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Cottage vacation rentals in St. Michaels

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Top-rated cottage rentals in St. Michaels

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Top guest favorite

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

4.96 out of 5 average rating, 420 reviews

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 charming exterior of a historic cottage is depicted, featuring a welcoming front porch and an American flag. Lush green landscaping with flowers adds a touch of color, while a stone pathway leads to the entrance. The house is set against a backdrop of trees.

Cottage in Rock Hall

4.88 out of 5 average rating, 136 reviews

Cottage with Modern Updates - Walk to Waterfront!

Historic cottage, fully renovated and located in the heart of Rock Hall. Features open living area, modern kitchen, sunny front porch, big fenced backyard, and patio with fire pit and picnic table. Enjoy everything the town has to offer - fishing, boating, festivals, dock bars, restaurants, shopping, & more. Walking distance to Main Street, marina, Harbor Shack, Waterman's Crab House, The Mainstay. A short drive to Eastern Neck National Wildlife Refuge, Washington College, historic Chestertown.

Top guest favorite

The charming beach house features a white picket fence and a welcoming front porch. A large anchor motif is displayed prominently above the door. Surrounding greenery provides a natural backdrop, enhancing the cozy exterior aesthetics in a tranquil setting.

Cottage in Lusby

4.98 out of 5 average rating, 280 reviews

Gettin to the point. ( Cove Point Beach)

Our beach house is for you to enjoy Cove Point Beach, which is only 500 ft away. The kitchen is fully stocked, or use the outdoor grill on the side of the house.PLEASE NON SMOKERS ONLY. One dog allowed on a cases by case bases with a one time pet fee of $65.00. No children under 8 years old. Walk to the beach, but only park your vehicle in our driveway, not on beach inlets. A gas fireplace in the living room. A beautiful sun porch area to enjoy. Enjoy walking on this private community beach.

A charming cottage sits at the water's edge, surrounded by lush greenery. A wooden staircase leads down from an elevated deck to the sandy beach. Two blue chairs are positioned on the deck, inviting relaxation as the sun sets in the background.

Cottage in Leonardtown

4.96 out of 5 average rating, 220 reviews

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

An aerial view highlights Rumbley Cottage's proximity to the shoreline and wetlands. The landscape features a mix of sandy beach, shallow waters, and expansive marshlands under a clear blue sky, offering a serene setting with natural beauty and tranquility.

Cottage in Westover

4.99 out of 5 average rating, 236 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

LAST MINUTE OPENING-09-27 to 10-03-25 !!!! Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

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 Saint Michaels

4.97 out of 5 average rating, 174 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Top guest favorite

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 Saint Michaels

4.98 out of 5 average rating, 251 reviews

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.

Top guest favorite

A charming cottage is visible beside a clear pool, surrounded by well-maintained green lawns. Two shaded umbrellas stand over cushioned lounge chairs by the water's edge, creating a comfortable outdoor space for relaxation. The inviting pool reflects the bright sky, enhancing the serene atmosphere.

Cottage in Easton

5 out of 5 average rating, 114 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

A wooden pier extends over calm waters at sunset, with the sun setting at the horizon. The scene features reflections of the colorful sky on the water's surface, creating a serene atmosphere. Smooth rocks line the edges of the pier.

Cottage in Stevensville

4.94 out of 5 average rating, 161 reviews

Cottage on the Bay - Kent Island

Chesapeake Bay Waterfront home on Kent Island! Enjoy year round big sky and water views from the comfort of the screened porch & family room. Fish & crab from the pier or take a dip in the bay. Open concept living and rear bedroom/rec room are perfect for relaxing and having fun with family & friends. Close to popular wedding venues, local marinas & charter fishing boats, restaurants, Tiki bars, beaches, golfing, parks, & bike trails.

Top guest favorite

A welcoming cottage exterior features a covered porch with seating, light fixtures, and colorful plantings. A walkway made of stone leads to the entrance, and the surrounding landscape is highlighted by well-maintained grass and nearby neighboring homes.

Cottage in California

4.97 out of 5 average rating, 248 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has an open floor plan that allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum featuring live concerts by top name bands.

Top guest favorite

The view from the deck features lush trees framing a sandy beach and the calm waters of the Potomac River. Two stylish planters filled with yellow flowers are positioned at the entrance, adding a pop of color to the serene landscape.

