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Holiday Rentals in Sherwood

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    Don't let other travellers get your favourite Sherwood area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 21 Rentals in Sherwood
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    The following rentals are within 25 kilometers of Sherwood.
    Stevensville, MD
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    McDaniel
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Seahorse Guest Cottage near the Bay, dog friendly1 / 17
    (5)Very good
    North Beach, MD
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    Easton
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Wi-Fi
    • Waterfront
    • Ocean Views
    • Washer
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4+ acres on Shipshead Creek off of St. Michaels road. Fully furnished (2 king and 4 twin beds), heated pool, deep water dock, tennis court,and pet friendly. Boat, Jet Ski, Paddle Board, Kayak, Canoe, and Bike rentals can be arranged-Inquire if interested The Space Pet Friendly waterfront...
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    Easton, Talbot County 21601
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    St. Michaels Waterfront Home W/Dock for 2 boats1 / 18
    (1)Excellent
    Neavitt
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Patio
    • Balcony
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2017
    VERY nice place and owner was excellent. Place building is old must has been well maintained. It is very clean and exceeded all our needs. Owner are excellent people!!
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    About this property
    Full renovations just completed on this newly-listed historic waterfront home. Sleeps five (1 King, 1 Queen, 1 Twin). Kick back, relax and enjoy the beautiful waterviews. Have crabs on the deck or cocktails on the dock. Features a new dock with 14 ft. and 16 ft. wide, deepwater boat slips. Bring...
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    Neavitt, Talbot County 21652
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    RESTORED WATERFRONT COTTAGE1 / 24
    (10)Excellent
    Royal Oak
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You can tell right away, from the warm sage green exterior and the peaceful creekside setting, that this charming vacation cottage promises a fun, relaxing getaway. With a 180 degree expanse of spectacular Oak Creek waterfront, the River House at Royal Oak is the pefect choice for year 'round...
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    Royal Oak, Talbot County 21662
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Stevensville, MD
    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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    Stevensville, Kent Island 21666
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    ENDLESS SUNSETS - The perfect getaway!1 / 11
    (5)Excellent
    Claiborne
    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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    Location Information
    Claiborne, Talbot County 21663
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Relaxing, Fun, Dog-Friendly Waterfront Cottage1 / 24
    (1)Excellent
    Churchton, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Washer
    • Grill
    • Internet Access
    • DVD Player
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 May 2016
    Stayed a few days in the cottage...there is another quarters for a couple next door at the main house ,and another room they are renting and working on expanding I...
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    About this property
    This sunny but cozy 3 bedroom/2 bath cottage is just the spot for a get-away on your own, with other couples/friends, or with big and small familie! Just steps from the water and nestled on a country-like acre in a surprisingly convenient corner of the Chesapeake Bay, this unique, quiet, scenic...
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    Location Information
    Churchton, Maryland 20733
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Tilghman Island Cottage for Six - Near Marina and Knapps Narrows Drawbridge1 / 20
    (6)Excellent
    Tilghman
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Satellite TV
    • Parking
    • Air Conditioning
    • Waterfront
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 July 2016
    We had an absolutely wonderful time. The cottage was clean and well appointed. We would definitely go back!
    Reviewed 8 October 2015
    Tilghman Cottage (the Roost) is a lovely place that makes you feel comfortable in every possible way. The house is very clean, bright, cosy, and yet spacious, fully equipped...
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    About this property
    Enjoy the beauty and tranquility of Tilghman Island from this bright and comfortable 3 bedroom, 2 bathroom cottage known for many years as the vacation rental 'The Roost.' Available for both short and long-term rentals, the cottage is located on a quiet residential street across from a marina...
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    Location Information
    Tilghman, Talbot County 21671
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    North Beach, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    All-Decked-Out Beach House is on the Western Shore of the Chesapeake Bay in the lovely Rose Haven/North Beach MD community. Fenced-in on a large corner lot directly across from Herrington on the Bay, 3 miles from Chesapeake Beach Bay Resort & Spa and 45 min. from DC this 3bed/1.5 bath offers...
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    North Beach, Calvert County 20714
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Luxury vacation condominum with private beach1 / 35
    (13)Excellent
    Chester, MD
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Hot Tub
    • Waterfront
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Secure Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 January 2016
    My family used this home for 10 days over Christmas and New Year. It was just perfect. Plenty of room for our Christmas tree, decorations and packages. Spotlessly clean bedrooms...
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    About this property
    Swan Cove Condominiums at Kent Narrows(#49064) with private beach and views of the Chesapeake bay! - Brand new luxury condominium with 3000 sq ft, 4 bedrooms, 3 ½ bathrooms, one large family room with open kitchen, one large sunny living room and dinning area. There are 2 king size bed, 2 queen...
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    Location Information
    Chester, Kent Island 21619
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Stevensville, MD
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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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    Location Information
    Stevensville, Kent Island 21666
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    Wittman
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Washer
    • Patio
    • Grill
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    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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    Stevensville, MD
    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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    Stevensville, Kent Island 21666
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)1 / 21
    (3)Excellent
    Chester, MD
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Patio
    • Satellite TV
    • Waterfront
    • Wi-Fi
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 January 2016
    We have stayed in this home several times and will return in July. It is a wonderful house with a private master suite at one end, two bedrooms with a 2nd bath at the other.The...
    Reviewed 29 July 2013
    First I would like to say thanks, to Harry, and Scott. They were the best host, I've encountered. They have a property, they can be proud of. The house was just excellent...
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    About this property
    Waterfront Rancher on 3 acres, centrally located between Washington DC, St. Michaels, Annapolis, and Baltimore. 4 Bed/2 Bath home with central air sleeps 8. This home has been in our family for over 50 years and is a special place. Over the years there have been many updates to the home. The...
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    Location Information
    Chester, Kent Island 21619
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3BR Stevensville House Overlooking Eastern Shore1 / 26
    (1)Excellent
    Stevensville, MD
    3 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    North Beach, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming restored cottage has all the luxury upgrades you could want!! Gourmet kitchen with granite counters and double-oven, 5-burner gas cooktop, and plenty of storage. Easy-to-enjoy gas fireplace, and ample space for entertaining and kids to play -- both indoors and out! Convenient to...
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    Location Information
    North Beach, Calvert County 20714
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Grandview at Pleasure Point1 / 34
    (10)Excellent
    Bozman
    8 Bedrooms, 6 Bathrooms, Sleeps 27 Quick View
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    Amenities & Details
    • 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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    Deale, MD
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Housekeeping Included
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Sauna
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the home and studio of local sculptor artist. This apartment includes the second and third floors, approximately 2,300 sf of space. Large and comfortable bedrooms, large bathrooms, showers have double heads, sauna in the main master-bath. We provide linens and towels. This apartment has a...
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    Location Information
    Deale, Maryland 20751
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Shady Side, MD
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Waterfront
    • Grill
    • Patio
    • Parking
    • Satellite TV
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If mesmerizing waterfront views, tidy and comfortable accommodations, and a private backyard are what you are longing for, then escape to this 2-bedroom, 1.5-bathroom vacation rental house in Shady Side, Maryland! With access to a private pier and dock, this quaint cottage that comfortably sleeps 5...
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    Location Information
    Shady Side, Maryland 20764
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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