Family-friendly vacation rentals in Edgewater

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.

4.96 out of 5 average rating, 268 reviews

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!

Two adirondack chairs in blue and teal are positioned on a wooden pier, facing the sunset over calm waters. A small white table sits between them, holding two coffee mugs. The vibrant orange and pink hues of the sky reflect on the water's surface.

4.98 out of 5 average rating, 185 reviews

Waterfront Chesapeake Bay Sunrises & Fishing Dock!

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!

4.98 out of 5 average rating, 211 reviews

The living room features a modern gray sectional sofa adorned with colorful cushions. A wooden coffee table rests on a large area rug, accompanied by two yellow accent chairs. Natural light enters through large windows, brightening the space and highlighting decorative wall art.

Bungalow in Edgewater

Peaceful Setting with Chic, Thoughtful Style

Settle down for a peaceful night's sleep in the four-poster bed at this tranquil cottage in the woods. The soft gray color palette along with beautiful hardwood floors creates a calm, fresh feel, while the screen porch offers a quiet spot for restful afternoons. This serene retreat sits minutes away from Annapolis. The waterfront community has a beach a short walk away for launching kayaks and taking relaxing strolls. There is also easy access to Baltimore, Washington, and the Eastern Shore.

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, 145 reviews

Luxury Modern Home on Water+Hotub- Annapolis 25min

Waterside mid-century modern home, perfectly appointed. Join with colleagues, family, and friends. Paddleboard, roast marshmallows, watch fireworks, take a hot tub or team building. Our "Flight Deck" is perfect for meetings and retreats. Breathtaking, peaceful grounds with an abundance of space. Approximately 2800 SF sits on a 3/4 acre property - perfect for lawn games and zip lining. 20x20 furnished deck + dock Mayo Beach and Beverly Triton 1 mile away. Within an hour of the DMV

5.0 out of 5 average rating, 217 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.

A living area features a comfortable sectional sofa and a modern accent chair, centered around a round coffee table. Light wood flooring complements the space, while tall windows are dressed with blue curtains. Decorative lamps and minimalist wall art enhance the room's design.

4.93 out of 5 average rating, 106 reviews

3 BRs House+Patio+Playground

Newly renovated and furnished entire house for your family! Spacious 3 bedrooms 1.5 bathrooms house, large backyard patio with gas grill and your own private playground for your kids! Brand new designer furnitures with a sense of home! Fully functional kitchen and large dining space, perfect to enjoy a great evening with your friends and family! Fit 3 cars in our private driveway. Minutes away from restaurants and grocery stores! 15 mins drive to Downtown Annapolis!

Superhost

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.

4.74 out of 5 average rating, 206 reviews

5.0 out of 5 average rating, 226 reviews

Guesthouse in Annapolis

Coastal Waterfront 1 Bedroom Cottage

Enjoy a peaceful waterfront getaway just 2 miles from Historic Downtown Annapolis and the U.S. Naval Academy. Located directly on the South River in a quiet neighborhood, this charming cottage features a full kitchen, 1 bedroom, washer/dryer, and sleeper sofa for up to 4 guests. Relax on the private patio with outdoor seating, grill, and fire pit, or enjoy the beautiful river views. Perfect for exploring Annapolis or simply unwinding by the water.

4.97 out of 5 average rating, 113 reviews

A spacious great room features large windows that offer sweeping views of the water. Comfortable seating arrangements with soft furnishings are complemented by a working fireplace. A staircase is visible in the background, leading to additional living spaces.

Home in Shady Side

Waterfront Sanctuary only 50 Min. From DC/Balt.

New full home renovation with gourmet kitchen, wide open floor plan, multiple guests rooms, and a bunk room that accommodates 12. An inviting space that welcomes any couple or a large extended family. This home sits with only three other homes on a private peninsula and has water access on both sides. It is conveniently located less than an hour from DC and Baltimore on the west coast of the Bay (no need to cross the Bay Bridge).

A newly renovated home is presented with light grey siding and blue accents. Two spacious decks with white railings create inviting outdoor spaces. Flower beds with blooming plants enhance the entryway, while leafy trees provide shaded areas around the property.

4.98 out of 5 average rating, 109 reviews

Captain’s Retreat! Newly Renovated - Beach House!

Beautiful newly renovated 3500 square foot 4 bedroom 2.5 bath home located in Arundel on the Bay. Steps to the Beach and a large community playground. With three large decks, enjoy nature, sitting with a glass of wine or coffee in the morning. Gourmet Kitchen opens to a deck with plenty of seating to enjoy outdoor entertaining. Perfect for large groups or multiple families. Custom solid wood bunk beds - Twin XL's over Kings!

4.9 out of 5 average rating, 554 reviews

A cozy living area is highlighted by red sofas and a decorative coffee table. A cheerful lamp casts warm light, while natural light filters through windows. The open layout leads to a dining space, accentuated by framed artwork on the walls.

Guest suite in Edgewater

South River Park Apartment

Located minutes from Annapolis, the in-law apartment offers access to Baltimore and DC in under an hour. The apartment offers its own entrance, full kitchen, one bathroom, one bedroom, tile floors, pullout sofa, Wifi, and parking. The apartment is registered with the Anne Arundel County Dept. of Inspections & Permits, #STR-15, for short term rentals.