Cottage in Hague

4.98 out of 5 average rating, 170 reviews

Potomac River cheerful cottage

Embark on a journey to the serenity of nature and the gentle lullaby of the Potomac River at the cottage. Escape the hustle and let the timeless embrace of water and tranquility rejuvenate your mind and soul. The private sandy beach (no public access) is steps away and awaits your footprints. Delight in the serene surroundings of the Northern Neck countryside. Two hours from DC, Richmond and Maryland.

A view of the sunset over Chesapeake Bay is captured from the deck, with warm hues reflecting on the water. The scene includes a grassy area leading to the shoreline and a subtle silhouette of a dock in the background.

Cottage in Deale

4.95 out of 5 average rating, 167 reviews

Chesapeake Bay Cottage

Cottage Located directly on the Chesapeake Bay. Includes sandy beach, yard, a screened in porch and deck. Two Kayaks to enjoy. Two bedroom plus den. Two full baths. Fully equipped kitchen.Kurig coffee maker and regular available. Master bedroom -queen size mattress. Second bedroom -a full-size mattress (double) third bedroom -a twin day bed with twin pullout. Both twin size mattresses.

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Popular amenities for St. Michaels cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

An inviting stone patio area features comfortable outdoor seating, framed by greenery. Light pours in through the open doors, leading to an interior space that includes minimalist decor and a spiral staircase. A hot tub is visible in the background, enhancing the tranquil setting.

Cottage in Annapolis

4.84 out of 5 average rating, 93 reviews

Waterfront cottage w/hot tub/ gated/ pier/ firepit

Top guest favorite

A tranquil beach scene presents soft sand leading to calm water, framed by an open sky dotted with clouds. A weathered log rests on the shoreline, while distant rocky formations add interest to the horizon.

Cottage in Saint Leonard

4.96 out of 5 average rating, 158 reviews

Block to Private Beach, Screened deck, Hot Tub

Top guest favorite

A serene water view is captured as the sun sets, casting warm hues of orange and pink across the sky. The calm surface of the water reflects the colorful clouds, while a pier extends into the scene, inviting leisure and tranquility.

Cottage in Woolford

5 out of 5 average rating, 76 reviews

Waterfront Cottage & Guesthouse Near Cambridge

A covered outdoor seating area is shown, featuring a rug and a wooden table surrounded by comfortable chairs. Green trees provide shade, and a view of the calm waterfront and distant shoreline can be seen, creating a serene outdoor space for relaxation.

Cottage in Lusby

4.94 out of 5 average rating, 16 reviews

Riverside Haven w/ Hot Tub

An aerial view showcases a rustic-modern house surrounded by greenery. Red pathways lead to the entrance, and a wooden deck is visible with steps leading up to the front door. In the background, a private pool and shaded seating areas offer outdoor relaxation options.

Cottage in Marion Station

4.77 out of 5 average rating, 48 reviews

Year Round Playground - Rare Rustic-Modern Getaway

A screened porch features a hanging bench swing with cushions in shades of blue and nautical motifs. A small chair stands nearby, adorned with a decorative pillow. Tall curtains frame the space, providing a relaxed and inviting atmosphere surrounded by greenery.

Cottage in Annapolis

4.86 out of 5 average rating, 109 reviews

Nautical Vibe Walk 2 Harbor Pubs USNA

A furnished deck is surrounded by greenery, featuring a dining set under a large umbrella. Comfortable seating and a patterned area rug enhance the space, with details such as a small decorative lantern and a heating lamp visible.

Cottage in Chesapeake Beach

4.54 out of 5 average rating, 26 reviews

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

Top guest favorite

A serene private dock overlooks a calm cove, with vibrant kayaks stacked nearby. A simple bench provides seating, surrounded by lush greenery and mist rising from the water's surface, inviting relaxation and peaceful reflections.

Cottage in Montross

4.93 out of 5 average rating, 103 reviews

Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach

Pet-friendly cottage rentals

Cottage in Deale

4.83 out of 5 average rating, 184 reviews

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

The exterior of a single-story cottage is framed by lush greenery and mature trees. A white picket fence encloses the front yard, which features a small lawn and a decorative tree. Gravel pathways lead to the front entrance, with a shaded area beside the house.

Cottage in Deale

4.91 out of 5 average rating, 170 reviews

Rockhold Creek Cottage

A charming blue cottage features a spacious front deck with wooden railings and steps leading up to the entrance. Large windows allow for ample natural light, while the surrounding grass lawn and trees enhance the outdoor setting.

