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.

4.96 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!

LocationValueIndoor spaces

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!

LocationFamilyHospitality

5.0 out of 5 average rating, 123 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

ValueLocationBathroom

4.99 out of 5 average rating, 152 reviews

A wooden dock extends over calm waters, leading to a charming home surrounded by trees. The house, featuring large windows, is illuminated as dusk approaches. Adirondack chairs are placed along the shoreline, inviting relaxation in the natural setting.

Home in Stevensville

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

FamilyValueOutdoor spaces

4.98 out of 5 average rating, 155 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!

FamilyValueLong stay

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

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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.

FamilyValueBreakfast

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, 102 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!

FamilyValueQuiet

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!

LocationValueCleanliness

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).

FamilyLocationHospitality

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!

LocationFamilyCheckout

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

This special place is close to everything. One block to the Naval Academy and one block to all the historic and downtown attractions. This in-law suite has a queen bed, full bath, sauna, kitchenette, seating area, and desk/dining table. Welcoming separate, quiet entrance with access to a lovely patio with seating and firepit. Twin bed can be set up and made up at guest request.

ValueFamilyAccess

Popular amenities for Edgewater house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 133 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

ValueLocationCheckout

Superhost

A large, two-story home with a welcoming front porch is set amidst a spacious green lawn. The house features a grey exterior with white trim and multiple windows, surrounded by trees and landscaping, creating a peaceful and private atmosphere.

Home in Severn

Large Home w/ Pool, Gym, 7 Bedrooms, Sleeps 21

ValueLocationCheck-in

4.86 out of 5 average rating, 228 reviews

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

LocationValueNearby

Superhost

Home in Waldorf

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

FamilyValueView

4.84 out of 5 average rating, 123 reviews

5.0 out of 5 average rating, 329 reviews

The outdoor area features a circular pool surrounded by colorful lounge chairs in yellow, blue, and white. Umbrellas in red and blue provide shade over a dining table with red chairs. Towering trees frame the view of the expansive waterfront beyond.

Home in Kent Narrows

Chester Riverfront At Kent Narrows

LocationValueDecor

4.96 out of 5 average rating, 140 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!

ValueFamilyGetting around

Superhost

Home in Fort Washington

Inground Pool | Hot Tub | Sauna | Theme Room

LocationValueLaundry

4.89 out of 5 average rating, 231 reviews

4.97 out of 5 average rating, 117 reviews

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.

Home in St. Michaels

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

LocationFamilyAmenities

Weekly house rentals

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!

FamilyValueCheck-in

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

ValueLocationParks

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

ValueLocationParks

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

FamilyLocationGetting around

A shaded seating area is arranged under a gazebo, featuring a woven outdoor sofa and chairs in warm orange cushions. A central fire pit table complements the setting, surrounded by a patterned outdoor rug on a paved surface, with a fenced backyard visible in the background.

4.96 out of 5 average rating, 155 reviews

Nautical Retreat 6 Guests • 3 BDR • 2 Baths

ValueLocationPets

An inviting front yard is presented, featuring a pathway of round stones leading to the entrance of a two-story guesthouse. Lush greenery is framed by ornamental plants and mulched beds, creating a serene outdoor setting surrounded by trees.

4.98 out of 5 average rating, 191 reviews

Quiet Waterfront

LocationFamilyRiver

A two-story blue house features a bright yellow front door and large windows, contributing to its modern curb appeal. The front yard is landscaped with green grass and flower beds. A paved driveway leads to a two-car garage, with a white picket fence visible in the background.

4.96 out of 5 average rating, 28 reviews

Londontowne Home | Beach | 3BR

LocationFamilyWi-Fi

A charming waterfront home is framed by clusters of trees and grasses. A gravel driveway leads up to the entrance, with a large porch visible. The architecture features large windows that allow for plenty of natural light, ensuring a bright and inviting atmosphere.

4.88 out of 5 average rating, 42 reviews

Chesapeake Bay Waterfront Escape

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Private house rentals

4.9 out of 5 average rating, 79 reviews

An open living area is highlighted, featuring a comfortable sectional sofa, a glass coffee table, and several armchairs. Natural light enters through multiple windows, illuminating the hardwood floor and decorative elements. A subtle area rug adds texture, providing a cozy space for gatherings.

Home in Riva

Charming Bright Spacious 3BR 2BT near South River

FamilyValueBarbecue

4.98 out of 5 average rating, 43 reviews

An aerial view showcases the stunning Heron House nestled on a waterfront point, surrounded by lush greenery and water. A spacious deck with outdoor seating and dining is visible, along with nearby boats docked along the shoreline under a twilight sky.

Home in Crownsville

Welcome to Heron House! Annapolis Waterfront Oasis

LocationFamilyBarbecue

A spacious living area is presented, featuring a large television mounted on a light-colored wall. Two comfortable sofas are arranged around a coffee table, with a textured rug beneath. Windows allow natural light to fill the space, complemented by soft furnishings and wall art.

4.97 out of 5 average rating, 90 reviews

Bright & Spacious 3BR/2.5BA Two-Story House

ValueFamilySleep quality

4.97 out of 5 average rating, 71 reviews

A modern kitchen features a large island with seating for four. Natural light pours in through wide windows overlooking the outdoor area. Appliances include a stainless steel refrigerator and a gas stove, while cabinets and shelves display kitchen essentials. The space is open and inviting.

Home in Harwood

Quiet Farm Stay near Annapolis

ValueFamilyNearby

The exterior of a charming, single-story house is depicted, featuring a well-maintained lawn bordered by trees and shrubs. A vibrant red door provides a welcoming focal point. The pathway leads to the entrance, complemented by stairs on either side, indicating accessibility.

5.0 out of 5 average rating, 43 reviews

The Red Door Cottage - Pet-Friendly!

FamilyLocationParks

5.0 out of 5 average rating, 34 reviews

A scenic waterfront view is captured at sunset, showcasing colorful skies reflected on calm waters. Several boats are moored at the docks, with greenery lining the shore. A red kayak rests on the grassy bank, contributing to the serene atmosphere.

Home in Shady Side

A Happy Place

FamilyLocationAccess

5.0 out of 5 average rating, 71 reviews

Home in Stevensville

Away at the Bay: New Home on the Chesapeake Bay!

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