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Oxford Vacation Rentals

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    Don't let other travelers get your favorite Oxford area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 22 Rentals in Oxford
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    Oxford
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Oxford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Oxford
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    The following rentals are within 10 miles of Oxford.
    Waterfront Vacation Home with Private Beach1 / 55
    (5)Average
    Trappe
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • Parking
    • Air Conditioning
    • Washer
    • Grill
    • DVD Player
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 23, 2015
    We had a blast. The property, although the actual house could use a bit of updating, is GORGEOUS. We did notice that the home definitely housed a pet or two but did not smell...
    Reviewed August 26, 2014
    Beautiful home and view of the bay. Private beach was amazing. Perfect for a group of friends or a couple looking to get away. I will definitely be staying here again!
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    About this property
    Beautiful, serene waterfront home on the Chesapeake Bay. One hour from the Atlantic Ocean (Ocean City, Assateague Island) and Annapolis, One and a half hours from Washington DC and Baltimore. Many nearby places worth visiting, including picturesque St. Michaels and the Blackwater Wildlife Refuge...
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    Location Information
    Trappe, Talbot County 21673
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    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
    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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Easton
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Internet Access
    • Parking
    • Private Yard
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great setting for a getaway relaxing weekend in a waterfront setting with a private beach. A variety of places to visit in the area, and fun outdoor activities. Two night minimum stay on weekends please. Swimming, fishing and lots of sunbathing. Amazing sunsets! This room is the master bedroom...
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    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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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 July 21, 2016
    We had an absolutely wonderful time. The cottage was clean and well appointed. We would definitely go back!
    Reviewed October 8, 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    RESTORED WATERFRONT COTTAGE1 / 24
    (10)Excellent
    Royal Oak
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Cambridge, MD
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Wi-Fi
    • Balcony
    • Parking
    • Satellite TV
    • Terrace
    • Washer
    • Private Yard
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern home that has accommodations for more than 10+, with 2 full living room areas, 3 and half baths, Xfinity cable, with flat screen TVs in each of 5 bedrooms. Master with 50", mini fridge, sofa,loveseat, and ensuite master bath. Home is minutes away from some of the finest Eastern Shore Seafood...
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    Location Information
    Cambridge, Maryland 21613
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Traveler-friendly cancellation policy
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    Amenities & Details
    • Private Yard
    • Internet Access
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great setting for a getaway relaxing weekend in a waterfront setting with a private beach. A variety of places to visit in the area, and fun outdoor activities. Two night minimum stay on weekends please. Swimming, fishing and lots of sunbathing. Amazing sunsets! This room is the master bedroom...
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    Location Information
    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cottage at Heron Cove, Chesapeake Bay, Cambridge1 / 39
    (8)Excellent
    Cambridge, MD
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Porch
    • DVD Player
    • Parking
    • Waterfront
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Cottage at Heron Cove is a cozy home situated on a scenic peninsula with water views from every window. Awake each morning to watch the sun glisten off the gentle waters. Explore ten acres of land and 1000 feet of shoreline. Relax on the wrap around screened in porch. Fish and crab from your...
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    Location Information
    Cambridge, Maryland 21613
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Year Round Estate on Bay / Fam. Reunions / Slps 281 / 35
    (15)Excellent
    Cambridge, MD
    7 Bedrooms, 7 Bathrooms, Sleeps 28 Quick View
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    Amenities & Details
    • DVD Player
    • Waterfront
    • Internet Access
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Satellite TV
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 30, 2016
    Lovely setting & a great location for sure. Nice big comfortable house. Great spot for big family reunion. This was our 2nd time we stayed here. Loved our first visit a...
    Reviewed August 3, 2012
    I would not change a single thing. Our family enjoyed the six day stay at this awesome place. The amenities were great, the location was central to other sights, and the...
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    About this property
    Captains Quarters on the Bay is a wonderful waterfront home with over 6,000+ Sq. Ft. of Living Space. Designer Appointed with All New Furnishings.7 Bedrooms with 6 Full Bathrooms, some with Jacuzzi/Whirlpool Baths. Gourmet Kitchen with Six Burner Stovetop and Triple Ovens. Large Game Room with...
