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Chester Vacation Rentals

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    Don't let other travellers get your favourite Chester area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 43 Rentals in Chester
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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
    (13)Excellent
    Chester
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    The following rentals are within 25 kilometres of Chester.
    Charming and Spacious Annapolis Victorian1 / 24
    (3)Excellent
    Annapolis, MD
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Waterfront House, Eastern Shore Chesapeake Bay1 / 34
    (21)Excellent
    Centreville, MD
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Air Conditioning
    • Porch
    • 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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Stevensville
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Ocean Views
    • Patio
    • Balcony
    • Washer
    • Central Heating
    • Terrace
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to our beautiful vacation home and enjoy the scenic view while having fun on the water. Love Point Bay Vacation Home is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. You will feel right at home, yet free of your everyday stress. Leave...
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    Stevensville, Kent Island 21666
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Beautiful Eastport Home, Walk to Naval Academy1 / 15
    (2)Excellent
    Annapolis, MD
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Terrace
    • Air Conditioning
    • Patio
    • Balcony
    • Wi-Fi
    • Secure Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 November 2016
    Beautifully decorated. Walking distance to Naval Academy. Plenty of sleeping space. Private outdoor space.
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    About this property
    Walk to the city docks and naval academy in this new (2014) luxury townhouse. The king bedroom suite also has a pullout twin bed for parents with small children. Enjoy the grand piano or relax by the gas fireplace. Cookout on the sunny patio. Visit local pubs and restaurants or just walk to...
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    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
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    Waterfront Cottage at Spring Cove1 / 15
    (2)Very good
    Rock Hall, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 September 2014
    My sisters and mother stayed three nights in this quaint house with great views of one of the marina's and cove area. The downstairs was perfect my mother, with a screened in...
    Reviewed 19 August 2014
    My family was looking for a relaxing getaway that would be an alternative to another week at the beach. We found the perfect spot at this cottage near Rock Hall. We rented with...
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    About this property
    The Cottage takes advantage of its unique environment with a large deck overlooking the extensive lawn and the tranquil waters of Spring Cove. The deck includes a dining set and barbeque grill.The first level includes a screened porch accessed through a first floor bedroom The Cottage is oriented...
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    Rock Hall, Maryland 21661
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    *BOOK NOW* Beautiful Cottage in historic Annapolis1 / 25
    (17)Excellent
    Annapolis, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Porch
    • Grill
    • Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2017
    My family just moved here in December 2016 and we needed a place to stay for a new months. It turned into 6 months and Alka B. was a wonderful landlord and was very helpful with...
    Reviewed 13 July 2017
    The location is amazing, especially for Navy football games! Plus the owner is right next door and very responsive for any questions or needs. Very accommodating and helpful...
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    About this property
    Half a block to walk to the Naval Academy Stadium and minutes away from stunning Annapolis town center. This adorable little cottage has lots of sleeping and great outdoor space. <BR>Sun Porch & Plenty of parking.<BR>A perfect place to relax and enjoy Annapolis, the property is available all year...
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    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Annapolis, MD
    3 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Washer
    • Internet Access
    • Patio
    • Balcony
    • Air Conditioning
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 September 2016
    Location quiet with good views.Disappointed that house was advertised with hot tub which was one of the main reasons this home was selected, and there was no hot tub. Owner...
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    About this property
    The ultimate Maryland retreat awaits you when you stay at this beautiful 3-bedroom, 3.5-bathroom vacation rental home on Oyster Creek. Up to 9 lucky guests will enjoy incredible views of the Chesapeake Bay and unbeatable maritime location close to the beach, boating, and fresh seafood. Whether you...
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    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 9
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    Captain's Quarters, a waterfront  couples retreat1 / 12
    (1)Excellent
    Rock Hall, MD
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 January 2017
    Lovely, comfortable,clean, friendly with direct access to dock and bay. Lovely views from the many windows. Space is bright and modern while still sortingva large claw foot tube...
