Holiday houses in Oxford

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Top-rated holiday rentals in Oxford

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Guest favourite

Farm stay in Madison

4.98 out of 5 average rating, 161 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.

24 Feb – 3 Mar

$227 NZD per night

Guest favourite

Cottage in Cambridge

4.98 out of 5 average rating, 108 reviews

Church Creek - waterfront cottage & pool - private

Close to Blackwater NWR and the Harriet Tubman Center, enjoy peaceful days at our secluded waterfront cottage on Church Creek. Two miles from a main road, and our closest neighbor is across a cove, our estate offers 50 acres of privacy and one of the best waterfront views on the Chesapeake. Enjoy a view from every window and nature all around you. Excellent walking, swimming (in-ground pool-May 3-Oct 1), great birding and bicycling. Launch your kayak from the backyard. Perfect private getaway!

24 Nov – 1 Dec

$403 NZD per night

Guest favourite

Cottage in Saint Michaels

4.98 out of 5 average rating, 423 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.

1–8 Mar

$399 NZD per night

Guest favourite

Guest suite in Cambridge

4.95 out of 5 average rating, 266 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 !

10–17 Feb

$281 NZD per night

Guest favourite

Home in Oxford

4.96 out of 5 average rating, 184 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.

21–28 Jan

$554 NZD per night

Guest favourite

Guest suite in Cambridge

4.95 out of 5 average rating, 400 reviews

Sailwinds Waterview Loft at Cambridge Creek

Waterview second story loft apartment in downtown Cambridge, MD with private entrance and secure bike storage! Located just 4 blocks from Route 50 and only 2 blocks from the Choptank River! This amazing space is within walking distance to seafood restaurants, shops, public boat ramp, beach, and parks! Close to all local attractions including the Choptank River Lighthouse, Sailwinds Park, Harriett Tubman UnderGround Railroad, Blackwater Refuge, Eagleman/Iron Man, and so many more!

17–24 Dec

$295 NZD per night

Guest favourite

Guesthouse in Easton

4.99 out of 5 average rating, 543 reviews

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for two individuals (No children under 8 years of age.), and please limit your visit to one vehicle only.

15–20 Oct

$269 NZD per night

Guest favourite

Apartment in Church Creek

4.97 out of 5 average rating, 371 reviews

Church Creek Natures' Rest

Nature's Rest is ideally located, just minutes to Blackwater Wildlife Refuge The Harriet Tubman Museum, as well as boat ramps for easy access to the Chesapeake Bay and it's tributaries for enjoying Maryland's Eastern Shore. We have plenty of parking, so bring your boat, bikes, and binoculars. Just mins from downtown Cambridge for dining & shopping. Discover the many quaint towns the area has to offer, come for a night, or stay as long as you'd like, look forward to meeting you.

12–19 Mar

$234 NZD per night

Guest favourite

Cottage in Saint Michaels

4.99 out of 5 average rating, 136 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

24 Sep – 1 Oct

$954 NZD per night

Guest favourite

Guest suite in Tilghman Island

4.96 out of 5 average rating, 114 reviews

Black Walnut Cove Retreat, Tilghman Island

Our waterfront studio retreat is a birdwatchers paradise. Located on beautiful Black Walnut Cove at the southern tip of Tilghman Island, you will be in a quiet neighborhood surrounded by water. Enjoy a quiet walk or bike ride along the Chesapeake Bay shoreline. You will have access to our dock and small boat ramp. Crabbing and fishing are a delight. Please note: 1) There is a 3-nt. minimum on holiday weekends. 2) Children between the ages of 1 and 5 are not permitted

8–15 Dec

$230 NZD per night

Guest favourite

Cottage in Saint Michaels

4.98 out of 5 average rating, 172 reviews

The Little Anchor Cottage, St. Michaels, MD

Welcome to the Little Anchor cottage in St. Michaels, Maryland! The cottage was built in late 1880s and is located in the charming Historic District, where you can enjoy the convenience of walking one block to the downtown shops and restaurants on S. Talbot street. And for another 5 to 15 minute walk, you can reach more waterfront dining on St. Michaels Harbor with its boat slips, boat ramps, the Chesapeake Bay Maritime Museum, Muskrat Park and Hollis Park.

13–20 Aug

$495 NZD per night

Guest favourite

Tiny home in Cambridge

4.99 out of 5 average rating, 154 reviews

Blackwater Refuge House on The Farm, water access

The Little House on The Farm is located on a beautiful family farm in rural Dorchester County! Located just 1.5 miles from the Blackwater Wildlife Refuge and Harriet Tubman National Park, This space is quaint,yet provides all the basics for a cozy welcoming getaway! Bring your bikes and cycle to the refuge and kayak in the Blackwater River. Kitchen is fully stocked for cooking. Coffee, tea and basic condiments and all linens and towels are provided.

2–9 Aug

$200 NZD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Oxford holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

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 holiday rentals in Oxford

Guest favourite

Home in Cambridge

4.99 out of 5 average rating, 139 reviews

Sunset Breezes - quiet waterfront retreat

2–9 Mar

$810 NZD per night

Guest favourite

Guesthouse in Oxford

4.99 out of 5 average rating, 81 reviews

The Nichols House Cottage

29 Jul – 5 Aug

$248 NZD per night

Guest favourite

Guesthouse in Cambridge

5.0 out of 5 average rating, 12 reviews

Camelot Cottage

30 Jan – 6 Feb

$165 NZD per night

Guest favourite

Cottage in Oxford

5.0 out of 5 average rating, 17 reviews

Historic Home in Heart of Oxford, MD

4–11 Dec

$457 NZD per night

Guest favourite

Cottage in Oxford

4.96 out of 5 average rating, 68 reviews

Tilghman Cottage I - Cheerful and Charming Oxford

30 Oct – 6 Nov

$531 NZD per night

Guest favourite

Guesthouse in Oxford

4.9 out of 5 average rating, 21 reviews

Newly Renovated Guest House

27 Jan – 3 Feb

$451 NZD per night

Guest favourite

Home in Oxford

5.0 out of 5 average rating, 37 reviews

Stunning Chesapeake waterfront home

13–20 Nov

$1,442 NZD per night

Guest favourite

Home in Oxford

5.0 out of 5 average rating, 24 reviews

Stewart Ave Retreat

19–26 Jan

$698 NZD per night

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Quick stats about holiday rentals in Oxford

Total rentals	20 properties
Wi-Fi availability	20 properties include access to Wi-Fi
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	980 reviews
Nightly prices starting at	$254 NZD before taxes and fees

Holiday houses in Oxford

Top-rated holiday rentals in Oxford

Farm stay in Madison

Cottage in Cambridge

Cottage in Saint Michaels

Guest suite in Cambridge

Home in Oxford

Guest suite in Cambridge

Guesthouse in Easton

Apartment in Church Creek

Cottage in Saint Michaels

Guest suite in Tilghman Island

Cottage in Saint Michaels

Tiny home in Cambridge

Holiday rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Oxford holiday rentals

Stay near Oxford's top sights

Other great holiday rentals in Oxford

Home in Cambridge

Guesthouse in Oxford

Guesthouse in Cambridge

Cottage in Oxford

Cottage in Oxford

Guesthouse in Oxford

Home in Oxford

Home in Oxford

Quick stats about holiday rentals in Oxford

Total rentals

Wi-Fi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore