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Cobb Island Holiday Rentals

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    Don't let other travellers get your favourite Cobb Island area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 21 Rentals in Cobb Island
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    Newly custom built cottage w/ modern amenities, quietly nestled among the Osprey1 / 18
    (10)Excellent
    Cobb Island
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    The following rentals are within 40 kilometres of Cobb Island.
    Shannon Point Lodge Peaceful and Private1 / 17
    (46)Excellent
    Kinsale, VA
    4 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
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    Parker Shores1 / 14
    (28)Very good
    Kinsale, VA
    3 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    Piney Point
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • Outdoor Dining Area
    • DVD Player
    • Parking
    • Grill
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully renovated cottage with immaculate interior and view from the most rooms of the Potomac River. We are not located on the river, but across the street that sees very little traffic. A water access easement runs from our door step to the Potomac River bulkhead. We love to spot the night lights...
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    Location Information
    Piney Point, Maryland 20690
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    New! Beachfront 4BR St. Leonard Cottage w/ Deck!1 / 24
    (1)Excellent
    Saint Leonard
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Air Conditioning
    • Internet Access
    • Patio
    • Washer
    • Satellite TV
    • Grill
    • Parking
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 August 2017
    This amazing beach house has everything. The location and views are awesome. You literally step off the deck into the shells and sand onto your own beach and swimming area...
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    About this property
    Escape your everyday hustle and bustle and discover a hidden treasure right on the Chesapeake Bay sands at this 4-bedroom, 1-bathroom St. Leonard vacation rental cottage. With comfortable accommodations to sleep 8, 1,200 square feet of well-appointed living space and easy access to surrounding...
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    Location Information
    Saint Leonard, Calvert County 20685
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    Waterfront Retreat on Monroe Bay-AMAZING SUNSETS!1 / 17
    (6)Excellent
    Colonial Beach, VA
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 May 2017
    We were very happy with our choice of a vacation rental.The location is amazing. We were right across the street from the bay. We ate crabs on the deck enjoying the view of the...
    Reviewed 21 December 2016
    I can not say enough about the wonderful vacation we had Sept, 2016. We rented a gulf cart and drove all over!! The location was excellent. The view was amazing! My Husband...
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    About this property
    Marina Sunset is situated on the upper level of a bayfront cottage. 'Incredible' best describes the sunset views of Monroe Bay from the front deck of this gorgeous vacation rental on the 'Point.' This beautifully decorated and fully equipped two-bedroom unit sleeps up to 5 and offers everything...
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    Location Information
    Colonial Beach, Virginia 22443
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    36283 Sunflower Blvd1 / 32
    (1)Excellent
    Piney Point
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
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    PET FRIENDLY* / Sleeps: 10 / View: Community / 3BR, 3BA townhome About this home: This spacious Bayside resort two-story 3-bedroom, 3-bath townhome - at approximately 1,800 square feet - offers just about everything you need for a relaxing vacation on the Delaware Coast. The first...
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    Piney Point, Maryland 19975
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Piney Point
    5 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View:  Lake  / Sleeps:  15 /  5BR , 4BA single family home About this home:   Just built & just listed for 2017 rentals! Be one of the first to vacation in 'Anchors Aweigh!' In The Shoals - Bayside resort's newest area, this two-story 5-bedroom, 4-bath coastal single family...
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    Piney Point, Maryland 19975
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 15
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    Piney Point
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
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    View:  Pond  / Sleeps:  14 /  5BR , 4BA single family home About this home:   Just built & just listed for 2017 rentals! Be one of the first to experience this upscale, beachy two-story 5-bedroom, 4-bath coastal single family vacation home, located in the exceptionally-amenitied...
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    Location Information
    Piney Point, Maryland 19975
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    36486 Wild Rose Circle1 / 45
    (1)Excellent
    Piney Point
    5 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
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    PET FRIENDLY* / 10% Military Discount** / View: Community / Sleeps: 15 / 5BR, 4BA single family home About this home: This spacious 5-bedroom, 4-bath single family home - approximately 3,800 square feet - is a great place to relax and enjoy your vacation. This lovely home sleeps 15...
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    Location Information
    Piney Point, Maryland 19975
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 15
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    Saint Leonard
    1 Bedroom, Sleeps 2 Quick View
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    • Waterfront
    • Outdoor Dining Area
    • Internet Access
    • Grill
    • Patio
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come relax at this charming updated one bedroom bungalow. It overlooks the waters of Wells Cove, a tributary to the Patuxent River which is itself, a tributary to the Chesapeake Bay. This cottage is secluded from the main house, surrounded by water and a wild flower meadow. Somewhat secluded from...
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    Location Information
    Saint Leonard, Calvert County 20685
    Holiday Rental House - 1 Bedroom, Sleeps 2
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    DREAM FAMILY HOUSE ON THE POTOMAC RIVER1 / 20
    (6)Very good
    Montross, VA
    4 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Housekeeping Included
    • Washer
    • Satellite TV
    • Waterfront
    • Grill
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 January 2017
    This home is everything I have ever dreamed of! By far the best relaxation retreat for myself and my family. Beautiful home well taken care of, I'm not to sure if the person...
