House holiday 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.

4.95 out of 5 average rating, 262 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!

Guest favourite

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, 181 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!

5.0 out of 5 average rating, 119 reviews

Modern Annapolis Getaway - 2 Free Parking Spaces

Modern 2 bedroom, 1 bath home located in the heart of historic Annapolis. Completely remodeled with free off-street parking. Located towards the end of a safe, quiet, dead end road, less than 3 miles from downtown Annapolis, the Naval Academy, the Annapolis Mall, St. John’s College, and the Navy-Marine Corps Memorial Stadium. Walk downtown or to the Annapolis Town Center, restaurants, shops, and so much more! -Wi-Fi -2 free parking spaces -Keurig Coffee -TV -Toothbrushes/Paste -Shampoo/Soaps

4.98 out of 5 average rating, 151 reviews

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!

A charming single-story cottage is presented, featuring a light-colored exterior and a welcoming front door. Dense greenery surrounds the home, while vibrant pink azaleas bloom in the foreground. A gravel pathway leads to the entrance, adding to the home's inviting curb appeal.

4.98 out of 5 average rating, 226 reviews

3BR/2BA Annapolis Cottage

Our cottage is located a little over a mile from downtown Annapolis, on a quiet peninsula close to the water. It is a short car ride to the heart of downtown and we have plenty of off-street parking. The trail can be used to walk/bike downtown and to Navy Stadium. The home recently had a complete renovation with an all-new kitchen, bathrooms, and hardwood floors throughout. Enjoy a tree-lined backyard with deck and gas grill. A clean comfortable space to relax while you enjoy Annapolis.

Guest favourite

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

A spacious living area showcases a comfortable sectional sofa and a leather armchair beside a decorative rug. A modern fireplace is framed by a white mantel, while a large television is mounted on the wall. A view of the stylish kitchen is visible in the background.

4.98 out of 5 average rating, 101 reviews

Downtown Annapolis Luxury House

Our downtown luxury Annapolis getaway is located 1.4 miles from Church Circle, which is the heart of downtown Annapolis. We are walking distance to all the amazing attractions in Annapolis. Our house is a lovely blend of comfort and style, making it an ideal retreat for families, friends, or colleagues traveling together! We are happy to offer early check-in and late checkouts if our bookings allow. Please contact us today and reserve our house for your next Annapolis getaway!

5.0 out of 5 average rating, 214 reviews

Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

Summer at The Cottage at Silver Water is effortless and indulgent. A sweeping waterfront lawn leads to a private shoreline for swimming, kayaking, and long days in the sun. Evenings bring golden skies, spectacular sunsets, and fires by the water’s edge. Inside, the cottage is beautifully designed with luxurious bedding, curated art, and thoughtful amenities that make every stay relaxed, refined, and unforgettable. See why all our guests only have a 5-Star experience.

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, 103 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!

4.97 out of 5 average rating, 168 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!

Your family will be close to everything when you stay at this centrally-located place. This home is located just 15 miles to Annapolis, 18 miles to the Naval Academy, and 30 miles to the heart of Washington, DC. Less then 8 miles to Rt 214, providing direct access to beltway, and other major highways. This charming home has as spacious fenced in yard, High Speed Internet, TV (Netflix & Hulu), outdoor seating and a fire pit. Want to get away? Bring the whole family!

4.97 out of 5 average rating, 110 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).

Guest favourite

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.