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    About this property
    Enjoy the gentle tidal waters of the Chesapeake Bay and its tributaries from your private overlook. The Captain’s Quarters at Spring Cove is a crisp and contemporary second floor living space with great water views. An exterior stairway leads to an ample deck where you can enjoy breakfast and...
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    Rock Hall, Maryland 21661
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Cape Saint Claire, MD
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Satellite TV
    • Private Garden
    • 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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    Cape Saint Claire, Maryland 21409
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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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
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 June 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.<BR><BR>We have taken great care and paid pain-staking...
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    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Charming Home close to historic district1 / 29
    (2)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
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 December 2016
    My two friends and I wanted a place to get away close to our homes in PA and we found it.Annapolis provided everything we were looking for and the house was beautiful and...
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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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    Annapolis, Maryland 21401
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Annapolis, MD
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Waterfront
    • Patio
    • Washer
    • Grill
    • 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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    Annapolis, Maryland 21032
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    Spacious, Modern Condo nr. Navy Stadium, downtown & Mall . Easy access route 501 / 6
    (2)Excellent
    Annapolis, MD
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Terrace
    • Satellite TV
    • Parking
    • Wi-Fi
    • DVD Player
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 June 2014
    We really enjoyed our stay at your condo. It was roomy and felt like home. It is in a very nice condo community which was very quiet. It was nice being able to cook and see into...
    Reviewed 12 November 2013
    My family of four stayed there for the weekend. We were there to watch the Navy-Hawaii football game. We could not find any hotel rooms in/around Annapolis that could host a...
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    About this property
    Large, open third floor condominium with cathedral ceilings. Large master bedroom has queen bed. 2nd bedroom has queen size bed. Large loft has two single beds. Although the condo can accommodate 6 for sleeping, I will generally only rent to parties of 4 or fewer. Dining room can seat 8 +...
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    Annapolis, Maryland 21401
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, 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
    • 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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    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Stevensville
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to our beautiful vacation home and enjoy the scenic view while having fun on the water. Love Point Bay Vacation Home is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. You will feel right at home, yet free of your everyday stress. Leave...
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    Location Information
    Stevensville, Kent Island 21666
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    * 3 Bedroom Rental House in Historic Rock Hall MD1 / 17
    (3)Excellent
    Rock Hall, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Satellite TV
    • Patio
    • DVD Player
    • Porch
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Spacious Home provides 3 Bedrooms and 2 bathrooms. Each room sleeps 2 people comfortably, and an old fashion cot is provided to sleep one more. This home is completely equipped with all the comforts of home. The Central location is in the heart of the Marina district, steps from Waterman’s...
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    Rock Hall, Maryland 21661
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Stevensville
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Patio
    • Waterfront
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you’re searching for the perfect place for a family retreat in Stevensville, look no further than this 5-bedroom, 2-bathroom vacation rental house which sleeps 12 in scenic Kent Island. Situated on the shores of Chesapeake Bay, this spacious home boasts 2,600 square feet, plenty of outdoor space...
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    Location Information
    Stevensville, Kent Island 21666
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    C/ean & Cozy1 / 10
    (1)Excellent
    Annapolis, MD
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 June 2017
    Very nice, clean, comfortable. Hostess was very accomodating. Would plan on staying there again if another trip to the area is warranted
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    About this property
    Our home is a 5 bedroom quality built home. This room is an office converted in to an extra bedroom space for guests to enjoy. It is located on the main level just inside the main entrance. It had double french doors which lock for privacy. Its a clean and cozy space and an expensive way to travel....
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    Location Information
    Annapolis, Maryland 21409
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Annapolis Waterfront very near USNA1 / 19
    (1)Excellent
    Annapolis, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Grill
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 April 2017
    A clean, peaceful retreat with spectacular views; that is exceptionally stocked!I had no need to buy anything! At one point, I asked the owner if/or where the hand mixer was...
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    About this property
    Waterfront timber frame large cottage in Annapolis, MD. Private, wooded setting with excellent views. Please inquire to the property owner for rates and quote. This house is an energy efficient 9 year old house perched atop a small bluff overlooking picturesque Mill Creek and an...
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    Location Information
    Annapolis, Maryland 21409
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    ENDLESS SUNSETS - The perfect getaway!1 / 11
    (5)Excellent
    Claiborne, MD
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Washer
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2015
    We were a group of two couples each with a young child. There was more than enough room for the 6 of us. The home is well located in Claiborne, about 5 min from downtown...
    Reviewed 10 October 2014
    Very new, very clean, very spacious, very comfortable. The family thoroughly enjoyed our stay here with plenty of room to spread out, a huge kitchen, meals on the deck and...
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    About this property
    Beautiful like new waterfront home on the Chesapeake Bay, 5 minute drive to Historic St. Michaels. Minutes to many quaint watermen villages. Shared waterside pool, beach, kayaks, small boat, childrens playset. The property was designed to take advantage of the incredible views of the Chesapeake...
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    Claiborne, Talbot County 21663
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Annapolis, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Private Garden
    • DVD Player
    • Patio
    • Air Conditioning
    • 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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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    McDaniel, MD
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Grill
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Stevensville
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Terrace
    • Waterfront
    • Balcony
    • Housekeeping Included
    • Ocean Views
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to our private luxury waterfront property that sits on 17 acres located on the Chester River where it meets the mouth of the Chesapeake Bay on Maryland's Eastern Shore. Get away from the city and enjoy the scenic view while having fun on the water. Love Point Bay Luxury Waterfront is at the...
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    Stevensville, Kent Island 21666
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    Wittman, MD
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Washer
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Shipwright Cottage is a fully-renovated 2 bedroom, 1 1/2 bath house that is a perfect getaway for couples or small families. Upstairs features two sleeping areas - a bedroom with two extra long twin beds that can be combined to make a king and an open, loft-style bedroom with a queen bed and...
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    Wittman, Talbot County 21676
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Annapolis, MD
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Known as the “Athens of America,” Annapolis is a city abundant with history and culture. This former capital of the United States has a little something for every interest and taste, whether you're a history buff, a sports enthusiast, or someone simply looking for a peaceful retreat!   Have the...
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    Location Information
    Annapolis, Maryland 21403
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3BR Stevensville House Overlooking Eastern Shore1 / 26
    (1)Excellent
    Stevensville
    3 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 May 2016
    From the moment you ride up the driveway you already know you are in for a wonderful experience. From the cathedral ceilings to the beautiful decor this home welcomes you. The...
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    About this property
    Have the ultimate Maryland getaway by staying at this remarkable Stevensville vacation rental home, surrounded by approximately 20 breathtaking acres of open space with picturesque Eastern Shore views. Whether you're in the mood for a relaxing escape in the great outdoors or a vacation filled with...
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    Location Information
    Stevensville, Kent Island 21666
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 8
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    Annapolis, MD
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Washer
    • Wi-Fi
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A perfect home to enjoy time in Annapolis!  Located on King George Street, walking distance to the Academy or downtown, this home is open year round with a 2-night minimum stay. It is an outstanding home for Weddings, Academy Events, Alumni Gatherings or Family Vacations.  This stunningly...
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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    Walk to Shops/Eateries Charming Cottage. Dogs Wel.1 / 50
    (1)Excellent
    Annapolis, MD
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Satellite TV
    • Grill
    • DVD Player
    • Housekeeping Included
    • Patio
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Sailors Crossing1 / 12
    (2)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 6 days ago
    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...
    Reviewed 2 weeks ago
    Stayed here in July...not one bad thing to say! Beautiful, charming, spacious, comfy home. Had an amazing relaxing weekend. Close to everything. Can't wait to go again!!!
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    About this property
    Sailors Crossing is a 3 bedroom, 2 bath home located in the heart of Rock Hall. 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 to the backyard, there's...
