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Chester House Rentals

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    25 Matching Rentals in the Chester AreaView all 38 rentals
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    DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-121 / 30
    (1)Excellent
    Chester
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)1 / 21
    (3)Excellent
    Chester
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Luxury vacation condominum with private beach1 / 35
    (15)Excellent
    Chester
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Chester
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Grill
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    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy all that Kent island has to offer--golfing, fishing, crabbing and the laid back island life!! Beautifully remodeled 4 Bedroom house in a great community close to Rt 50 and mins from the Bay Bridge!! Whether you are on Maryland's picturesque Eastern shore for its beaches & water activities...
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    Chester, Kent Island 21619
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    The following rentals are within 15 miles of Chester.
    Annapolis, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Private Yard
    • DVD Player
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We bought and renovated this rowhouse in 2007 for a second home for friends and family to stay when they visited and it eventually evolved into one of the most popular rental properties in all of Historic Annapolis. A former ' Home of the Week' in the Capital Gazette it is also one of the most...
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    Annapolis, Maryland 21401
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Halos'Haven Vacation Rental1 / 15
    (3)Very good
    McDaniel, MD
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We stayed at Halos Haven for a girls getaway weekend. Location and property were lovely. Great space for large groups. Having rented homes many times in the past, this...
    Reviewed July 13, 2018
    A group of us stayed at this house for a weekend and it was perfect. The pool was a perfect temperature, the kayaks were easily accessible and the view was amazing. We also...
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    About this property
    Halo's Haven is a true piece of Heaven!! Bring your boat and your bathing suit. Twenty picturesque acres on a beautiful point of land off of the Chesapeake Bay near historic St. Michael's, Maryland. This property is beautifully landscaped, has a waterfront pool, pool house with bathroom, boat dock...
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    McDaniel, St. Michaels 21647
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Sailors Crossing1 / 12
    (3)Excellent
    Rock Hall, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 7, 2017
    Beautiful home with many amenities, clean and comfortable. Awesome screened-in porch, great place to enjoy your morning coffee. Community park right behind home with tennis...
    Reviewed August 15, 2017
    House was great. Plenty of room to hang out and have fun with a large group and the grill was a plus. Just down the street from an awesome restaurant on the water and a short...
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    About this property
    Sailors Crossing is a 3 bedroom, 2 bath home located in the heart of Rock Hall. Parking is limited to 3 cars. The dining room seats 6 and the kitchen is roomy enough for several cooks and helpers. If it's crab you're after, the screened porch provides enough room for the group or take the feast out...
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    Rock Hall, Maryland 21661
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Stevensville
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Hot Tub
    • Washer
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Space Newly updated features make this property relaxing and highly desirable! Breathtaking views of the Chester River where it meets the mouth of the Chesapeake Bay on Maryland's Eastern Shore. Beautiful cathedral ceilings with a stone stacked fireplace. This is an entertainers delight or a...
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    Location Information
    Stevensville, Kent Island 21666
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    Beautiful Murray Hill Home (Annapolis)1 / 30
    (3)Very good
    Annapolis, MD
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Washer
    • Grill
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 21, 2015
    Owner has everything imaginable in the home that you would ever need for a vacation getaway. The house has lots of room so you have your privacy when needed. Beautiful...
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    About this property
    Our beautifully-appointed home pays homage to the Colonial Period. It comfortably sleeps eight guests with four bedrooms and 2.5 baths. It boasts elegant dining and living rooms. Enjoy the quiet street and an easy stroll to downtown Annapolis. We have taken great care and paid pain-staking...
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    Location Information
    Annapolis, Maryland 21401
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Cape Saint Claire, MD
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
    • Private Yard
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    located in a safe residential neighborhood with free parking. We are close to shopping, restaurants and the Chesapeake Bay; just minutes drive to the naval academy and downtown Annapolis. Our space is super clean, super spacious, and super comfortable! We are committed to providing you a great...
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    Location Information
    Cape Saint Claire, Maryland 21409
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Cottage 2 at Grandview Pleasure Point1 / 9
    (1)Excellent
    Bozman, MD
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Porch
    • Patio
    • Grill
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, valences, sofas, wing and lounge chairs and collectibles. All the cottages are fully furnished including solaria porch, gas fireplaces,...
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    Location Information
    Bozman, Talbot County 21612
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Charming Home close to historic district1 / 31
    (4)Excellent
    Annapolis, MD
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Wi-Fi
    • Grill
    • Porch
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 19, 2017
    This is a great house to rent with another couple or with a family. The house is Within easy walking distance to all the fun in downtown And the waterfront. It has all the...
    Reviewed August 20, 2017
    We had a lovely stay in this spacious and tastefully furnished house. It was perfect for my husband and I and our three boys (8, 14 and 16). The rooms were larger than I...
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    About this property
    A Charming detached one-family home located in one of the most vibrant neighborhoods of Annapolis. Perfectly located in a quiet residential street, only 0.8 miles from the United States Naval Academy and a short walk from Main street. The home is situated only a few steps away from West street and...
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    Location Information
    Annapolis, Maryland 21401
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stevensville
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Patio
    • Ocean Views
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Picture yourself sipping morning coffee on the deck watching the charter boats get ready for the big stripers, as the dawn breaks over another perfect day. A modern day home with expansive Captains Quarters and Master Bath overlooking the Chesapeake Bay perfect for the fisherman yet classy enough...
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    Location Information
    Stevensville, Kent Island 21666
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    Charming and Spacious Annapolis Victorian1 / 19
    (6)Excellent
    Annapolis, MD
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Air Conditioning
    • Parking
    • Grill
    • Wi-Fi
    • Washer
    • Porch
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Great house, lots of space everything you want, nice small touches. Owner is very responsive to questions and very friendly. Highly recommended and we would use it again.
