Oxford vacation rentals

We found 338 vacation rentals — enter your dates for availability

Discover a selection of 14 homes and other vacation rentals in Oxford that are perfect for your trip. Whether you’re staying in a vacation home with your kids or with friends, you'll find the amenities you need and want, which might include WiFi and a washer and dryer. Whatever you're looking for, you'll be able to choose a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Oxford

Showing deals for:Aug 15 - Aug 22
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Find out more about Oxford

Find out more about Oxford

Why visit Oxford

  1. Charming waterfront: Relax along the scenic waterfront, perfect for leisurely strolls and enjoying picturesque views.
  2. Historic architecture: Explore quaint houses and historic structures that showcase the town's rich heritage.
  3. Outdoor activities: Engage in family-friendly adventures with access to national parks and marinas for recreation.
  4. Cultural experiences: Discover local art and unique attractions in nearby Dorchester County.
  5. Diverse accommodations: Choose from a range of vacation rentals, including cozy cottages and luxurious waterfront homes.

Popular types of accommodation in Oxford

Explore the charm of Oxford with a variety of vacation rentals to suit every traveler’s needs. Whether you're seeking a cozy private vacation home, a stylish apartment, or a quaint cottage, Oxford has it all. Popular options include the inviting Oxford House, the spacious Easton Home, and luxurious waterfront cottages. Choose the perfect stay for your getaway and enjoy all that this picturesque destination has to offer.

  • Houses: The most sought-after option for visitors to Oxford, offering spacious and comfortable accommodations for families or groups.
  • Apartments: A popular choice for couples or solo travelers seeking convenience and a home-like atmosphere during their stay.
  • Cottages: These charming, quaint retreats provide a cozy and picturesque setting for a relaxing getaway.
  • Condos: Ideal for those wanting modern amenities and shared facilities while enjoying a vacation in Oxford.
  • House Boats: A unique option for travelers looking to experience life on the water in a fun and adventurous way.**

Top attractions in Oxford

Oxford, Maryland is perfect for outdoor and family adventures, offering a range of attractions including national parks, historic houses, and marinas. Visitors can immerse themselves in local culture and enjoy outdoor activities while exploring the scenic beauty of the area. Don't miss the opportunity to view the charming houses that define this quaint town, making your trip a memorable experience.

  1. Chesapeake Bay Maritime Museum: Located 7 miles from Oxford, this maritime museum offers a deep dive into the rich culture and heritage of the Chesapeake Bay. Visitors can explore historic vessels, engaging exhibits, and scenic waterfront views, making it a perfect spot for maritime enthusiasts.
  2. Oxford Museum: Nestled in the heart of Oxford, this history museum showcases local history and cultural artifacts, providing a fascinating glimpse into the town's past and its maritime heritage.
  3. Talbot County Visitor Center: Situated 8 miles from Oxford, this visitor center is your gateway to outdoor adventures. It offers information for families looking to explore the beautiful landscapes and recreational activities the area has to offer.

Things to do recommended for couples

Ready for a romantic getaway in Oxford, Maryland? Visit St. Michaels Winery for a charming experience just 7 miles away, or indulge in relaxation at Talbot Massage, 9 miles away. Don’t forget to explore Layton's Chance Vineyard and Winery, a lovely 20-mile trip filled with wine and romance!

Things to do recommended for families

Your family will have a blast at Chesapeake Beach Water Park, located 20 miles from Oxford. With thrilling water slides and family-friendly attractions, it's the perfect spot for adventure and entertainment, ensuring a memorable day for everyone!

Things to do recommended for groups

In Oxford, Maryland, groups can enjoy a show at the Avalon Theatre, located 8 miles away, or shop for gear at Easton Cycle and Sport, 9 miles away. For outdoor enthusiasts, the Hog Neck Golf Course, 11 miles away, offers a fantastic golfing experience.

What do I need to keep in mind when booking a vacation in Oxford

When planning your trip, whether you're traveling with a group, with family, bringing your pets, or seeking extended stays, it's important to prioritize your needs. Here are some helpful booking tips for Vrbo to enhance your experience.

  • Traveling to Oxford with a group: Think about how many bedrooms you require, as well as any additional features like a full kitchen or outdoor area for group gatherings. The good news is that you can easily filter for these options and more on Vrbo.
  • Traveling to Oxford with young kids: Traveling with young kids can be a bit of a challenge. It's important to prioritize their comfort and safety, along with finding age-appropriate amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Oxford: For many families, a vacation wouldn't be the same without their furry companions. If you can relate, take a look at Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds to ensure that your whole family feels comfortable and at home.
  • Planning for a long term stay visiting Oxford: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Oxford

Oxford, Maryland, is a charming destination perfect for outdoor adventures and family-friendly fun. Nestled on the Eastern Shore, this walkable town offers beautiful scenery and a friendly atmosphere. Explore nearby Dorchester County for unique attractions, art, and excursions that highlight the area’s rich culture. Enjoy relaxing moments along the waterfront and immerse yourself in the local community, making your vacation an unforgettable experience.

