans, ducks, & geese. The dock stretches 200 feet into the river with 3 berths for boats and seating for your enjoyment. Wildlife abounds; you may find yourself crabbing and fishing all day. Yes, our crabbing is excellent!The unique, secluded neighborhood consists of a single, mile-long road on its own peninsula with Dorchester's finest homes, stretching far into the Little Choptank River. The quiet street invites scenic bike rides or long walks to watch the sunsets.Mosquito Control measures provided for your comfort,The Area: A local country store, restaurant and boat ramp is 5 minutes away and the Chesapeake Bay, with its fishing, cruising, and endless sunsets, is out your window.The town of Cambridge is ten minutes away, with a pre-civil war, Victorian inspired downtown, and countless restaurants and shops. It’s not much further to visit the Maryland towns of Oxford, Easton, or Saint Michael's to walk the streets, take in the restaurants, or visit art shops and galleries. On the property, relax! Go no further than the shoreline to find great swimming, crabbing, fishing, sunning, or boating. The sandy beaches are a luxury all year long, and the heated pool provides for a warm swim during those colder days and nights in May and September/October**. Endless porches and a stone fire pit is the centerpiece for many nighttime get-togethers.In the neighborhood, bike or walk down the neighborhood's 'private' peninsula and enjoy marvelous sunrises and sunsets among the finest of Maryland's summer and weekend retreats.Sports both on water and land.Fishing Creek provides wide, almost endless passages for quiet kayaking, fishing, or pleasure boating. The waterskiing is excellent. The other side of the peninsula faces the Chesapeake Bay and Madison Bay and provides an open door to sailing or to the many top fishing spots. In town, there are boats to rent for a sail on the Choptank. Bike tours from all over the world flock to the eastern shore because it is flat, the roads are good quality, the traffic is light, and the sights are endless. Blackwater Refuge offers world-class nature views, and you can also bike in Easton, Saint Michaels, and Oxford, and there are many bike tour maps available to the visitor.There are two fantastic golf links nearby. The River Marsh course at the Hyatt Chesapeake is renowned. Hog Neck (18 miles) has a four-star rating from Golf Magazine. There are three additional courses between starting just nine miles away."Hot Tub" as listed is a Jetted Jacuzzi tub in the Master bath. We have a Steam Shower as well.* - Additional charge for groups larger than 14** - Pool heated *only* in May and between mid-September and closing for a fee** - Pets: One (1) dog (only) is permitted with a required pet fee and refundable pet deposit during any stay. All pet signs including hair waste etc. must be removed by the guest.** - Outdoor (only) security cameras face the driveway and waterAbout pets:Pets allowed: dogs less than 50 lbs per pet (limit one pet total).Must ask at booking. A fee plus deposit required..About checkOut:Check out before 10:30 AM.About children:Children allowed: ages 0-17.Love kids! House designed with a kids' floor!.About customRules:Signed rental agreement required. See full house rules thanks..Security: WiFi door lock for convenience for you & your guests. Exterior security cameras onsite; facing water and away from house,Pets: 1 dog. Not allowed on furniture or off-leash. Fully-refundable deposit req'd + $150 pet fee. Required to manage turnaround for the next guest.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.We take this seriously, thanks.About minBookingAge:Minimum age to rent: 30.About events:No events allowed.Only small, indoor parties.

3 Bedroom, 2 bath house on the Bay side of Hoopers Island on the Chesapeake Bay. Large yard and screened in deck on the Bay to catch our beautiful sunsets! Full kitchen, fireplace, washer/dryer. Master bedroom and Bedroom 2 can be configured with one King bed, or 2-twin beds. Close proximity to Riverside Lodge where we offer fishing and crabbing charters and where you can utilize kayaks and boat docking, Free county boat ramp within 1/2 mi; slips for larger boats can be arranged.About pets:Pets allowed: dogs and cats (limit 2 total).$75 pet fee per pet.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.

This charming century old Eastern Shore farmhouse is situated on Brooks Creek in the heart of the Chesapeake Bay. It is rendered as a "telescope" house that has 5 bedrooms, sleeps 18 comfortably with 3.5 baths along with an outdoor shower. Every room has waterfront views. We offer a game room, children's playroom, ping pong table, kayaks, canoe and enjoy fishing and crabbing off the pier. You may also "chill" around the in-ground swimming pool.You can choose to eat your Maryland steamed crabs on the massive stone patio sitting around the fire pit or inside the screened in porch while enjoying gorgeous sunsets.Excursions include strolling the nearby towns of Cambridge, Easton and St. Michaels and exploring the Black Water Refuge to view the outdoor life in their natural habitat.Experience the true quiet and serenity of this Eastern Shore destination at Sunset Bay.Would prefer multiple weeks and seasonal rentals, rates negotiated.Weddings can be booked as well.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:Events allowed: weddings.Maximum event attendees: 1,Up to 200.