Oxford holiday rentals

From simple studios to luxe lofts, find holiday rentals that are right for you on Airbnb.

Holiday rentals in Oxford

$355 SGD UR 2nd Home - near beach in Oxford
26 reviews

Oxford is the perfect place for a quiet weekend away with friends/family or a romantic get-away. Walk to a quiet beach on the Tred Avon River & ride the bikes from one waterfron... read more
13 reviews

Escape the hustle and bustle of city life. Relax and travel back in time to historic Oxford, MD, a modern day Mayberry. Oxford, located on the Eastern Shore, is both Maryland'... read more
$219 SGD Sailboat in Historic Oxford, MD
12 reviews

Experience the very best of Eastern Shore living while staying aboard a large, (62') comfortable catamaran sailboat in walking distance to Oxford. Docked in a secure and private... read more
$476 SGD Red Shake Cottage
3 reviews

Step out and walk to everything, including The Strand, a small beach great for relaxing in the sun and enjoying an afternoon picnic. We love this cottage for many reasons - the... read more
$637 SGD Oxford home in walkable location.
3 reviews

Great newer home in the heart of Oxford. Come experience all the Eastern Shore of Maryland has to offer! Five great restaurants within walking distance. Park the car and rel... read more
$497 SGD Memory Lane
2 reviews

Quaint Cottage within walking distance of town, close to the water and all things Oxford. We call this 1900 circa cottage gem "Memory Lane" for the wonderful memories you will ... read more

Favourite Oxford holiday rentals

$319 SGD Martini Cottage
4 reviews

Two bedroom recently renovated Sears Cottage in Heart of Historic Oxford. Walk to restaurants, parks and easy distance to St. Michaels via the Oxford Bellvue Ferry. A great spo... read more
$135 SGD Chill in The Crib! Easton, Maryland
84 reviews

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized be... read more
$351 SGD St. Michaels area Waterfront Home w/Deepwater Dock
4 reviews

Lovingly restored waterfront historic home just minutes from St. Michaels. Located in a quiet waterman's village, Seth's Landing provides tranquility and beautiful surroundings... read more
$263 SGD Miles Aweigh Cottage
6 reviews

Our cottage is less than a mile from St. Michaels town center. Restaurants, shopping, Chesapeake Maritime Museum, Easton-Tilghman Island. Bike, walk or drive...our home has bee... read more
$1278 SGD Iron Man MD Family(s) Location
1 review

Within walking distance to start/finish point of race and both bike & run goes by our house. Cheer on participants from shaded side yard. Well lived in family home with 1.75 bat... read more
$535 SGD Avalon - Penthouse - 2 night min
24 reviews

Third floor 3 Bedroom Penthouse Flat with Harbor View and efficiency style kitchen. Private in town location with spectacular view. TV, Pool Table, Foosball in Flat. Walk to al... read more

More holiday rentals in Oxford

$234 SGD Perfect St. Michaels Getaway
25 reviews

Shipwright Cottage is a fully-renovated idyllic getaway located in the Bay Hundred area of the Chesapeake Bay just 8 miles outside of St. Michaels, MD. Bikes and kayaks included... read more
$284 SGD The Brakers- Bedroom 1
1 review

My place is close to Great Marsh Park. You’ll love my place because of the coziness. My place is good for couples, solo adventurers, and business travelers. read more
1 review

This beautiful 3 bedrooms cottage just outside of the historic town of St. Michaels, MD offers waterfront relaxation, dock, kayaks, fire pit, hot tub, Cable TV and internet serv... read more

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