Oxford vacation rentals

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Top-rated vacation rentals in Oxford

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

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Guest favorite

Farm stay in Madison

4.98 out of 5 average rating, 162 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.

Mar 7 – 14

G$25,766 GYD per night

Guest favorite

Cottage in Saint Michaels

4.98 out of 5 average rating, 425 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.

Nov 15 – 22

G$42,676 GYD per night

Superhost

Tiny home in Cambridge

4.89 out of 5 average rating, 496 reviews

Blackwater Tiny Cabin on Snakehead Creek

The Solar Powered Tiny Cabin is located on a farmette 5 min away from Blackwater Refuge! It is an affordable and unique way to visit and enjoy all that Cambridge and Blackwater Refuge have to offer! Staying the cabin will make your visit even more memorable!The Tiny Cabin is now located 50 steps away from Pitcher Dam Creek which leads to the Little Blackwater! Kayaks on site! Bring your fishing rod to catch popular Snakeheads! 15 minute drive to Route 50, downtown Cambridge, shopping and dining!

Nov 9 – 16

G$18,153 GYD per night

Guest favorite

Guest suite in Cambridge

4.96 out of 5 average rating, 267 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 !

Sep 8 – 15

G$28,053 GYD per night

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.

Jul 24 – 31

G$65,507 GYD per night

Guest favorite

Home in Cambridge

4.99 out of 5 average rating, 141 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.

Feb 2 – 9

G$88,892 GYD per night

Guest favorite

Guesthouse in Easton

4.99 out of 5 average rating, 545 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.

Jan 25 – 30

G$29,946 GYD per night

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.

Feb 19 – 26

G$27,361 GYD per night

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.

Sep 15 – 22

G$111,584 GYD per night

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

Oct 23 – 30

G$30,120 GYD per night

Guest favorite

Cottage in Saint Michaels

4.98 out of 5 average rating, 174 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.

Aug 13 – 20

G$54,856 GYD per night

Guest favorite

Tiny home in Cambridge

4.99 out of 5 average rating, 156 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.

Aug 21 – 28

G$22,299 GYD per night

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

Loft in Lusby

5.0 out of 5 average rating, 311 reviews

Coastal Treetop Retreat w/ Private Beach Access

Jan 30 – Feb 6

G$26,427 GYD per night

Guest favorite

Cottage in Cambridge

4.98 out of 5 average rating, 108 reviews

Church Creek - waterfront cottage & pool - private

Mar 12 – 19

G$44,682 GYD per night

Guest favorite

Guesthouse in Annapolis

4.9 out of 5 average rating, 206 reviews

Calico Cottage Guest House, king bed, free parking

Jan 10 – 17

G$20,406 GYD per night

Guest favorite

Cottage in California

4.97 out of 5 average rating, 193 reviews

Cozy Little Cottage

Sep 7 – 14

G$18,502 GYD per night

Guest favorite

Tiny home in Solomons

4.95 out of 5 average rating, 538 reviews

“Cabana by the Bay”-tiny home on a pier!

Dec 4 – 11

G$29,758 GYD per night

Guest favorite

Home in Cambridge

4.9 out of 5 average rating, 146 reviews

Jewell on the Chesapeake

Aug 2 – 9

G$38,488 GYD per night

Guest favorite

Apartment in Cambridge

4.92 out of 5 average rating, 101 reviews

Little Slice of Cambridge. Newly listed, 2 bedroom

Mar 16 – 23

G$30,140 GYD per night

Guest favorite

Guesthouse in Grasonville

4.9 out of 5 average rating, 203 reviews

Eastern Shore Charm on Winchester Creek

Oct 2 – 9

G$27,439 GYD per night

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Other great vacation rentals in Oxford

Guest favorite

Guesthouse in Oxford

4.99 out of 5 average rating, 81 reviews

The Nichols House Cottage

Aug 3 – 10

G$29,033 GYD per night

Guest favorite

Guesthouse in Cambridge

5.0 out of 5 average rating, 13 reviews

Camelot Cottage

Oct 6 – 13

G$18,344 GYD per night

Guest favorite

Cottage in Oxford

4.96 out of 5 average rating, 68 reviews

Tilghman Cottage I - Cheerful and Charming Oxford

Jan 27 – Feb 3

G$59,795 GYD per night

Guest favorite

Cottage in Oxford

5.0 out of 5 average rating, 17 reviews

Historic Home in Heart of Oxford, MD

Jun 11 – 18

G$50,191 GYD per night

Guest favorite

Guesthouse in Oxford

4.9 out of 5 average rating, 21 reviews

Newly Renovated Guest House

Feb 3 – 10

G$48,731 GYD per night

Guest favorite

Home in Oxford

5.0 out of 5 average rating, 37 reviews

Stunning Chesapeake waterfront home

Oct 4 – 11

G$178,424 GYD per night

Superhost

Home in Cambridge

5.0 out of 5 average rating, 6 reviews

High St. Art Gallery Suite

Sep 2 – 9

G$26,405 GYD per night

Guest favorite

Home in Oxford

5.0 out of 5 average rating, 24 reviews

Stewart Ave Retreat

Apr 9 – 16

G$79,299 GYD per night

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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
G$31,273 GYD 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 air conditioning, over 10 homes with wifi, 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

Loft in Lusby

Cottage in Cambridge

Guesthouse in Annapolis

Cottage in California

Tiny home in Solomons

Home in Cambridge

Apartment in Cambridge

Guesthouse in Grasonville

Other great vacation rentals in Oxford

Guesthouse in Oxford

Guesthouse in Cambridge

Cottage in Oxford

Cottage in Oxford

Guesthouse in Oxford

Home in Oxford

Home in Cambridge

Home in Oxford

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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