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Pet-friendly home rentals near Chesapeake Bay

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Top-rated pet-friendly home rentals near Chesapeake Bay

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
The vintage A-frame home is nestled amongst trees, featuring a deck with a canopy in the foreground. A stone path leads to the entrance, where large windows allow for ample natural light. The surrounding landscape is adorned with greenery and decorative plants.
Cabin in Lusby

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

4.92 out of 5 average rating, 267 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
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
Top guest favourite
A comfortable living area is framed by large windows showcasing a vibrant sunset over the water. Soft furnishings include two chairs with decorative pillows and a coffee table. Plants are positioned thoughtfully, enhancing the serene atmosphere.
Home in North Beach

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces

A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l dates**

5.0 out of 5 average rating, 186 reviews
Top guest favourite
Home in Montross

Waterfront, 3 Beaches, Dock + Kayaks, Potomac

Relax - Star Gaze - Kayak/Paddleboard - Hike - Fish - Swim - Beach & more! ☀️ Waterfront w/Dock 👨‍🍳 Gas griddle 🛶 Kayaks/Paddleboard 🔥 Fire pit ⛱️ 3 Community Beaches 🎯 Gameroom 🐶 Dogs OK (Max 2) ⚡️EV Outlet The Riverside Retreat in the Northern Neck of VA is the perfect spot to relax and connect with nature. We offer a peaceful sanctuary that families & small groups love to visit! Book your getaway today or ❤️ us for next time!

4.98 out of 5 average rating, 158 reviews
Top guest favourite
A private dock extends into the calm water, featuring a wooden platform and seating areas. A vibrant blue paddleboard rests on the grassy shoreline, while an in-ground trampoline is seen nearby. The scene is framed by trees under a clear blue sky.
Home in Montross

Waterfront home, private dock

Relax right next to the water in this tranquil Montross getaway. Fish, crab, kayak, paddleboard, or just sit on the swing and watch dolphins, eagles, herons, and stingrays from your private dock. Dine outdoors on the spacious deck, spend some some quality family time with an in-ground trampoline, tree swing, cornhole, bocce ball, spikeball, and a unique custom-built treehouse. Or just stay inside, relax, and enjoy the views, with an indoor electric fireplace and jacuzzi bathtub.

4.97 out of 5 average rating, 108 reviews
Top guest favourite
Home in White Stone

1891 Coastal Charmer: fully renovated farmhouse

Built in 1891, this farmhouse has been totally renovated by a professional designer. The Cottage is filled with coastal colors and accessories so it feels fun and updated but still retains the feeling of walking into a well loved family beach cottage. We are pet friendly as any beach cottage should be and love seeing our guests and their pets enjoying the cottage. Follow the cottage on social media @ BlueOysterCottage for more pictures, design ideas and local places to visit.

4.99 out of 5 average rating, 149 reviews
Top guest favourite
A serene view of a cove with gentle waves lapping against a sandy shore. The calm water reflects the clear blue sky and nearby greenery. Footprints are visible in the sand, leading toward the water's edge.
Cottage in Reedville

"Dragonfly" Waterfront Cottage on Chesapeake Bay

Bayfront beach vacation? Kayak out to dolphins? Breathtaking sunrises & sunsets? Yes, please! Relaxation and fun await at 'Dragonfly', a gorgeous cottage right on the Chesapeake Bay with spectacular views from every room. Nestled on acres and acres of waterfront, this magical property has its own cove for all the swimming, kayaking, SUP boarding and fishing you can manage. If you love nature, bring your water shoes and sense of adventure and we will take care of the rest!

4.91 out of 5 average rating, 233 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
Cottage in Charlestown

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity, a large soaking tub, a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels...

4.96 out of 5 average rating, 295 reviews
Guest favourite
Aerial view of a spacious house surrounded by lush greenery, with a private pier extending into the water. The house features a large, wrap-around porch and several trees dotting the landscape, creating a natural and serene setting by the water.
Home in Scotland

Spacious Gorgeous Waterfront Home with Sunset View

Dreamy weekends on the water, the perfect getaway for the entire family and friends in the southern tip of St Mary’s peninsula. This gorgeous newly remodeled house with 5 Bedroom 3.5 Bath sleeps 10 very comfortably. Wake up with amazing water views and access to the water with your own private pier. Spend your day crabbing, fishing, kayaking, or paddle boarding. Amazing beaches at Point Lookout State Park, just a few minutes away. High speed internet, WiFi, and cable.

