Vacation rentals in Royal Oak

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Top-rated vacation rentals in Royal Oak

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

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. 19 – 26

$319 CAD per night
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. 16 – 23

$182 CAD per night
Guest favourite

Home in Oxford

4.97 out of 5 average rating, 183 reviews

The Oxford House

Enjoy water views from the backyard or visit with friends on the screened in porch. The light and airy, 3bd, 2bath house is a short walk to Oxford’s best restaurants and favorite ice-cream shop. You can find the best beach in oxford only 75 yards from our front door or take the Ferry to the neighboring town of Saint Michaels, Maryland. You will love the scenic views and historical charm of this little town, the Oxford house has a central location allowing you to walk or bike to everything.

Mar. 12 – 19

$444 CAD per night

Popular amenities for Royal Oak vacation rentals

Other great vacation rentals in Royal Oak

Guest favourite

Condo in Oxford

4.98 out of 5 average rating, 112 reviews

Cozy Oxford Getaway

Apr. 5 – 12

$273 CAD per night
Guest favourite

Apartment in Lexington Park

5.0 out of 5 average rating, 310 reviews

Adorable Waterfront Apartment Weekend Getaway

Jan. 14 – 21

$137 CAD per night
Superhost

Tiny homes in Cambridge

4.89 out of 5 average rating, 492 reviews

Blackwater Tiny Cabin on Snakehead Creek

Nov. 29 – Dec. 6

$125 CAD per night
Guest favourite

Home in Saint Michaels

4.91 out of 5 average rating, 138 reviews

Dr. Miller house. Best location-in the heart town

Sep. 12 – 19

$436 CAD per night
Guest favourite

Apartment in Greenwood

4.97 out of 5 average rating, 469 reviews

Beach Highway Hobby Farm

Sep. 14 – 21

$112 CAD per night
Guest favourite

Apartment in Church Creek

4.97 out of 5 average rating, 369 reviews

Church Creek Natures' Rest

Dec. 6 – 13

$188 CAD per night
Guest favourite

Cottage in Easton

5.0 out of 5 average rating, 83 reviews

Cottage on Solitude Creek, Hot Tub & Firepit

Apr. 17 – 24

$578 CAD per night
Guest favourite

Guesthouse in Oxford

4.99 out of 5 average rating, 81 reviews

The Nichols House Cottage

Jul. 25 – Aug. 1

$199 CAD per night
Guest favourite

Guesthouse in Cambridge

5.0 out of 5 average rating, 12 reviews

Camelot Cottage

Jun. 10 – 17

$140 CAD per night
Superhost

Home in Royal Oak

4.79 out of 5 average rating, 14 reviews

Poplar Lane: the heart of the Eastern Shore

Jul. 12 – 19

$604 CAD per night
Guest favourite

Home in Newcomb

5.0 out of 5 average rating, 28 reviews

Saint Michaels Waterfront Home

Nov. 6 – 13

$888 CAD per night
Guest favourite

Home in Easton

5.0 out of 5 average rating, 17 reviews

Eastern Shore Retreat!

Nov. 23 – 30

$688 CAD per night

Destinations to explore

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