  • Annapolis: Annapolis, located 27 miles from Oxford, is a charming city rich in history and coastal beauty. Known for its vibrant atmosphere, it offers a great blend of family-friendly activities and outdoor adventures. Wander through the historic district, visit the United States Naval Academy, or enjoy a day at the beach. Shopping enthusiasts will appreciate the local malls and boutiques, while foodies can indulge in fresh seafood from waterfront restaurants. With its picturesque waterfront and engaging cultural scene, Annapolis is a must-visit destination.
  • St. Michaels: Just 7 miles from Oxford, St. Michaels is a delightful town that attracts visitors with its romantic charm and outdoor experiences. Stroll along the scenic boardwalk, explore recreational areas, or relax at the family-friendly beach. This quaint town is known for its rich maritime heritage, with art galleries and shops reflecting local craftsmanship. The nearby lake offers opportunities for water activities and fishing, making it a perfect getaway for families and couples alike. St. Michaels is a charming stop for any traveler seeking a peaceful escape.
  • Bellevue: Bellevue is a hidden gem located only 1 mile from Oxford, offering a relaxing beach experience and entertainment options. The area is known for its beautiful family beaches and scenic lookouts, perfect for picnicking and enjoying picturesque sunsets. Visitors can unwind by the water, indulge in local eateries, or simply soak up the sun. Bellevue's close proximity to Oxford makes it an ideal spot for a quick getaway, where you can enjoy a blend of leisure and local charm.

Best time to go to Oxford

If you're planning a trip to Oxford, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January36.0°F (2.2°C)Light RainMostly SunnyModerately LowSlightly High
February38.5°F (3.6°C)Light RainMostly SunnyAverageSlightly Low
March44.8°F (7.1°C)Light RainMostly SunnyAverageSlightly Low
April55.0°F (12.8°C)Light RainMostly SunnyAverageAverage
May64.0°F (17.8°C)Light RainMostly SunnyAverageAverage
June72.9°F (22.7°C)Light RainMostly SunnyModerately HighAverage
July78.1°F (25.6°C)Light RainMostly SunnyModerately HighSlightly High
August76.3°F (24.6°C)Light RainMostly SunnyModerately HighSlightly High
September70.5°F (21.4°C)Light RainMostly SunnyAverageAverage
October60.6°F (15.9°C)Light RainMostly SunnyAverageAverage
November48.9°F (9.4°C)Light RainMostly SunnyModerately LowSlightly Low
December41.9°F (5.5°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate significantly. Moreover, booking an extended stay often results in substantial savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to narrow your search by price, location, and type of vacation rental.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll earn OneKeyCash™ on the full booking amount. Being the organizer certainly has its perks! Join our One Key rewards program to unlock exclusive savings for members and accumulate OneKeyCash™ on eligible stays. Sign up today and begin your journey to savings.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers an easy-to-use platform for planning your travels. You can create new trips, resume planning from where you last stopped, or manage and organize your travel details all in one place. You'll see your saved or booked properties neatly sorted into categories like Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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.

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)
  • 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)
  • Hog Neck Golf Course (11.4 mi / 18.4 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!

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 / 13.9 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 / 14.9 km)
  • Bill Burton Fishing Pier State Park (9.6 mi / 15.4 km)

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.

Frequently asked questions

How much does it cost to rent a vacation rental in Oxford?
The average price for a vacation rental in Oxford can vary based on factors like property type, length of stay and season. Whether you prefer a sprawling villa with room to move around or a cozy cabin ideal for just you and the kids, just enter your dates of travel to find some great-value stays.
How much does it cost to rent a beach house in Oxford?
When you travel and the style and size of the property will help determine the cost of your beachside vacation rental. Enter your Oxford travel dates to view your available options on Vrbo. Did someone just say “hot tub”? Use our filters to select the features and amenities you need.
What are the top attractions for families in Oxford?
If you’re looking for some family-friendly fun near the center of Oxford, head over to Oxford Museum.
How old do you have to be to rent a vacation rental in Oxford?
The minimum age is usually 16, 18 or 21. It can differ between properties on Vrbo, so check the rules of your chosen Oxford vacation home before booking your escape.
How long can I rent a vacation rental in Oxford for?
The length of time you can rent a vacation rental in Oxford is down to the property. Just enter your selected dates to look at a list of options offering extended stays. With tons of amenities like kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you’re sure to discover somewhere perfect to call your home away from home in Oxford.
Does Vrbo offer discounts for vacation homes in Oxford?
Whether you’re interested in one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to score some fabulous deals and discounts on Vrbo. From weekend trips to extended vacations, we’ve got you covered for your next Oxford escape.

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