Family-friendly holiday rentals in Rock Hall

The Fisherman's Lodge at the 1858 Monkton Hotel

Love the outdoors? Love to fish, hike, bike, kayak? All of the above? The Monkton Hotel is a registered landmark that sits on the NCR trail, which runs along the Gunpowder River, home for some of the best trout fly fishing in the country. This fully renovated apartment, themed the "Fisherman's Lodge", is on the second floor and has the latest amenities. Nothing in the area matches the charm, convenience and history. An electric bike store, tube rental and great cafe are all in the same building.

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

3 bedroom home with pool and game room

Forget your worries in this spacious and serene space. 5 miles outside of the town of Centreville. 15 miles to Chestertown. Custom built home sits on 4 acres in the middle of a 200 acre farm. First floor master bedroom and master bath. Living room, half bath, kitchen and dining area. Large back porch facing pool. Second story has full bathroom and two bedrooms. Each bedroom has an extra room inside. Also upstairs is a game room with a pool table. 1-king bed 1-full bed 1- queen bed 1- twin

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away.

In Town, Rock Hall, Fenced-In Yard, 1 blk to Water

In Town, Amazing Location on Walnut Street, Rock Hall Clean, Quiet & Beautiful Rancher, Large Fenced in Yard! 1 Bedroom (Queen) 1 Bedroom (Queen) Sun Room (Twin) Daybed Only 1 block from the Chesapeake Bay. Perfect for your weekend getaway or longer stay. Tastefully updated 2-bedroom, 1 bath ranch home. Located JUST one block from marinas, restaurants, Public Landing and Rock Hall Harbor. Three blocks from Ferry Park Beach. A beautiful and safe stroll or bike ride to Main Street (1.5 mile)

The Blissful Retreat @theblissfulretreat

Serene space nestled in the woods; with water views. You have your own private cottage on our 10 acre property to watch the sunsets and enjoy the nature all around. You'll spot deer, bunnies, frogs, turtles, birds and so much more from the lovely front porch! As a Nurse I can guarantee our space has always been cleaned and sanitized to the highest standards, regular use of a ozone light. Check us out on insta for more blissfulness - theblissfulretreat and FB- theblissfulretreatrockhall

Cozy 3-bedroom home w/ Hot tub & firepit

This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

Harbor View Haven | Waterfront w/ Hot Tub + Dock!

BNB Breeze Presents Harbor View Haven This exquisite waterfront property offers a captivating retreat to relax and recharge with stunning views and an array of desirable features! With a serene waterfront location, this idyllic home provides a picturesque setting for unplugging and experiencing outdoor enjoyment. Your extensive amenity list includes: 💦 Hot Tub 🔥 Outdoor Gas Fireplace ☕️ Jura Espresso Machine 🚤 Private Dock + Kayaks 🚴 Bikes for Exploring 🏓 Ping-Pong Table 🌅 Bay Views

Ft. Smallwood Overlook. Waterfront with Kayaks!

Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

Waterfront historic district 1BR Apartment

Take it easy at this unique and peaceful riverfront getaway. Third floor, one bedroom apartment with its own private rooftop deck and beautiful views of the Chester River. Located at the end of a street on the water, but still in the historic district offering convenience and privacy. A short stroll to everything Chestertown has to offer. Off street parking. Kayaks or canoe available with notice or bring your own. Enjoy coffee and sunrise from deck or Adirondacks. NO CLEANING FEE!

Cozy 1920's Bungalow Near Water/Local Attractions

Updated 1920's bungalow near all Rock Hall has to offer. Blocks away from the Bay, marinas and center of town. Coffee shop, grocery and other shops 2 blocks away. Walk to several restaurants. Cozy and very comfortable. Quiet street, and peaceful at night. This house is an ideal Rock Hall location. This home is well stocked, so most condiments, coffee, tea, sodas and water are included. There are also many toiletry and first aid products. No need to bring soap or shampoo.