Discover a selection of 174 vacation rentals in Oxford that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $419 per night, and houses and cottages are popular options for a stay in Oxford. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Oxford
Destination guide

Sometimes you wanna go where everybody knows your name

Dreaming of a quaint town where everybody knows your name? Then an Oxford vacation rental may be calling your name. The picturesque waterfront town is one of Maryland’s oldest towns, and was once a colonial port. A storybook setting, complete with pristine views of the Eastern shoreline, make it a wonderful spot to spend a lazy summer weekend or get away from life’s crazy chaos for a while. Whether you’re fond of people- or boat-watching, sitting riverside, or noshing on a tasty treat, you’ll find plenty of opportunities to do it all here.

Things to do

Take a dip, or a day trip, or a wine sip

First stop, history! At the Oxford Museum, you’ll glean a better understanding of the area while viewing fascinating exhibits and over 2500 artifacts. The Oxford-Bellevue Ferry is a bold example of the area’s venerability: It dates from 1683 and has been in service since 1836! If you prefer to spend time in the water, head to Strand Beach and take a dip. If you don’t mind daytripping, a visit to St. Michaels Winery, approximately half an hour away, offers a mouth-watering opportunity to sample some of Maryland's best wines.


By land or by sea, Oxford has you covered

Attention, landlubbers and seafarers: You’re in the right place. Once you settle into your Oxford vacation rental, you’ll be engulfed in a world of activity. Bring the family to Oxford Park and enjoy a relaxing picnic while watching sailboats float past. Indulge your inner historian with a self-guided walking tour of the town—don’t miss the genuine Victorian-era homes that capture a special charm all of their own. Whimsical boutiques are jam-packed with special mementos and antiques. Of course, Oxford is synonymous with water, and you can enjoy plenty of maritime fun while you’re here. Fishing or ferrying, anyone?


Oxford: a town for all seasons

Its proximity to the water means that summertime never ventures into brutally hot territory. That’s great news if you’ve booked an Oxford vacation rental hoping to soak up the sunshine—just be mindful of the mid-season humidity! Summer presents average highs in the upper 70s, with a dramatic cooling that arrives by fall. Winter is expectedly brisk and sometimes snowy, and an average high of 35 degrees means you’ll want to pack a parka, a hat, and a pair of gloves. Spring—especially March—can be rainy. Don't forget the rain boots!

Natural features

It’s a shore thing in Oxford

Situated along the south shores of the Tred Avon River, Oxford is characterized by its aquatic ambiance and waters that seem to shimmer from nearly every angle. All riverside roads have plenty of seating space. If you’ve got “watch an amazing sunset” on your bucket list, perch yourself on a bench at Pleasant Street and enjoy the view. There’s also a lovely sandy beach where sitting and doing nothing is perfectly acceptable—and possibly preferable. Animal sightings are likely limited to fish, but anyone who enjoys a fresh catch will appreciate that.

How to get there

Transportation to and around Oxford

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 9.4 mi (15.1 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), which is 41.1 mi (66.1 km) away.

How many vacation rentals are available around Oxford?

Our 2021 property listings offer a large selection of 174 vacation rentals around Oxford. From 155 house rentals to 21 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.