Oxford holiday rentals

We found 354 holiday rentals — enter your dates for availability
Discover a selection of 11 homes and other holiday rentals in Oxford that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll have the amenities that you expect and more, which might include parking and a fireplace. At the end of the day, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Oxford

Showing deals for:6 Nov - 13 Nov

Dining
Marina
Private kitchen
Living area
Exceptional
(63 reviews)

Chesapeake Houseboat Getaway on Kent Island, Maryland

Stevensville

9% off
AU$2,650
for 7 nights, 1 houseboat
AU$379 per night
includes taxes & fees
Chesapeake Houseboat Getaway on Kent Island, Maryland
View from Foyer into Great Room
Pool
View from Pier back to house!
screened porch
Exceptional
(145 reviews)

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Easton

8% off
AU$11,207
for 7 nights, 1 home
AU$1,601 per night
includes taxes & fees
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Outdoor dining
Private kitchen
Interior
Room
Exceptional
(20 reviews)

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

Annapolis

16% off
AU$7,652
for 7 nights, 1 home
AU$1,093 per night
includes taxes & fees
Captain's Retreat! Newly Renovated - few steps from the beach!
Delightful front garden welcomes you when approaching house from driveway
Shaded view of wrap-around deck; stainless Saber outdoor gas grill
Custom, open-concept home (photo prior to new red-oak hardwood flooring)
"Overlook on Dun's Cove" -- luxury, year-round waterfront vacation rental
Exceptional
(161 reviews)

Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels

Sherwood

10% off
AU$3,155
for 7 nights, 1 home
AU$451 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Living area
Exterior
Private kitchen
Interior
Exceptional
(64 reviews)

Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay

Cambridge

8% off
AU$11,125
for 7 nights, 1 home
AU$1,589 per night
includes taxes & fees
Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay
Living Room with flat screen TV and sleeper sofa
View down the lane
Dining Room - Seats 6
Sit and stay a while!
Exceptional
(122 reviews)

Perfect Waterview Cottage - St. Michaels Getaway

Wittman

8% off
AU$2,870
for 7 nights, 1 cottage
AU$410 per night
includes taxes & fees
Perfect Waterview Cottage - St. Michaels Getaway
Interior
Private kitchen
Room
Living area
Exceptional
(10 reviews)

3-bedroom waterfront retreat in Secretary, Maryland

Secretary

8% off
AU$4,468
for 7 nights, 1 home
AU$638 per night
includes taxes & fees
3-bedroom waterfront retreat in Secretary, Maryland
Interior
Dining
Living area
Private kitchen
Exceptional
(10 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

12% off
AU$4,508
for 7 nights, 1 cottage
AU$644 per night
includes taxes & fees
Charming Waterfront Cottage Retreat near St. Michaels
Living area
Be ready to float! Bring your own inner tubes  and tennis shoes!
Interior
Exterior detail
Exceptional
(143 reviews)

Charming cottage along water with private pier, near St. Michaels Winery

Bozman

12% off
AU$2,942
for 7 nights, 1 cottage
AU$420 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Property grounds
Living area
Private kitchen
Living area
Exceptional
(5 reviews)

Lovely 2-bedroom waterfront cottage in charming Wittman

Wittman

8% off
AU$3,156
for 7 nights, 1 cottage
AU$451 per night
includes taxes & fees
Lovely 2-bedroom waterfront cottage in charming Wittman
Private kitchen
Exterior
Living area
Property grounds
Exceptional
(19 reviews)

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman

8% off
AU$4,160
for 7 nights, 1 cottage
AU$594 per night
includes taxes & fees
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Comfortable family room with reclining sofa, Smart TV and remote controlled window shades.
Light and bright dining room with space for 6 (plus a high chair).
Recently renovated kitchen with quartz countertops, stainless steel appliances, and all the gadgets, tools, and amenities you need to cook wonderful meals.
Light and bright dining room with space for 6 (plus a high chair).
Exceptional
(7 reviews)

Cozy Cottage with Beach Access

Annapolis

7% off
AU$4,414
for 7 nights, 1 home
AU$631 per night
includes taxes & fees
Cozy Cottage with Beach Access
Interior
Property grounds
Private kitchen
Water view from the kitchen
Exceptional
(29 reviews)