A bright living room features a dark sofa adorned with decorative pillows, paired with a wooden coffee table on a patterned rug. A decorative wall with framed pictures adds character, while natural light enters through the large windows covered by light curtains.

4.94 out of 5 average rating, 126 reviews

Relaxing Turkey Point Retreat-Steps to the marina!

Relax and unwind at our peaceful retreat by the water. Steps to the marina and Turkey Point Island, enjoy a quiet stay away. Just 20 minutes from downtown Annapolis, with some of the best food in town close by. Whether you’re here for a quick visit or need a place for a longer term stay, we’ve got you covered!

Popular amenities for Edgewater family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 217 reviews

Guest suite in Arnold

Pet-Friendly King Suite + Kitchen | Near Annapolis

4.99 out of 5 average rating, 142 reviews

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

4.97 out of 5 average rating, 100 reviews

A serene waterfront view is captured, featuring lush green grass leading to a private patio area with a hot tub. In the background, a rainbow arches over the water, framed by a cloudy sky. The cozy apartment stands nearby, enhancing the tranquil setting.

Guest suite in Annapolis

Bay View Studio Apartment

4.87 out of 5 average rating, 118 reviews

Cottage in Annapolis

Charming City Retreat. Walk-harbor, eateries.USNA

4.83 out of 5 average rating, 203 reviews

Cottage in Deale

Waterfront Cottage@ChesapeakeParadise Hot Tub/Dogs

4.95 out of 5 average rating, 314 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

A covered porch is shown with a hanging egg chair and a gray sectional sofa. Soft cushions are placed on the seating area. Beyond the railing, the tranquil waters of Chesapeake Bay can be seen, complemented by lush greenery and nearby homes.

4.88 out of 5 average rating, 200 reviews

Charming Annapolis Water View Home

4.86 out of 5 average rating, 438 reviews

A wooden pier extends over calm water, featuring two adirondack chairs positioned at the end. Sunlight reflects off the water's surface, surrounded by green foliage and trees. The view includes distant trees lining the shore.

Bungalow in Deale

Cozy waterfront getaway on the Bay

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 147 reviews

Guest suite in Annapolis

Annapolis Garden Suite

4.98 out of 5 average rating, 155 reviews

Home in Deale

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

A tranquil bedroom features a spacious bed adorned with a patterned throw and neatly arranged pillows. A modern lamp and decorative mirror enhance the ambiance, while natural light enters through a unique shaped window. A soft towel is elegantly rolled on the bed.

4.93 out of 5 average rating, 206 reviews

The Navy House-Walk or Shuttle Downtown! 3 bd

4.97 out of 5 average rating, 473 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

A serene outdoor patio area features manicured hedges and a stone path. A seating arrangement is visible, surrounded by greenery. A colorful flag and artwork hang on the fence, while flowering trees add a natural touch to the space, providing a cozy atmosphere.

4.96 out of 5 average rating, 269 reviews

Historic Downtown in-law suite

4.97 out of 5 average rating, 170 reviews

The exterior of a two-story home is displayed, featuring a light-colored façade, white porch railings, and a chimney. A neatly manicured lawn surrounds the house, complemented by tall trees in the background and a clear blue sky above.

Home in West River

Cozy waterview home in West River!

4.99 out of 5 average rating, 167 reviews

A spiral staircase leads to a lofted sleeping area in a well-lit living space. Warm wood tones are present in the furniture and flooring. A small kitchen area is visible, along with a dining table set for four. Lighting fixtures enhance the modern feel.

Guesthouse in Annapolis

Garden View, 1 Bedroom and a Loft.

A charming single-story house is presented with a light gray exterior and a prominent teal door. Symmetrical landscaping frames the entrance, featuring neatly trimmed hedges and colorful plants. A concrete pathway leads to the front steps, inviting guests into a welcoming atmosphere.

4.94 out of 5 average rating, 119 reviews

Hidden Wine Cellar | Eastport Retreat

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 180 reviews

A living area features a gray couch adorned with decorative pillows against a light wall. A recliner is positioned nearby, and a wall-mounted Smart TV is visible. A dresser with a plant sits below the TV. Natural light streams in through nearby windows.

Condo in Annapolis

1st Floor Condo in Annapolis

Apartment in Stevensville

A modern living area features a light-colored sofa adorned with a teal throw blanket. A round wooden table accompanied by metal chairs is positioned nearby. A decorative mirror and an abstract painting are displayed on the wall, while a stone fireplace adds a subtle touch of warmth.

Boutique by the Bay

4.97 out of 5 average rating, 316 reviews

4.98 out of 5 average rating, 204 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

4.99 out of 5 average rating, 127 reviews

An aerial view captures the expansive property, featuring a large home surrounded by lush green lawns and mature trees. A heated in-ground pool is visible in the backyard, adjacent to a serene water body, with an expansive landscape enhancing the tranquil setting.

Cabin in St. Michaels

True St. Michaels 6 Acre Waterfront w/heated pool

4.99 out of 5 average rating, 255 reviews

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

Superhost

Home in Waldorf

Private Pool | Modern | Lux 4 BR Retreat | Near DC

4.84 out of 5 average rating, 123 reviews

4.99 out of 5 average rating, 129 reviews

Farm stay in Huntingtown

Luxury Farmette -Private & Secluded-1hr to DC