Discover a selection of 259 vacation rentals in Oxford, MD 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 $200 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

Activities and attractions in Oxford

Do you want to find attractions to visit while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that Oxford has to offer. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • St. Michaels Winery (7.1 mi / 11.4 km)
  • Hog Neck Golf Course (11.4 mi / 18.4 km)
  • Easton Cycle and Sport (8.6 mi / 13.9 km)
  • Talbot Massage (8.6 mi / 13.9 km)
  • Phillips Wharf Environmental Center (8.8 mi / 14.2 km)
  • Bay Country Shop (10.8 mi / 17.4 km)

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

Exploring the natural landscape of Oxford

Travelers enjoy Oxford for its riverfront and beaches. Whether you're an active traveler or just want to appreciate the scenery, Oxford is a great place to get out in nature. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Great Marsh Park (8.7 mi / 14 km)
  • Bill Burton Fishing Pier State Park (9.6 mi / 15.4 km)
  • Harriet Tubman Underground Railroad National Historical Park (16.5 mi / 26.5 km)
  • Blackwater National Wildlife Refuge (18.3 mi / 29.4 km)
  • Long Wharf Park (9.3 mi / 15 km)
How to get there

Transportation options to and around Oxford

The nearest airport is in Baltimore Washington Intl. Airport (BWI), located 43.3 mi (69.7 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Easton, MD (ESN-Easton - Newnam), which is 10.4 mi (16.7 km) away.

What are the top vacation rentals in or near Oxford?

The heart wants what it wants, and right now it wants to go on vacation. It's time to pack your suitcase and zip off to one of these top vacation rentals in or near Oxford:

  • Around 60 miles from the center of Oxford, it's hard to beat "Gorgeous Direct Ocean Front Condo Overlooking Pool And Beach". It has 1 bedroom and a range of amenities including an elevator and nearby whale-watching activities.
  • "Brand New Renovation In Historic District With 2 Parking Spots" also promises an awesome stay, offering 2 bedrooms, towels, an oven and more. It's around 30 miles from Oxford.

For even more great options, use the search bar at the top of the page to find the perfect Oxford vacation rental for you.

What are the best tiny house vacation rentals in or near Oxford?

For an unforgettable vacation experience, book a tiny house rental in Oxford. A word of warning though — after you've stayed in a tiny house, the urge to downsize and move into one of these pocket-sized digs will be tough to resist!

  • Unwind and clear your mind at "Annapolis Waterfront "tiny House" In Garden Setting". Located in Parole, a hair dryer and an iron and ironing board are a couple of amenities on offer here.
  • Alternatively, book a couple of nights at "A Serene Tiny Home Experience". Situated in Parole, this itty-bitty abode comes with an oven and a nearby river.

What are the top-rated vacation rentals for weekend getaways in or near Oxford?

Clock out on Friday afternoon and then forget all about the office. If you're ready for some relaxation and fun, these properties in and around Oxford promise a memorable weekend getaway:

  • Spend your whirlwind escape at "Peaceful Cambridge Home On Jenkins Creek", which is around 8 miles to the south of central Oxford. There's plenty of adventure and nature to discover around here. Go cycling and kayaking or simply delight in the sights of Galesville Heritage Museum and Bill Burton Fishing Pier State Park.
  • Alternatively, find your home away from home at "Charming Historic Home Just Steps From Main Street". Stay in and put your feet up, or get active and try cycling and sailing. When you're ready to explore more of the area, visit Hart-Miller Island State Park and Maryland Zoo. This charming vacation rental is around 25 miles northwest of Oxford.

Can I find studio apartments for rent in and around Oxford?

Generally small, easy on the pocketbook and well located, it's not hard to fall for the appeal of a studio apartment. Settle into one of these vacation rentals and get acquainted with Oxford up close:

  • Make "Annapolis Waterfront "tiny House" In Garden Setting" your home for a few days or more. This top vacation rental features amenities including a stovetop and a microwave oven.
  • Another great choice is "Beautiful Condo - Water View Near City Dock". Make use of a fridge, a TV and other amenities during your stay.

With the money you save on your studio apartment, you can afford to discover more of Oxford. Cultural attractions like ARTFX Gallery of Fine Crafts and Arts and OXOXO Gallery will help you understand the character of this destination.

Can I find short term rentals in or near Oxford?

