Rent a Vacation Home: Hotels and Bed and Breakfasts are nice, but sometimes you want the room, freedom and amenities that a vacation home provides. We are happy to provide a selection of Chesapeake Bay region homes available as vacation rentals. When you click on the "more information" links below, you will be taken to the Vacation Home Rentals  website, where you can make booking arrangements. A Chesapeake Bay vacation rental house may be the perfect option for family gatherings, reunions, or just a quiet getaway. Many of the vacation rentals available are waterfront, while others have convenient downtown locations. Rentals vary in size from cottages to large luxury properties. Please take a look at the rentals listed below. Vacation Rental Owner?  Join Vacation Home Rentals and attract renters to your property.
 
Three Bedroom Restored Waterfront Cottage, St. Michaels, MD Charming beautifully restored 100 year old cottage is surrounded by waterfront. Beautiful views from all sides. Rent boats and catch crabs. The house has its own pier. Perfect location between Easton and St Michaels only 1 1/2 hours from Baltimore or Washington. Spend a relaxing vacation at the River House. The house has central AC, high speed cable internet and TV, washer/dryer, new kitchen, and all amenities. Beautiful sun porch and two decks. The house also has 3 full baths. The house has a fireplace. More Information.
 
Waterfront Estate -Duxburry Point Manor with pool & dock, St. Michaels, MD This enchanting Manor home overlooking the broad waters of Leadenham Bay, has a pool, a dock (with a covered boat house) and a floating 18ft dock to tie the canoes and kayaks up to.. Surrounded by tall, shady trees and wonderfully landscaped gardens, this ?Lady of the Bay? home as we call it, offers privacy and comfort with incredible style.
With 5 bedrooms (all en suite), a formal living room, dining room, large eat in farmhouse kitchen and a wonderful screened-in porch, along with an outside deck, this home exudes all the warmth and comfort of an English country house - it is not easy to leave Duxbury!!
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Leeds Creek Manor. Waterfront with Pool, Dock, Tennis Court, St. Michaels, MD The Manor on Leeds Creek. This Eastern Shore colonial (circa 1800) is one of the most private and prestigious vacation rental homes in Talbot County. The Manor is surrounded by 35 acres of woods and farmlands with breathtaking water views, a private cove, dock, boat house, large pool and tennis court.
The flowing layout of five bedrooms, 4 bathrooms, formal dining and living rooms, large eat in kitchen, library/den and screened in porch look out over rambling landscaped grounds to the waters of Leeds Creek. More Information
 Romantic Vacation Cottage, Tilghman Island, MD Ideal accommodations for a truly memorable honeymoon or intimate celebration, this newly remodeled cottage sits quietly across the bridge on Tilghman Rd just 10 miles outside of beautiful St. Michaels. The property features a modern & fully equipped kitchen, all new appliances, brand new carpet, flooring & fixtures throughout, washer/dryer, linens, full bath/shower + a very private and lovely fenced yard, front & rear decks, as well as an outdoor "crab steamer." More Information.
 Romantic Waterfront Sunsets, Kent Island, MD This wonderful waterfront retreat provides spectacular sunset views over the Chesapeake Bay. Enjoy and relax on the dock, by the pool or in the hot tub. If you have a boat, arrangements can be made to tie up at the Marina just one block away. Only an hour from downtown Washington or Baltimore, you can use this relaxing location to explore museums, fine restaurants or go to the Atlantic Shore beaches. Historic Annapolis is also just across the Bay. Jet ski rentals are also nearby. But you will likely find it hard to leave the tranquility and the majestic views of the incredible Chesapeake.
The house has two bedrooms, living room, kitchen, loft, screened porch and three full baths. Sleeps 7 in 1 king, two queen and one single bed. Master bedroom has king and private bath. Second bedroom has two queen beds. Loft has a day bed and generous game area for kids.
