Pet-friendly vacation rentals in Rock Hall

4.97 out of 5 average rating, 472 reviews

A spacious living area features large windows that allow natural light to fill the space, showcasing views of the surrounding greenery. Comfortable seating is arranged around a low table, with a television mounted on the wall, and decorative shelves filled with various items.

Cottage in Annapolis

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.

The single-story ranch home is set on a spacious lot adorned with a mix of grass and fallen leaves. Blue shutters frame the windows, and a welcoming front porch is furnished with several chairs. A two-car garage is visible to the left.

4.98 out of 5 average rating, 111 reviews

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)

4.95 out of 5 average rating, 314 reviews

A serene waterfront scene is captured at dusk, featuring a dock illuminated by soft lighting. A swing sits beneath a large tree, providing a peaceful spot to relax while overlooking the calm water.

Home in Grasonville

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.

4.97 out of 5 average rating, 133 reviews

The outdoor area features a spacious concrete saltwater pool surrounded by lounge chairs and tables. The house showcases a light-colored façade with multiple entrances, large windows, and umbrellas providing shade, all set against a backdrop of lush greenery.

Home in Stevensville

Beautiful Kent Island Getaway with Pool

PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a spacious bonus room for all your family entertaining. You will love the open floor plan with cathedral ceilings with a beautiful stone fireplace. The Master bedroom with jacuzzi tub. Surround sound music system. Desk with computer. Separate pool house with kitchen and bathroom great for entertaining. Outside features includes a Concrete saltwater pool (not heated) with huge fenced in backyard and KOI pond. Porches back and front.

Bungalow in Sparrows Point

The living area features a spacious layout with large windows allowing natural light to fill the room. Two patterned armchairs are positioned around a central console with a television. A light fixture hangs from the ceiling, complementing the hardwood flooring and neutral wall colors.

Boatyard Bungalow, 6 beds; 2 Full Baths-Waterfront

The original schoolhouse for Edgemere that was built in 1898 and converted to a residential home/marina in the 1950s. With over 2,200 sq. ft., it's a perfect environment for wedding venue preparations, family and friend reunions. Please don't exceed maximum number of twelve (12) guests at any one time in the house, during the day; or ten (10) staying the night in the house. Additional Pirate & Mermaid Bath House on property should extra toilets and showers be needed from April-November only.

4.95 out of 5 average rating, 169 reviews

Guest suite in Chestertown

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. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate a portion of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

4.99 out of 5 average rating, 256 reviews

4.99 out of 5 average rating, 142 reviews

A Bullfrog hot tub is situated under a wooden gazebo, with water glistening in sunlight. A plush robe is draped over the edge alongside a straw hat and a rolled towel. A grassy area and wooden privacy fence complete the serene outdoor setting.

Home in Cape St. Claire

Beach Access, Hot Tub, Pet Friendly, Fully Fenced

A serene escape awaits you at our cozy hot tub 4-bedroom retreat, minutes away from Historic Downtown Annapolis. As the sun sets, the deck comes alive under the soft glow of string lights beckoning you to unwind in our 8-person Bullfrog hot tub or outdoor firepit where your worries will melt away! Indulge in the culinary delights of fresh local seafood and world-renowned crabcakes just moments away. Truly indulge in our paradise getaway and experience everything Annapolis has to offer!

5.0 out of 5 average rating, 217 reviews

Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

Autumn at The Cottage at Silver Water is peaceful, cozy, and a little magical. Crisp days invite you to kayak, explore the shoreline, or enjoy the changing colors. Evenings bring golden skies, spectacular sunsets, cool breezes, and fires by the water. Inside, the cottage is warm and inviting, with luxurious bedding, curated art, and thoughtful amenities for a relaxed, memorable stay. Come experience autumn at Silver Water—and see why every guest has given their stay five stars.

Superhost

A wooden dock extends into a calm body of water, reflecting the blue sky and surrounding trees. The serene scene is framed by lush green foliage, enhancing the tranquil atmosphere of the creek.

Cabin in Worton

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.

4.89 out of 5 average rating, 120 reviews

4.96 out of 5 average rating, 105 reviews

A cozy outdoor seating area is set up on a grassy lawn, facing the water. Adirondack chairs and a low sofa surround a fire pit, creating a welcoming space for relaxation. A private dock extends into the Chester River, offering scenic views of the water.

