Oxford holiday homes

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:25 Dec - 1 Jan

View from Foyer into Great Room
Pool
Dining table- seats 10!
View from Pier back to house!
Exceptional
(146 reviews)

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

Easton

8% off
NZ$14,302
for 7 nights, 1 home
NZ$2,043 per night
includes taxes & fees
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Interior
The view off of the point, breathtaking.
Pool
Another view from above.
Exceptional
(46 reviews)

Grandview- Main House

Bozman

25% off
NZ$8,403
for 7 nights, 1 home
NZ$1,200 per night
includes taxes & fees
Grandview- Main House
View of St. Michaels Harbor from Town Park in front of Thomas Harrison House
View of Side of Harrison House and St. Michaels Harbor from Locust Street
Rear Porch for relaxing or for barbecues!
View of St Michaels Harbor from french doors in Living Room, and from Side Patio
Exceptional
(145 reviews)

Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!

St. Michaels

8% off
NZ$10,900
for 7 nights, 1 home
NZ$1,557 per night
includes taxes & fees
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
Dining
Interior
Living area
Interior
Excellent
(6 reviews)

Spacious waterfront house in charming Royal Oak with WiFi, AC, dock

Royal Oak

9% off
NZ$15,463
for 7 nights, 1 cottage
NZ$2,209 per night
includes taxes & fees
Spacious waterfront house in charming Royal Oak with WiFi, AC, dock
Private kitchen
Dining
Living area
Interior
Exceptional
(11 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

8% off
NZ$6,902
for 7 nights, 1 cottage
NZ$986 per night
includes taxes & fees
Charming Waterfront Cottage Retreat near St. Michaels
Private kitchen
Exterior
Living area
Property grounds
Exceptional
(25 reviews)

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

Tilghman

8% off
NZ$5,196
for 7 nights, 1 cottage
NZ$742 per night
includes taxes & fees
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Interior
Living area
Dining
Exterior
Exceptional
(51 reviews)

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

Stevensville

8% off
NZ$11,456
for 7 nights, 1 home
NZ$1,637 per night
includes taxes & fees
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Dining Room - Seats 6
View down the lane
Custom kitchen
Living Room with flat screen TV and sleeper sofa
Exceptional
(122 reviews)

Perfect Waterview Cottage - St. Michaels Getaway

Wittman

8% off
NZ$3,490
for 7 nights, 1 cottage
NZ$499 per night
includes taxes & fees
Perfect Waterview Cottage - St. Michaels Getaway
Property grounds
Private kitchen
Interior
Interior
Exceptional
(7 reviews)

Arcadia Shores on the Cove.

Easton

8% off
NZ$8,529
for 7 nights, 1 home
NZ$1,218 per night
includes taxes & fees
Arcadia Shores on the Cove.
Living area
Private kitchen
Interior
Property grounds
Exceptional
(10 reviews)

3-bedroom waterfront retreat in Secretary, Maryland

Secretary

8% off
NZ$6,101
for 7 nights, 1 home
NZ$872 per night
includes taxes & fees
3-bedroom waterfront retreat in Secretary, Maryland
Living area
Be ready to float! Bring your own inner tubes and tennis shoes!
Exterior detail
Living area
Exceptional
(144 reviews)

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

Bozman

12% off
NZ$3,606
for 7 nights, 1 cottage
NZ$515 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Private kitchen
Living area
Exterior
Interior
Exceptional
(415 reviews)

Stay in the HEART of Saint Michaels!

St. Michaels

17% off
NZ$3,571
for 7 nights, 1 home
NZ$510 per night
includes taxes & fees
Stay in the HEART of Saint Michaels!
Private kitchen
Property grounds
Water view from the kitchen
Interior
Exceptional
(36 reviews)

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Annapolis

8% off
NZ$8,878
for 7 nights, 1 home
NZ$1,268 per night
includes taxes & fees
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Dining
Outdoor dining
Living area
Private kitchen
Exceptional
(13 reviews)

High Water Guest House<br>

Cambridge

8% off
NZ$5,113
for 7 nights, 1 home
NZ$730 per night
includes taxes & fees
High Water Guest House<br>
Private kitchen
Terrace/patio
Living area
Back yard and fire pit
Exceptional
(49 reviews)