4.89 out of 5 average rating, 168 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

Popular amenities for pet-friendly home rentals near Chesapeake Bay

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Top guest favourite
A serene dock extends over calm waters, surrounded by lush greenery. A small orange kayak is secured nearby. In the background, a custom waterfront home is nestled among tall trees, providing a natural and tranquil setting.
Home in Mechanicsville

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

5.0 out of 5 average rating, 105 reviews
Top guest favourite
A sunset view is revealed over the Chesapeake Bay, with warm colors reflecting on the water. Wooden deck furniture is positioned to enjoy the scenery, framed by tall trees along the shoreline. Gentle waves are visible in the foreground, enhancing the serene atmosphere.
Home in Lusby

Waterfront Home on the Chesapeake Bay-Pvt Beach

4.95 out of 5 average rating, 186 reviews
Guest favourite
A serene waterfront view is presented, featuring a wooden dock extending over still water. Lush green grass fills the foreground, while trees line the opposite bank, creating a natural backdrop under a partly cloudy blue sky.
Home in Woolford

Waterfront Getaway with Dock

4.93 out of 5 average rating, 194 reviews
Top guest favourite
Four black Adirondack chairs are positioned in a grassy area facing a tranquil body of water. Lush green reeds frame the water's edge, with a blue sky and scattered clouds above. A small dock is visible in the distance, adding to the serene setting.
Home in Belle Haven

Bay Breeze Home on private waterfront

4.97 out of 5 average rating, 159 reviews
Guest favourite
An aerial view captures a spacious property bordered by water on two sides. A sandy beach area extends along the shoreline, surrounded by trees. The house features a large deck facing the water, and the landscape showcases a mix of greenery and open space.
Home in Heathsville

Private Beach Oasis, Arcade & Theater

4.9 out of 5 average rating, 105 reviews
Top guest favourite
The exterior of a single-story beach house is visible, featuring white siding and landscaped areas. A stone pathway leads to a cozy outdoor seating area with light cushions. Lush greenery and mature trees are present, contributing to a serene atmosphere.
Home in Lusby

Cove Point Cottage with Chesapeake Bay views

4.98 out of 5 average rating, 257 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

4.95 out of 5 average rating, 262 reviews
Guest favourite
An aerial view of a serene waterfront property is depicted, showcasing a spacious home surrounded by trees. A private dock extends into the calm waters, reflecting the trees along the shoreline, highlighting the tranquil setting.
Home in Heathsville

The Hideaway at Mill Creek

4.93 out of 5 average rating, 157 reviews

Pet-friendly home rentals with a pool

Top guest favourite
A serene beach area is depicted at sunset, with soft waves lapping against a sandy shore. The water reflects golden hues, and trees line the distant shoreline, creating a peaceful natural setting.
Barn in Cobbs Creek

The Barn at Pond Point - Riverfront Home

4.95 out of 5 average rating, 145 reviews
Guest favourite
A charming two-story cottage is set on a lush green lawn, with a clear view of the Chesapeake Bay in the background. The cottage features large windows and a sloped roof, with a small wooden addition on one side, surrounded by well-maintained grass.
Tiny home in Cape Charles

The Laughing King Retreat Honeymoon Island Cottage

4.98 out of 5 average rating, 360 reviews
Superhost
Home in Irvington

Magical wooded cottage pool +priv hottub walk2town

4.95 out of 5 average rating, 180 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

4.97 out of 5 average rating, 131 reviews
Guest favourite
A serene view of a private beach meets the calm waters of the bay under a clear blue sky. Gentle waves lap at the sandy shore, with a wooden dock extending into the water. Soft grasses frame the beach area, contributing to the tranquil atmosphere.
Villa in Montross

Beach Retreat

4.85 out of 5 average rating, 127 reviews
Top guest favourite
Home in Irvington

The Rosé Retreat: Pool-Screened Porch-RELAX

4.99 out of 5 average rating, 133 reviews
Top guest favourite
Home in Cobbs Creek

Million $ Views! Pool! Private Hot Tub! EV Charger

4.91 out of 5 average rating, 181 reviews
Top guest favourite
A clear blue pool is framed by wooden decking and lush greenery. The inviting water reflects the sky, and the pool features a set of steps for easy access. Surrounding the pool are wooden railings, adding to the private feel of the outdoor space.
Flat in Irvington

Pelican Place, Cozy Retreat | Pool | Walk to Tides

5.0 out of 5 average rating, 133 reviews

Private, pet-friendly home rentals

Guest favourite
A spacious deck offers breathtaking views of the water at sunset, with a stunning orange and pink sky. Four Adirondack chairs are arranged around a brown wicker coffee table, complemented by striped cushions. The serene water reflects the evening sky, creating a tranquil atmosphere.
Cottage in Onancock

A "True" Chesapeake Bay Waterfront Experience!

