Cottage vacation rentals in Annapolis

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.

4.96 out of 5 average rating, 413 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 exterior of a charming white cottage is displayed, featuring a sloped roof and inviting porch steps. Large windows allow natural light to fill the home, with vibrant pink flowers enhancing the front yard. A manicured lawn completes the welcoming entrance.

4.98 out of 5 average rating, 119 reviews

Miller Cottage - near Navy Stadium

Miller Cottage is a charming 1920s style cottage in the quiet neighborhood of Homewood and 1 mile to Church Circle/West Street and the state capital of Maryland, and 1 ½ miles to the City Dock. One bedroom with queen bed with an en suite bathroom with shower. Pull out couch for additional sleeping in the living room. Open plan living room, dining room and kitchen. Nautical furnishings, in a warm, bright home. Within walking distance of the Navy Marine Corp Stadium (about 6 tenths of a mile)

4.99 out of 5 average rating, 161 reviews

A breathtaking sunrise is captured over calm waters, creating a stunning reflection of vibrant hues of orange, pink, and purple. The private pier is visible on the right, complementing the serene landscape of trees on the distant shore and a tranquil island in the background.

Cottage in Edgewater

Waterfront Chesapeake Bay Sunrises w/Private PIER!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

An open living and dining area is highlighted, featuring a spacious sectional couch and a dining table set with placemats. Light-colored walls and vaulted ceilings contribute to the airy ambiance. The kitchen is visible in the background, equipped with modern amenities.

4.93 out of 5 average rating, 207 reviews

Secluded Cottage_ A+ Amenities in Historic Dwntwn

Beautifully restored 1928 cottage w/ open floor plan & vaulted ceilings provide a homey vibe Enjoy Historic Annapolis Towncenter in your backyard Jack & Jill bath separates queen bedrooms. Comfortable full-size daybed = 3beds Hardwood floors adorn common areas Gourmet kitchen w/ extensive granite countertops, breakfast bar & amenities Dining table & chairs, extra-large comfy couch nestled between 2 chaise lounge chairs, 55" Roku tv, electric FP, towels, linens, pvt laundry, and more!

A cozy living area features a decorative fireplace with a white brick surround. A colorful artwork of sailboats adorns the wall above the mantel. A small boat decoration and a vase with yellow flowers decorate the coffee table, creating a warm focal point in the room.

4.94 out of 5 average rating, 189 reviews

Charming Cottage 2 parking spot easy walk downtown

Discover this charming, fully furnished cottage ideally accommodating up to six guests. Nestled on a serene street within walking distance of downtown, the United States Naval Academy, and the Navy and Marine Corps Stadium, this delightful space features a tranquil screened front porch, inviting living areas, and two bedrooms (one queen, two twin beds) with all bedding and linens provided. The lower level offers a full-size futon and a designated office area for added comfort and convenience.

4.91 out of 5 average rating, 198 reviews

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

Home away from home

This is a small house with private parking close to Baltimore and Annapolis. I have one queen size Murphy bed, one single pull out couch. It has an updated kitchen, updated bathroom, walk-in closet, Internet and heating and cooling. I also have a pellet stove. my kitchen is fully stocked with dishes, knives, forks, pots and pans. The bathroom has towels and rugs. I tried to add all the amenities to make it as comfortable as home. Look at pet rules under the other things to note section.

4.97 out of 5 average rating, 180 reviews

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

Ft. Smallwood Overlook. Waterfront with Kayaks!

Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

Cottage in Saint Michaels

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.

4.97 out of 5 average rating, 167 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.

4.74 out of 5 average rating, 185 reviews

A spacious sleeping area features a comfortable bed with a neutral headboard and two bedside tables with lamps. Natural light enters through the large windows, complemented by soft curtains. A small wooden table with a chair and an air conditioning unit are also visible in the room.

Cottage in Edgewater

Waterview Studio on a sunset corner

Book more than 2 days and get up to 15% off. Last painted in June 2021, new toilet and Tempurpedic mattress top. New wood floor installed in 2024. Private and comfortable studio in a centenary house with independent entrance in a quiet neighborhood surrounded by the waters of the South River. The house is divided in two independent and private units. Great for outdoor lovers. Ideal for gate away, temporary stays for work, vacation or relaxing from the stressful life.

5 out of 5 average rating, 110 reviews

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

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

4.94 out of 5 average rating, 160 reviews

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

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.

4.83 out of 5 average rating, 183 reviews

A shaded outdoor area features a glass-top dining table surrounded by six chairs, situated on lush green grass. Nearby, additional loungers invite relaxation, under the canopy of a large tree with vibrant foliage, overlooking a calm waterfront view.

