Vacation rentals in Oxford

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Top-rated vacation rentals in Oxford

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite

Farm stay in Madison

4.98 out of 5 average rating, 159 reviews

Madison Nature Getaway

We're on 106 acres minutes away from Cambridge, Blackwater NWR, Harriet Tubman URR State Park and two public boat ramps for access to Chesapeake Bay. Hike our trails and enjoy bird watching, wildlife photography and fishing on our award winning tree farm and relax by our pond. Bring your bikes, binoculars and kayaks and enjoy the surrounding area. We have a gas grill and a screened pavilion for our guests for parties and meals. FRIENDS OF BLACKWATER NWR MEMBERS & MILITARY RECEIVE A 10% DISCOUNT.

Aug. 18 – 25

$182 CAD per night
Guest favourite

Cottage in Saint Michaels

4.98 out of 5 average rating, 418 reviews

St. Michaels-Historic Dist. Margaret Wells House

The Margaret Wells House is in the heart of the Historic District between the main street and water. Enjoy a total renovation of this charming home. A short walk to the water's edge, Inn at Perry Cabin, Chesapeake Bay Maritime Museum, restaurants, shops, winery, brewery and local market. A perfect spot for a couple's Shore weekend getaway or attending a wedding, nearby. Our nightly pricing includes coffee, tea, fresh linens on beds, hand-milled natural soap, fresh bath towels and wash cloths.

Mar. 1 – 8

$320 CAD per night
Guest favourite

Guest suite in Cambridge

4.95 out of 5 average rating, 265 reviews

Oakley Suite

5 minute walk to restaurants and shops, 3 min.to the water. Ideal setting with lovely rear patio and garden with entrance to private family room. Stairs to upper level with 2 very large and private guest rooms. Landing at top of steps presents a convenience station with Keurig, microwave, and mini fridge. This Suite is completely private and includes 2 bedrooms, bath, family room, convenience station, and rear patio, all for one price! 1st floor Owners Suite available as well for a total of 8 !

Aug. 21 – 28

$204 CAD per night

Popular amenities for Oxford vacation rentals

Stay near Oxford's top sights

Doc's Sunset Grille13 locals recommend
Scottish Highland Creamery17 locals recommend
Oxford-Bellevue Ferry16 locals recommend
Capsize OXMD10 locals recommend
Robert Morris Inn11 locals recommend
Latitude 386 locals recommend

Other great vacation rentals in Oxford

Superhost

Home in Cambridge

4.89 out of 5 average rating, 110 reviews

Dorothy's Chesapeake Delight

Apr. 4 – 11

$232 CAD per night
Guest favourite

Home in Cambridge

4.99 out of 5 average rating, 134 reviews

Sunset Breezes - quiet waterfront retreat

Oct. 30 – Nov. 6

$478 CAD per night
Guest favourite

Home in Saint Michaels

4.97 out of 5 average rating, 238 reviews

Miles Aweigh

Apr. 18 – 25

$611 CAD per night
Superhost

Tiny homes in Cambridge

4.89 out of 5 average rating, 492 reviews

Blackwater Tiny Cabin on Snakehead Creek

Oct. 27 – Nov. 3

$136 CAD per night
Guest favourite

Cottage in Cambridge

4.99 out of 5 average rating, 107 reviews

Church Creek - waterfront cottage & pool - private

Dec. 24 – 31

$321 CAD per night
Guest favourite

Guest suite in Saint Michaels

4.78 out of 5 average rating, 327 reviews

Gorgeous Cottage: Easy Walk into St Michaels Town!

Aug. 4 – 11

$242 CAD per night
Guest favourite

Home in Saint Michaels

4.91 out of 5 average rating, 151 reviews

Small Historic House Downtown St Michaels

Jan. 13 – 20

$287 CAD per night
Guest favourite

Guesthouse in Oxford

4.99 out of 5 average rating, 81 reviews

The Nichols House Cottage

Jul. 24 – 31

$199 CAD per night
Guest favourite

Cottage in Oxford

5.0 out of 5 average rating, 17 reviews

Historic Home in Heart of Oxford, MD

Sep. 29 – Oct. 6

$368 CAD per night
Guest favourite

Home in Oxford

5.0 out of 5 average rating, 22 reviews

Stewart Ave Retreat

Mar. 19 – 26

$455 CAD per night
Guest favourite

Cottage in Oxford

4.97 out of 5 average rating, 65 reviews

Tilghman Cottage II

Jan. 1 – 8

$507 CAD per night
Guest favourite

Home in Oxford

5.0 out of 5 average rating, 37 reviews

Stunning Chesapeake waterfront home

Jan. 2 – 9

$879 CAD per night

Quick stats about vacation rentals in Oxford

Total rentals

20 properties

Wifi availability

20 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

970 reviews

Nightly prices starting at

$163 CAD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Talbot County
  5. Oxford