
Alquileres vacacionales en casas en Shady Side
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Casas vacacionales con las mejores calificaciones en Shady Side
Los huéspedes están de acuerdo: estas casas tienen excelentes calificaciones, entre otras cosas, por su ubicación y limpieza.

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.
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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!
FamiliarCalidad-precioParques

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!
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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!
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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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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.
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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!
FamiliarCalidad-precioEspacios interiores

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.
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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.
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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).
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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!
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The Little Gypsy BoHome
Escape to a private Chesapeake Bay retreat with stunning water views and sunsets. Located in peaceful Tracy’s Landing, this coastal home offers relaxed charm and resort-style amenities. Enjoy a saltwater pool, private beach, sauna, steam shower, canoe, and outdoor spaces. Perfect for families, couples, or friends, with easy access to Annapolis and D.C. Relax, recharge, and make unforgettable memories.
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Comodidades populares de las casas vacacionales en Shady Side
Casas vacacionales con piscina

Beautiful Kent Island Getaway with Pool
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Miles Aweigh
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Large Home w/ Private Pool, Gym, Sauna, 7 Bedrooms
Calidad-precioFamiliarCondición

Historic Rousby Hall, Waterfront, Pool, Beach
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*Brand New | Modern Farmhouse | Lux 4 BR | Near DC
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Gorgeous, Waterfront Home Is Perfect for Families!
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Chester Riverfront At Kent Narrows
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Inground Pool | Hot Tub | Sauna | Theme Room
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Casas vacacionales por semana

Kent Island Waterfront Home with Amazing Sunsets
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Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces
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3 BRs House+Patio+Playground
Calidad-precioFamiliarMascotas

Charming Historic 2 Bedrooms on the Chesapeake Bay
Calidad-precioUbicaciónPlaya

Private Waterfront Home W/ Hot Tub, Dock & Kayaks
FamiliarCalidad-precioAcceso

Sunset Breezes - quiet waterfront retreat
FamiliarCalidad-precioCaminata

Charming Coastal/Country Home w/3 Acres & Sauna!
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A Happy Place
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Casas vacacionales privadas

Franklin At The Bay
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Cozy Bayside Retreat
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Private & Peaceful | Water Views, Big Deck, Games
VistaHospitalidadComodidad

Chesapeake Bay Waterfront Escape
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Zen Sunset Retreat (ZSR) on the Waterfront
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Charming Stay Near the Bay- w/Beach Passes!
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Modern Farmhouse | 12.5 Acres & 2 Fire Pits
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The Mermaid Cottage | Walk to Beach | Pet Friendly
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Destinaciones 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
- Parque Nacional
- FedExField
- Universidad Johns Hopkins
- Oriole Park en Camden Yards
- Parque Federal Hill
- Capital One Arena
- Cementerio Nacional de Arlington
- Parque Costero de Georgetown
- Monumento a Washington
- Playa de Betterton
- Museo Nacional de Historia y Cultura Afroamericana
- Puerto Nacional
- CFG Bank Arena
- Howard University
- Smithsonian National Zoological Park
- Centro de Convenciones de Baltimore
- Museo de la Biblia
- Museo Nacional del Aire y el Espacio
- Patterson Park
- Museo de Arte Americano Smithsonian





