Oxford vacation rentals

We found 345 vacation rentals — enter your dates for availability

Discover a selection of 12 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.

Holiday rentals with weekly discounts - Oxford

Showing deals for:Aug 21 - Aug 28

Image gallery for Captain's Retreat! Newly Renovated - few steps from the beach!

Exterior
9.8 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)

Captain's Retreat! Newly Renovated - few steps from the beach!

Annapolis

17% off
Price is $799
$5,592 for 7 nights
All fees included
Captain's Retreat! Newly Renovated - few steps from the beach!

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Find out more about Oxford

Why visit Oxford

  • Outdoor Activities: Enjoy a range of outdoor pursuits, from hiking to beachcombing, set against stunning natural landscapes.
  • Historic Sites: Discover fascinating history museums that highlight the cultural heritage of the area.
  • Charming Marina: Visit the picturesque marina, perfect for boating and enjoying waterfront views.
  • Scenic Getaways: Experience the beauty of nearby Easton and the serene Madison Nature Getaway for romantic outings.
  • Diverse Accommodations: Choose from cozy cottages to luxurious rentals that cater to all traveler preferences.

Popular types of accommodation in Oxford

Discover the perfect getaway in Oxford with our diverse selection of vacation rentals. From cozy private homes and charming cottages to modern apartments, we have options to suit every traveler. Whether you need a spacious bedroom for the family, select hotels for a luxurious stay, or extended stays with all the comforts of home, you’ll find it here. Enjoy amenities like hot tubs and more for a truly relaxing experience.

  • Houses: The top choice for visitors in Oxford, offering spacious accommodations perfect for families or groups.
  • Cottages: A charming option, these cozy retreats capture the essence of Oxford's scenic beauty.
  • Apartments: Ideal for solo travelers or couples, providing a comfortable and convenient home base.
  • Condos: A popular choice with modern amenities, perfect for those seeking a blend of comfort and luxury.
  • Cabins: A rustic lodging option, great for those wanting a peaceful getaway in nature.**

Top attractions in and around Oxford

Oxford, Maryland, is a delightful destination for outdoor enthusiasts and beach lovers alike. Visitors can explore urban parks, a charming marina, and fascinating history museums that showcase the area's cultural heritage. Whether you're traveling with family or seeking a scenic getaway, Oxford offers a variety of attractions that cater to diverse interests, ensuring a memorable vacation experience for everyone.

  • Oxford Museum: A charming history museum located in the heart of Oxford, it offers visitors a glimpse into the region's rich cultural heritage and history through engaging exhibits and local artifacts.
  • Chesapeake Bay Maritime Museum: Situated 7 miles away, this maritime museum showcases the maritime history of the Chesapeake Bay, featuring interactive exhibits, historic boats, and stunning waterfront views.
  • Gerry Boyle Park at Great Marsh: Located 9 miles from Oxford, this urban park is perfect for families, offering scenic trails, picnic areas, and opportunities for outdoor activities amidst natural beauty.

Things to do recommended for couples

Oxford, Maryland, offers charming waterfront strolls along the Tred Avon River. Indulge in a romantic dinner at a local seafood restaurant, and take a sunset sail for unforgettable views. Don't forget to explore the quaint streets filled with historic charm and cozy shops for a perfect couple's getaway.

Things to do recommended for families

Families visiting Oxford, Maryland can explore the charming Oxford Museum, enjoy a scenic bike ride along the picturesque waterfront, and take a family-friendly cruise on the Tred Avon River for stunning views and a chance to spot local wildlife.

Things to do recommended for groups

Groups visiting Oxford, Maryland, can enjoy a scenic boat tour on the Tred Avon River, explore the charming local shops, and savor fresh seafood at waterfront restaurants. Don’t miss the chance to visit the historic Oxford Museum for a glimpse into the town's rich maritime heritage.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, family, or pets, or if you're considering longer stays, it's important to prioritize your preferences when searching. Here are some helpful Vrbo booking tips for you.

  • Traveling to Oxford with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group activities. The good news is that you can easily filter for these options and many more on Vrbo.
  • Traveling to Oxford with young kids: Traveling with young kids can present some challenges. It's important to prioritize their comfort and safety, along with providing suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions is a smart move.
  • Taking your pets with you to Oxford: For many, a family vacation isn't truly fulfilled without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Oxford: If you're in search of vacation rentals that offer 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 near Oxford

Experience the charm of Oxford, Maryland, a picturesque getaway perfect for outdoor enthusiasts and beach lovers alike. In early autumn, the vibrant foliage creates a stunning backdrop for exploring nearby Easton, known for its historic sites and family-friendly atmosphere. Don't miss the serene Madison Nature Getaway, ideal for romantic excursions and scenic adventures. With its humid summers and inviting community, Oxford offers a delightful blend of relaxation and exploration for every traveler.