Cottage in Colonial Beach

4.84 out of 5 average rating, 112 reviews

Bungalow Private Beach & Dock Colonial Beach Water

The entrance features double glass doors framed by a wooden deck. Seasonal potted plants, including vibrant flowers and greenery, are arranged on either side, while a small pumpkin adds a festive touch. A decorative light fixture hangs nearby, enhancing the welcoming appearance.

Cottage in Glen Burnie

4.91 out of 5 average rating, 206 reviews

Home away from home

A charming cottage is nestled among lush trees, featuring a spacious yard of green grass. Ample sunlight filters through the leaves, casting playful shadows. The exterior showcases a combination of windows and porch areas, offering a welcoming appearance in a serene environment.

Cottage in Pasadena

4.97 out of 5 average rating, 186 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

Top guest favorite

A dining area is presented with a modern table surrounded by white chairs, offering a casual atmosphere. Natural light pours in through large windows. A beach-themed artwork depicting a tropical scene enhances the setting, while a coffee bar is conveniently located nearby.

Cottage in North Beach

4.96 out of 5 average rating, 173 reviews

Bell Estates I Beautiful Cottage I *Beach Passes*

A quaint yellow cottage is framed by a wooden fence and natural greenery. The front porch features colorful doors and multiple windows, allowing ample light to enter. A deck extends from the house, providing a welcoming space for relaxation amidst the surrounding trees.

Cottage in Port Republic

4.78 out of 5 average rating, 195 reviews

Shewell’s Cottage by the Shore

Top guest favorite

An outdoor deck features comfortable seating with two rocking chairs and an outdoor sofa, arranged around a propane fire pit. A vibrant orange umbrella provides shade, overlooking the tranquil water of Nomini Creek, with lush greenery and a private dock in the background.

Cottage in Montross

4.98 out of 5 average rating, 182 reviews

Newly Renovated 2BR Waterfront Cottage with Dock

Private cottage rentals

Top guest favorite

The cottage is set in a peaceful wooded area, featuring a sloping green lawn and surrounding trees. A stone pathway leads to the porch, which is bordered by a white railing. The clear blue sky and sunlight enhance the serene atmosphere.

Cottage in Hollywood

5 out of 5 average rating, 45 reviews

The Little Blue Cottage

An open living area features plush seating arrangements in soft tones, complemented by a coffee table and an elegant fireplace beneath a mounted TV. Natural light filters through sheer curtains, enhancing the warm atmosphere of the space.

Cottage in Annapolis

4.94 out of 5 average rating, 18 reviews

Wonderful Cottage Nestled On Chesapeake Bay

A classic two-story house is showcased, featuring white siding and contrasting black shutters. A vibrant red door serves as a focal point. The front steps are flanked by neatly trimmed shrubs, and a green lawn extends to the sidewalk, providing an inviting entrance.

Cottage in Cambridge

4.98 out of 5 average rating, 47 reviews

Cozy 3-bedroom cottage steps away from the water.

A cozy outdoor space features a circular arrangement of blue Adirondack chairs surrounding a firepit, set on gravel. A wooden picnic table sits underneath an umbrella, while a spacious green lawn is framed by a wooden fence and trees in the background.

Cottage in Grasonville

4.85 out of 5 average rating, 73 reviews

CoastalBeachCottage*BayViews*Close2WeddingVenues

Top guest favorite

A serene view of a serene water landscape is showcased, featuring a double rainbow arching across the sky. Reflections of the rainbow are visible on the water's surface. A private pier extends into the water, surrounded by lush greenery.

Cottage in East New Market

4.96 out of 5 average rating, 69 reviews

Cottage on Cabin Creek

Top guest favorite

An aerial view of the waterfront cottage highlights a well-maintained exterior surrounded by lush green grass and trees. The serene water and distant horizon are visible, along with two private docks extending into the bay.

Cottage in Rock Hall

5 out of 5 average rating, 88 reviews

Overton Farm Cottage

A two-story cottage is presented, featuring a spacious screened porch and a gently sloped front lawn. Lush greenery frames the house, which is highlighted by a stone façade and white railing. Steps lead to the porch, inviting relaxation in a tranquil setting.

Cottage in Annapolis

4.94 out of 5 average rating, 84 reviews

Peaceful Escape: Bay Ridge Cottage by the Bay

A white picket fence lines the edge of a grassy area, overlooking a calm bay. The water reflects the blue sky and scattered clouds, creating a serene atmosphere. The distant shoreline is subtly visible, adding depth to the tranquil view.

Cottage in Chesapeake Beach

4.93 out of 5 average rating, 61 reviews

Cliffside Bay Cottage: Pet-Friendly, Easy DC Drive

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