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Oxford Holiday Rentals

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Our top choices for Oxford holiday rentals

10.0 out of 10, Exceptional, (7)
The price is NZ$433
includes taxes & fees
11 Jan - 12 Jan 2026
Station House East: Upscale Loft in the Historic District Cambridge, MD
9.8 out of 10, Exceptional, (43)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is NZ$449
includes taxes & fees
5 Jan - 6 Jan 2026
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
10.0 out of 10, Exceptional, (10)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is NZ$605
includes taxes & fees
5 Jan - 6 Jan 2026
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
9.6 out of 10, Exceptional, (20)
"The place was wonderful beautiful views of harbor, extremely clean and well appointed. Great restaurants we ate at RAR, great beer and food. Christopher’ Corner great dinner food fabulous and cocktails, highly recommend. Blackwater Cafe wonderful breakfast. "
United States
deb j.
The price is NZ$594
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
9.8 out of 10, Exceptional, (11)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
United States
Lauren V.
The price is NZ$610
includes taxes & fees
14 Jan - 15 Jan 2026
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Apartment in Cambridge

Sailwinds Loft at Cambridge Creek
10.0 out of 10, Exceptional, (24)
"What a great place to relax after exploring and enjoying the area. Definitely will visit again "
United States
Chris S.
The price is NZ$436
includes taxes & fees
31 Dec - 1 Jan 2026
Sailwinds Loft at Cambridge Creek
8.4 out of 10, Very good, (6)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is NZ$478
includes taxes & fees
12 Jan - 13 Jan 2026
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
10.0 out of 10, Exceptional, (50)
"Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!"
United States
Karen L.
The price is NZ$638
includes taxes & fees
6 Jan - 7 Jan 2026
Beautiful Waterfront Retreat in Cambridge!

Holiday Home in Woolford

Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (51)
"Great place, will stay again"
United States
Matt S.
The price is NZ$478
includes taxes & fees
6 Jan - 7 Jan 2026
Waterfront Getaway with Dock

Holiday Home in Denton

Turnbridge Manor
9.8 out of 10, Exceptional, (12)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is NZ$1,044
includes taxes & fees
31 Dec - 1 Jan 2026
Turnbridge Manor
9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is NZ$783
includes taxes & fees
29 Jan - 30 Jan 2026
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
10.0 out of 10, Exceptional, (14)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is NZ$905
includes taxes & fees
2 Jan - 3 Jan 2026
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
The price is NZ$1,498
includes taxes & fees
8 Jan - 9 Jan 2026
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
8.8 out of 10, Excellent, (9)
"This home was everything we needed and more! It was spacious, clean and a beautiful location! There was a leak in the ceiling and the owners were very responsive and fixed it right away. Definitely recommend this stay."
United States
Priscilla A.
The price is NZ$1,013
includes taxes & fees
2 Jan - 3 Jan 2026
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is NZ$717
includes taxes & fees
6 Jan - 7 Jan 2026
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Oxford Hotel Reviews

Find out more about Oxford

Everything you need to know about Oxford holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oxford holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oxford holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oxford holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oxford. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oxford holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oxford holiday rentals we have selected for you start as low as NZ$638 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oxford rentals

At Expedia, we put the best Oxford holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oxford rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oxford holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oxford. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Oxford?

Yes, there are holiday rentals close to the most popular sights in Oxford, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the riverfront in Oxford. Make sure you have time to check out the cathedral and waterfront during your trip.

What are some of the best holiday rentals that Oxford has to offer?

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. : This holiday home rental outside of Oxford is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a pool table.

How many holiday rentals are there in Oxford?

With 13 Expedia holiday rentals, you're guaranteed to find just the right place for your Oxford stay.

What can I see and do in Oxford?

Explore the area and cultural attractions such as Oxford Museum, or visit one of the family-friendly sights such as Chesapeake Bay Maritime Museum. In the wider area, you’ll find Saint Michaels Village and St. Michaels Winery.

What are holiday rentals like in Oxford?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oxford. Holiday rentals feature extras such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a small group gathering.