  • St. Michaels: St. Michaels is a charming town located 7 miles from Oxford, known for its stunning waterfront and quaint streets. This picturesque destination offers a perfect blend of outdoor activities and scenic beauty. Visitors can stroll along the boardwalk, enjoy recreational areas by the bay, and relax on family-friendly beaches. Popular attractions include the local beach and the vibrant marina, where you can experience the area's rich maritime history. St. Michaels is ideal for those looking to unwind while soaking in the coastal charm.
  • Cambridge: Situated 10 miles from Oxford, Cambridge is a delightful city that beckons with its beautiful waterfront and vibrant community. Known for its outdoor experiences, visitors can explore the scenic boardwalk, relax at the beach, and shop at the local shopping center. The city’s attractions include the picturesque esplanade and the scenic bay, offering opportunities for boating, fishing, and enjoying nature. Cambridge is a fantastic destination for travelers seeking a blend of recreation and relaxation amidst breathtaking scenery.
  • Bellevue: Just 1 mile from Oxford, Bellevue is a quaint village that provides a peaceful retreat for those seeking outdoor adventures. With its proximity to the beach and bay, visitors can indulge in various water activities or explore the nearby national state park. Bellevue's natural beauty and serene environment make it an excellent choice for nature lovers and families looking to enjoy a day outdoors. This charming village offers easy access to stunning landscapes and recreational opportunities, making it a must-visit destination.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January36.0°F (2.2°C)Light RainMostly SunnyModerately LowSlightly Low
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 HighSlightly High
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 LowAverage
December41.9°F (5.5°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is a breeze

Are you eager to save on your upcoming travels? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient platform for you to plan new adventures, manage your travel arrangements, and keep track of your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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

What is the best area to stay in Oxford, Maryland, United States of America when booking a vacation rental?
When considering the best area to stay in Oxford, Maryland for a vacation rental, the charming waterfront neighborhoods offer a delightful experience. One standout area is the historic district, where you can immerse yourself in the town's rich maritime heritage. This area is dotted with lovely old homes and picturesque streets, making it great for leisurely strolls. You'll find yourself close to the Oxford-Bellevue Ferry, a fun and scenic way to explore the nearby towns across the Tred Avon River.

Another appealing neighborhood is the area surrounding the waterfront parks, where beautiful views and recreational activities abound. This location provides easy access to local attractions, such as the scenic Oxford Town Park, which is popular for picnics and outdoor relaxation. The nearby Oxford Museum also offers insights into the town's history and culture, adding depth to your stay.

Overall, Oxford has a selection of charming properties that cater to various preferences, whether you're looking for a cozy cottage or a more expansive waterfront home.
How much does it cost to rent a vacation home in Oxford?
Prices for vacation rentals in Oxford vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Oxford to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Oxford vacation house rentals?
You can find great discounts on house rentals in Oxford on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Oxford?
For renting a beach house in Oxford, consider the picturesque waterfront along the Tred Avon River. This charming area features a variety of vacation rentals that typically offer amenities such as private docks, outdoor seating areas, and spacious backyards superb for family gatherings. Many properties here provide easy access to both the river for kayaking and the nearby beaches, making it an ideal spot for water enthusiasts.

The neighborhood around the Oxford-Bellevue Ferry offers a quaint atmosphere with beautiful views of the water and surrounding landscapes. Rentals in this area may include features like screened porches, fire pits for evening gatherings, and well-equipped kitchens that facilitate a comfortable stay. Guests can enjoy the serene environment while being just a short drive away from local shops and restaurants in Oxford.

Additionally, the nearby public beaches and parks provide opportunities for picnicking, fishing, and exploring nature trails. This region is superb for those seeking a peaceful retreat with a blend of water activities and a charming, small-town experience.
What is the most popular type of vacation rental accomodation in Oxford?
In Oxford, vacation houses are the most popular type of rental accommodation, with around 11 available in the area. These homes are typically located in serene neighborhoods, providing a peaceful retreat for visitors. Most vacation houses feature multiple bedrooms, fully equipped kitchens, and spacious living areas, allowing guests to comfortably gather and relax. Many properties also offer outdoor spaces, such as gardens or patios, great for enjoying the picturesque views of the surrounding landscape.
Are there any family house rentals in Oxford?
In Oxford, Maryland, there are several family-friendly house rentals available. The charming town offers a variety of accommodations, many of which are situated near the waterfront, providing easy access to outdoor activities like kayaking and fishing. Properties often include spacious living areas, full kitchens for preparing family meals, and outdoor spaces great for enjoying the beautiful views of the Tred Avon River.