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Annapolis

8% off
AU$6,983
for 7 nights, 1 home
AU$998 per night
includes taxes & fees
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Terrace/patio
Living area
Room
Interior
Exceptional
(7 reviews)

Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels

St. Michaels

17% off
AU$3,399
for 7 nights, 1 home
AU$486 per night
includes taxes & fees
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
fridge with ice maker
Outdoor dining
upstairs offers 2 bedrooms including 1 queen and 4 twin (bunks)
Exterior detail
Exceptional
(30 reviews)

Eastern Shore Waterside Cottage Near St. Michaels

Neavitt

8% off
AU$3,401
for 7 nights, 1 cottage
AU$486 per night
includes taxes & fees
Eastern Shore Waterside Cottage Near St. Michaels
Boutiques and vintage shops are right outside your door
The beautiful marina is just 4 blocks away
Marina
Interior
Exceptional
(10 reviews)

Station House East: Upscale Loft in the Historic District Cambridge, MD

Cambridge

7% off
AU$1,464
for 7 nights, 1 apartment
AU$209 per night
includes taxes & fees
Station House East: Upscale Loft in the Historic District Cambridge, MD
Dining
Living area
Private kitchen
Interior
Exceptional
(48 reviews)

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Stevensville

8% off
AU$9,284
for 7 nights, 1 home
AU$1,326 per night
includes taxes & fees
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Exterior
Exterior
Living area
Dining
Exceptional
(27 reviews)

Spacious waterfront home with amazing views, private pier, fishing and crabbing.

Cambridge

8% off
AU$6,715
for 7 nights, 1 home
AU$959 per night
includes taxes & fees
Spacious waterfront home with amazing views, private pier, fishing and crabbing.
Front and side view of Blades House from Locust St.
St. Michaels Harbor from Park down street
Large screened porch with ceiling fan allows outdoor dining and relaxing.
Eating area in panelled Family Room. Eat here, in dining room, or on porch!
Exceptional
(150 reviews)

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St. Michaels

8% off
AU$4,122
for 7 nights, 1 cottage
AU$589 per night
includes taxes & fees
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Exterior
Marina
Living area
Marina
Exceptional
(13 reviews)

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Cambridge

8% off
AU$2,976
for 7 nights, 1 apartment
AU$425 per night
includes taxes & fees
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Oxford

  • Scenic waterfront views: Enjoy picturesque vistas along the waterfront, perfect for relaxing strolls and tranquil moments.
  • Outdoor activities: Explore the local marina and urban parks, ideal for picnics and leisurely outdoor pursuits.
  • Rich history: Visit the town's history museum to gain insights into Oxford's fascinating heritage.
  • Charming architecture: Wander through historical streets lined with quaint buildings that reflect the town's character.
  • Serene atmosphere: Experience a peaceful retreat in a welcoming environment, ideal for families and couples alike.

Popular types of accommodation in Oxford

Discover Oxford, Maryland, a charming city offering a variety of holiday rentals. From cosy private holiday homes and quaint cottages to modern apartments, there is something for everyone. Explore local attractions and landmarks, ensuring a memorable stay in this welcoming destination. Oxford holiday rentals provide transparency, savings, and reassurance for your next getaway, making it an ideal choice for travellers seeking a comfortable and enjoyable experience.

  • Private Holiday Homes: The top choice for visitors, offering spacious and comfortable living, perfect for families and groups.
  • Cottages: Quaint and charming, these properties provide a cosy retreat ideal for a romantic getaway or a peaceful escape.
  • Apartments: Conveniently located and self-contained, apartments are excellent for those seeking a home-like feel during their stay.
  • Condos: Blending comfort with modern amenities, condos are a popular option for those wanting a bit more luxury.
  • Cabins: Nestled in nature, cabins offer a rustic experience, perfect for immersing yourself in the scenic beauty of the area.**

Top attractions in and around Oxford

Oxford, Maryland, is a charming destination perfect for outdoor enthusiasts and families alike. Visitors can enjoy scenic water views while exploring the local marina and urban park, ideal for leisurely strolls or picnics. The town also boasts a history museum, offering insights into its rich heritage. With its inviting atmosphere and beautiful surroundings, Oxford is a delightful spot for a relaxing holiday experience.

  • Oxford Museum: Discover local heritage at this history museum, showcasing Oxford's rich past with engaging exhibits and cultural artefacts.
  • Chesapeake Bay Maritime Museum: Explore maritime history with exhibits celebrating seafaring traditions, located 11km from Oxford.
  • St. Michaels Marina: Enjoy a blend of adventure and outdoor fun at this marina, offering beach vibes and water-based activities 11km from Oxford.

Things to do recommended for couples

For a romantic getaway in Oxford, Maryland, enjoy a leisurely sail on the charming Tred Avon River or take a sunset stroll along the picturesque waterfront. Indulge in a candlelit dinner at a local eatery, savouring the fresh seafood and delightful views.

Things to do recommended for families

Families visiting Oxford, Maryland, can explore charming local parks, enjoy interactive exhibits at local museums, and participate in community events, offering a delightful blend of history and fun for all ages.

Things to do recommended for groups

Explore Oxford, Maryland by visiting local historical sites and enjoying group culinary tours. Discover charming heritage centres and enjoy bespoke dining experiences that offer insights into American history and culture.

*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

Whether you're journeying with a group, as a family, accompanied by your pets or seeking extended stays, ensure you filter by the appropriate priorities. Here are some Stayz booking tips for you.

  • Traveling to Oxford with a group: Consider how many bedrooms you require, in addition to facilities like a fully-equipped kitchen or an outdoor area for group get-togethers. Fortunately, you can apply filters for all these features, and more, on Stayz.
  • Traveling to Oxford with young kids: Traveling with young children can be demanding. It is essential to prioritise their comfort and safety, and to ensure the availability of age-appropriate facilities, such as a private swimming pool. It is also advisable to consider your closeness to attractions that are suitable for families.
  • Taking your pets with you to Oxford: For many, a family holiday isn’t complete without their four-legged companion in tow. If this resonates with you, explore Stayz properties that welcome pets. Most pet-friendly accommodations provide feeding bowls and beds, ensuring that every member of the family feels right at home.
  • Planning for a long term stay visiting Oxford: If you are seeking holiday lets offering discounts for extended stays of a month or more, you have come to the right place. By utilising the appropriate filter, you can effortlessly locate and secure savings on monthly rentals. You might also consider including options such as a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Oxford

Oxford, Maryland offers an idyllic waterfront getaway with charming Oxford and a quiet escape along the Oxford Strand. Explore the historical streets and scenic vistas, perfect for a family-friendly or romantic excursion. Enjoy the unique atmosphere of Oxford, where a visit promises a delightful blend of outdoor adventures and serene coastal charm.

  • St. Michaels: Located 11km from Oxford, St. Michaels is a charming city renowned for its scenic outdoor attractions. Visitors can enjoy a boardwalk, expansive recreational areas and delightful coastal experiences, including family-friendly beach outings along the bay. The city's picturesque setting makes it an ideal destination for those seeking a blend of natural beauty and vibrant local culture.
  • Easton: Situated 13km from Oxford, Easton offers a captivating mix of outdoor charm and seaside allure. The city provides attractive boardwalks, bustling shopping centres and ample recreational spaces. Its coastal attractions, including the bay and family beach, are perfect for those looking to immerse themselves in scenic landscapes and enjoy leisurely strolls along the waterfront.
  • Cambridge: At a distance of 16km from Oxford, Cambridge presents a delightful coastal retreat with a mix of outdoor enjoyment and urban conveniences. Explore its scenic boardwalk, recreational areas and shopping centres, while the local bay and esplanade offer a refreshing seaside experience. Cambridge stands as a splendid destination for visitors seeking both tranquillity and engaging local attractions.

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 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 Stayz is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Furthermore, extending your stay can often result in significant savings. To discover the ideal Stayz property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Stayz Trips: Planning as easy as it gets

Stayz’s Trip Board offers a handy space to create new journeys, resume where you left off, or review and arrange your plans. You can find properties you have saved or booked organised into Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Take in the picturesque beauty of Oxford

Enjoy the cathedral and other features of Oxford. Renowned for its sailing, riverfront and beaches, this city welcomes all visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Oxford

Are you hoping to discover attractions to visit while you're in the area? Venture out of your cosy holiday rental and check out everything that makes Oxford a one-of-a-kind holiday spot. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Hog Neck Golf Course (11.4 mi / 18.4 km)
  • Phillips Wharf Environmental Center (8.8 mi / 14.2 km)
  • Bay Country Shop (10.8 mi / 17.4 km)

