
Renta de casas vacacionales en Shady Side
Busca y reserva casas únicas en Airbnb
Las mejores casas en Shady Side
Los huéspedes están de acuerdo: estas casas tienen excelentes calificaciones por su ubicación y limpieza, entre otros aspectos.

Chesapeake Waterfront-3 En Suites-Fire Pit-Kayaks
There's nothing like being directly on the water! Relax and rejuvenate in this Chesapeake waterfront estate home which includes private pier, hot tub and fire pit. Crab or fish off the pier or take the kayak out to see the Chesapeake bay wildlife. Try out paddle boarding! Sit around the fire pit at night or watch the stars at night while soaking in the hot tub. Cook wonderful meals in our well-equipped kitchen. Or try some our local restaurants. Great place for families or multi family groups.
FamiliarUbicaciónJacuzzi
Calificación promedio: 4.99 de 5; 181 evaluaciones
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!
ValorUbicaciónLavandería
Calificación promedio: 4.95 de 5; 266 evaluaciones
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!
UbicaciónFamiliarEspacios exteriores
Calificación promedio: 4.98 de 5; 184 evaluaciones
Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home
Fabulous 4-5 bedroom 3-bath (majority of a larger house) with spectacular views on a lush, waterfront point! Shady waterfront lawns & sunny pier, breezy open spaces, sparkling views & wildlife. Couples & groups love our wonderful, nature-filled spot, a fun, relaxing, serene retreat on the WEST shore of the Chesapeake (close proximity to D.C., Annapolis, Baltimore)! Crabbing, kayaks, fire pit, and hot tub on two country-like acres. See “NEW Amazing” for whole 6-7 bed 4 ba listing of same house.
UbicaciónFamiliarPrecisión
Calificación promedio: 4.85 de 5; 104 evaluaciones
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.
ValorFamiliarCalidad del sueño
Calificación promedio: 4.99 de 5; 151 evaluaciones
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!
ValorFamiliarDistribución
Calificación promedio: 4.98 de 5; 153 evaluaciones
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
ValorUbicaciónDecoración
Calificación promedio: 4.99 de 5; 145 evaluaciones
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.
ValorFamiliarCerca
Calificación promedio: 5.0 de 5; 216 evaluaciones
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!
ValorUbicaciónLimpieza
Calificación promedio: 4.97 de 5; 169 evaluaciones
Waterfront w/ Private Pier, 35 Mins to Annapolis
Shady Side is a quaint town located 35 min. from Annapolis and an hour from Washington, D.C or Baltimore. This waterfront home is perfect for families or small groups looking for a relaxing getaway on the Chesapeake Bay. Enjoy the wrap-around screened porch, private pier with ladder for swimming, large yard, and an incredible view of the Bay Bridge. Free public boat ramp 5 minutes away in Parish Creek. Listed for 8 people max. Contact us for approval of 1-2 more.
FamiliarValorAcceso
Calificación promedio: 4.91 de 5; 123 evaluaciones
Hannah’s Hideaway
Cottage style with water view of Rockhold Creek. Water taxi right out front of house to take you to local restaurants. Crabbing excursions or fishing charters available for extra cost. Dog friendly. Local restaurants all within 1 mile from location. Fenced in back yard. Picnic table and fire pit to have own personal crab feasts or cookout. Many local restaurants with outside musicians.Grocery store and gas/liquor stores within 5 minutes from house.
UbicaciónFamiliarHospitalidad
Calificación promedio: 4.99 de 5; 161 evaluaciones
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).
FamiliarUbicaciónWifi
Calificación promedio: 4.97 de 5; 112 evaluacionesAmenidades populares de las casas en Shady Side
Casas con alberca

The Little Gypsy BoHome
ValorFamiliarVista
Calificación promedio: 4.99 de 5; 255 evaluaciones
Beautiful Kent Island Getaway with Pool
UbicaciónFamiliarHospitalidad
Calificación promedio: 4.97 de 5; 133 evaluaciones
Historic Rousby Hall, Waterfront, Pool, Beach
FamiliarUbicaciónRío
Calificación promedio: 4.99 de 5; 178 evaluaciones
Large Home w/ Pool, Gym, 7 Bedrooms, Sleeps 21
FamiliarUbicaciónMascotas
Calificación promedio: 4.86 de 5; 226 evaluaciones
Private Pool | Modern | Lux 4 BR Retreat | Near DC
ValorUbicaciónHospitalidad
Calificación promedio: 4.84 de 5; 122 evaluaciones
Gorgeous, Waterfront Home Is Perfect for Families!
UbicaciónValorCerca
Calificación promedio: 4.96 de 5; 140 evaluaciones
Inground Pool | Hot Tub | Sauna | Theme Room
UbicaciónValorWifi
Calificación promedio: 4.89 de 5; 231 evaluaciones
Chester Riverfront At Kent Narrows
ValorUbicaciónEspacios exteriores
Calificación promedio: 5.0 de 5; 328 evaluacionesCasas disponibles por semana