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 Chesapeake Bay Luxury Vacation Home, Kent Island, Md Welcome to Baydreams vacation home, a luxury waterfront vacation home situated near the Kent Narrows in Queen Anne's County, on the Eastern Shore of Maryland. Book the comfort and convenience of a 4 bedroom home offering a unique lodging to the discriminating traveler that other accommodations do not. Enjoy a few quiet and relaxed days with someone special, close friends or family on the grandeur of the three mile wide Chester River with your own scenic balcony, deck and pier, an oasis when you just want to be away from it all for awhile. Sleeps 10 adults. Welcome to your hideaway on a safe and quiet street where you are conveniently located near everything an Eastern Shore vacation has to offer. Newly decorated interior with nautical themes and a carefully landscaped exterior make Baydreams your waterfront home away from home. Layback into one of our Adirondack chairs as you lie next to the bubbling, heated hot tub and spot seagulls diving for fish in the distance. Relax on your private deck. Take a nap in the plush king, or queen beds or have a seat at the backyard tiki bar while enjoying a glass of tea. Leisurely prepare full course meals in the kitchen designed after a ships galley. Entertain with the available games in the scenic family room. Go canoeing or rowing off your private ramp into the Chester River. Use our bicycles to go on a little adventure. Kent Island has a 5 mile wooded and paved bike trail.
The main home, Baydreams (3Bedroom, 2 bath) can be rented to smaller parties of 6 or less at a lower nightly rate for those who do not need the Bay Cottage Suite. The Suite features a separate bedroom with a plush King Bed, full functioning eat in kitchen, waterfront Living Room with pull out Queen sleeper sofa, a fireplace and panoramic views of the Chester. There is also a full bath and screened in porch and use of the laundry facilities. More Information.
 Lovely waterfront home on South River Chesapeake Bay, Annapolis MD You'll love the stunning 180-degree view of the South River, just off the Chesapeake Bay near Annapolis. The location is incredible. Just six miles from Annapolis and the United States Naval Academy. The home is 15 miles from Baltimore/Washington International Airport and 40 minutes to Washington, D.C. (15 miles to the nearest Metro stop). The home feels so secluded yet it is just minutes away from great restaurants, shopping and marinas. The house is in a quaint, quiet neighborhood, perfect for evening strolls and morning walks. More Information
  Waterfront Home with New Dock Mill Creek, Patuxent River Bring your boat to this waterfront home on Mill Creek, a major tributary of the the Patuxent River. The large brick home has 3 bedrooms and 2 full bathrooms, a sunroom, eat-in kitchen, dining room, air conditioning, garage and laundry facilities. The spacious deck faces the new dock, which has a 4-6 foot depth. The lush one + acre of land is plenty of space for sunning, picnicing, and watching the boats pass by. Downtown Solomons Island is less than five minutes away and the Chesapeake is less than 10 minutes by boat. More Information
 Circa 1795 restored townhouse in Fells Point, Baltimore, MD Lancaster House is a completely restored 1795 townhouse in the heart of Baltimore's fascinating Fells Point historic district. The house retains the character of a 200+ year old building, but has been completely updated and tastefully furnished. More Information
 Row House - Inner Harbor, Convention Center, Camden Yards Baltimore, MD Beautifully rehabbed 150 year old Row House on one of the most beautiful blocks in Baltimore. The front features a street full of Bradford Pear Trees, best seen in early spring....out back you'll find a 10 x 15 deck overlooking a quaint back yard, a parking pad for 1 car, and a small neighborhood park just steps away....views of both Camden Yards and Raven's Stadium from the rear deck.
On the inside you'll find 2400 square feet of contemporary loft style living! More Information
 Harbor Cottage with quiet beach famous for fossils St. Leonard, MD Delightful cottage on Flag Harbor with view of the Chesapeake and a short walk to the large sand beach, great for swimming, boating, fishing, fossil hunting, walking. Harbor and bay view from the deck, fully equipped with quality furnishings and complete kitchen. AC and heat. Two queen beds and one full sized sleep sofa.Well behaved dogs only, please. Museums, restaurants, antiques, golf, state parks, hiking trails, charter/rental boats all nearby. Only 1 hour from Washington DC. More Information
 "The Bay Breeze Cottage II" at the Chesapeake Bay 2 Miles East of Chesapeake Bay Bridge Tunnel - Ocean Park, VA Beach "The Bay Breeze Cottage II", a two-bedroom duplex cottage, is conveniently located just two miles east of the Chesapeake Bay Bridge Tunnel in the bayside community of Ocean Park. Only a three-minute stroll to lovely Lynnhaven Beach, the cottage is located at 2247 Powhatan Avenue, Virginia Beach, Virginia 23455.
The cottage offers two spacious bedrooms with comfortable queen beds, plus a deluxe inflatable queen that may easily set up in the large great room. The great room is highlighted with natural yellow-pine wainscoting, a large sectional sofa and a 52" big-screen television with DVD player. The bright eat-in kitchen is fully equipped with a appliances including a dishwasher.
