Oxford Vacation Rentals

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Vacation Rentals in Oxford

Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (25)
"My family and I enjoyed our stay at the Carpenter Alley Cottage in Saint Michaels! The location was perfect -- walking distance from everything! Appreciated that there was a ground floor bedroom for my parents so they didn't have to climb the stairs and my daughter loved having her own bunk bed room! I did have a few questions about the cottage and the check-in process and my inquiries were all met with a prompt response. Would love to stay here again! (One note though is that it is a smaller,...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Exterior
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (19)
"We have nothing but great things to say about Adam and his beautiful home! He was so accommodating and the home was comfortable and spacious for our family of 5! Couldn’t have had a better experience :)"
The price is $135
$327 total
includes taxes & fees
May 27 - May 28
Relax on Kent Island in 3 Bedroom Home w/Waterview
Property grounds
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (106)
"Wonderful return visit to St Michaels. This time at a fantastic historical home in perfect location. Home was everything you could ask for and more. Park your car and walk anywhere, within a very quiet neighborhood, yet minutes from all St Michaels offers. Highly recommend this Property and host."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
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Property grounds
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
10.0 out of 10, Exceptional, (151)
"Quaint yet period correct. Plenty of room with decent kitchen. Especially love location and screaned back porch. Have stayed in house several times and does not disappoint!! Will go again for sure!"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Fridge, microwave, stovetop, dishwasher
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (4)
"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (104)
"Loved this historic house! Perfect location, peaceful neighborhood and walking distance to entire town."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Outdoor pool
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (21)
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (127)
"A lovely cottage to stay in. Lots of old world charm and location is unbeatable when want to stay in St. Michaels"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Fridge, microwave, oven, stovetop
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
10.0 out of 10, Exceptional, (31)
"One of the best properties I have stayed at. With all the amenities, you never need to leave the home. We enjoyed the views, the quietness of the area, and the wildlife. We nicknamed two beautiful ducks…Sonny and Cher! The house is very clean, the checkin checkout procedures were very easy. The host communicated all the details plus additional suggestions. We are definitely returning very soon."
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
Fridge, microwave, oven, stovetop
Waterfront Cottage on the Eastern Shore
The price is $599
$1,134 total
includes taxes & fees
Jun 17 - Jun 18
Waterfront Cottage on the Eastern Shore
Property grounds
Chesapeake Houseboat Getaway on Kent Island, Maryland
10.0 out of 10, Exceptional, (7)
"My husband and I and our dog had a lovely getaway on "Julia's Arc". This was our first time on a Houseboat and it was a wonderful experience. So much light! And the movement of the boat was just enough to be comforting. The home was very clean and beautifully adorned with great attention to detail. Julia, the host, was very responsive and very generous in doing all she could to make our trip as comfortable and pleasurable as possible. The views over the water were gorgeous and we really...
Chesapeake Houseboat Getaway on Kent Island, Maryland
Interior
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
10.0 out of 10, Exceptional, (6)
"My sisters and I (5 total) visited in early November. Kent Island Time was a perfect fit. We were impressed by the cleanliness, spacious rooms, and well-equipped common areas. The best feature was the waterfront location. Even in November, we were able to sit outside on the patio and enjoy a glass of wine as we watched the amazing sunset. We all agreed we would absolutely stay again in the future."
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (61)
"The house was lovely. We had 3 days of rain but the view and the beach made it interesting at all times. The hosts make sure you have everything you need for your comfort and entertainment. This is by far the best appointed house we have rented. Thank you for a wonderful week!"
Mid-Century Modern and Marvelous on the Bay
Pool
Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
Fridge, microwave, oven, stovetop
The Middle Point Cabin in Saint Michaels
9.8 out of 10, Exceptional, (47)
"Looked just like the pictures. Everything was new clean and comfortable. Enclosed patio was a hit with our cat."
The Middle Point Cabin in Saint Michaels
Beach nearby
Waterfront, cozy cottage with private pool on 27 acres of privacy
9.8 out of 10, Exceptional, (85)
"We came for the Ironman 140.6 and we lucked out finding this lovely cottage! It was the perfect location, the property was beautful, and the house was very clean and had everything we needed. Dave and Cindy were so kind and helpful! They welcomed us to the property, gave us restaurant recommendations, let us pick some figs, and were very helpful when I left something behind. We would love to stay again!"
Waterfront, cozy cottage with private pool on 27 acres of privacy
Terrace/patio
Eastern Shore Waterside Cottage Near St. Michaels
10.0 out of 10, Exceptional, (5)
"We loved Waterside Cottage. It was so quite & the crabbing was wonderful which is what we were looking for. Topher was wonderful to work with both before we arrived & on the day of arrival. My husband is already asking if we can book it again next year."
Eastern Shore Waterside Cottage Near St. Michaels
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (196)
"We came here for the St. Michaels Running Festival. The location was perfect for navigating the morning race traffic. It was also the perfect spot to avoid the extra foot traffic. We will definitely be back."
Relaxing Waterfront Cottage Near St Michaels, Maryland
Bay Views |Breezy point Beach: 4BD 2BA King bed
10.0 out of 10, Exceptional, (1)
"The house was clean and quiet. The hosts were helpful and available for communication. This is a lovely house for a vacation away from crowds and by the beach."
The price is $172
$488 total
includes taxes & fees
May 22 - May 23
Bay Views |Breezy point Beach: 4BD 2BA King bed
Pool
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
10.0 out of 10, Exceptional, (1)
"This was the most peaceful and perfect property. I felt like I was on vacation and able to relax! We would definitely return if we are in the area again."
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
Don't see what you're looking for?
See all available properties in Oxford
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.

Oxford Vacation Rental Travel Info

Number of vacation rentals
24
Popular accommodation
Oxford private vacation homes
Known landmarks
St. Michaels Winery, Avalon Theatre and Academy of the Arts
International airport
Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)

Other types of properties in Oxford you may be interested in

Street view
The Oxford Inn
3.0 star property
9.4 out of 10, Exceptional, (222)
"the dining is SUPERB"
The price is $175
$193 total
includes taxes & fees
May 22 - May 23
The Oxford Inn
Ecotours
Sandaway Suites & Beach
3.0 star property
9.2 out of 10, Wonderful, (115)
"I took a solo trip and picked the perfect spot. This family owned inn is great for a family trip, a romantic getaway, or for a quiet escape by yourself. The owners are such a welcoming family and made me feel very like VIP. I will be going back and recommend Sandaway to anyone looking for that getaway in the Eastern Shore. Thank you Gibson Family for a wonderful experience!"
The price is $230
$253 total
includes taxes & fees
May 22 - May 23
Sandaway Suites & Beach
Fridge, microwave, oven, stovetop
Newly Renovated Guest House located in Oxford MD
10.0 out of 10, Exceptional, (7)
"A great getaway but could even be better if you were to have a comfortable lounger in the living room as well as a couple of loungers in the garden. Despite the lounger issue I would definitely rent again"
Newly Renovated Guest House located in Oxford MD
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.

Everything you need to know about Oxford vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oxford vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oxford vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oxford in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $135 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oxford rentals

At Expedia, we put the best Oxford vacation 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 vacation.

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 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?

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife: This vacation home near Oxford offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Oxford?

With 14 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 St. Michaels Winery and Avalon Theatre.

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.

Recent reviews of Oxford properties
Expedia verified reviews

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton

5/5 Excellent
"The staff went above and beyond, very helpful and responsive. CLEAN rooms and common areas. We will stay again "
A verified traveler stayed at Fairfield Inn & Suites by Marriott Easton
Posted 2 days ago
Fairfield Inn & Suites by Marriott Easton