Book Holiday Homes in Oxford

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Featured Holiday Homes in Oxford

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Cambridge MD
When you stay at this vacation home in Cambridge, you'll be on the waterfront and 14 minutes by car from Christ Rock Park.
Opens in a new windowPrivate 2 Acre Waterfront Family Retreat with Pool & Pier
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 MD
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.
Opens in a new windowBeautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!

Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!

Madison MD
Located in Madison, this vacation home is on the waterfront, within a 15-minute drive of Blackwater National Wildlife Refuge and Harriet Tubman Underground Railroad ...
Opens in a new windowAmazing views waterfront 3-bedroom home in Madison with a 190 foot pier!
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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
Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views

Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views

Tilghman Island MD
When you stay at this vacation home in Tilghman, you'll be on the waterfront, just steps from Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowBayfront Retreat Near St. Michaels | Private Dock • Sunset Views
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
Thorneton Point Estate

Thorneton Point Estate

Easton MD
Located in Easton, this vacation home is on the waterfront, within a 10-minute drive of Saint Michaels Village and St. Michaels Winery.
Opens in a new windowThorneton Point Estate
Stylish Home on the Choptank River (with Tidal Beach)

Stylish Home on the Choptank River (with Tidal Beach)

Preston MD
Located in Preston, this vacation home is by the sea, within a 15-minute drive of Gilpin's Point Landing and Williston Lake.
Opens in a new windowStylish Home on the Choptank River (with Tidal Beach)
GRATITUDE FARM - A Tranquil Waterfront Renovated Farmhouse - Bozman, MD

GRATITUDE FARM - A Tranquil Waterfront Renovated Farmhouse - Bozman, MD

Bozman MD
Located in Bozman, this vacation home is on the waterfront, within a 15-minute drive of Neavitt Park and Perry Cabin Park.
Opens in a new windowGRATITUDE FARM - A Tranquil Waterfront Renovated Farmhouse - Bozman, MD
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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
234 Holiday Homes
Lowest Price
AU$286
Highest Price
AU$633
Popular accommodation
Private 2 Acre Waterfront Family Retreat with Pool & Pier, Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac, Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!, Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets, Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views, Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways, Thorneton Point Estate, Stylish Home on the Choptank River (with Tidal Beach), GRATITUDE FARM - A Tranquil Waterfront Renovated Farmhouse - Bozman, MD

Top trending hotels in Oxford

Sandaway Suites & Beach

Sandaway Suites & Beach

3 out of 5
103 West Strand Road Oxford MD
Fully refundableReserve now, pay when you stay
The price is AU$286 per night from 12 Apr to 13 Apr
AU$286
12 Apr - 13 Apr
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$401 per night from 31 Mar to 1 Apr
AU$401
31 Mar - 1 Apr
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$633 per night from 5 Apr to 6 Apr
AU$633
5 Apr - 6 Apr
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.