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    Location Information
    Cambridge, Maryland 21613
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 28
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    Cedar Point Chesapeake Bay Waterfront Cottage1 / 21
    (5)Very good
    Cambridge, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming waterfront cottage on 6.5 private acres sits among swans and eagles on Marylands beautiful Eastern Shore. This professionally deorated cottage is packed with modern ammenities and charm. Saltwater Pool, Dock with seating, boat slip, water and electric; canoes and kayaks, woodburning...
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    Location Information
    Cambridge, Maryland 21613
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Trappe
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Private Yard
    • Internet Access
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great setting for a getaway relaxing weekend in a waterfront setting with a private beach. A variety of places to visit in the area, and fun outdoor activities. Two night minimum stay on weekends please. Swimming, fishing and lots of sunbathing. Amazing sunsets! This room is the master bedroom...
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    Location Information
    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cambridge, MD
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Central Heating
    • Patio
    • Waterfront
    • Balcony
    • Washer
    • Grill
    • DVD Player
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From the hosts that have maintained a five star ratings on our cottage vacation rental, we would like to invite you to enjoy a special vacation in our four bedroom 3 full bath luxury estate home in the heart of the Chesapeake Bay. The house has just undergone a complete remodeling and...
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    Location Information
    Cambridge, Maryland 21613
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Cambridge, MD
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Wi-Fi
    • Balcony
    • Air Conditioning
    • Washer
    • Terrace
    • Parking
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on the beautiful Eastern Shore of Maryland, Cambridge has been named one of the best ten small towns in the U.S. and is a boater's dream! The house has four private suites, full gourmet kitchen, three sitting areas, and two car garage. Check out the Dorchester County Tourism page for...
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    Location Information
    Cambridge, Maryland 21613
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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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 November 14, 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 June 9, 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
    Rental Home - 8 Bedrooms, 6 Bathrooms, Sleeps 27
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    Year Round Waterfront Prop. (Sleeps 18 )1 / 28
    (4)Excellent
    Cambridge, MD
    5 Bedrooms, 4 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Satellite TV
    • Washer
    • Grill
    • Internet Access
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautifully designer furnished waterfront home is located in a very private setting overlooking the Chesapeake Bay and Little Choptank River. The property features magnificent water views, a private dock, fire pit, a large fenced swimming pool, large deck (partially covered), playground and...
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    Location Information
    Cambridge, Maryland 21613
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 18
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    Fishing Cove on the Chesapeake Bay1 / 20
    (2)Excellent
    Cambridge, MD
    8 Bedrooms, 6 Bathrooms, Sleeps 23 Quick View
    Traveler-friendly cancellation policy
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    • Washer
    • Terrace
    • Waterfront
    • Balcony
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 13, 2016
    We had 14 people for thanksgiving..house had everything we needed! The kitchen was fully stocked with all the necessary cooking implements. And the 2 refrigerators were very...
    Reviewed December 5, 2016
    Our church group (11 men of all ages) had a most excellent weekend at this house and would be delighted to return some day. With only one person per bed, though, the max...
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    About this property
    Fishing cove is an 8 bedroom, 6 bath waterfront house tucked away in a lush pine forest that we rent on a monthly, weekly or weekend basis. Our waterfront vacation rental home on Maryland's Eastern Shore is on a very private cove with its own pier. The house is wheelchair accessible and the main...
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    Location Information
    Cambridge, Maryland 21613
    Rental Home - 8 Bedrooms, 6 Bathrooms, Sleeps 23
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    Cambridge, MD
    8 Bedrooms, 6 Bathrooms, Sleeps 22 Quick View
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    Amenities & Details
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the best of beautiful Cambridge when you book this magnificent 8-bedroom, 6-bathroom vacation rental house that comfortably sleeps 22. Featuring a splendid waterfront location on a private lane, along with a private outdoor pool, this home promises a memorable retreat! The moment you...
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    Location Information
    Cambridge, Maryland 21613
    Rental Home - 8 Bedrooms, 6 Bathrooms, Sleeps 22
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    Baltimore-Washington Intl Airport
    43.2 miles from Oxford
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