Book Holiday Homes in Oxford

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Featured Holiday Homes in Oxford

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

Royal Oak
With a stay at this vacation home in Royal Oak, you'll be on the waterfront, and 7.8 mi (12.6 km) from Saint Michaels Village and 8.3 mi (13.3 km) from St. Michaels ...
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

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

Cambridge
Located in Cambridge, this vacation home is on the waterfront, within a 15-minute drive of Spocott Windmill and Richardson Maritime Museum.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
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
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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~
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge
The price is AU$601 per night from 8 Sept to 9 Sept
AU$601
8 Sept - 9 Sept
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.
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!

"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!

3 out of 5
East New Market
With a stay at this vacation home in East New Market, you'll be within a 15-minute drive of Bay Country Shop and Meredith House.
"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!
Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels

St 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.
Dollhouse in Central Historic St Michaels
River Front, Private Single Family Home

River Front, Private Single Family Home

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.
River Front, Private Single Family Home
Peaceful Queenstown Home w/ Deck & Grill!

Peaceful Queenstown Home w/ Deck & Grill!

Queenstown
With a stay at this vacation home in Queenstown, you'll be within a 10-minute drive of Queenstown Premium Outlets and Wye Oak State Park.
Peaceful Queenstown Home w/ Deck & Grill!
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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
254 Holiday Homes
Lowest Price
AU$150
Highest Price
AU$601
Popular accommodation
RANCH AT ROYAL OAK- Exclusive waterfront pool pier, NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock, Walk to Everything House, 25-50% Off~Private Beach~Hot Tub~Fire Table~, Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, "Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!, Dollhouse in Central Historic St Michaels, River Front, Private Single Family Home, Peaceful Queenstown Home w/ Deck & Grill!

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$497 per night from 7 Oct to 8 Oct
AU$497
7 Oct - 8 Oct
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.
Sandaway Suites & Beach
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$431 per night from 28 Sept to 29 Sept
AU$431
28 Sept - 29 Sept
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.
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 refundable
The price is AU$150 per night from 6 Oct to 7 Oct
AU$150
6 Oct - 7 Oct
includes taxes & fees
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.