Pet-friendly holiday rentals in St. Michaels

4.98 out of 5 average rating, 205 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

La Casita on Harris Creek is an architecturally unique guest house situated on a private 40-acre farm in the heart of the Chesapeake Bay, 5 min by car to Saint Michaels, MD. The guesthouse, adjacent to the owner's main farm house, features an upstairs loft, open plan first floor TV/WiFi, full bath/shower, galley kitchen/ cook top stove, microwave, stainless refrigerator, microwave, stainless refrigerator. An adjacent private pool is available for guests. TALBOT COUNTY LICENSE NUMBER STRN 26-39

Outdoor spacesWalkabilityCleanliness

4.97 out of 5 average rating, 104 reviews

A comfortable living room features plush seating arrangements, including reclining chairs and a spacious sofa. A coffee table sits in the center, complemented by a large television mounted above a brick fireplace. Bookshelves filled with titles line the walls, adding a cozy touch.

Home in Easton

4 bdrm, 3 bath, 2,700 sqft whole house on 1 acre

Bring the whole family to my spacious house. 3 bathrooms for everyone to get ready. 2 king beds and 2 queen beds across 4 bedrooms. Huge living room, kitchen, and dinning room. Enjoy a sun room and fenced in back yard. Fresh eggs from backyard chickens. Merry Maids regularly cleans the bathrooms and kitchen. The basement, garage, and shed are for storage, and are not part of the rental. While quiet just outside of the city, there maybe some highway noise or farm animal noise. Large driveway

PetsOutdoor spacesWi-Fi

4.92 out of 5 average rating, 272 reviews

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 spacesWi-Fi

4.97 out of 5 average rating, 477 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.

WalkabilityOutdoor spacesKitchen

4.95 out of 5 average rating, 317 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.

PetsWalkabilityCleanliness

4.94 out of 5 average rating, 109 reviews

Lush green grass leads to the waterfront, where the calm water reflects the surroundings. Two white Adirondack chairs sit invitingly under the shade of tall trees, providing a serene spot for relaxation. A wooden dock extends into the water, enhancing the picturesque setting.

Home in Neavitt

Waterfront, Dog friendly, St Michaels home

Lovingly restored waterfront historic home just minutes from St. Michaels. Located in a quiet waterman's village, Seth's Landing provides tranquility and beautiful surroundings. Up for a little adventure? Bring your watercraft of choice - house has dock with two deepwater boatslips. Or bring your bikes - great area for biking! Or rent any of these from local business and have delivered to house. Great for couples and small families. Due to proximity to water, not good for young children.

PetsOutdoor spacesCleanliness

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.

4.96 out of 5 average rating, 222 reviews

Historic Berkeley Hall in the heart of town

Berkeley hall is centrally located in historic Saint Michaels. Park your car and walk to everything! Great shops, restaurants and 3 blocks to the water. First floor includes a high ceiling parlor that connects to a lovely side porch and large kitchen. There is a mahogany staircase that takes you to the 2nd floor that has 2 master suites. One has a king bed the other has a queen bed w/ ladder to loft which is best for kids -has a twin size futon sofa bed. Perfect home for a romantic getaway.

Outdoor spacesWalkabilityBiking

5.0 out of 5 average rating, 190 reviews

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**

Outdoor spacesPetsBackyard

5.0 out of 5 average rating, 220 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.

Outdoor spacesPetsBathroom

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.

PetsWalkabilityAmenities

4.99 out of 5 average rating, 380 reviews

4.97 out of 5 average rating, 310 reviews

A serene waterfront scene is framed by a sprawling tree. Boats are moored along the docks, with calm water reflecting the sky. Quaint buildings line the shore, and a bench is positioned on the grass, inviting quiet contemplation of the picturesque surroundings.

Cottage in St. Michaels

The Little Anchor Cottage, St. Michaels, MD

Welcome to the Little Anchor cottage in St. Michaels, Maryland! The cottage was built in late 1880s and is located in the charming Historic District, where you can enjoy the convenience of walking one block to the downtown shops and restaurants on S. Talbot street. And for another 5 to 15 minute walk, you can reach more waterfront dining on St. Michaels Harbor with its boat slips, boat ramps, the Chesapeake Bay Maritime Museum, Muskrat Park and Hollis Park.

Outdoor spacesPetsAccuracy

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.

4.97 out of 5 average rating, 118 reviews

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

Harbor Hideaway's in- town location and now featuring a PRIVATE POOL is a rare find. Steps away from everything that SM's has to offer. HH is a 1940’s - 1 1/2 story cottage loaded with thoughtful amenities. Airy and appointed with modern/ comfortable furnishings, resort quality linens, a well stocked kitchen; this 2 bdrm /2 B cottage is sure to please! Perfect for 1 to 2 couples, girls' wknds, small family, or anyone just in need of a relaxing getaway.

WalkabilityOutdoor spacesHospitality

Popular amenities for St. Michaels pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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

Outdoor spacesPetsFamily

4.88 out of 5 average rating, 146 reviews

4.98 out of 5 average rating, 294 reviews

The living room features a light-toned couch centered in the space, complemented by a decorative coffee table. A reclined green chair and a lamp beside it provide additional seating. The open kitchen is visible in the background, with light cabinetry and full size appliances.

Home in Shady Side

Canary Pointe-A popular getaway for 2!

PetsWalkabilityQuiet

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.

4.99 out of 5 average rating, 146 reviews

Luxury Modern Home on Water+Hotub- Annapolis 25min

Outdoor spacesWalkabilityComfort

4.96 out of 5 average rating, 141 reviews

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!

Outdoor spacesWalkabilityFamily

4.93 out of 5 average rating, 198 reviews

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

WalkabilityPetsWi-Fi

4.98 out of 5 average rating, 156 reviews

Home in Deale

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

PetsOutdoor spacesCleanliness

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.

4.95 out of 5 average rating, 274 reviews

Annapolis Area Waterside Retreat

Outdoor spacesWalkabilityRiver

4.97 out of 5 average rating, 135 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

PetsOutdoor spacesDecor

Pet-friendly home rentals with a pool

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.

4.99 out of 5 average rating, 99 reviews

Waterfront | Pool | Hot tub | Beach Access

Outdoor spacesWalkabilityBeach

4.94 out of 5 average rating, 148 reviews

Guest suite in Annapolis

Annapolis Garden Suite

PetsWalkabilityQuiet

4.98 out of 5 average rating, 164 reviews

Home in Montross

Waterfront, Dock+Kayak, Firepit, Gameroom, Potomac

PetsOutdoor spacesTV

4.94 out of 5 average rating, 219 reviews

Guest suite in Arnold

Pet-Friendly King Suite + Kitchen | Near Annapolis

PetsOutdoor spacesSleep quality

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

WalkabilityPetsBiking

4.92 out of 5 average rating, 197 reviews

4.92 out of 5 average rating, 234 reviews

A private beach area is depicted with soft, sandy ground, featuring two beach chairs under a blue umbrella. Calm waters extend to the horizon, complemented by a wooden dock and a distant view of the opposite shore under a clear, blue sky.

Home in Montross

The Glebe

Outdoor spacesWalkabilityQuiet

Superhost

A serene swimming pool is featured in a private outdoor area, surrounded by a stone deck. Two white lounge chairs are positioned nearby, with trees providing a shaded atmosphere. The clear water glistens under a partly cloudy sky, inviting relaxation.

4.9 out of 5 average rating, 198 reviews

House in Edgewater Maryland

PetsWalkabilityBathroom

4.84 out of 5 average rating, 128 reviews

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

WalkabilityOutdoor spacesBarbecue

Private, pet-friendly home rentals

4.9 out of 5 average rating, 326 reviews

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

Outdoor spacesWalkabilityHiking

Apartment in St. Michaels

Downtown St. Michaels | Porch + Pet-Friendly

WalkabilityPetsComfort

4.96 out of 5 average rating, 27 reviews

5.0 out of 5 average rating, 39 reviews

A bridge control house is observed beside a two-lane road. The structure is painted in light colors, with the name 'KNAPPS ARROWS BRIDGE' displayed. A raised section of the bridge is visible, allowing boats to pass underneath. Lush greenery is seen in the background.

Home in Tilghman Island

The Getaway

PetsOutdoor spacesBarbecue

5.0 out of 5 average rating, 21 reviews

Cozy, Family-Friendly Log Cabin-St. Michaels

PetsOutdoor spacesSleep quality

4.97 out of 5 average rating, 35 reviews

Cottage in St. Michaels

Lovely Waterfront Cottage on 2 acres, St. Michaels

PetsWalkabilityFamily

Guesthouse in St. Michaels

An elevated view of a green two-story house is surrounded by tall trees, with water visible in the background. The layout includes a wraparound porch and landscaped shrubbery, leading to a winding drive that approaches the front entrance.

Secluded water, private sitting room, full bath!

PetsOutdoor spacesRiver

5.0 out of 5 average rating, 49 reviews

4.96 out of 5 average rating, 45 reviews

A serene sunset is captured over calm waters, with vibrant oranges and yellows reflecting on the surface. The horizon blends into deep blues and subtle cloud formations, while the shoreline features a natural landscape leading to the water's edge.

Home in Tilghman Island

Panoramic water views

Outdoor spacesPetsLayout

Superhost