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Pet-friendly holiday rentals in Stevensville

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Quick stats about holiday rentals that are pet-friendly in Stevensville

  • Nightly prices starting at

    Stevensville holiday rentals start at €104 per night before taxes and fees

  • Verified guest reviews

    Over 910 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Stevensville rentals

  • 4.9 Average rating

    Stevensville stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated pet-friendly home rentals in Stevensville

Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
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.

4.97 out of 5 average rating, 470 reviews
Guest favourite
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.

4.95 out of 5 average rating, 310 reviews
Top guest favourite
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

This Rhode River home is your perfect getaway to the Annapolis area - whether you’re looking to get away to a unique home overlooking incredible sunsets, a fun weekend with friends along the water, a family trip to the Chesapeake, or a private work retreat away from the bustle of the city, this home has it all. The house is a short drive from DC or Baltimore and unlike any Airbnb this side of the Chesapeake - it is on a 3 acre marina just minutes from Annapolis but private and away from it all!

4.95 out of 5 average rating, 262 reviews
Top guest favourite
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.
Home in Rock Hall

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)

4.98 out of 5 average rating, 110 reviews
Top guest favourite
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.

4.97 out of 5 average rating, 131 reviews
Top guest favourite
Home in Deale

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier

Waterfront Enjoyment: A 3-bedroom, 2-bathroom home! This charming one-story house in Churchton, Maryland, is perfect for families. It includes 8 acres of land and over 700 feet of waterfront on Broadwater Creek, ideal for fishing, crabbing, paddleboarding, and kayaking. Discover the charming town of Deale, Maryland, with its easy entry to the Chesapeake Bay. Relax and enjoy this property! There's a brand-new 140-foot dock with beautiful views of the bay, ideal for catching crabs and fish!

4.98 out of 5 average rating, 151 reviews
Guest favourite
A spacious living area is highlighted by large windows allowing natural light. Modern furniture includes a sectional sofa and accent chairs, complemented by a sleek coffee table. A large television is mounted on the wall, while indoor greenery adds a touch of nature.
Home in Edgewater

Luxury Modern Home on Water+Hotub- Annapolis 25min

Waterside mid-century modern home, perfectly appointed. Join with colleagues, family, and friends. Paddleboard, roast marshmallows, watch fireworks, take a hot tub or team building. Our "Flight Deck" is perfect for meetings and retreats. Breathtaking, peaceful grounds with an abundance of space. Approximately 2800 SF sits on a 3/4 acre property - perfect for lawn games and zip lining. 20x20 furnished deck + dock Mayo Beach and Beverly Triton 1 mile away. Within an hour of the DMV

4.99 out of 5 average rating, 145 reviews
Top guest favourite
Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

Summer at The Cottage at Silver Water is effortless and indulgent. A sweeping waterfront lawn leads to a private shoreline for swimming, kayaking, and long days in the sun. Evenings bring golden skies, spectacular sunsets, and fires by the water’s edge. Inside, the cottage is beautifully designed with luxurious bedding, curated art, and thoughtful amenities that make every stay relaxed, refined, and unforgettable. See why all our guests only have a 5-Star experience.

5.0 out of 5 average rating, 214 reviews
Top guest favourite
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.
Guest house in Stevensville

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, 363 reviews
Top guest favourite
Home in Chestertown

The Garden Estate: Historic Town Center Home

Step back in time without sacrificing luxury. Nestled in Chestertown’s historic district, this rebuilt 19th-century estate blends grand character with modern comfort, just 4 blocks from Washington College. Sprawling across a rare town-center acre, the sanctuary features magnificent gardens, a fenced yard, a fire pit, and a Weber grill for evenings under the stars. Inside, find a flawless layout designed for privacy, rest, and premium comfort.

5.0 out of 5 average rating, 252 reviews
Guest favourite
Guest suite in Arnold

Captains Quarters Oasis Near Annapolis, Sleeps 4

This updated suite is designed for comfort & convenience. Enjoy a king bed and a (queen bed) LoveSac sofa perfect for 2-4 guests. The suite includes a private en-suite bathroom, high-speed internet, a fully furnished kitchen, and a coffee bar to make you feel right at home. Located just 4 miles from Annapolis, you're close to all the best spots. Whether you’re here to relax or explore, this suite has everything you need!

4.95 out of 5 average rating, 214 reviews
Top guest favourite
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

This special place is close to everything. One block to the Naval Academy and one block to all the historic and downtown attractions. This in-law suite has a queen bed, full bath, sauna, kitchenette, seating area, and desk/dining table. Welcoming separate, quiet entrance with access to a lovely patio with seating and firepit. Twin bed can be set up and made up at guest request.

4.96 out of 5 average rating, 260 reviews

Popular amenities for Stevensville pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Guest favourite
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

4.96 out of 5 average rating, 105 reviews
Top guest favourite
The exterior of a two-story home is displayed, featuring a light-colored façade, white porch railings, and a chimney. A neatly manicured lawn surrounds the house, complemented by tall trees in the background and a clear blue sky above.
Home in West River

Cozy waterview home in West River!