    Reviewed May 17, 2018
    Home had lots of rooms in various configurations which were great for our multi-generational family visit. Even toys for the toddlers! Host super helpful, even found us a...
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    About this property
    The Perfect House for a Navy Football Game Weekend!! This is a beautiful historic property within walking distance of downtown Annapolis and the Navy-Marine Corps Stadium. With six bedrooms (two queen beds, three fulls and two twins) the house could comfortably sleep up to 12. Additional rooms...
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    Location Information
    Annapolis, Maryland 21405
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Rock Hall, MD
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Parking
    • Air Conditioning
    • Washer
    • Grill
    • Private Yard
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on one of the prettiest streets in Rock Hall, the Bay Cottage offers 2 bedrooms and 1 full bathroom. A fully equipped kitchen, gas grill and outdoor seating pulls the family together for mealtimes or enjoy our local restaurants which are just a short walk. Pets are welcomed on this fenced...
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    Location Information
    Rock Hall, Maryland 21661
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Annapolis, MD
    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Grill
    • Balcony
    • Terrace
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming Annapolis home, just 150 feet from the water, with floor to ceiling windows overlooking the expansive waters of the Chesapeake Bay. Water views from almost every room. Features 4 bedrooms and 4 bathrooms with luxury upgrades, viking kitchen appliances, comfortable couches for sleeping...
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    Location Information
    Annapolis, Maryland 21403
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    Waterfront House, Eastern Shore Chesapeake Bay1 / 34
    (22)Excellent
    Centreville, MD
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Air Conditioning
    • Porch
    • Cable/satellite TV
    • Grill
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We welcome your inquiries and would be glad to answer any questions you have before booking. In response to inquiries and booking requests, we will send you our standard rental agreement for your information and approval. This house is on the estate of John Raskob, builder of the Empire State...
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    Centreville, Maryland 21617
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Annapolis, MD
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Waterfront
    • Patio
    • Washer
    • Grill
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your family will thank you for choosing this Severn River Waterfront Retreat for Vacation! From the moment you enter this 5 bedroom home you will appreciate the spectacular views of the Severn River. Four of the five bedrooms view the Severn River, so your family will love waking up to views of...
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    Location Information
    Annapolis, Maryland 21032
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    Walk to Shops/Eateries Charming Cottage. Dogs Wel.1 / 51
    (2)Excellent
    Annapolis, MD
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Grill
    • DVD Player
    • Housekeeping Included
    • Patio
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2017
    We stayed at the cottage for an extended period of time and it was very enjoyable. The house itself was well put together and had everything that we could have needed. The...
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    About this property
    This City-inspected vintage cottage in Upper Eastport, located on a cul de sac, is a short walk to the Historic Harbor & just blocks from Spa Creek. History, waterfront, rooftop restaurants, wine bars, sailing, kayaking and more. We have everything here in Annapolis - USNA, sailing, culture,...
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    Location Information
    Annapolis, Maryland 21403
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Annapolis, MD
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Yellow House is a magnificent Waterfront Property, with interior and exterior appointments, that are truly outstanding-76 five Star reviews can be viewed on our sister site-vacation rentals by owner dot com. 230476 With its magazine worthy gardens, and spacious 6 bedrooms, designed and...
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    Location Information
    Annapolis, Maryland 21403
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    Main House at Grandview at Pleasure Point1 / 34
    (12)Excellent
    Bozman, MD
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    What a terrific week we had . Young and old enjoyed our stay. Perfect weather and plenty of crabs made our visit special. Grandview is the perfect family vacation spot.
    Reviewed June 19, 2018
    The drive way to Grand View Cottages is gravel right beside a cemetery on the left of MD 579-S. I am describing this so you would not pass it thinking the next asphalted...
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    About this property
    Main House: Beautiful NEW kitchen... Featuring two interior eating/serving areas, custom french windows that open to a sitting area on the porch, 4 bedrooms & Enclosed Sleeping Porch 2 ½ baths, fireplace, 3 TV’s, DVD, cable, wireless internet, large living room, dinning room, screened porch,...
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    Location Information
    Bozman, Talbot County 21612
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    Bozman, MD
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The ambiance of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, new sleep sofas, wing chairs and sleeper lounge chairs, as well as antiques, reproductions and other eclectic furnishings All the...
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    Bozman, Talbot County 21612
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Charming Townhouse - Steps to City Dock and USNA1 / 7
    (1)Terrible
    Annapolis, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Outdoor Dining Area
    • DVD Player
    • Central Heating
    • Internet Access
    • Grill
    • Patio
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Shellback house is a three bedroom, one and 1/2 bath historic townhouse in the heart of Downtown Annapolis with a private garden. The house has views of Ego Alley (Annapolis Waterfront) from the front stoop and the master bedroom. BOOK NOW FOR 2015 LEGISLATIVE SESSION AT STIPEND RATES! Please...
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    Location Information
    Annapolis, Maryland 21401
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Annapolis, MD
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Private Yard
    • Parking
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk to historic City Dock, waterfront restaurants, U.S. Naval Academy. Open, sunny floor plan ideal for entertaining. Craftsman style 3 BRM + den + office + front porch swing + screened back porch + game room + ample parking. Well-furnished. Sleeps 6-8 comfortably or up to 10 with available...
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    Location Information
    Annapolis, Maryland 21403
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Annapolis, MD
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • DVD Player
    • Balcony
    • Washer
    • Parking
    • Porch
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    HOUSE This fully renovated, circa 1890 ,Victorian house is located in the middle of the Eastport peninsula . The house is within walking distance, or a three minute taxi ride, to downtown historic Annapolis and the US Naval Academy, as well as shopping, several marinas, theater, numerous...
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    Location Information
    Annapolis, Maryland 21403
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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