Book Holiday Homes in Oxford

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Featured Holiday Homes in Oxford

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

St. Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 5-minute walk of Higgins Yacht Yard and Marina and Muskrat Park.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Bay Breeze - Charming 3BR Waterfront Home on the Chester River

Bay Breeze - Charming 3BR Waterfront Home on the Chester River

Grasonville
When you stay at this vacation home in Grasonville, you'll be within a 10-minute drive of Chesapeake Exploration Center and Queenstown Premium Outlets.
Bay Breeze - Charming 3BR Waterfront Home on the Chester River
Relax on Kent Island in 3 Bedroom Home w/Waterview

Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville
The price is AU$443 per night from 13 Apr to 14 Apr
AU$443
includes taxes & fees
13 Apr - 14 Apr
Located in Stevensville, this vacation home is within a 15-minute drive of Romancoke Wharf County Park and Matapeake State Park.
Relax on Kent Island in 3 Bedroom Home w/Waterview
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Tranquil  Beautiful Waterfront  Near Historic St. Michaels & Royal Oak

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

easton
With a stay at this vacation home, you'll be centrally located in Easton, within a 10-minute drive of Saint Michaels Village and St. Michaels Winery.
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Easton
When you stay at this vacation home in Easton, you'll be on the waterfront and 14 minutes by car from Hog Neck Golf Course.
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Walk to Everything House

Walk to Everything House

Saint Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 5-minute walk of Muskrat Park and Higgins Yacht Yard and Marina.
Walk to Everything House
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

2 out of 5
Cambridge
Located in Cambridge, this vacation home is within a 15-minute walk of Harriet Tubman Museum and Educational Center and Richardson Maritime Museum.
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
25-50% Off~Private Beach~Hot Tub~Fire Table~

25-50% Off~Private Beach~Hot Tub~Fire Table~

Stevensville
Located in Stevensville, this vacation home is on the waterfront, a 1-minute drive from Romancoke Wharf County Park and 10 minutes from Matapeake State ...
25-50% Off~Private Beach~Hot Tub~Fire Table~
Serene Waterfront Minutes from St Michaels.

Serene Waterfront Minutes from St Michaels.

Easton
Located in Easton, this vacation home is on the waterfront, a 5-minute drive from Saint Michaels Village and 6 minutes from St. Michaels Winery.
Serene Waterfront Minutes from St Michaels.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Oxford Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Oxford vacation homes are the perfect way for you to wing it.

Holiday houses in Oxford let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Oxford in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Oxford adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oxford with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Oxford vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Oxford Holiday Homes essential information

Accommodation
232 Holiday Homes
Lowest Price
AU$185
Highest Price
AU$506
Popular accommodation
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, Bay Breeze - Charming 3BR Waterfront Home on the Chester River, Relax on Kent Island in 3 Bedroom Home w/Waterview, Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak, Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac, Walk to Everything House, Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC, 25-50% Off~Private Beach~Hot Tub~Fire Table~, Serene Waterfront Minutes from St Michaels.

Top trending hotels in Oxford

Newly Renovated Guest House located in Oxford MD

Newly Renovated Guest House located in Oxford MD

Oxford
Located in Oxford, this guesthouse is on the waterfront, within a 5-minute drive of Play Ball Dog Park and Oxford Museum.
Newly Renovated Guest House located in Oxford MD
Downtown Oxford | Outdoor Dining | Character Filled

Downtown Oxford | Outdoor Dining | Character Filled

Oxford
With a stay at this vacation home in Oxford, you'll be a 1-minute walk from Play Ball Dog Park and 12 minutes by foot from Oxford Museum.
Downtown Oxford | Outdoor Dining | Character Filled
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
The price is AU$506 per night from 14 Apr to 15 Apr
AU$506
includes taxes & fees
14 Apr - 15 Apr
Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 6 minutes from Dorchester County Visitors ...
Hyatt Regency Chesapeake Bay
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St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundableReserve now, pay when you stay
The price is AU$185 per night from 13 Apr to 14 Apr
AU$185
includes taxes & fees
13 Apr - 14 Apr
When you stay at St Michaels Inn in St. Michaels, you'll be in the historical district, within a 5-minute drive of St. Michaels Winery and Chesapeake Bay Maritime ...
St Michaels Inn
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See all available properties in Oxford
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.