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:6 Nov - 13 Nov

Exterior
Marina
Exterior
Exterior
Exceptional
(63 reviews)

Chesapeake Houseboat Getaway on Kent Island, Maryland

Stevensville

9% off
NZ$3,190
for 7 nights, 1 houseboat
NZ$456 per night
includes taxes & fees
Chesapeake Houseboat Getaway on Kent Island, Maryland
Our home!   Total of 2 .5 acres!
Baja Deck with umbrella- sit in pool on plastic adirondack chairs and read!
Exterior
Perfection!
Exceptional
(145 reviews)

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

Easton

8% off
NZ$13,991
for 7 nights, 1 home
NZ$1,999 per night
includes taxes & fees
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Outdoor dining
Exterior
Beach
Living area
Exceptional
(20 reviews)

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

Annapolis

16% off
NZ$9,337
for 7 nights, 1 home
NZ$1,334 per night
includes taxes & fees
Captain's Retreat! Newly Renovated - few steps from the beach!
Relax, enjoy the fire, and splendid views in the cherry lounging furniture
"Overlook on Dun's Cove" -- luxury, year-round waterfront vacation rental
View of Dun's Cove and property from private pier, accommodates boats up to 40'
Custom, open-concept home (photo prior to new red-oak hardwood flooring)
Exceptional
(161 reviews)

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

Sherwood

10% off
NZ$3,797
for 7 nights, 1 home
NZ$542 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Exterior
Aerial view
Aerial view
Exterior
Exceptional
(64 reviews)

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

Cambridge

8% off
NZ$13,896
for 7 nights, 1 home
NZ$1,985 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
Welcome to Shipwright Cottage!
View from the end of the lane
Custom kitchen
Exceptional
(122 reviews)

Perfect Waterview Cottage - St. Michaels Getaway

Wittman

8% off
NZ$3,428
for 7 nights, 1 cottage
NZ$490 per night
includes taxes & fees
Perfect Waterview Cottage - St. Michaels Getaway
Miscellaneous
Miscellaneous
Outdoor dining
Miscellaneous
Exceptional
(10 reviews)

3-bedroom waterfront retreat in Secretary, Maryland

Secretary

8% off
NZ$5,482
for 7 nights, 1 home
NZ$783 per night
includes taxes & fees
3-bedroom waterfront retreat in Secretary, Maryland
Private kitchen
Exterior
Exterior
Exterior
Exceptional
(10 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

12% off
NZ$5,530
for 7 nights, 1 cottage
NZ$790 per night
includes taxes & fees
Charming Waterfront Cottage Retreat near St. Michaels
Living area
Catch up with friends...
Living area
Property grounds
Exceptional
(143 reviews)

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

Bozman

12% off
NZ$3,542
for 7 nights, 1 cottage
NZ$506 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Bathroom
Living area
Room
Bathroom
Exceptional
(5 reviews)

Lovely 2-bedroom waterfront cottage in charming Wittman

Wittman

8% off
NZ$3,798
for 7 nights, 1 cottage
NZ$543 per night
includes taxes & fees
Lovely 2-bedroom waterfront cottage in charming Wittman
Property grounds
Exterior
Calm broad vistas
Exterior
Exceptional
(19 reviews)

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

Tilghman

8% off
NZ$5,103
for 7 nights, 1 cottage
NZ$729 per night
includes taxes & fees
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Bright and spacious primary suite with queen bed, Smart TV, and stunning private bathroom that you have to see to believe!
Comfortable family room with reclining sofa, Smart TV and remote controlled window shades.
Recently renovated kitchen with quartz countertops, stainless steel appliances, and all the gadgets, tools, and amenities you need to cook wonderful meals.
Cozy cottage a block from Chesapeake Bay - with 2 bedrooms and 2 baths, outdoor living, and all the comforts of home.
Exceptional
(7 reviews)

Cozy Cottage with Beach Access

Annapolis

7% off
NZ$5,417
for 7 nights, 1 home
NZ$774 per night
includes taxes & fees
Cozy Cottage with Beach Access
Private kitchen
Property grounds
Water view from the kitchen
Bathroom
Exceptional
(29 reviews)

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Annapolis

8% off
NZ$8,461
for 7 nights, 1 home
NZ$1,209 per night
includes taxes & fees
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Outdoor dining
Exterior
Terrace/patio
Outdoor dining
Exceptional
(7 reviews)

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

St. Michaels

17% off
NZ$4,090
for 7 nights, 1 home
NZ$584 per night
includes taxes & fees
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
rockers looking out on to the property/water also has dining table
SUP Board onto Duck Cove from the private dock
Exterior
wrap around porch with rockers and dining area
Exceptional
(30 reviews)

Eastern Shore Waterside Cottage Near St. Michaels

Neavitt

8% off
NZ$4,091
for 7 nights, 1 cottage
NZ$584 per night
includes taxes & fees
Eastern Shore Waterside Cottage Near St. Michaels
Interior
Large dining table seats 8
Fully stocked kitchen includes all major appliances
Private kitchen
Exceptional
(10 reviews)

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

Cambridge

7% off
NZ$1,762
for 7 nights, 1 apartment
NZ$252 per night
includes taxes & fees
Station House East: Upscale Loft in the Historic District Cambridge, MD
Terrace/patio
Exterior
Exterior
Miscellaneous
Exceptional
(48 reviews)

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

Stevensville

8% off
NZ$11,676
for 7 nights, 1 home
NZ$1,668 per night
includes taxes & fees
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Living area
Property grounds
Exterior
Outdoor dining
Exceptional
(27 reviews)

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

Cambridge

8% off
NZ$8,130
for 7 nights, 1 home
NZ$1,161 per night
includes taxes & fees
Spacious waterfront home with amazing views, private pier, fishing and crabbing.
Large screened porch with ceiling fan allows outdoor dining and relaxing.
Front and side view of Blades House from Locust St.
Town Park and harbor view 1/2 block from house. Farmer's market in park on Sat.
Rear of house with Screened Porch and Patio great for barbecuing!
Exceptional
(150 reviews)

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

St. Michaels

8% off
NZ$5,055
for 7 nights, 1 cottage
NZ$722 per night
includes taxes & fees
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Marina
Parking
Exterior
Beach
Exceptional
(13 reviews)

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Cambridge

8% off
NZ$3,583
for 7 nights, 1 apartment
NZ$512 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
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

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

    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)
  • 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, Bookabach 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 Bookabach 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 Bookabach. 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 Bookabach 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 Bookabach 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 Bookabach. 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 Bookabach 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 Bookabach'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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