4.97 out of 5 average rating, 168 reviews
Guest favourite
A bright living room features a dark sofa adorned with decorative pillows, paired with a wooden coffee table on a patterned rug. A decorative wall with framed pictures adds character, while natural light enters through the large windows covered by light curtains.
Home in Edgewater

Relaxing Turkey Point Retreat-Steps to the marina!

4.94 out of 5 average rating, 125 reviews
Top guest favourite
The living room features a chandelier, a decorative mirror above the fireplace, and a cozy seating area with two armchairs and a chaise lounge. A colorful area rug covers the floor, while a small table and lamp provide additional lighting.
Home in St. Michaels

Historic Berkeley Hall in the heart of town

4.96 out of 5 average rating, 217 reviews
Guest favourite
A shaded seating area is arranged under a gazebo, featuring a woven outdoor sofa and chairs in warm orange cushions. A central fire pit table complements the setting, surrounded by a patterned outdoor rug on a paved surface, with a fenced backyard visible in the background.
Home in Annapolis

Nautical Luxe Retreat 6 Guests • 3 BDR • 2 Baths

4.96 out of 5 average rating, 150 reviews
Top guest favourite
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!

4.95 out of 5 average rating, 197 reviews
Top guest favourite
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, 127 reviews
Top guest favourite
Home in Stevensville

Away at the Bay: New Home on the Chesapeake Bay!

5.0 out of 5 average rating, 68 reviews

Pet-friendly home rentals with a pool

Top guest favourite
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

4.98 out of 5 average rating, 200 reviews
Guest favourite
Guest suite in Annapolis

Annapolis Garden Suite

4.94 out of 5 average rating, 145 reviews
Top guest favourite
The facade of a historic farmhouse is presented with a covered porch, featuring white railings and columns. An American flag is displayed prominently. Yellow chrysanthemums are placed near the entrance, with a brick pathway leading to the front door, framed by large green shutters.
Farm stay in Chestertown

Piney Grove Farm

4.97 out of 5 average rating, 110 reviews
Top guest favourite
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

4.99 out of 5 average rating, 251 reviews
Superhost
Home in Waldorf

*Brand New | Modern Farmhouse | Lux 4 BR | Near DC

4.83 out of 5 average rating, 119 reviews
Guest favourite
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)

4.97 out of 5 average rating, 116 reviews
Guest favourite
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

4.87 out of 5 average rating, 117 reviews
Top guest favourite
Home in Stevensville

*Waterfront* 5BR w/ Pool + Firepit on Kent Island!

5.0 out of 5 average rating, 21 reviews

Private, pet-friendly home rentals

Top guest favourite
A wooden pier stretches into the water, flanked by lush greenery. A rainbow arcs above the serene landscape, with gentle waves lapping at the edge of the sandy shore. Trees and homes line the distant banks, completing the tranquil waterfront scene.
Place to stay in Glen Burnie

The Crab House - a Private, Waterfront Guest House

4.94 out of 5 average rating, 408 reviews
Top guest favourite
A spiral staircase leads to a lofted sleeping area in a well-lit living space. Warm wood tones are present in the furniture and flooring. A small kitchen area is visible, along with a dining table set for four. Lighting fixtures enhance the modern feel.
Guest house in Annapolis

Garden View, 1 Bedroom and a Loft.

4.99 out of 5 average rating, 165 reviews
Top guest favourite
Two blue Adirondack chairs are positioned on a leaf-covered area, facing a tranquil body of water. Surrounding trees provide a natural frame, with autumn foliage adding warm colors. In the background, a wooden dock and shelter are visible along the water's edge.
Cottage in Annapolis

Waterfront farm retreat for vacation & telework

4.98 out of 5 average rating, 162 reviews
Guest favourite
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.
Bungalow in Sparrows Point

Boatyard Bungalow, 6 beds; 2 Full Baths-Waterfront

4.95 out of 5 average rating, 168 reviews
Guest favourite
The main living area features a comfortable wicker chair with a blue cushion, complemented by a separate white armchair. Natural light pours in through several large windows with blinds, illuminating the light wood flooring and a cozy throw blanket draped over a nearby chair.
Houseboat in Stevensville

Chesapeake Houseboat Getaway

4.87 out of 5 average rating, 77 reviews
Guest favourite
A charming bayfront home is nestled in a landscaped yard. The exterior features blue siding, a welcoming front porch, and well-maintained gardens. An American flag is displayed prominently, while a sidewalk leads up to the entrance, surrounded by lush greenery and colorful flower beds.
Home in Stevensville

Bay Views Just Minutes from Annapolis

4.79 out of 5 average rating, 24 reviews
Guest favourite
A serene outdoor space features six Adirondack chairs facing the sunset over the bay. The horizon is lined with soft clouds, and a picnic table is set in the distance on a grassy area, providing a perfect spot for relaxation.
Home in Stevensville

Beachside Dream

4.89 out of 5 average rating, 89 reviews
Top guest favourite
A charming cottage is set amidst tall trees, featuring a dark exterior complemented by large windows. Soft lighting illuminates the entrance, where two welcoming chairs are placed on the porch, creating an inviting atmosphere for relaxation.
Cottage in Stevensville

Off The Chart Stays

5.0 out of 5 average rating, 37 reviews

Destinations to explore