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 "The Bay Breeze Cottage III" 2 Miles East of the Chesapeake Bay Bridge - Virginia Beach, VA "The Bay Breeze Cottage III" lies in the bayside community of Ocean Park on a quiet street lined with native water oaks, just steps from the wide Ocean Park Beach. From the beach, you'll enjoy awesome views of the Chesapeake Bay Bridge Tunnel as well as Cape Henry and Fort Story.
The cottage consists of two attached units...the front cottage has two bedrooms and one bathroom, a roomy great room highlighted by yellow pine wainscoting, and a fully-equipped kitchen. There's a small private side yard for lounging and grilling. The rear unit provides three bedrooms, a bath an a half, a large great room accented with yellow pine wainscoting, a dining room, and a fully-equipped kitchen. Outside is a private fenced yard shaded by an ancient water oak. Best of all, a spacious ( 16' X 28' ) new deck provides lots of space for outdoor living.
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SUN-E-BANK GUESTHOUSE - Minutes from Marinas Reedville, VA Home sits on 1/2 acre property. First level has one bed room with twin beds, large living room with a queen sofa bed, large dinning room, bathroom, a Florida room, a den with one double size sofa bed, and kitchen. The kitchen is stocked with everything you need to serve a meal. The second level has two bedrooms. One bedroom has four twin beds, the other three twin beds. Located in Northumberland County on the Chesapeake Bay you are minutes from marinas, and the historical town of Reedville. The town offers waterfront dinning and The Fishermans Museum. Stroll down Main Street where you will find Historical Homes and sites going back before the turn of the century.
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3 Story Beach House Overlooking the Chesapeake Bay, Cape Charles, VA Great Beach house, called "THE VIEW", with a 55' x 10' wrap around porch 1 lot off the town beach on the Chesapeake Bay. This 3 story house has 2nd story deck that allows 2 second floor bedrooms to open onto second floor deck overlooking the beach and Chesapeake bay. The second story also has a Master Suite with a den and master bath with Jacuzzi tub and separate shower. The house also has a separate garage with rentable 1 bedroom apartment above the Garage. The house is golf cart distance to 1 Arnold Palmer and 1 Jack Nicholas Golf courses and equidistant to a 280 slip Mariner with 3 restaurants and shopping Plaza. More Information.
 Nottingham Cottage- Beach town Chesapeake Bay, Cape Charles, VA Restored home in quaint Chesapeake Bay beach town featuring signature golf and luxury marina w/ pool of "Bay Creek". 3 bedroom 2 full bath restored home w/ all new everything.
Why not stay-in luxury? More Information
 "Alexander's Cottage" Cape Charles, VA Stay in one of the first homes in town. The home has been renovated, but still retains the Victorian charm of yesteryear. Delightful master suite with king size bed and footed tub. Two additional queen bedrooms with bath. In addition, 2 roll away beds. Come enjoy the unique experience of Cape Charles. We are a small Victorian town that can offer you a great get away adventure. More Information
 Hawthorn Cottage, 2 blocks from the beach, Colonial Beach, VA Hawthorn Cottage, just 90 minutes away from the Washington, DC area, is the perfect weekend escape from the hectic hustle and bustle of the city. This cozy 3 bedroom, 1 bath Cottage is located in the town of Colonial Beach just steps away from the water and within walking distance to the towns amenities. More Information.
 Twin Maples Cottage, 3 Bedrooms Colonial Beach, VA Twin Maples Cottage is a spacious and comfortable *pet friendly* vacation cottage in Colonial Beach, close to town and the beach/boardwalk. Colonial Beach is a golf cart community on the Potomac River. It is surrounded by an area rich in our country's history. Antique/second-hand shops, great restaurants, coffee shops, wineries, state parks, and historical sites are all within either walking distance or a short driving distance from the cottage.
The cottage has three bedrooms and two full bathrooms. There are two large screened in porches, and a fenced-in yard for your dogs or kids to play in.
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Griffin Cottage - Water view 2 Bedroom Cottage Colonial Beach, VA Water view 2bdr, 1 bath cottage with spacious yard facing the Potomac River. Eat in kitchen, living room, large deck for entertaining. 1 Queen Bed, 1 Double Bed, 1 Sofa Bed. Air Conditioning. Located in the portion of town which allows golf cart use. Golf cart and bicycle rentals available nearby. More Information
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