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Pet-friendly home rentals near Chesapeake Bay

Find and book unique pet-friendly homes on Airbnb

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 --

PetsOutdoor spacesWifi

4.92 out of 5 average rating, 272 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!

Outdoor spacesWalkabilityBathroom

4.95 out of 5 average rating, 274 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!

PetsOutdoor spacesFamily

4.98 out of 5 average rating, 156 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**

WalkabilityOutdoor spacesCheckout

5.0 out of 5 average rating, 190 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

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, feed the Alpacas, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

WalkabilityOutdoor spacesShared spaces

4.96 out of 5 average rating, 270 reviews
Guest favourite
A metal tray filled with freshly steamed crabs sits on a wooden table. The crabs are coated with seasoning and display vibrant orange-red shells. In the background, natural light filters through a screened porch, adding a warm ambiance to the scene.
Home in Onancock

Escape To A “True” Chesapeake Waterfront Property!

Get away from it all... The Thicket Point Fish Camp is a true Chesapeake Bay waterfront property and the perfect place to escape for the best of the Eastern Shore. Located just 5 miles from downtown Onancock, VA, and everyday conveniences, this property is one of a kind! This is the "Bayview House", an updated 1950's cape cod featuring lots of original features with many modern upgrades. It sits on our 44-acre property along with our "Sunset House" - also available on Airbnb.

Outdoor spacesPetsAccuracy

4.88 out of 5 average rating, 103 reviews
Top guest favourite
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.

Outdoor spacesPetsAmenities

5.0 out of 5 average rating, 220 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.

PetsWalkabilityBeach

4.99 out of 5 average rating, 151 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!

Outdoor spacesWalkabilityView

4.92 out of 5 average rating, 239 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...

Outdoor spacesWalkabilityHospitality

4.96 out of 5 average rating, 304 reviews
Top guest favourite
A wooden dock extends over calm waters, leading to a charming home surrounded by trees. The house, featuring large windows, is illuminated as dusk approaches. Adirondack chairs are placed along the shoreline, inviting relaxation in the natural setting.
Home in Stevensville

Kent Island Waterfront Home with Amazing Sunsets

Kick back at this cheerful waterfront escape on Thompson Creek—a favorite for families & wedding guests! With easy, local access to eight nearby venues, it’s the perfect home base. Enjoy sunsets, boating, and all Kent Island adventures. Thompson Creek leads to the Chesapeake Bay, with Annapolis, Kent Narrows, and St. Michaels close by. Relax on the screened‑in porch, and enjoy a remote feel with shops minutes away.

WalkabilityOutdoor spacesCondition

4.99 out of 5 average rating, 155 reviews
Top guest favourite
The charming exterior of a waterfront cottage, featuring a white picket fence and a welcoming front deck. Large windows allow for natural light, while vibrant surroundings enhance the coastal feel. The front porch is partially shaded by lush greenery, inviting relaxation and enjoyment of the outdoors.
Cottage in North Beach

Cozy Waterfront Cottage - Pet Friendly

Original waterfront cottage in North Beach is perfect for a small family or two couples. Beautiful sunrises and moonrises over the boardwalk from the front deck. Walk to restaurants and nightlife, stroll the boardwalk, chill on the beach or go to the spa or charter fishing in Chesapeake Beach. Pet friendly. Beach Passes, umbrella and chairs included. 2 bedrooms plus a twin daybed that pulls out to queen bed.

WalkabilityPetsNearby

4.96 out of 5 average rating, 112 reviews

Popular amenities for pet-friendly home rentals near Chesapeake Bay

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

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

PetsOutdoor spacesDecor

4.95 out of 5 average rating, 317 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

Outdoor spacesPetsHiking

4.97 out of 5 average rating, 114 reviews
Guest favourite
Home in Montross

Riverfront Home w/Dock · Fire Pit · Kids Play Area

Outdoor spacesPetsGetting around

4.92 out of 5 average rating, 106 reviews
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.

PetsOutdoor spacesCheckout

5.0 out of 5 average rating, 109 reviews
Guest favourite
Home in Montross

Waterfront, Dock+Kayak, Firepit, Gameroom, Potomac

WalkabilityPetsQuiet

4.98 out of 5 average rating, 164 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

WalkabilityOutdoor spacesCheck-in

4.98 out of 5 average rating, 164 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

Outdoor spacesPetsNearby

4.98 out of 5 average rating, 264 reviews
Top 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

WalkabilityOutdoor spacesBathroom

4.93 out of 5 average rating, 198 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

PetsWalkabilityLocation

4.95 out of 5 average rating, 148 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.
Guesthouse in Stevensville

Waterfront-View of Bay from your Bed

WalkabilityPetsLong stay

4.99 out of 5 average rating, 380 reviews
Top 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 homes in Cape Charles

The Laughing King Retreat Honeymoon Island Cottage

WalkabilityOutdoor spacesIndoor spaces

4.98 out of 5 average rating, 364 reviews
Top guest favourite
An aerial view captures a spacious home set on a wooded parcel adjacent to a serene body of water. The exterior features a large swimming pool surrounded by decking, with a manicured lawn and tall trees creating a natural boundary.
Home in Cambridge

Gorgeous, Waterfront Home Is Perfect for Families!