Water Views - Close to Downtown Annapolis

Annapolis

5% off
NZ$6,685
for 7 nights, 1 home
NZ$955 per night
includes taxes & fees
Water Views - Close to Downtown Annapolis
Marina
The beautiful marina is just 4 blocks away
Boutiques and vintage shops are right outside your door
Private kitchen
Exceptional
(11 reviews)

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

Cambridge

7% off
NZ$2,057
for 7 nights, 1 apartment
NZ$294 per night
includes taxes & fees
Station House East: Upscale Loft in the Historic District Cambridge, MD
Living area
Marina
Property grounds
Exterior
Exceptional
(14 reviews)

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Cambridge

8% off
NZ$3,670
for 7 nights, 1 apartment
NZ$524 per night
includes taxes & fees
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Dining
Exterior
Living area
Private kitchen
Exceptional
(28 reviews)

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

Cambridge

8% off
NZ$8,441
for 7 nights, 1 home
NZ$1,206 per night
includes taxes & fees
Spacious waterfront home with amazing views, private pier, fishing and crabbing.

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    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

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)
  • 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)
  • Triple Creek Winery (14.3 mi / 23 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 best area to stay in Oxford when booking a holiday rental?
When considering a holiday rental in Oxford, Maryland, the area around the waterfront offers a charming experience with picturesque views and a tranquil atmosphere. This part of Oxford is known for its historical significance and natural beauty, making it an ideal place for visitors looking to enjoy a peaceful getaway.In this neighbourhood, you'll find lovely properties that often feature scenic vistas of the Tred Avon River. The area is dotted with quaint cottages and more upscale homes, providing a variety of options for holiday rentals. With its rich maritime heritage, staying here allows easy access to delightful attractions such as the Oxford Museum, where you can delve into the local history, and the iconic Oxford-Bellevue Ferry, which offers a unique way to explore the surrounding areas.Additionally, the serene environment is great for outdoor enthusiasts, with opportunities for kayaking, cycling, and leisurely walks along the waterfront.
Where are the best areas for renting a beach house in Oxford?
For renting a beach house in Oxford, Maryland, the picturesque waterfront along the Tred Avon River is a prime area to consider. Properties in this region often come with stunning views, private docks, and easy access to the river for kayaking or paddleboarding. Many homes feature outdoor spaces such as large decks or patios, superb for relaxing and enjoying the serene surroundings.Additionally, the area near the Oxford-Bellevue Ferry offers charming cottages that exude a classic Eastern Shore aesthetic. These accommodations frequently include amenities like fully equipped kitchens, spacious living areas, and sometimes even private gardens. The proximity to local attractions, such as the quaint shops and restaurants in the town centre, enhances the overall experience for travellers.For those looking to explore beyond the immediate vicinity, there are opportunities for cycling along the scenic roads or taking leisurely strolls along the waterfront.
What is the most popular type of holiday rental accomodation in Oxford?
In Oxford, holiday houses are the most popular type of holiday rental, with about 44 available throughout the charming town. These properties often provide a spacious and comfortable setting, featuring multiple bedrooms, fully equipped kitchens, and inviting living areas. Many holiday houses also include outdoor spaces such as gardens or decks, allowing guests to enjoy the picturesque views of the surrounding area. With their home-like atmosphere, these rentals are ideal for families or groups looking to relax while exploring the local attractions, such as the scenic waterfront and nearby parks.
Are there any family house rentals in Oxford?
In Oxford, Maryland, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The charming neighbourhoods offer properties that typically feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces great for kids to enjoy. Many homes also provide amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay for all.Visitors can take advantage of the town's picturesque setting by exploring nearby attractions like the scenic waterfront, where families can indulge in activities such as kayaking or fishing. The local area is also rich in history, with opportunities to learn about the town's maritime heritage.
Can I rent a holiday home with a pool or hot tub in Oxford?
In Oxford, Maryland, there are several holiday homes available for rent that feature pools or hot tubs, making it a lovely destination for relaxation and leisure. The town is situated along the picturesque Tred Avon River, where visitors can enjoy serene waterfront views and outdoor activities. Many of the rentals in this area come equipped with private pools, hot tubs, and spacious outdoor areas, ideal for families or groups looking to unwind after a day of exploring.Travellers can expect amenities such as fully equipped kitchens for self-catering, comfortable living spaces, and some properties may even offer access to kayaks or bicycles for a more active holiday experience.
Are there pet-friendly house rentals in Oxford?
In Oxford, Maryland, there are several pet-friendly house rentals available, making it an excellent choice for travellers looking to enjoy a getaway with their furry companions. The charming waterfront area offers a variety of holiday properties, many of which feature amenities such as private docks, outdoor patios, and spacious living areas that are great for relaxation.Visitors can expect fully equipped kitchens, allowing for convenient meal preparation, and many homes come with access to beautiful views of the Tred Avon River. The town is known for its peaceful atmosphere and picturesque scenery, providing a serene backdrop for a holiday with pets.Furthermore, the nearby Oxford-Bellevue Ferry is a delightful experience for both humans and pets, allowing easy access to the surrounding areas.
Are there any remote work holiday rentals in Oxford?
In Oxford, Maryland, there are several remote work holiday rentals available, with around 44 options to choose from. This quaint waterfront town offers a peaceful setting ideal for those looking to combine work and relaxation. Many of the properties come equipped with amenities such as dedicated workspaces, including desks and ergonomic chairs, ensuring a comfortable environment for productivity. High-speed Wi-Fi is commonly available, allowing for seamless connectivity during your stay.Beyond the work aspect, the charming atmosphere of Oxford provides opportunities to unwind. The town is known for its picturesque views along the Tred Avon River, and nearby attractions include local galleries and quaint shops. Travellers can also enjoy outdoor activities like boating and fishing, making it an excellent choice for a balanced work-life experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Oxford?
In Oxford, popular rental amenities include kitchens, allowing guests to prepare their own meals, and coffee or tea makers for a warm beverage at any time. Onsite parking is readily available, making it convenient for those travelling by car. Many properties also feature gardens, providing a lovely space for relaxation outdoors, as well as porches or lanais where visitors can enjoy the fresh air and scenic views.
When is the best time to visit Oxford for a holiday rental?
The best time to visit Oxford for a holiday rental is during the peak season from June to August, with July being particularly popular. This vibrant period sees an influx of visitors enjoying the picturesque charm of the town, particularly its waterfront activities and the serene beauty of the Chesapeake Bay. The warm, sunny weather, with temperatures typically ranging from the mid-teens to low 30s Celsius, creates a friendly space great for outdoor exploration.During these summer months, you can indulge in a variety of activities, from kayaking and sailing to leisurely strolls along the scenic harbour. The town's delightful restaurants and cafes are also bustling, offering fresh seafood and local flavours that enhance your experience.For those seeking a more affordable option, consider visiting in December. While this month tends to be quieter, it offers a unique charm with festive decorations and a peaceful ambiance. You can enjoy cosy walks along the water and take in the tranquillity that Oxford has to offer during the off-peak season.Ultimately, your choice will depend on whether you gravitate towards the lively summer atmosphere or prefer the calm and charm of winter.
What are the top attractions in Oxford?
In Oxford, Maryland, visitors can enjoy a range of charming attractions that highlight the area's rich maritime history and picturesque scenery. The Oxford-Bellevue Ferry offers a delightful experience, allowing travel across the Tred Avon River while taking in beautiful views of the surrounding landscape. The historic Oxford Museum provides insights into the town's past, showcasing local artefacts and the maritime heritage of the Eastern Shore.For outdoor enthusiasts, the nearby parks and waterfront areas offer opportunities for boating, fishing, and kayaking. The serene Oxford waterfront is superb for leisurely strolls and enjoying the tranquil atmosphere. Additionally, the local art scene can be explored through various galleries featuring works by regional artists, contributing to the town's quaint, artistic charm.
Are all fees included in the Oxford holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Oxford holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Oxford with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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.
Are there any discounts for Oxford holiday homes?
You can find great discounts on holiday homes in Oxford on Bookabach, 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.
Can I change or cancel my Oxford holiday home booking on Bookabach?
To find Oxford holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Oxford?
A long-stay holiday home in Oxford is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Oxford holiday home?
Book your Oxford holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Oxford?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Oxford to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers 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, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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