Book Holiday Homes in Oxford

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Featured Holiday Homes in Oxford

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge MD
The price is AU$518 per night from 5 Jan to 6 Jan
AU$518
5 Jan - 6 Jan 2026
includes taxes & fees
A stay at this vacation home places you in the heart of Cambridge, steps from Long Wharf Park and Choptank River Lighthouse.
Opens in a new windowCozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Cambridge MD
Located in Cambridge, this vacation home is on the waterfront, within a 15-minute drive of Spocott Windmill and Richardson Maritime Museum.
Opens in a new windowNEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford MD
Located in Woolford, this vacation home is in a rural location, within a 10-minute drive of Blackwater National Wildlife Refuge and Harriet Tubman Underground ...
Opens in a new windowThe Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
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Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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

St. Michaels MD
With a stay at this vacation home in St. Michaels (Downtown St. Michaels), you'll be steps from Higgins Yacht Yard and Marina and 3 minutes by foot from Muskrat ...
Opens in a new windowDowntown St. Michaels | Walk to Shops, Restaurants and Nightlife
Heart of Tilghman Island | Pet Friendly | Perfect for Weddings Guests & Families

Heart of Tilghman Island | Pet Friendly | Perfect for Weddings Guests & Families

Tilghman Island MD
With a stay at this vacation home in Tilghman, you'll be within a 5-minute walk of Talbot County Library Tilghman Branch and Tilghman Watermen’s Museum.
Opens in a new windowHeart of Tilghman Island | Pet Friendly | Perfect for Weddings Guests & Families
Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

Easton MD
With a stay at this vacation home in Easton, you'll be on the beach, and 6.6 mi (10.7 km) from Saint Michaels Village and 7.3 mi (11.7 km) from St. Michaels ...
Opens in a new windowWoodwind Manor on the Tred Avon minutes to St Michaels and Easton.
 Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Woolford MD
A stay at this vacation home places you in the heart of Woolford, and within a 15-minute drive of Blackwater National Wildlife Refuge.
Opens in a new window Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Cambridge MD
With a stay at this vacation home in Cambridge, you'll be on the waterfront, and 6.1 mi (9.9 km) from Christ Rock Park and 6.5 mi (10.5 km) from Snows Turn ...
Opens in a new windowYear Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Sherwood MD
When you stay at this vacation home in Sherwood, you'll be on the waterfront, within a 5-minute drive of Back Creek Community Park and Knapp's Narrows Marina ...
Opens in a new window6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
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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$190
Highest Price
AU$949
Popular accommodation
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock, The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks, Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, Heart of Tilghman Island | Pet Friendly | Perfect for Weddings Guests & Families, Woodwind Manor on the Tred Avon minutes to St Michaels and Easton., Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock, Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28, 6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Top trending hotels in Oxford

Sandaway Suites & Beach

Sandaway Suites & Beach

3 out of 5
103 West Strand Road Oxford MD
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
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$336 per night from 1 Jan to 2 Jan
AU$336
1 Jan - 2 Jan 2026
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 Meredith House.
Opens in a new windowHyatt Regency Chesapeake Bay
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3 out of 5
3206 Main St Grasonville MD
The price is AU$190 per night from 28 Dec to 29 Dec
AU$190
28 Dec - 29 Dec
includes taxes & fees
A stay at Hilton Garden Inn Kent Island Marina places you in the heart of Grasonville, a 3-minute drive from Chesapeake Exploration Center and 7 minutes from ...
Opens in a new windowHilton Garden Inn Kent Island Marina
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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$949 per night from 30 Dec to 31 Dec
AU$949
30 Dec - 31 Dec
includes taxes & fees
A stay at Inn at Perry Cabin places you in the heart of St. Michaels, steps from Perry Cabin Park and 8 minutes by foot from Higgins Yacht Yard and Marina.
Opens in a new windowInn at Perry Cabin
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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.

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