Book Holiday Homes in Oxford

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Oxford

Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels

St Michaels MD
Stay at this holiday home in St. Michaels. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Muskrat Park and Clint S. Bradley Park are ...
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
Stay at this holiday home in Cambridge. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Ragged Island and Spocott Windmill are located ...
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
Stay at this holiday home in Tilghman. Enjoy a garden, laundry facilities and balconies. Popular attractions Tilghman Watermen’s Museum and Talbot County Library ...
Opens in a new windowWaterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
Save an average of 15% on thousands of hotels when you're signed in
Historic Waterfront Estate with Pool & Pet-Friendly  – Perfect for Fall Getaways

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

Oxford MD
Stay at this holiday home in Oxford. Enjoy private pools, a garden and laundry facilities. Popular attractions Oxford Museum and Royston Island are located ...
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
Stay at this holiday home in Woolford. Enjoy private pools, laundry facilities and patios. Popular attractions Ragged Island and Spocott Windmill are located ...
Opens in a new window"Endless Summer" Waterfront on the Chesapeake Bay!
Waterfront Getaway with Dock

Waterfront Getaway with Dock

Woolford MD
Stay at this holiday home in Woolford. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Harriet Tubman Underground Railroad National Historical ...
Opens in a new windowWaterfront Getaway with Dock
Waterfront Sunset Bayview: sleeps 6

Waterfront Sunset Bayview: sleeps 6

Chester MD
Stay at this holiday home in Chester. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Bodkin Island and Chesapeake Bay Environmental 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
Stay at this holiday home in Neavitt. Enjoy free Wi-Fi, a garden and tennis courts. Popular attractions Neavitt Park and Phillips Wharf Environmental Center ...
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
Stay at this holiday home in St. Michaels. Enjoy free Wi-Fi, private pools and laundry facilities. Popular attractions Back Creek Park and Clint S. Bradley Park ...
Opens in a new windowMinutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
Don't see what you're looking for?
See all available properties in Oxford
View all properties
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
225 Holiday Homes
Lowest Price
NZ$352
Highest Price
NZ$1,114
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 NZ$352 per night from 28 May to 29 May
NZ$352
28 May - 29 May
includes taxes & fees
Stay at this beach hotel in Oxford. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the property condition in their reviews. Popular attractions ...
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
Stay at this holiday home in Oxford. Enjoy private pools, a garden and laundry facilities. Popular attractions Oxford Museum and Royston Island are located ...
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 NZ$523 per night from 19 May to 20 May
NZ$523
19 May - 20 May
includes taxes & fees
Stay at this beach resort in Cambridge. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the pool and the helpful staff in their reviews. ...
Opens in a new windowHyatt Regency Chesapeake Bay
Save an average of 15% on thousands of hotels when you're signed in
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
The price is NZ$1,114 per night from 31 May to 1 June
NZ$1,114
31 May - 1 June
includes taxes & fees
Stay at this luxury hotel in St. Michaels. Enjoy free Wi-Fi, free valet parking and a full-service spa. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowInn at Perry Cabin
Don't see what you're looking for?
See all available properties in Oxford
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.