Cottage in Deale

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Savor our three-bedroom Cottage in this peaceful western shore spot, enjoy two acres of green space, the pier, kayaks, swings, fire pit, shady lawns & sun-drenched loungers, local waterfront dining or eat in, close to Washington, D.C., Annapolis, & Baltimore at this honeymoon-worthy country-like micro-resort. Due to the current COVID-19 situation, we have offered SPECIAL discounts for longer-term rentals

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Popular amenities for Annapolis cottage rentals

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Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.91 out of 5 average rating, 102 reviews

An above-ground swimming pool is surrounded by greenery, providing a relaxing outdoor space. The pool features a white safety gate and steps for easy access. On either side, tall palm-like plants add a touch of nature, while two small tables with stools offer seating nearby.

Cottage in Bryans Road

The Potomac House: 13 acre riverfront property

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.

4.86 out of 5 average rating, 108 reviews

Nautical Vibe Walk 2 Harbor Pubs USNA

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.

4.84 out of 5 average rating, 89 reviews

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

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

4.58 out of 5 average rating, 24 reviews

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

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Pet-friendly cottage rentals

4.89 out of 5 average rating, 131 reviews

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

Cottage with Modern Updates - Walk to Waterfront!

Cottage in Saint Michaels

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.

4.98 out of 5 average rating, 241 reviews

The Little Anchor Cottage, St. Michaels, MD

4.87 out of 5 average rating, 153 reviews

A serene water view is presented, featuring a calm lake that reflects a cloudy sky and surrounding trees. The stillness of the water enhances the scenery, showcasing a harmonious blend of natural elements against a backdrop of soft blues and whites.

Cottage in Wittman

Perfect St. Michaels Getaway

4.85 out of 5 average rating, 130 reviews

A serene waterfront scene is displayed, showcasing a calm body of water bordered by lush greenery. A pier extends into the water, with boats moored nearby. In the distance, various structures line the shore, surrounded by nature, under a softly lit sky.

Cottage in Pasadena

Chesapeake Cottages- 2 Quaint Waterfront Retreats

4.9 out of 5 average rating, 168 reviews

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

Rockhold Creek 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.

5 out of 5 average rating, 12 reviews

Wonderful Cottage Nestled On Chesapeake Bay

4.79 out of 5 average rating, 186 reviews

A spacious living area is presented with light-colored tile flooring, featuring a large bed with soft bedding. A dark sofa sits near a modern television, and a decorative shelving unit contrasts with the neutral walls. Natural light enhances the inviting environment.

Cottage in Old Town

THE PRINCE COTTAGE WITH PRIVATE PARKING GARAGE!!!

4.93 out of 5 average rating, 54 reviews

A charming bayside cottage is visible from the water, surrounded by lush green trees. A private dock extends into the calm water, offering ample space for relaxation and fishing, and leading up to the welcoming entrance of the home.

Cottage in Edgewater

Waterfront Cottage with Private Pier

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Private cottage rentals

5 out of 5 average rating, 23 reviews

The exterior of the cottage is showcased with a light-colored facade and a welcoming front porch. Surrounded by lush greenery, the yard offers a serene atmosphere. A screened-in porch on one side enhances the outdoor living space, inviting relaxation and connection with nature.

Cottage in Oxford

Sailor's Cottage - Private Waterfront

A charming one-story cottage is surrounded by lush greenery and colorful flower beds. The well-maintained lawn features clusters of lavender-colored flowers, complemented by shrubs and bushes, creating an inviting atmosphere. The front porch, with steps leading up, adds to the home's welcoming appeal.

4.93 out of 5 average rating, 29 reviews

Bay View Beach Cottage, plan your family vacation

4.87 out of 5 average rating, 183 reviews

The exterior of a charming beach cottage is visible, featuring a sloped roof and multiple windows. A green street sign indicates the intersection of Chesapeake Avenue and 7th Street. Lush green grass and shrubs surround the property's fence.

Cottage in North Beach

Full house rental in Twin Beach. 1 bk from the Bay

4.87 out of 5 average rating, 46 reviews

A cozy cottage exterior is presented with a stone patio featuring four white Adirondack chairs surrounding a small table. A flagpole with an American flag stands nearby, while trees and greenery provide a peaceful backdrop.

Cottage in Easton

Loon Cottage on Leeds Creek

5 out of 5 average rating, 45 reviews

A wide view of the Chesapeake Bay features a vibrant rainbow arching across a cloudy sky. A wooden deck and a thatched-roof area are visible in the foreground, while boats are docked at the piers along the water's edge.

Cottage in Essex

The Little House of Rockaway Beach, Maryland

The renovated cottage features a white exterior with blue accents, surrounded by lush greenery. A small porch with a light blue railing leads to the entrance. A brick pathway and outdoor seating area are visible in the well-maintained yard.

4.98 out of 5 average rating, 48 reviews

Charming Waterfront Cottage on Historic Property

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.

4.94 out of 5 average rating, 82 reviews

Peaceful Escape: Bay Ridge Cottage by the Bay