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

Oxford Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Oxford vacation rentals

A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

1. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (39 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is ￥24,814
￥40,727 total
includes taxes & fees
Sep 1 - Sep 2
Sailwinds Loft at Cambridge Creek
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

2. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (25 reviews)
"Lovely terrace style town house in a lovely location in close proximity to the Marina and other amenities. Beautiful place to relax."
United States
Robert
The price is ￥24,814
￥59,224 total
includes taxes & fees
Sep 8 - Sep 9
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

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 ￥13,448
￥43,945 total
includes taxes & fees
Sep 1 - Sep 2
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

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 ￥44,218
￥88,276 total
includes taxes & fees
Sep 2 - Sep 3
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A covered outdoor dining area with a table and chairs, overlooking a body of water and trees.

5. Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (45 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
The price is ￥60,034
￥75,801 total
includes taxes & fees
Sep 8 - Sep 9
Sunset Breezes - quiet waterfront retreat

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 ￥23,053
￥73,344 total
includes taxes & fees
Sep 1 - Sep 2
Family Beach House: Spacious Deck, Grill & Views
A wooden interior with a dining area, sofas, and a table.

7. 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, (14 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 traveler
The price is ￥65,509
￥117,972 total
includes taxes & fees
Sep 29 - Sep 30
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
A spacious living room with a large TV, blue sofa, and a ceiling fan.

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)
"Anne is a great host, always responded promptly regardless of time.Property is huge! Lots of patio space, and included kayaks for us to use. Next time in the area will definitely stay there"
United States
Ramon A.
The price is ￥69,159
￥122,520 total
includes taxes & fees
Sep 1 - Sep 2
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

9. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is ￥40,023
￥67,879 total
includes taxes & fees
Sep 1 - Sep 2
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

10. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is ￥43,625
￥74,300 total
includes taxes & fees
Sep 1 - Sep 2
Plum Point Cottage #17
A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

11. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (17 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is ￥57,632
￥98,762 total
includes taxes & fees
Sep 1 - Sep 2
Turnbridge Manor

12. Waterfront Escape with Pool Nature Lover Paradise

Waterfront Escape with Pool Nature Lover Paradise
Stevensville
10.0 out of 10, Exceptional, (3 reviews)
"N"
United States
Maria S.
Waterfront Escape with Pool Nature Lover Paradise
Three birds perched on a wooden structure by the water.

13. 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, (76 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is ￥136,077
￥231,337 total
includes taxes & fees
Sep 7 - Sep 8
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A two-story house with a red roof, a brick chimney, and a small porch.

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
6.8 out of 10, (3 reviews)
"The place was very clean and Host was ok the shopping was six miles away, not in walking distance, we had no pets on this trip."
United States
Anonymous traveler
The price is ￥115,265
￥168,168 total
includes taxes & fees
Sep 2 - Sep 3
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

15. Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stay by MD's 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 ￥136,077
￥231,337 total
includes taxes & fees
Sep 1 - Sep 2
Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
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

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

8/10 Good
"under beds needs better cleaning. bathroom toilet seat needs cleaning (room 519) tighten. faucet needs maintenance both tub and sink."
Reynold 1-night trip
Posted less than an hour ago
Hilton Garden Inn Kent Island Marina

Find out more about Oxford

Search for holiday rentals in Oxford on Expedia! You can easily find your home rentals, villas, holiday apartments in Oxford using one of the methods below:

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  • Enter your travel dates to view the best deals on holiday rentals in Oxford while they last

Look no further and take a look at our great range of rental properties in Oxford!

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.