4.94 out of 5 average rating, 191 reviews
Top guest favourite
A wooden deck is shown overlooking a serene pond, framed by lush trees. A dining table with chairs is set for outdoor enjoyment, while soft natural light reflects off the water's surface, creating a peaceful ambiance.
Farm stay in Onancock

Private romantic pet friendly waterfront cottage

4.99 out of 5 average rating, 347 reviews
Top guest favourite
Place to stay in White Stone

Unique style, Waterfront Dock,Yard,Kayaks,SUP,King

4.99 out of 5 average rating, 126 reviews
Guest favourite
A two-story cabin made of wood stands beside a serene pond, surrounded by tall pine trees. The cabin features large windows and a spacious deck with rocking chairs, inviting peaceful moments by the water's edge.
Cabin in Cape Charles

Ultimate Cabin Farm Stay Cape Charles

4.96 out of 5 average rating, 258 reviews
Guest favourite
Cottage in Deale

Waterfront Cottage@ChesapeakeParadise Hot Tub/Dogs

4.83 out of 5 average rating, 201 reviews
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

4.97 out of 5 average rating, 470 reviews
Guest favourite
A serene sunset is captured over calm waters, with hues of orange and gold reflecting on the surface. Silhouettes of trees frame the scene, while a dock extends into the bay, creating a tranquil coastal atmosphere.
Cottage in Painter

Cottage by the bay location1/2 blockto the bay

4.91 out of 5 average rating, 125 reviews
Top guest favourite
A serene sunset casts vibrant hues of pink and orange across the water. The pier is seen in the distance, with the silhouette of a bridge spanning the horizon. Two figures are visible swimming, creating gentle ripples in the calm water.
Tiny home in Solomons

“Cabana by the Bay”-tiny home on a pier!

4.96 out of 5 average rating, 740 reviews

Pet-friendly home rentals with a hot tub

Superhost
A scenic waterfront view is captured, featuring a spacious green yard with a double swing and a hammock situated under a tall tree. Calm waters reflect the sky, creating a serene atmosphere. Lush greenery lines the shore, enhancing the peaceful setting.
Home in Cambridge

Waterfront Oasis! Hot tub! 2+ acres - Sleeps 8

4.88 out of 5 average rating, 141 reviews
Superhost
A shaded outdoor seating area is positioned on a wooden deck, facing the water. Comfortable blue cushioned chairs surround a matching sofa, with a white coffee table in the center. Lush greenery and a calm river view create a serene environment.
Cottage in Elkton

Sunset River Shack -amazing waterfront view

4.9 out of 5 average rating, 109 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

4.99 out of 5 average rating, 145 reviews
Top guest favourite
A serene outdoor area features six Adirondack chairs arranged on a grassy bluff, offering expansive views of the Chesapeake Bay. The water reflects the blue sky dotted with white clouds, while a small sailboat glides across the horizon.
Cabin in North East

Waterfront Cabin on the Chesapeake

4.97 out of 5 average rating, 201 reviews
Top guest favourite
Home in Deale

Chesapeake Waterfront-3 En Suites-Fire Pit-Kayaks

4.99 out of 5 average rating, 178 reviews
Guest favourite
The living room features a high, wooden ceiling with large windows allowing natural light to fill the space. A comfortable arrangement of sofas and chairs offers ample seating, complemented by a stylish area rug. A modern fireplace adds warmth to the inviting design.
Home in Perry Hall

Gunpowder Retreat

4.98 out of 5 average rating, 149 reviews
Top guest favourite
The exterior of a blue Swiss chalet A-frame house is showcased against a clear sky. The property features decorative windows and is surrounded by well-maintained landscaping, including colorful flowers and greenery.
Chalet in Port Tobacco Village

Riverfront Retreat-HotTubIDock|Fenced YardINear DC

4.99 out of 5 average rating, 111 reviews
Top guest favourite
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

4.99 out of 5 average rating, 142 reviews

Quick stats about pet-friendly home rentals near Chesapeake Bay

  • Total holiday rentals

    Explore 2,750 holiday rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay holiday rentals start at €9 per night before taxes and fees

  • Verified guest reviews

    Over 116,930 verified reviews to help you choose

  • Family-friendly holiday rentals

    2,000 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    350 properties feature pools

  • Rentals with dedicated workspaces

    1,750 properties have a dedicated workspace

  • Wifi availability

    2,670 of Chesapeake Bay holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chesapeake Bay rentals

  • 4.8 Average rating

    Chesapeake Bay stays are highly rated by guests – averaging 4.8 out of 5!

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