Oxford vacation rentals

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Top-rated vacation rentals in Oxford

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Guest favorite

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.

Guest favorite

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!

Guest favorite

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.

Guest favorite

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 !

Guest favorite

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.

Guest favorite

Home in Cambridge

4.99 out of 5 average rating, 139 reviews

Sunset Breezes - quiet waterfront retreat

Enjoy our waterfront home styled after historic bay lighthouses. Relax by the water in a hammock under the tall pines. Gather with family and friends around the fire pit. Take in the beautiful water sights while paddling in a kayak, canoe, or paddleboard. Laugh with family and friends while playing corn hole, croquet, or bocce ball waterside. Photograph abundant wildlife - bald eagles, blue herons, osprey, deer, turkey and numerous waterfowl. Dine on the deck while enjoying beautiful sunsets.

Guest favorite

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!

Guest favorite

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.

Guest favorite

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.

Guest favorite

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.

Guest favorite

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

Guest favorite

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.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Oxford vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

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 vacation rentals in Oxford

Guest favorite

Guest suite in Saint Michaels

4.78 out of 5 average rating, 330 reviews

Gorgeous Cottage: Easy Walk into St Michaels Town!

Guest favorite

Apartment in Lexington Park

5.0 out of 5 average rating, 313 reviews

Adorable Waterfront Apartment Weekend Getaway

Guest favorite

Home in Cambridge

4.9 out of 5 average rating, 146 reviews

Jewell on the Chesapeake

Guest favorite

Cottage in Wittman

4.9 out of 5 average rating, 134 reviews

"Wittman Cottage"

Guest favorite

Apartment in Greenwood

4.97 out of 5 average rating, 477 reviews

Beach Highway Hobby Farm

Guest favorite

Loft in Lusby

5.0 out of 5 average rating, 310 reviews

Coastal Treetop Retreat w/ Private Beach Access

Guest favorite

Cottage in California

4.97 out of 5 average rating, 192 reviews

Cozy Little Cottage

Guest favorite

Guesthouse in Grasonville

4.9 out of 5 average rating, 203 reviews

Eastern Shore Charm on Winchester Creek

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Other great vacation rentals in Oxford

Guest favorite

Cottage in Oxford

4.96 out of 5 average rating, 68 reviews

Tilghman Cottage I - Cheerful and Charming Oxford

Guest favorite

Guesthouse in Oxford

4.9 out of 5 average rating, 21 reviews

Newly Renovated Guest House

Guest favorite

Home in Oxford

5.0 out of 5 average rating, 37 reviews

Stunning Chesapeake waterfront home

Guest favorite

Home in Oxford

5.0 out of 5 average rating, 24 reviews

Stewart Ave Retreat

Superhost

Home in Cambridge

5.0 out of 5 average rating, 4 reviews

High St. Art Gallery Suite

Guest favorite

Home in Cambridge

5.0 out of 5 average rating, 30 reviews

Small, peaceful getaway

Guest favorite

Cottage in Easton

5.0 out of 5 average rating, 83 reviews

Cottage on Solitude Creek, Hot Tub & Firepit

Superhost

Home in Cambridge

5.0 out of 5 average rating, 4 reviews

Magical Waterfront Home-Dock, Firepit, family fun!

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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
980 reviews
Nightly prices starting at
$150 before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Oxford?
Yes! Work meets play with ease at over 10 vacation rentals in Oxford featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly house rentals in Oxford?
Oxford has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Oxford?
Experience the best of Oxford with our house rentals, starting at about $200 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Oxford have wifi?
Absolutely! We offer over 10 house rentals with wifi in Oxford. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oxford have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Oxford. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Oxford?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Oxford vacation rentals

Top-rated vacation rentals in Oxford

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Oxford vacation rentals

Stay near Oxford's top sights

Other great vacation rentals in Oxford

Guest suite in Saint Michaels

Apartment in Lexington Park

Home in Cambridge

Cottage in Wittman

Apartment in Greenwood

Loft in Lusby

Cottage in California

Guesthouse in Grasonville

Other great vacation rentals in Oxford

Cottage in Oxford

Guesthouse in Oxford

Home in Oxford

Home in Oxford

Home in Cambridge

Home in Cambridge

Cottage in Easton

Home in Cambridge

Quick stats about vacation rentals in Oxford

Total rentals

Wifi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Oxford?

Are there family-friendly house rentals in Oxford?

How much does it cost to stay in house rentals in Oxford?

Do house rentals in Oxford have wifi?

Do house rentals in Oxford have air conditioning?

What are the most popular amenities for House Rentals in Oxford?

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