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    Location Information
    Rock Hall, Maryland 21661
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Annapolis, MD
    5 Bedrooms, 3 Bathrooms, Sleeps 20 Quick View
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    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Ocean Views
    • Hot Tub
    • Internet Access
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfort & Style: Enjoy stunning Chesapeake Bay Views, Beach, Pier, Boat Slips, Park, Water Access, Fire Pit, Patio Heater and more! Charming cottage & detached studio/game room (both upgraded in 2013) offer gourmet kitchen with new stainless steel appliances, a second full kitchen in garden...
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    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 20
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    Grandview at Pleasure Point1 / 34
    (10)Excellent
    Bozman, MD
    8 Bedrooms, 6 Bathrooms, Sleeps 27 Quick View
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    • Satellite TV
    • Patio
    • Internet Access
    • Washer
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 November 2016
    We thoroughly enjoyed our stay in one of the little cottages on the property. We arrived late Friday night and the property sign was not lit up, so it took a while to find it...
    Reviewed 9 June 2015
    Perfectly situated on the water. The views are amazing, as is the pool. There is a huge lawn which is perfect for children of all ages. A short drive to St. Michael's, which is...
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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
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 27
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    Annapolis, MD
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Private Garden
    • Parking
    • Wi-Fi
    • 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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    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Edgewater, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 2000 square foot apartment is in a beautiful, gated resort marina. The apartment is completely new with high end kitchen and bathrooms, cathedral ceilings and an amazing view all the way down the South River. The marina offers all kinds of activities including a waterfront restaurant, Jet...
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    Edgewater, Maryland 21037
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 12
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    Annapolis, MD
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Patio
    • Terrace
    • DVD Player
    • Central Heating
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is in a very nice, safe neighborhood (two blocks to firehouse and 2 blocks to police station) within walking distance to historic downtown Annapolis. It is also less than a block to the Navy football stadium and easily walkable to grocery store, pharmacy, liquor store and...
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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Annapolis, MD
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Washer
    • DVD Player
    • Secure Parking
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Balcony
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Best location in Eastport ,We restored this lovely victorian house over the past sixteen years. The upstairs is modern and has all the great amenities that a renovated building provides. anderson windows to keep the place warm and toasty. Seperate heating/air conditioning controls.Wooden floors,...
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    Location Information
    Annapolis, Maryland 21403
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Rock Hall, MD
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Washer
    • Grill
    • Parking
    • Porch
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming 3 bed / 1 bath single family home with screened in front porch. Relax on the rocking chairs as you take in the charm of this lovely town on one of the prettiest streets in Rock Hall. Ample parking, large back yard with BBQ, tables and chairs to relax with family and friends after spending...
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    Location Information
    Rock Hall, Maryland 21661
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Amazing Waterfront Annapolis & easy walk downtown1 / 24
    (1)Very good
    Annapolis, MD
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Waterfront
    • Hot Tub
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 October 2015
    Myself and five coworkers rented this house for a meeting. As we are from different areas across the country we usually meet at hotels. I thought we would try something...
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    About this property
    A Peaceful Oasis Overlooking Annapolis Waterfront and easy walking distance to downtown. Check out this great video of the home & property. Cut and paste the following link: AnnapolisWaterfrontRentals..om This incredible home has 100' of floor-to-ceiling windows nestled in the tree canopy for...
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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Annapolis, MD
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Satellite TV
    • Air Conditioning
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My place is good for couples, solo adventurers, and business (URL HIDDEN) school just down the street , Great location for naval academy parents for parents day etc. A gourmet kitchen if you prefer to cook your own meals or cook your fish you have caught on your fishing trip on the bay,we can...
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    Location Information
    Annapolis, Maryland 21403
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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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<BR>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
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Annapolis, MD
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    This is the newly renovated 780 sf studio unit that is on the ground floor of a main house that is similarly titled and on the same property. Striking and dramatic 8700 - 9000 sf contemporary, new loft style renovation of the main house with exposed structure and mechanical systems that serves as...
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    Location Information
    Annapolis, Maryland 21401
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Annapolis, MD
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Waterfront
    • 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
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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