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces
FamiliarUbicaciónCerca
Calificación promedio: 5.0 de 5; 189 evaluaciones
Luxury Waterfront Annapolis/ Private Beach & Dock
ValorFamiliarPlaya
Calificación promedio: 5.0 de 5; 147 evaluaciones
Huge 4 BR Beach House | Fire Pit | Fenced Yard
ValorUbicaciónBaño
Calificación promedio: 4.97 de 5; 197 evaluaciones
Sunset Breezes - quiet waterfront retreat
ValorUbicaciónHospitalidad
Calificación promedio: 4.99 de 5; 227 evaluaciones
Captain’s Retreat! Newly Renovated - Beach House!
UbicaciónFamiliarAccesibilidad
Calificación promedio: 4.98 de 5; 109 evaluaciones
Charming Historic 2 Bedrooms on the Chesapeake Bay
FamiliarValorSalida
Calificación promedio: 4.9 de 5; 114 evaluaciones
Charming Annapolis Water View Home
UbicaciónFamiliarCocina
Calificación promedio: 4.87 de 5; 199 evaluaciones
Nautical Retreat 6 Guests • 3 BDR • 2 Baths
FamiliarValorDistribución
Calificación promedio: 4.96 de 5; 154 evaluacionesCasas privadas

West River Waterfront w/ Pier, Kayaks & Bay Views
FamiliarUbicaciónTranquilo
Calificación promedio: 4.83 de 5; 23 evaluaciones
Peaceful Coastal Escape | Water Views + Hot Tub
UbicaciónFamiliarTV
Calificación promedio: 5.0 de 5; 17 evaluaciones
The Wise Quack 2 - A Taste of the Chesapeake Bay!
FamiliarUbicaciónAccesibilidad
Calificación promedio: 4.89 de 5; 38 evaluaciones
Franklin At The Bay. Bay Adventures!
FamiliarUbicaciónLlegada
Calificación promedio: 4.85 de 5; 27 evaluaciones
Cozy Bayside Retreat
UbicaciónHospitalidadCalidad del sueño
Calificación promedio: 5.0 de 5; 5 evaluaciones
Private & Peaceful Water Views, Big Deck, Games
UbicaciónTranquiloAcceso
Calificación promedio: 5.0 de 5; 6 evaluaciones
Kent Island Waterfront | Swim Spa + Sauna + Beach
ValorUbicaciónTranquilo
Calificación promedio: 5.0 de 5; 28 evaluaciones
Chesapeake Bay Waterfront Escape
FamiliarValorEspacios exteriores
Calificación promedio: 4.88 de 5; 41 evaluacionesDestinos para explorar
- Nueva York Alquileres vacacionales
- Filadelfia Alquileres vacacionales
- Washington Alquileres vacacionales
- Ocean City Alquileres vacacionales
- Pittsburgh Alquileres vacacionales
- Virginia Beach Alquileres vacacionales
- Raleigh Alquileres vacacionales
- Jersey City Alquileres vacacionales
- Newark Alquileres vacacionales
- Baltimore Alquileres vacacionales
- Richmond Alquileres vacacionales
- Atlantic City Alquileres vacacionales
- M&T Bank Stadium
- National Mall
- Casa Blanca
- Centro de Convenciones Walter E. Washington
- Nationals Park
- FedExField
- Universidad Johns Hopkins
- Federal Hill Park
- Oriole Park en Camden Yards
- Capital One Arena
- Cementerio Nacional de Arlington
- Parque Costero de Georgetown
- Howard University
- Playa de Betterton
- Monumento a Washington
- Museo Nacional de Historia y Cultura Afroamericana
- National Harbor
- CFG Bank Arena
- Centro de Convenciones de Baltimore
- Smithsonian National Zoological Park
- Museo de la Biblia
- Museo Nacional del Aire y del Espacio
- Museo de Arte Americano Smithsonian
- Parque Patterson





