Holiday Rentals in Oxford

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Holiday Rentals in Oxford

Downtown Oxford | Outdoor Dining | Character Filled

Downtown Oxford | Outdoor Dining | Character Filled

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (24)
"Our weekend stay at Julia’s Arc was truly the perfect weekend!!! The location is perfect and the boat is so clean, cozy, beautifully decorated, and generously stocked. We felt so calm and happy during our whole stay. The top deck is a perfect spot to have a cup of coffee or watch the sunset. Plus, the host, Julia was so accommodating and sweet. We really hope to go back soon! "
Chesapeake Houseboat Getaway on Kent Island, Maryland

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (244)
"The only thing I can say is that the online listing really doesn’t do justice to how amazingly stunning Rob & Clarissa’s place is. My family and I decided last minute that we wanted to spend a weekend on the bay. I never expected it to be so beautiful! We got there late in the evening and we were speechless when we woke up to the most beautiful view of the water. My son had an amazing time between playing in the loft or in the playhouse outside, kayaking, and paddle boating. My parents “settled”...
Family and Pet-Friendly, Waterfront with Pier

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

9.8 out of 10, Exceptional, (9)
"This house is huge and has lots of different indoor and outdoor gathering spaces so the kids and adults in our group of three families didn’t have to be on top of each other in one living space the whole time. Big firepit area and huge lawn were great, and we enjoyed the kayaks and canoe. There’s a place to buy fresh crabs, oysters, and shrimp very close by, and the house has everything you need for a crab night. The owner was incredibly responsive and kind."
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (34)
"Clean, Spacious, and exactly as advertised! "
The price is €245
includes taxes & fees
20 Apr - 21 Apr
Relax on Kent Island in 3 Bedroom Home w/Waterview

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

10.0 out of 10, Exceptional, (7)
"The Lighthouse cottage was super clean & comfortable, beautifully decorated and stocked with supplies, and located on a lovely block overlooking water l. As a bonus, it was walking distance from downtown’s many shops and restaurants. "
The price is €337
includes taxes & fees
17 Apr - 18 Apr
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (39)
"This place is great. From the layout, to the sauna, screened in porch and backyard, the owners have thought hard about what features make for a luxurious, comfortable and fun experience. They were also very helpful with all aspects of the process - booking, arrival times, access to the home, help with what to do while there. "
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (39)
"Stayed at the rental for a day sandwiched between two nights. Perfect for R&R. "
The price is €254
includes taxes & fees
21 Apr - 22 Apr
Waterfront Getaway with Dock

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

9.6 out of 10, Exceptional, (4)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is €503
includes taxes & fees
15 May - 16 May
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
7.4 out of 10, Good, (3)
"Next time we will wait until its a little warmer! Safe and clean marina. Great views! Peaceful and quiet. "
Floating 2 bed 2 bath condo stunning views of the bay

Eastern Shore Waterside Cottage Near St. Michaels

10.0 out of 10, Exceptional, (19)
"Had a great visit. House was perfect and the area is absolutely gorgeous"
Eastern Shore Waterside Cottage Near St. Michaels

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (34)
"Great location with two parking spots and a small yard. Great for family vacation. "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock

10.0 out of 10, Exceptional, (16)
"Our 5th year traveling to the eastern shore of Maryland. The house was great. Loved everything about Pool"
Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (12)
"Great house, great owner, family had a blast! Thank you!"
Waterfront Sunset Bayview: sleeps 6

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (33)
"The perfect Thanksgiving. House was just right for family of three although more people would have been fine too. Lived the crab shack and played lots of pool and ping pong. Kitchen well stocked. Owners were prompt in responding to any questions. We would come back in a heartbeat."
The price is €469
includes taxes & fees
19 Apr - 20 Apr
Beautiful Waterfront Retreat in Cambridge!

Waterfront Property, kayaks, private dock, near town

9.8 out of 10, Exceptional, (150)
"Wonderful! Cranbrook is beautifully decorated, is in an amazing location and the views are spectacular!. Lots of period pieces with descriptions - great historical info. Large dining room and additional eating area, nice sitting areas, kitchen is well appointed. Stairs to bedrooms but a pullout on main level. Historic house so bedrooms are walk thru but fine with us! Room for multiple remote work stations. We’ll be back."
Waterfront Property, kayaks, private dock, near town

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

9.4 out of 10, Exceptional, (22)
"This property offered a truly magnificent stay. We were delighted by its gorgeous and clean environment, the peaceful atmosphere, and the impressive array of amenities. Finding a place that could comfortably accommodate our group of 20 for a two-day family and friends trip with a private indoor pool, hot tub, billiard table, table tennis, kayaks, and a private deck exceeded our expectations. The accommodations were spacious and spotless upon arrival, and we appreciated the ample supply of...
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

9.6 out of 10, Exceptional, (114)
"The house is quaint and very clean. It could use a refresh. Can't beat the location. You can walk to everything. "
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

25-50% Off~Private Beach~Hot Tub~Fire Table~

10.0 out of 10, Exceptional, (22)
"Our girls' weekend at this VRBO was absolutely perfect! From the moment we walked in, we were blown away by the gorgeous interior and stunning views. The house was fully equipped with everything we needed, making our stay incredibly comfortable and convenient. The hot tub was a huge hit and added an extra touch of luxury to our getaway.The beds were incredibly comfortable, and the entire house was spotlessly clean upon our arrival. We truly appreciated the attention to detail.The host was...
25-50% Off~Private Beach~Hot Tub~Fire Table~

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

10.0 out of 10, Exceptional, (12)
"very serene, peaceful home on the bay! Amazing getaway! "
The price is €561
includes taxes & fees
29 Apr - 30 Apr
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
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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Other types of properties in Oxford you may be interested in

Downtown Oxford | Outdoor Dining | Character Filled

Downtown Oxford | Outdoor Dining | Character Filled

Newly Renovated Guest House located in Oxford MD

9.8 out of 10, Exceptional, (19)
"Clean and somewhat comfortable. "
Newly Renovated Guest House located in Oxford MD

Hyatt Regency Chesapeake Bay

4.0 star property
8.8 out of 10, Excellent, (1002)
"Great spot."
The price is €241
includes taxes & fees
6 May - 7 May
Hyatt Regency Chesapeake Bay
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.

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?

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks: This holiday home rental outside of Oxford is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, 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 selection of games.

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 St. Michaels Winery and St. Michaels Marina.

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.