Just because you only have a few short days off work doesn't mean you have to spend it in a bleak hotel. Go on vacation but still have the home comforts you love at one of these short-term rentals in or around Oxford:

  • "Peaceful Cambridge Home On Jenkins Creek" is near the center of Oxford, which means you'll have plenty of things to keep you on the go. Explore notable attractions like Annapolis Bowl and Eisenhower Golf Course when you're not hanging out in your cozy digs.
  • "Charming Historic Home Just Steps From Main Street" is another wonderful option. We recommend adding Walden Golf Club and Crofton Bowl to your travel itinerary when you're ready to sightsee.

What are the best romantic weekend getaways in or near Oxford?

Whether spent in a cabin, an apartment or a lodge, a romantic weekend getaway is one of the best ways to spice up your love life. Whisk your other half off for a couple of relaxing days at one of these appealing escapes in or near Oxford:

  • Sneak off on Friday afternoon for a few passionate nights at "Brand New Renovation In Historic District With 2 Parking Spots". Located around 30 miles from Oxford, it comes with lots of nice touches, including beauty services and a fireplace.
  • "Water Front Retreat - Sunrise And Sunset Water Views" is another top option that's sure to impress. It's about 30 miles from Oxford and has beauty services and a fireplace.

What are the best large group vacation rentals in or near Oxford?

Big groups mean huge fun. They also mean finding someplace that'll easily fit your whole gang. Check out our large group vacation rentals in or around Oxford and get your loved ones together under one roof:

  • You'll have loads of space to move around at "240' Private Beachfront @kent Island Love Point". Around 25 miles north of Oxford, this grand property has 5 bedrooms accommodating up to 26 guests. Top amenities include a nearby waterfront and a kitchen.
  • Invite up to 15 of your favorite people to "Waterfront Insta - Worthy Sunsets 5bedroom W" and fill the place with laughter and love. This popular option has 5 bedrooms and is around 25 miles to the south of central Oxford. It's crammed with features to keep large groups happy and comfortable, including an ocean view and a firepit.

What are the best houses for rent with a pool in or near Oxford?

Nothing spells fun like a pool. Blow up your inflatable swan and check out these houses in or near Oxford that come with this must-have amenity:

  • Pack your swimsuit and book a few days at "Annapolis Waterfront "tiny House" In Garden Setting". There are plenty of other convenient amenities here, including a fridge and a microwave oven.
  • "Premier St. Michaels Cottage - T. Blades House" is the kind of place you go to get away from it all and enjoy your surroundings, starting with its inviting pool. A microwave oven and on-site watersports are also on hand to make your visit a memorable one.

Not sure what to pack for your Oxford getaway? This impressive destination has a humid subtropical climate. In summer, you can expect average temperatures ranging from 70 ºF to 80 ºF. Check out our selection of Oxford vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more ideas about where to stay.

What are the best large family vacation rentals in or near Oxford?

No matter if your ideal escape is up in the mountains or on the beach, you'll enjoy it even more if you share it with loved ones. Choose one of these large family vacation rentals in or near Oxford and bring the whole crew:

  • Get your nearest and dearest under the same roof at "Water Front Retreat - Sunrise And Sunset Water Views", which has 3 bedrooms sleeping up to 8 guests. This getaway is located 30 miles to the north of Oxford and comes with amenities such as a dining table and cable/satellite TV services.
  • "Charming Historic Home Just Steps From Main Street" is also a top pick for families. It's around 25 miles to the northwest of Oxford, has 3 bedrooms and accommodates up to 8 guests. Handy amenities here include a toaster and a DVD player.

If you're in the mood to do some sightseeing, there are plenty of family-friendly attractions nearby to put on your to-do list. National Aquarium in Baltimore, Six Flags America and Maryland Zoo are good places to start.

Can I find family cabin rentals in or near Oxford?

Get away from it all and treat the people you love to a vacation of a different kind. Stay in one of these family cabin rentals in or near Oxford and get the camping experience — but with all the comforts of home!

  • "Stunning Views From Waterfront Log Cabin With Fireplace On The Chesapeake Bay" - Located around 25 miles southwest of central Oxford, this family-friendly escape comes with a swimming pool and a kitchen.
  • "Chesapeake Cabin" - Rally the troops and spend a few nights or longer at this welcoming rental, which is around 25 miles to the northwest of Oxford. You'll have access to beach sun loungers, a barbecue grill and a great deal more.

For more options, use the search bar at the top of the page and adjust the filters to find the Oxford vacation rental that's perfect for your needs.