Book Holiday Homes in Oxford

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Featured Holiday Homes in Oxford

Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels

St Michaels MD
With a stay at this vacation home in St. Michaels (Downtown St. Michaels), you'll be within a 5-minute walk of Muskrat Park and Higgins Yacht Yard and ...
Opens in a new windowDollhouse in Central Historic St Michaels
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Cambridge MD
With a stay at this vacation home in Cambridge, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay and Spocott Windmill.
Opens in a new windowWaterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Tilghman Island MD
When you stay at this vacation home in Tilghman, you'll be on the waterfront, within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowWaterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
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Historic Waterfront Estate with Pool & Pet-Friendly  – Perfect for Fall Getaways

Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways

Oxford MD
Located in Oxford, this vacation home is on the waterfront, within a 10-minute drive of Play Ball Dog Park and Oxford Museum.
Opens in a new windowHistoric Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways
"Endless Summer" Waterfront on the Chesapeake Bay!

"Endless Summer" Waterfront on the Chesapeake Bay!

Woolford MD
When you stay at this vacation home in Woolford, you'll be 14 minutes by car from Blackwater National Wildlife Refuge.
Opens in a new window"Endless Summer" Waterfront on the Chesapeake Bay!
Waterfront Getaway with Dock

Waterfront Getaway with Dock

Woolford MD
The price is AU$371 per night from 21 May to 22 May
AU$371
21 May - 22 May
includes taxes & fees
Located in Woolford, this vacation home is on the waterfront, within a 10-minute drive of Blackwater National Wildlife Refuge and Harriet Tubman Underground ...
Opens in a new windowWaterfront Getaway with Dock
Waterfront Sunset Bayview: sleeps 6

Waterfront Sunset Bayview: sleeps 6

Chester MD
With a stay at this vacation home in Chester, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay and Chesapeake Exploration Center.
Opens in a new windowWaterfront Sunset Bayview: sleeps 6
Stunning views at WATERFRONT St Michaels area historic home, dog friendly

Stunning views at WATERFRONT St Michaels area historic home, dog friendly

Neavitt MD
When you stay at this vacation home in Neavitt, you'll be on the waterfront and 3 minutes by foot from Neavitt Park.
Opens in a new windowStunning views at WATERFRONT St Michaels area historic home, dog friendly
Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock

Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock

St. Michaels MD
Located in St. Michaels, this vacation home is on the waterfront, within a 10-minute drive of St Michaels Nature Trail and Higgins Yacht Yard and Marina.
Opens in a new windowMinutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
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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
231 Holiday Homes
Lowest Price
AU$290
Highest Price
AU$915
Popular accommodation
Dollhouse in Central Historic St Michaels, Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW, Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets, Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways, "Endless Summer" Waterfront on the Chesapeake Bay!, Waterfront Getaway with Dock, Waterfront Sunset Bayview: sleeps 6, Stunning views at WATERFRONT St Michaels area historic home, dog friendly , Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock

Top trending hotels in Oxford

Sandaway Suites & Beach

Sandaway Suites & Beach

3 out of 5
103 West Strand Road Oxford MD
The price is AU$290 per night from 28 May to 29 May
AU$290
28 May - 29 May
includes taxes & fees
With a stay at Sandaway Suites & Beach in Oxford, you'll be 0.3 mi (0.5 km) from Oxford Museum and 8 mi (12.9 km) from St. Michaels Winery.
Opens in a new windowSandaway Suites & Beach
Historic Waterfront Estate with Pool & Pet-Friendly  – Perfect for Fall Getaways

Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways

Oxford MD
Located in Oxford, this vacation home is on the waterfront, within a 10-minute drive of Play Ball Dog Park and Oxford Museum.
Opens in a new windowHistoric Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
The price is AU$431 per night from 19 May to 20 May
AU$431
19 May - 20 May
includes taxes & fees
Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 5 minutes from Eastern Shore Hospital ...
Opens in a new windowHyatt Regency Chesapeake Bay
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Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
The price is AU$915 per night from 31 May to 1 June
AU$915
31 May - 1 June
includes taxes & fees
A stay at Inn at Perry Cabin places you in the heart of St. Michaels, within a 15-minute walk of Perry Cabin Park and Saint Michaels Town Hall.
Opens in a new windowInn at Perry Cabin
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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.