Exploring the natural landscape of Oxford

Travellers enjoy Oxford for its riverfront and beaches. Whether you're an adventurous traveller or just want to take in the scenery, Oxford is a great place to get out in nature. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Gerry Boyle Park at Great Marsh (8.7 mi / 13.9 km)
  • Long Wharf Park (9.3 mi / 14.9 km)
  • Blackwater National Wildlife Refuge (18.5 mi / 29.8 km)
  • Northern Chesapeake Bay (21.4 mi / 34.4 km)
  • Romancoke Wharf County Park (16 mi / 25.8 km)
  • Royston Island (3.2 mi / 5.1 km)

Seasonal weather in Oxford

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 24°C.

Transport options to and around Oxford

The nearest airport is in Easton, MD (ESN-Easton - Newnam), located 10.4 mi (16.7 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), which is 42.6 mi (68.5 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Oxford?
Houses are the most popular style of holiday home in Oxford, according to our data. Even if you've got a different idea in mind, Stayz has properties in loads of sizes and shapes. Look through our options to find your ideal fit.
How much does it cost to rent a holiday home in Oxford?
The average price for a holiday home in Oxford is based on a number of factors, such as property type, length of stay and time of year. Whether you're searching for a sprawling villa with space for extended family or a quaint cabin just enough for two, just add your travel dates to find stays with fantastic value.
How much does it cost to rent a beach house in Oxford?
Prices for beach houses in Oxford differ depending on the type and size of the property and when you plan to travel. Just enter your travel dates into Stayz and how many guests to see available options and prices. From there you can use our filter tool to tailor your search results by amenities, nearby activities, ratings and more.
Are there pet-friendly holiday homes in Oxford?
There certainly are. You can choose from nine holiday homes that welcome pets in Oxford on Stayz. Our furry kids deserve a break too, so simply use our search function for pet-friendly holiday homes to book a pad where Spot can join in the fun.
What are popular home amenities in Oxford?
When it comes to home amenities that people are searching for in Oxford, a swimming pool, a beach view and a water view are the most popular. With Stayz holiday homes, you'll enjoy choices to suit your taste and style, whether you're going on a holiday with your partner, your friends or even pets.
Are there large group holiday homes in Oxford?
There are six holiday properties in Oxford that can sleep five or more guests. From family getaways to events like a friend's birthday, these stays have ample space to gather with the people that matter the most.
Are there holiday homes in Oxford that welcome kids?
Gather your whole crew for a fun-packed adventure in Oxford at one of our nine family-friendly holiday properties. Many of these stays provide amenities that are great for trips with the little ones, like laundries, extra bedrooms and swimming pools. Simply check the "Properties good for families" filter box and pick your favourite.
What are the top attractions for families in Oxford?
Keep your kids occupied at these top family-friendly attractions in Oxford:
  • Chesapeake Bay Maritime Museum
  • Oxford Museum
  • St. Michaels Museum
Can I find two-bedroom holiday homes in Oxford?
Choose from three two-bedroom properties in Oxford. Put your little ones in the second room or fill it with a couple of your best buddies. There's ample space for whoever's fortunate enough to be coming along for the ride.
Are there holiday homes with WiFi in Oxford?
Whether you want to stay in touch with the news, check emails or surf social media, there are nine holiday homes with WiFi in Oxford. Check the "WiFi" box when searching on Stayz and stay connected on your holiday.
How can I find holiday homes with air conditioning in Oxford?
Pick your travel dates and then use the filter tool to locate holiday homes with air conditioning in Oxford on Stayz. With eight air-conditioned properties to choose from here, you can look forward to a comfy and cool stay.
How old do you have to be to rent a holiday home in Oxford?
We advise checking with the Oxford holiday home you'd like on Stayz as age restrictions differ. However, generally it's 16, 18 or 21.
How long can I rent a holiday home in Oxford for?
It's down to the Oxford property. To see all available options offering extended stays, simply type your dates and number of people into Stayz's search page. You can look forward to having the entire property to yourself, along with amenities such as air conditioning, a kitchen and a backyard where the kids can run and play. Be on the lookout for long-term stays that offer weekly or monthly discounts.

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