    Reviewed 8 September 2016
    We rented the house over a long weekend with 10 adults and 3 babies. We also rented the pontoon boat.The house is as large, well stocked, and amazingly located as the listing...
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    About this property
    WATERFRONT HOME Private 574 feet/175 meters of Waterfront - Mean Low Tide 4 feet/1.22 meters 4700 sq. ft/1433 sq. meters of Open Floor Plan home on 2.1 acres/8498.4 sq. meters Four Bedrooms each with private bathrooms and a powder room off living room Handicap Friendly In-law Suite - Kitchen,...
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    Location Information
    Montross, Virginia 22520
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 14
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    Warsaw, VA
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Plan your next Virginia escape to ‘JuJu’s Place,’ a 3-bedroom, 2.5-bathroom vacation rental house in Warsaw. This 1,800-square-foot home has the capacity to comfortably sleep 7 guests, making it the perfect home-away-from-home for families or friends traveling together. The open front and back yard...
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    Location Information
    Warsaw, Virginia 22572
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Super Cute, 2 Bedroom, 1 Bath, Furnished Cottage1 / 15
    (7)Average
    Colonial Beach, VA
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
    • Washer
    • Grill
    • Air Conditioning
    • Porch
    • Patio
    • Satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 August 2016
    Clean and comfortable- close to everything you need. Home is private and quiet but close to the activities
    Reviewed 16 August 2016
    I rented this unit with my parents. The rental is advertised as a house with air conditioning. Renters should be aware that this house does not have central air. The unit has 1...
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    About this property
    Super cute, furnished cottage on the point. 2 bedroom, 1 bath, kitchen, sunroom, covered back patio. Renovated bathroom, hardwood floors, fenced yard. Come relax and enjoy a sunset walk around the point. Nestled on a quiet street two blocks from the Potomac River and two blocks from Monroe Bay....
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    Location Information
    Colonial Beach, Virginia 22443
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    Port Tobacco
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Internet Access
    • Balcony
    • Parking
    • Satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Circa 1930's-style french mansion house located on three acres in historic Port Tobacco, Maryland. Rosewood Manor BnB is the Bed and Breakfast of Choice in Charles county, Southern Maryland. Just a 10 minute drive from Crain Highway (301) Visitors Welcome Center, 12 minutes from the greater...
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    Location Information
    Port Tobacco, Maryland 20677
    Private Room - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Port Tobacco
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Terrace
    • Grill
    • Housekeeping Included
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Elegant French Style Bed and Breakfast, located in the historic area of Port Tobacco, Md. Large spacious rooms all with private bath, skylight, sofa, wing chair, writing desks, ceiling and wall mouldings and chandeliers. Some with balcony and Fireplace. All with large spacious closets. Linens...
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    Location Information
    Port Tobacco, Maryland 20677
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Stunning Pond House in Coles Point1 / 32
    (1)Excellent
    Coles Point, VA
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Satellite TV
    • DVD Player
    • Parking
    • Air Conditioning
    • Grill
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2016
    Myself and a few friends ending up spending a enjoyable weekend at this home. I would highly recommend it to anyone looking to get a away from it all for a few days.
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    About this property
    This vacation getaway is on a private lot on a 16 acre pond perfect for canoeing and kayaking, opening to the Potomac River. You are welcome to use our canoe and kayaks during your stay. The house sleeps 10 people in beds, two bedrooms are on the main level (one bedroom with a queen bed and one...
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    Location Information
    Coles Point, Virginia 22469
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Port Tobacco
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Circa 1930's style French mansion house located on three acres in historic Port Tobacco. All rooms are large spacious well appointed, beautifully decorated with private baths, writing desks, sofa or wing chairs, Flat Screen TV, some with Fireplace, some with balcony. All rooms include full...
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    Location Information
    Port Tobacco, Maryland 20677
    Private Room - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Colonial Beach, VA
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
    • Satellite TV
    • Washer
    • Air Conditioning
    • DVD Player
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take leisure to the next level on your upcoming coastal retreat by reserving 'The Blue Crab Cottage,' a traditional bungalow-style Colonial Beach vacation rental home. This cottage has 3 bedrooms, 1 spacious bathroom, and enough sleeping arrangements for 5 guests. Found just 2 blocks from the beach...
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    Location Information
    Colonial Beach, Virginia 22443
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Kinsale, VA
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Parking
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tween is located at Sandy Point, Virginia on the Northern Neck. The house is on the waterfront of the Potomac River where it is approximately five miles across to the Maryland shores. You look out onto the Chesapeake Bay from the porch. The beach is sand and the water has a gradual depth increase -...
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    Location Information
    Kinsale, Virginia 22488
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Saint Leonard
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a peaceful beach getaway? Located in quiet Long Beach overlooking Flag Harbor Yacht Haven marina, this cottage is a few minutes walk to the sandy beach along cliffs famous for fossils from the Miocene. The shallow water is safe for children to swim, and a favorite for fishermen and...
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    Location Information
    Saint Leonard, Calvert County 20685
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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