WalkabilityPetsTV

4.96 out of 5 average rating, 141 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

Outdoor spacesPetsFamily

4.99 out of 5 average rating, 255 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

Outdoor spacesWalkabilityCheckout

4.84 out of 5 average rating, 128 reviews
Guest favourite
An aerial view of the house showcases a spacious deck with comfortable seating, surrounded by a railing. A dock extends into the water, equipped with a covered boat lift. Lush greenery borders the property, providing a serene backdrop.
Home in Montross

Coastal Waterfront Escape Fire Pit, Dock & Kayaks

WalkabilityOutdoor spacesCheck-in

4.96 out of 5 average rating, 107 reviews
Superhost
Home in Irvington

Gothic Cottage, Hot Tub, Walk to Town

PetsWalkabilityDecor

4.95 out of 5 average rating, 186 reviews

Private, pet-friendly home rentals

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

WalkabilityOutdoor spacesParking

4.97 out of 5 average rating, 477 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

PetsOutdoor spacesCondition

4.99 out of 5 average rating, 354 reviews
Guest favourite
A wooden staircase illuminated by soft lights leads down to a private dock. Reflections of trees and evening sky are seen on the calm water of St. Leonard Creek. A sailboat is moored at the end of the dock, adding to the serene waterside ambiance.
Cabin in Lusby

Peaceful Waterfront Retreat on The Bay

WalkabilityPetsComfort

4.9 out of 5 average rating, 326 reviews
Superhost
An aerial view showcases a lush green landscape surrounding a peaceful shoreline. The sandy beach meets calm waters, framed by dense trees. The varied colors of the water create a serene contrast against the vibrant greenery, presenting a tranquil natural setting.
Cottage in Lusby

Hot Tub Hideaway by Shark Tooth Shores

WalkabilityPetsParking

4.82 out of 5 average rating, 105 reviews
Guest favourite
A natural rock fire pit is surrounded by several Adirondack chairs, offering a comfortable gathering space. The serene waterfront is visible in the background, with trees lining the shore and a dock extending into the water.
Cabin in Reedville

Dinna Fash-3 BR Waterfront Log Cabin

Outdoor spacesWalkabilityAmenities

4.96 out of 5 average rating, 315 reviews
Top guest favourite
The image captures a serene waterfront scene, showcasing a long wooden dock extending into the calm river. Lush greenery lines the riverbank, while a clear blue sky with scattered clouds provides a picturesque backdrop. The tranquil water reflects the surrounding landscape.
Apartment in Lexington Park

Historic St. Mary's City, MD

Outdoor spacesWalkabilityKitchen

4.97 out of 5 average rating, 628 reviews
Top guest favourite
Place to stay in White Stone

Beacon Bay: Waterfront, Large yard, Kayaks, SUP, KING

PetsOutdoor spacesView

4.99 out of 5 average rating, 131 reviews
Guest favourite
Cottage in Deale

Waterfront Cottage@ChesapeakeParadise Hot Tub/Dogs

Outdoor spacesPetsPool

4.83 out of 5 average rating, 204 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

PetsOutdoor spacesLayout

4.88 out of 5 average rating, 146 reviews
Guest favourite
An outdoor dining area is showcased on a spacious deck featuring a round table set with dishes and floral arrangements. Several wooden chairs surround the table, while a large umbrella provides shade. The scenic view of the Chesapeake Bay extends in the background.
Home in Huntingtown

Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck

Outdoor spacesWalkabilityFamily

4.98 out of 5 average rating, 105 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

WalkabilityOutdoor spacesQuiet

4.97 out of 5 average rating, 203 reviews
Top guest favourite
A spacious deck features a large dining table surrounded by white chairs, overlooking a private pool and a serene pond. String lights are hung above, enhancing the outdoor setting. Leafless trees are visible in the background against a partly cloudy sky.
Home in Edgewater

Waterfront | Pool | Hot tub | Beach Access

PetsOutdoor spacesTV

4.99 out of 5 average rating, 99 reviews
Guest favourite
Apartment in Upper Marlboro

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

PetsOutdoor spacesNearby

4.94 out of 5 average rating, 224 reviews
Top guest favourite
Home in Deale

Chesapeake Waterfront-3 En Suites-Fire Pit-Kayaks

Outdoor spacesPetsIndoor spaces

4.99 out of 5 average rating, 183 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

PetsWalkabilityIndoor spaces

4.89 out of 5 average rating, 114 reviews
Guest favourite
A grand deck is viewed, featuring two white rocking chairs overlooking a vibrant sunset over the water. The sky is filled with shades of pink and orange, reflecting on the calm ocean surface. A dark wicker seating area is visible to the right.
Home in Buckroe Beach

Exclusive Beachfront Home w/ 180° Views & Hot Tub!

Outdoor spacesWalkabilityBeach

4.96 out of 5 average rating, 115 reviews

Quick stats about pet-friendly home rentals near Chesapeake Bay

  • Total vacation rentals

    Explore 2,780 vacation rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay vacation rentals start at $14 CAD per night before taxes and fees

  • Verified guest reviews

    Over 122,630 verified reviews to help you choose

  • Family-friendly vacation rentals

    1,970 properties offer extra space and kid-friendly amenities

  • Vacation rentals with a pool

    350 properties feature pools

  • Rentals with dedicated workspaces

    1,700 properties have a dedicated workspace

  • Wifi availability

    2,700 of Chesapeake Bay vacation 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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