A waterfront street lined with trees and a white building with a balcony.

Oxford Vacation Rentals

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Our top choices for Oxford vacation rentals

1. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is CA $221
CA $360 total
includes taxes & fees
Oct 6 - Oct 7
Sailwinds Loft at Cambridge Creek

2. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (14 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is CA $242
CA $550 total
includes taxes & fees
Oct 27 - Oct 28
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

3. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is CA $120
CA $402 total
includes taxes & fees
Oct 6 - Oct 7
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

4. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is CA $415
CA $804 total
includes taxes & fees
Oct 6 - Oct 7
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

5. More, than just a place to sleep - welcome home!

More, than just a place to sleep - welcome home!
Cambridge
The price is CA $425
CA $566 total
includes taxes & fees
Oct 6 - Oct 7
More, than just a place to sleep - welcome home!

6. Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is CA $205
CA $653 total
includes taxes & fees
Oct 7 - Oct 8
Family Beach House: Spacious Deck, Grill & Views

7. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (67 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is CA $295
CA $358 total
includes taxes & fees
Oct 18 - Oct 19
Waterfront Getaway with Dock

8. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford
9.6 out of 10, Exceptional, (35 reviews)
"Beautiful piece of property and clean, comfortable accommodations! Would definitely return if plan to be in that area again!!"
United States
Joyce F.
The price is CA $489
CA $924 total
includes taxes & fees
Oct 6 - Oct 7
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

9. WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
9.0 out of 10, Wonderful, (15 reviews)
"Very spacious home. 4 bedrooms and 4 baths. Great basement for watching TV with a large group. Home is about 15 minutes from downtown Cambridge."
United States
Anonymous traveller
The price is CA $474
CA $906 total
includes taxes & fees
Oct 6 - Oct 7
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

10. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is CA $1,139
CA $1,976 total
includes taxes & fees
Oct 6 - Oct 7
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

11. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is CA $388
CA $658 total
includes taxes & fees
Oct 6 - Oct 7
Plum Point Cottage #17

12. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is CA $513
CA $870 total
includes taxes & fees
Oct 6 - Oct 7
Turnbridge Manor

13. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is CA $998
CA $1,796 total
includes taxes & fees
Oct 6 - Oct 7
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

14. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Stevensville
8.0 out of 10, Very good, (5 reviews)
"We arrived and the air conditioning was broken.The owner did not inform us but installed portable AC’s running vents out of doors that would not close or lock. The old AC unit was installed incorrectly &BR below flooded by 12 am. contacted owner and then was told not to run AC & we would be refunded. Covered mattresses that were being soaked, cleaned up flood, washed all bedding. Owner said trying to find us another rental but there were none & I had service dog. If we moved we would miss...
United States
Suzanne R.
The price is CA $1,026
CA $1,502 total
includes taxes & fees
Oct 6 - Oct 7
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Oxford. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Oxford?

Yes, we have vacation rentals close to well known local attractions 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 vacation rentals in Oxford?

Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways: Visitors like this Oxford vacation home rental. It is located on a river and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Oxford?

With 11 Expedia vacation rentals, you're sure 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 a family-friendly sight such as Chesapeake Bay Maritime Museum. In the larger area, you’ll find Saint Michaels Village and St. Michaels Winery.

What are vacation rentals like in Oxford?

Vacation rentals are privately owned accommodations you can book for several days or longer in Oxford. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips.