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Compare 193 Vacation Homes in Oxford with updated reviews, rates, and availability.

"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!😁"

Nature,Outdoors,Scenery,Water,Waterfront

"We had the most wonderful time at this charming house on Tillman Island! While the pics are great, it is even better in person. The house is perfectly nestled on the waterway, offering stunning views. The backyard pool was a true highlight, and we spent countless hours splashing around, the pool in the sun."

Cambridge Vacation Rental | 7BR | 5.5BA | Stairs Required | 10,333 Sq Ft

" 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...

Welcome to the waterfront Seize the Bay with a private pier (boat pictured not included in rental).

"Despite the rainy weather from hurricane Debby, our family enjoyed our stay at this house/ property. The property was well appointed and we didn’t need for anything. We loved the porch, the dock and the water views. The house was very clean and there was plenty of space to spread out if needed. It was a peaceful getaway. Our hosts were wonderful and were easy to contact and helpful with information. "

"Stayed for three nights with a few friends with a focus on birding. The house is in a great location for "

SAR 1,656 total

includes taxes & fees

3 Dec - 4 Dec

"Owner canceled the day before with no notice"

Welcome to the Beachcomber on Kent Island, uniquely situated between a marina and a beach.

"We enjoyed our time here. The location is perfect, right on the water with beautiful sunset views. I thought the home could have some more seating space in the main living room area, but it worked well for our family of 5 (4 adults, 1 child). There was a bit of a musty smell throughout the duration of the stay, but it didn't hinder our enjoyment of the property. We'd definitely stay there again."

"We would love to return to Travelers Rest! Spacious home with separate master suites, waterfront views, large efficient kitchen, large private property, fairly isolated and within easy striking distance to Easton and St Michaels. We’ve rented many homes in this area and Travelers Rest is among the best. "

"Excellent experience."

SAR 987 total

includes taxes & fees

2 Dec - 3 Dec

"Four of my friends and I stayed at this cute home for a ladies' weekend (two nights) in St. Michaels. We are in our early 40's and all agreed that the location of this home is superb. We walked to dinner each night (Limoncello and Ruse, both great) and enjoyed the wonderful shops in the lovely downtown area. The location of this home cannot be beat if you want to park your car upon arrival and not have a need to use it again during your stay. We had three cars, two of which fit in the driveway...

"The house was amazing! From the moment the front door opened it was a visual feast. The views are incredible, it's quiet, private and very relaxing. There were personal elements reflecting the current and original owners which we found very interesting and the attention to detail throughout was superb! Everything was incredibly well stocked with a multitude of extras. "

"Perfect large space on a quiet and pretty area. Really great space. "

"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."

"Every morning I made coffee, lit the fire pit on the dock and spent at least from 30 minutes before sunrise to 30 after. Used Merlin to identify bird calls. Heard and saw bald eagles, a belted kingfisher and an eastern bluebird. Watched a great blue heron fishing. Heard many many different birds. Truly an awesome location to slow down and enjoy the moment "

SAR 1,047 total

includes taxes & fees

15 Dec - 16 Dec

"I highly recommend staying here for a cozy couples weekend. It was absolutely beautiful and quiet. The host was so nice and made us feel welcome. I can’t wait to stay here again."

SAR 1,361 total

includes taxes & fees

11 Dec - 12 Dec

Taylors Island Vacation Rental | 3BR | 2.5BA | 2,100 Sq Ft | 1-2 Steps Required

"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. "

Aerial view of property- river, dock, pergola , pool behind house

"We enjoyed our time at the house very much. We went out to dinner only once and the rest of the time we ate in. We grilled two nights and made a roast one night. The views and the pool were more than you could imagine."

Enjoy gorgeous sunsets, fish & crab from the pier

"comfortable and very cozy. Wonderful crabbing and sunsets."

"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...

"Great rental experience. Barb was fantastic at communicating. The house was perfect for our group, including some adults and some young children. Yard and dock were a blast for playing and fishing. "

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Other property types in Oxford

Charming Cottage on a quite creek of the Chesapeake Bay with private pool.

"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"