Home in Chestertown

River front cottage with private dock & water fun

Private cottage on the banks of the Chester River. Sleeps 8-14. Private dock with plenty of water activities. This property offers relaxation and serenity as soon as you pull in! Located right on the water with spectacular views of the Chester River, the house is renovated in a cozy, casual farmhouse style. While you will love the house you will spend your days outside enjoying life on the river thanks to your private access to the water and lots of water fun!

Guesthouse in Stevensville

The image captures a serene evening scene by the pool with a view of the setting sun over the water. Sunlight filters through trees, creating a warm glow. Poolside lounge chairs are visible, along with a clear pool reflecting the colorful sky.

Waterfront-View of Bay from your Bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

4.99 out of 5 average rating, 371 reviews

4.97 out of 5 average rating, 103 reviews

Home in Chestertown

High Tide & Hound

Welcome to your perfect getaway in the heart of historic Chestertown! This charming home is just two minutes from the iconic High Street Wharf, where you can enjoy scenic views, fishing, and waterfront strolls. We’re proudly family friendly , pet friendly, so bring your furry friends along for the adventure. Whether you’re here for the festivals, the river, or just to relax this is your ideal place. Comfortable , private, and conveniently located.

Popular amenities for Rock Hall pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

Superhost

The exterior of the waterfront home showcases a spacious wooden deck with a ramp leading to double glass doors. The structure is framed by large windows, and the surrounding greenery adds a natural touch to the entryway.

Home in Essex

Waterfront getaway Essex, MD

4.78 out of 5 average rating, 100 reviews

4.96 out of 5 average rating, 268 reviews

A serene outdoor patio area features manicured hedges and a stone path. A seating arrangement is visible, surrounded by greenery. A colorful flag and artwork hang on the fence, while flowering trees add a natural touch to the space, providing a cozy atmosphere.

Home in Annapolis

Historic Downtown in-law suite

4.95 out of 5 average rating, 199 reviews

A cozy living area features a gray sectional sofa with a yellow throw draped over it. Wood accents and a patterned area rug complement the warm hardwood floors. An adjacent dining space is visible, showcasing a rustic brick wall and a dining table with elegant lighting.

Home in Fells Point

Charming 4 bedroom home just steps to the water!

4.98 out of 5 average rating, 129 reviews

A large flat-screen television is mounted on a brick wall above a stone fireplace. The screen displays a colorful scene of hot air balloons against a blue sky. Surrounding the fireplace are potted plants and shelves filled with DVDs, adding to the cozy atmosphere.

Home in Glen Burnie

Glen Burnie Escape

4.98 out of 5 average rating, 121 reviews

A modern kitchen features dark wood cabinetry and light-colored countertops. Stainless steel appliances, including a stove and microwave, are visible. An island with two high chairs is illuminated by a stylish light fixture, while sliding glass doors provide access to the outdoor area.

Home in Joppatowne

Two bedroom small ranch with beautiful forest view

4.96 out of 5 average rating, 138 reviews

The lighthouse replica is shown from an elevated angle, surrounded by trees and located beside the water. A wrap-around deck is visible, along with the charming architectural details of the structure and the contrasting red roof.

Home in North East

Red Point Lighthouse

4.97 out of 5 average rating, 145 reviews

A single-story home is set amidst a lush, green lawn, surrounded by trees and natural vegetation. The exterior features a light-colored facade with a welcoming front entry and flower beds to the sides, enhancing the serene atmosphere of the wooded location.

Home in Greensboro

Cozy 2 bedroom home on wooded private lane

4.96 out of 5 average rating, 267 reviews

Sailboats are moored in a serene marina, with soft waves reflecting the sunlight. The docks are lined with wooden posts, guiding the view to a lush green shoreline in the background. A peaceful atmosphere is created by the gentle ripples and warm evening light.

Home in Edgewater

Annapolis Area Waterside Retreat

Pet-friendly home rentals with a pool

4.98 out of 5 average rating, 204 reviews

A modern guesthouse features a peaked roof and large windows, set against a vibrant sunset sky. The surrounding landscape includes wild grasses and a paved pathway, suggesting a serene connection to nature.

Cottage in St. Michaels

La Casita on Harris Creek, St. Michaels

Farm stay in Cockeysville

The Master's Suite · King Suite, Hunt Valley

4.95 out of 5 average rating, 147 reviews

4.94 out of 5 average rating, 147 reviews

Guest suite in Annapolis

Annapolis Garden Suite

Guesthouse in Stevensville

The side view of a historic brick house is shown, featuring a gabled roof with multiple chimneys. The whitewashed brick exterior contrasts with the green trim around the windows and door. The well-maintained lawn surrounds the structure, complemented by mature trees in the background.

Circa 1700 Chesapeake Colonial Home

4.92 out of 5 average rating, 197 reviews

4.99 out of 5 average rating, 255 reviews

A spacious living area features two comfortable sofas, one draped with a soft blanket. Natural light streams through large windows, highlighting the wooden flooring. A small wooden table is visible in the background, and a decorative piece hangs above the mantel.

Home in Tracys Landing

The Little Gypsy BoHome

4.97 out of 5 average rating, 117 reviews

A charming blue cottage is depicted with a gabled roof and white columns framing the entrance. Lush green bushes line the pathway, providing an inviting approach. Clear blue skies and tall trees are visible in the background, enhancing the peaceful setting.

Home in St. Michaels

SM's Premier Rental Heated Pool (closes 10/27)

4.9 out of 5 average rating, 119 reviews

A private swimming pool is surrounded by lounge chairs and landscaped greenery. The clear blue water reflects sunlight, and a white fence offers privacy. The pool area includes a concrete deck, creating an inviting space for relaxation and enjoyment.

Home in Chesapeake City

The Mint Cottage in Chesapeake City

4.87 out of 5 average rating, 121 reviews

A cozy sleeping area features a spacious bed with cotton bedding and decorative pillows. Natural light enters through a window, highlighting the minimalist design. An ottoman rests at the foot of the bed, with a bedside table and a storage unit visible in the space.

Tiny home in Glen Burnie

Secluded Tiny House With your own Private Pool

Private, pet-friendly home rentals

4.96 out of 5 average rating, 304 reviews

A cozy living area features a brown leather sofa next to a white coffee table. A decorative rug with star patterns lies on the floor. A green potted plant adds a natural touch, complemented by a television on a media unit. Light enters from the window.

Apartment in Chester

Cozy Waterfront Apartment Chester, MD

4.91 out of 5 average rating, 92 reviews

A blue two-story home is featured, with a welcoming front porch surrounded by greenery and blooming flowers. The driveway leads to a pair of blue garage doors. Sunlight highlights the textured roof and soft colors of the exterior, set against a backdrop of tall trees.

Townhouse in Rock Hall

Walking Distance to Marinas & Main St!

4.95 out of 5 average rating, 37 reviews

Chesapeake Bay Retreat W/Breathtaking Views

A spacious bedroom is illuminated by natural light from a window with light-colored blinds. A large bed with a dark headboard is centered in the room, accompanied by two pillows. Nearby, a floor lamp and a decorative curtain add soft accents to the neutral-toned walls.

4.91 out of 5 average rating, 56 reviews

The Blue Jimmy

A spacious outdoor deck is shown, featuring a wooden dining table and four Adirondack chairs. The serene waterfront view overlooks the Chesapeake Bay, with lush greenery extending towards the horizon. A BBQ grill is positioned nearby, complementing the relaxed atmosphere.

4.86 out of 5 average rating, 21 reviews

Relaxation by the Bay!

Superhost

A charming bayside cottage is shown with a light-colored exterior and a star accent. Several bicycles are lined up on the grass, ready for exploration. A large tree is present nearby, enhancing the outdoor space, while a pathway leads to the entrance.

4.89 out of 5 average rating, 45 reviews

Bayside cottage steps from the harbor

The image captures a serene sunset over calm waters, with soft hues of orange and pink reflecting on the surface. Silhouetted figures can be seen sitting on a rocky outcrop, while the shoreline is framed by gentle waves rolling onto the beach.

5.0 out of 5 average rating, 12 reviews

Bayside Breeze