Visitors can explore nearby attractions such as the Oxford-Bellevue Ferry, which offers a scenic ride across the river, or take leisurely strolls through the quaint streets lined with historic homes and gardens.
Can I rent a vacation home with a pool or hot tub in Oxford?
In Oxford, Maryland, there are several vacation homes available for rent that feature pools and hot tubs. This charming waterfront town offers a tranquil setting along the Chesapeake Bay, making it an ideal retreat for travelers seeking relaxation. Many of the available rentals come with amenities such as private pools, outdoor decks, and hot tubs, great for enjoying the serene surroundings. Additionally, travelers can expect fully equipped kitchens, spacious living areas, and sometimes even waterfront views, enhancing their overall experience. Find your rental in Oxford with a pool or a hot tub.
Can I find long-stay vacation rentals in Oxford?
A long-stay vacation rental in Oxford is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Oxford?
In Oxford, Maryland, travelers can find several pet-friendly house rentals that cater to those looking to enjoy a getaway with their furry companions. Many of these homes are situated along the waterfront, offering stunning views and easy access to the water for activities like kayaking or paddleboarding. Expect amenities such as spacious backyards, screened porches, and fully equipped kitchens that make for a comfortable stay.

The charming neighborhood features local parks and nature trails, superb for walks with pets. The nearby Oxford-Bellevue Ferry provides a great experience for visitors and their pets as they cross the Tred Avon River.
Are there any remote work vacation rentals in Oxford?
In Oxford, Maryland, there are some vacation rentals available that cater to remote work needs, with around 11 options to choose from. Many of these properties are equipped with essential amenities for a productive work-from-home experience, including dedicated desks and comfortable desk chairs. Travelers can also expect free Wi-Fi, allowing for seamless connectivity during working hours. Some rentals may even offer additional conveniences such as printers, ensuring that guests can manage their professional tasks efficiently while enjoying the picturesque surroundings of this charming waterfront town. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Oxford vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Oxford with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Oxford?
In Oxford, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature coffee and tea makers, ensuring that travelers can enjoy a warm beverage at their convenience. Onsite parking is commonly available, making it easy for visitors to explore the charming town and its surroundings. Additionally, rentals often come with gardens, offering a serene space for relaxation, as well as porches or lanais where guests can unwind and appreciate the peaceful atmosphere.
When is the best time to visit Oxford for a vacation rental?
The best time to visit Oxford, Maryland for a vacation rental is during the peak season from June to August. This vibrant period attracts visitors eager to enjoy the picturesque waterfront and indulge in outdoor activities such as sailing, fishing, and exploring the charming town with its historic architecture. With warm temperatures averaging in the high 70s to mid-80s Fahrenheit, the summer months create an inclusive setting for leisurely strolls along the docks and enjoying the local cuisine.

July stands out as the most popular month, and you'll find the town buzzing with energy as families and friends gather to soak up the sun and participate in community events. The weather is great for water-based adventures and taking in the natural beauty surrounding Oxford.

For travelers seeking a more budget-friendly experience, consider planning your visit in December. While this is the low season, the town offers a cozy charm adorned with holiday decorations, and you can enjoy a peaceful getaway with fewer crowds. It's an excellent time for those who appreciate a serene atmosphere while still exploring local shops and enjoying winter activities.

Ultimately, the best time to visit Oxford depends on your preferences—whether you're drawn to the lively summer scene or the tranquil beauty of winter.
How early should I book a Oxford vacation rental?
Book your Oxford vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Oxford, Maryland, United States of America?
In Oxford, Maryland, visitors can enjoy a charming small-town atmosphere with several popular attractions. The Oxford-Bellevue Ferry is a popular spot, offering scenic views as it transports travelers across the Tred Avon River. The town's waterfront is superb for leisurely strolls and features picturesque views of the marina and surrounding landscapes.

For those interested in history, the Oxford Museum showcases local artifacts and provides insights into the town's maritime heritage. The nearby Cattail Creek is ideal for kayaking and paddleboarding, making it a great place for outdoor enthusiasts.

Additionally, the quaint shops and galleries in the town center offer unique local crafts and art, while the surrounding area boasts beautiful gardens and nature trails, superb for leisurely exploration.
Can I change or cancel my Oxford home rental booking on Vrbo?
To find Oxford vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Oxford vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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