Holiday Rentals in Oxford

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Holiday Rentals in Oxford

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (112)
"Perfect stay in a historic home in the heart of town."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (68)
"The ratings were Exceptional, so I was skeptical. However, it was beyond exceptional. The most well equipped rental we have seen. Great location. Well stocked. Excellent communication with the host. Couldn’t have asked for anything more. Definitely recommend, and will stay here again when in the area. We had a great time."
Mid-Century Modern and Marvelous on the Bay
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (216)
" The Cottage is located on Harris Creek and it has everything that you need to really "kick back" and enjoy all of the amenities and scenery. The large modern kitchen is well stocked for all of your culinary needs and the side deck and grill are perfect for your outdoor dining. It is our third time vacationing at such a lovely place and close by are great restaurants, shops, boating, fishing, swimming, or just doing NOTHING!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (132)
"Fine stay pretty quiet off season"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (17)
" October 11-14, 2024, we rented the “Willoughby” for a family reunion. Let me start out by saying this home is amazing. It looks exactly as pictured based on the website photos. It was even better than I expected. If you are considering this property, I highly recommend booking it! Believe me when I say the Willoughby is a rare gem. The location of the home is perfect and extremely private. The grounds are pristine and the view of the water is breathtaking. The home sits on the Hudson...
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Chesapeake Houseboat Getaway on Kent Island, Maryland
9.6 out of 10, Exceptional, (19)
"We loved our stay. It was particularly nice to get away from all the "hustle and bustle" of the Sailboat Show. The unit was well-equipped and comfortable. We loved the upper deck! In fact, we had morning coffee, on day, and watched 2 eagles in a nearby tree. "
Chesapeake Houseboat Getaway on Kent Island, Maryland
Walk to Everything House
10.0 out of 10, Exceptional, (72)
"We thoroughly enjoyed the convenience of walking to shops, restaurants, and waterfront! Residence was charming and clean! Only minor issue was we couldn’t locate the iron- just the ironing board! We still had fun but we’re just a bit wrinkled!😁"
Walk to Everything House
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
10.0 out of 10, Exceptional, (31)
"House was spacious, clean, and exactly as described in the listings. We had a great time!"
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
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
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (24)
"We loved everything about the Kent Island House! Would book again in a hot minute"
Pool and Bay Views on wrap around deck in Kent Island
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
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
9.8 out of 10, Exceptional, (9)
"Our stay was amazing. The house is beautiful. The views and peaceful location were completely used. We had many fun game nights and dinners around the table, the kitchen easily provided many happy meals. The gas grill, the fire pit were easy to use. The kayaks were a lot of fun. Sitting on the dock enjoying the peaceful quiet mornings was rejuvenating. The pool chairs and umbrellas were really nice. A ping pong table in the garage was a ton of fun too. The extra fridge/freezer was handy and the...
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (29)
"I had a fantastic stay in Stevensville! The house was cozy, clean, and exactly as described. It had all the essentials for a comfortable visit, and the location was perfect for a peaceful getaway. The host was attentive, friendly, and made sure I had everything I needed to feel at home. I especially appreciated the thoughtful touches around the house that made it feel welcoming. I highly recommend this place to anyone looking for a relaxing and enjoyable stay, and I would definitely return in...
The price is €232
includes taxes & fees
6 Nov - 7 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview
St. Michaels Waterfront Home
9.6 out of 10, Exceptional, (25)
"Excellent property ! Had everything we needed and wanted and more. Waterfront views and shorebirds beautiful ! We hope to revisit !!! "
St. Michaels Waterfront Home
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (168)
"We went to St. Michael’s for a wedding. The cottage was great. Very charming. The location was perfect. We could walk everywhere. We had great communication with the host. He was very accommodating. We will stay there again. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (31)
"Other than arriving with no sheets on beds, no towels, and no basic toiletries or kitchen cleaning set, place is very good. Cleaning service, owner, or property management firm mismanaged the prep for our arrival. Absence of sheets, towels, etc. was rectified in a bit more than 1 hour. Nice place and superb location for seeing the village. Quiet, but right in the middle of all shops, farmers market, restaurants, etc. There was a bit of a pet odor in the 1st floor bedroom. Only other comment is...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
10.0 out of 10, Exceptional, (7)
"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
Private 9 acre Family Retreat on the Chesapeake Bay
10.0 out of 10, Exceptional, (8)
"House was loaded with activities for all ages. So much to do and see. Host was outstanding! Friendly and extremely accommodating."
Private 9 acre Family Retreat on the Chesapeake Bay
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (114)
"Waters edge is just a few steps away to sit and watch boats come in and out. So cute and the most amazing artifacts decorating the place made it even more captivating. Short walk to coffee, food and shopping local. The owner was responsive and kind as well as super easy to work with. Will definitely return."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Bay Views & Fire Pit: Taylor’s Island Retreat
9.8 out of 10, Exceptional, (10)
"This is a hidden jewel. We had so much fun fishing and crabbing. The home was everything you could ever ask for. We will definitely be back next year for a longer stay. If you are looking for some peace and quiet, this is the place to be. Thank you to the owners for making this a great place. "
Bay Views & Fire Pit: Taylor’s Island Retreat
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

The Oxford Inn
3.0 star property
9.4 out of 10, Exceptional, (237)
"The staff were friendly and accommodating. "
The Oxford Inn
Newly Renovated Guest House located in Oxford MD
10.0 out of 10, Exceptional, (16)
"Quiet area, clean, fresh, attractively and comfortably decorated accompanied by excellent service by the host. Recommend highly!!"
Newly Renovated Guest House located in Oxford MD
Sandaway Suites & Beach
3.0 star property
9.2 out of 10, Wonderful, (130)
"It was a very relaxing stay!!"
The price is €202
includes taxes & fees
6 Nov - 7 Nov
Sandaway Suites & Beach
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?

Mid-Century Modern and Marvelous on the Bay: This holiday home rental outside Oxford is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a private garden and 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 Avalon Theatre.

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.