
Family-friendly holiday rentals in Rock Hall
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Rock Hall
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Cottage with Modern Updates - Walk to Waterfront!
Historic cottage, fully renovated and located in the heart of Rock Hall. Features open living area, modern kitchen, sunny front porch, big fenced backyard, and patio with fire pit and picnic table. Enjoy everything the town has to offer - fishing, boating, festivals, dock bars, restaurants, shopping, & more. Walking distance to Main Street, marina, Harbor Shack, Waterman's Crab House, The Mainstay. A short drive to Eastern Neck National Wildlife Refuge, Washington College, historic Chestertown.

Cheerful & Spacious Shore Life Beauty!
Welcome to our charming yet peaceful abode & island oasis where sailing, marine life, & bay exploration exceed the standard! This exceptional home is conveniently located to a variety of high quality restaurants, parks, outdoor activities, spas, beaches, wedding venues, & other entertainment including live music, hunting, & antiquing while also being 20-minutes from Annapolis & 1-hour from Baltimore City & DC. Let this be your definitive choice for a magical destination you'll forever remember.

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

Beautiful Waterfront Chestertown Getaway
Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running options. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

Inspiration Guest Suite @ Cinnamon By The Bay
Inspiration is a cozy, bright studio with a full-size bed, seating area, kitchenette, and workspace. It is located upstairs in the Cinnamon By The Bay Inn. Main Street shopping, Java Rock coffee shop, and The Mainstay music venue are right outside the front entrance. Ferry Beach, Eastern Neck Wildlife Refuge, museums, charter fishing, kayaking, and marinas are a short walk or drive. Enjoy stunning sunsets and lively conversations on the community deck. Suite is limited to 2 guests.

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.

Welcome Aboard!
Unique accommodations on a comfortably equipped 43 foot Hatteras yacht, just a 5 minute drive to historic downtown Annapolis and the Naval Academy. 15 minute drive to the Navy Stadium, 15 minutes drive to Rt 50. THIS LISTING IS FOR ACCOMODATIONS ONLY; BOAT MAY NOT BE DRIVEN! Forward cabin has bunk beds. Aft cabin has a queen bed. Fully equipped galley (kitchen) with 2-burner cook top, microwave/oven, fridge, toaster oven and Keurig. Boat has WIFI, heat, AC and hot water!

Cabin on the Creek ~ Kayaks and Fire Pit
Unwind in our cabin tucked away on a private lane mins from Chestertown. We are situated on 6.5 wooded acres, perched up on 100’ bluff overlooking Churn Creek, a tributary off the Chesapeake Bay. Idyllic water views framed by a canopy of oak trees. Enjoy nature as you relax outside by the fire pit or stroll down to the ‘point’ to take in wildlife, or take a kayak out to explore the creek and water fowl. Deer come up through the woods and are often spotted on the property.

Sea Dreamer
Tranquil TIDAL, riverfront, split-level home. Rent the spacious lower level with 2 bedrooms, full custom kitchen, large living room (TVs, sleeper sofas, massage chair), dining/office space, and full bath with luxury shower. Includes soaps, towels, hairdryer. Kitchen equipped for cooking, includes full fridge. Patio with grill/fire-pit, lounging and kayaks. Convenient: 25 min to BWI, 45min to Annapolis, 60min to DC. Ideal for relaxing and exploring!

Beautiful Baycation Stay
This Baycation stay is perfect for friends and family looking for a waterfront stay just 25 minutes from BWI Airport, Downtown Baltimore and Downtown Annapolis. Offering amenities like kayaks, crabbing, paddle boards, firepit, WiFi with all streaming services and toiletries to make sure you have everything in case you forget. There is a home office space set up! Kitchen stocked for home cooking, relaxing, and a guest book for eating out.
Popular amenities for Rock Hall family-friendly rentals
Family-friendly home rentals with a hot tub

Kone Oasis- hot tub, pool, theater/game rm.

Beautiful, quiet waterfront house. Lots of room!

Waterfront Cottage@ChesapeakeParadise Hot Tub/Dogs

Wigwam Lodge ~ HotTub ~ MasterSuite~Woodland Views

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

Luxe Winter Retreat- 5 Star

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

Affordable, Cozy Retreat 4 Miles from Annapolis
Family- and pet-friendly home rentals

Nautical Luxe Retreat 6 Guests • 3 BDR • 2 Baths

Glen Burnie Escape

Patterson Park Penthouse with Rooftop Deck!

Historic Downtown in-law suite

Annapolis Garden Suite

Watch Deer from a Farm Cottage

Waterfront-View of Bay from your Bed-Steamy Sauna

Canary Pointe-A popular getaway for 2!
Family-friendly home rentals with a pool

Bay Breeze Retreat

Rollingside: Two-Room Guest Suite

The Mint Cottage in Chesapeake City

Luxury 4 Bedroom - Pool/HotTub/Fire Pit

A home away from home

1st Floor Condo in Annapolis

Coastal Waterfront 1 Bedroom Cottage

The Little Gypsy BoHome
When is the best time to visit Rock Hall?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $280 AUD | $280 AUD | $280 AUD | $280 AUD | $350 AUD | $336 AUD | $353 AUD | $371 AUD | $322 AUD | $316 AUD | $322 AUD | $306 AUD |
| Avg. temp | 1°C | 3°C | 7°C | 13°C | 18°C | 23°C | 26°C | 25°C | 21°C | 14°C | 8°C | 4°C |
Quick stats about holiday rentals that are family-friendly in Rock Hall

Total holiday rentals
Explore 30 holiday rentals in Rock Hall

Nightly prices starting at
Rock Hall holiday rentals start at $169 AUD per night before taxes and fees

Verified guest reviews
Over 1,230 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Rock Hall holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Rock Hall rentals

5 Average rating
Rock Hall stays are highly rated by guests—averaging 5 out of 5!
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- Family-friendly rentals Kent County
- Family-friendly rentals Maryland
- Family-friendly rentals United States
- Georgetown University
- Walter E Washington Convention Center
- National Mall
- M&T Bank Stadium
- Nationals Park
- The White House
- District Wharf
- National Museum of Natural History
- Capital One Arena
- Baltimore Convention Center
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- Arlington National Cemetery
- Howard University
- Betterton Beach
- Sandy Point State Park
- Georgetown Waterfront Park
- Washington Monument
- Patterson Park
- National Harbor
- Smithsonian American Art Museum
- Six Flags America
- The Pentagon
- Johns Hopkins University




