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Vacation Rentals in Oxford, Maryland

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about Oxford

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Oxford, Maryland vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Oxford are added and updated every week!

Compared to hotels, Oxford vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Oxford, Maryland Vacation Rentals and Tourism

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Oxford things to do

 

Sail Selina II

This was by far the best part of our amazing trip to St. Michael's. We went on the champagne cruise. The boat is beautiful. The views were breathtaking. The...read more

 

Carpenter Street Saloon

Some of the other reviews sum the experience up pretty well. The atmosphere and service are definitely laid back and I certainly wouldn't recommend...read more

 

Chesapeake Bay Maritime Museum

YES! This is a fabulous museum for any age group, with plenty of hands-on activities to keep people interested and really enhance the learning. I hadn't...read more

 

St. Michaels Winery

I've been here twice. The more recent visit took place just two days ago. We had the dry red tasting, and unfortunately I did not find most of the wines to...read more

 

Tricycle and Run

My wife and I were biking around St. Michael's on Memorial Day, and my wife's bike seat broke. I called Tricycle and Run to see if they were open and could...read more

 

Calico Toys and Games

Wow. This is like the BEST toy store I've ever seen. And it's not a chi-chi, "we're all wood and German-made and you're all Very Involved in Your...read more

 

Sailwinds Park

Our annual rest stop. 2 hours from home on the way to Ocean City, MD. Clean bathrooms. Great view & if you have children, a great little park for play...read more

 

Riverhouse at Easton Club Golf Course

My cousin just had her wedding here last weekend and everything went very smoothly (minus the weather which didn't cooperate till the VERY last minute)....read more

 

St. Michaels Concours d'Elegance

With the help of Cole Porter: It's delightful, it's delicious, it's d'Elegance You can tell at a glance what a swell event this is for romance You can...read more

 

Shore Pedal & Paddle

With a variety of options available, this shop has something for everyone. The equipment is well maintained. The staff well versed in all matters...read more

 

Avalon Performing Arts Theater

Perfect place to see great live music, hilarious comedians, or have fun on New Years Eve. I for one have done all of the above and this historic venue never...read more

 

Fitness RX

Sunday morning, 9am. I'm in from out of town and just want to get in a workout. Fitness Rx looked like one of the few open gyms at that time. The owner,...read more

 

Richardson Maritime Museum

Excellent museum in downtown Cambridge, within walking distance of the marina. It's larger than it appears from outside and has many rooms to explore. The...read more

 

Caroline Country Club Inc

New Chef, new menus, new environment. Food was delicious... If this is the first Friday dinner; I can't imagine what this place will grow to!! Great...read more

 

Lucky Dog Catamaran Company

My wife and I and the kids took a 2 hour ride aboard this Catamaran while staying in Cambridge, MD at the Hyatt. Capt Kimber is really cool and laid back....read more

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Fabulous Fall Cottage Getaway! Enjoy cozy views and Inn next door.
Oxford Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $181 - $263 /nt
    $1,125 - $1,800 /wk
 
 
 
 
 

81 reviews write a review

Sunrises AND Sunsets, Panoramic Views with Pool and Deepwater Dock, Sleeps 10
Oxford House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 5
  • rates (USD) $700 - $850 /nt
    $4,500 - $5,700 /wk
 
 
 
 
 

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Waterfront Family Retreat with Deepwater Dock
Oxford House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 16
  • baths 2
  • rates (USD) $490 - $800 /nt
 
 
 
 
 

8 reviews write a review

Darling in town cottage with private sandy beach, dock, Comb for Seaglass!
Oxford Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $418 - $498 /nt
    $1,580 - $2,255 /wk
 
 
 
 
 

33 reviews write a review

Historic, Renovated, Darling, Love the Front Porch -Walk to Everything Oxford
Oxford Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 4
  • baths 2
  • rates (USD) $353 - $407 /nt
    $1,510 - $1,745 /wk
 
 
 
 
 

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In Town Oxford Waterfront Perfect - Steps from Town Beach
Oxford Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • sleeps 8
  • baths 3
  • rates (USD) $637 - $709 /nt
    $2,585 - $2,985 /wk
 
 
 
 
 

2 reviews write a review

Private Dock & Pool - Minutes to St Mikes & Easton - Kayaks on Creek
Oxford Cottage Rental Picture
  • bedrooms 4
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $469 - $909 /nt
    $2,327 - $4,242 /wk
 
 
 
 
 

22 reviews write a review

Family friendly cottage near park and center of town. Adorable!
Oxford Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $461 - $548 /nt
    $1,980 - $2,280 /wk
 
 
 
 
 

29 reviews write a review

Perfect for capturing last family memories--plenty of space and things to do!
Oxford House Rental Picture
  • bedrooms 7
  • rental type House
  • owner badgeowner badge
  • sleeps 22
  • baths
  • rates (USD) $974 - $1,578 /nt
    $4,042 - $8,134 /wk
 
 
 
 
 

48 reviews write a review

Waterfront Point, Views from all sides, Love the Pool and Kitchen
Oxford Cottage Rental Picture
  • bedrooms 4
  • rental type Cottage
  • sleeps 9
  • baths
  • rates (USD) $686 - $1,054 /nt
    $2,455 - $4,559 /wk
 
 
 
 
 

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Steps from Oxford Beach... and Eastern Shore's Best Ice Cream!
Oxford Cottage Rental Picture
  • bedrooms 4
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $478 - $598 /nt
    $2,030 - $2,330 /wk
 
 
 
 
 

17 reviews write a review

5 Acres, Kayaks, Pool, Cooks Kitchen,Screened Porch, Big Yard for FBall games
Oxford House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths 5
  • rates (USD) $764 - $1,228 /nt
    $3,957 - $7,948 /wk
 
 
 
 
 

13 reviews write a review

Quaint Historic In Town - Walk to Everything, Near Waterfront Town Park
Oxford Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $361 - $430 /nt
    $1,505 - $1,715 /wk
 
 
 
 
 

14 reviews write a review

Charming Waterfront Cottage Close To St. Michaels (1/2 mile from The Oaks)
Oxford Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • sleeps 7
  • baths
  • rates (USD) $375 - $625 /nt
 
 
 
 
 

4 reviews write a review

Exceptional Waterfront Property 10% Fall Discount
Oxford Estate Rental Picture
  • bedrooms 5
  • rental type Estate
  • owner badgeowner badge
  • sleeps 10
  • baths 7
  • rates (USD) $900 - $1,000 /nt
    $3,500 - $6,300 /wk
 
 
 
 
 

3 reviews write a review

Beautiful and Very Private Historic Waterfront Estate House
Oxford Estate Rental Picture
  • bedrooms 6
  • rental type Estate
  • owner badgeowner badge
  • sleeps 12
  • baths
  • rates (USD)
 
 
 
 
 

8 reviews write a review