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.

Guest favorite

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

$108 per night
Guest favorite

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

$180 per night
Guest favorite

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 !

Nov 17 – 24

$129 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

Guest favorite

Apartment in Church Creek

4.97 out of 5 average rating, 369 reviews

Church Creek Natures' Rest

Dec 6 – 13

$115 per night
Superhost

Home in Cambridge

4.89 out of 5 average rating, 110 reviews

Dorothy's Chesapeake Delight

Apr 4 – 11

$128 per night
Guest favorite

Home in Cambridge

4.99 out of 5 average rating, 134 reviews

Sunset Breezes - quiet waterfront retreat

Oct 22 – 29

$274 per night
Guest favorite

Home in Saint Michaels

4.97 out of 5 average rating, 238 reviews

Miles Aweigh

Aug 12 – 19

$419 per night
Superhost

Tiny home in Cambridge

4.89 out of 5 average rating, 492 reviews

Blackwater Tiny Cabin on Snakehead Creek

Nov 29 – Dec 6

$73 per night
Guest favorite

Cottage in Cambridge

4.99 out of 5 average rating, 107 reviews

Church Creek - waterfront cottage & pool - private

Feb 28 – Mar 7

$179 per night
Guest favorite

Home in Saint Michaels

4.91 out of 5 average rating, 151 reviews

Small Historic House Downtown St Michaels

Dec 21 – 28

$167 per night
Guest favorite

Guest suite in Saint Michaels

4.78 out of 5 average rating, 327 reviews

Gorgeous Cottage: Easy Walk into St Michaels Town!

Jun 11 – 18

$134 per night
Guest favorite

Tiny home in Solomons

4.95 out of 5 average rating, 530 reviews

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

Mar 20 – 27

$124 per night
Guest favorite

Guesthouse in Grasonville

4.9 out of 5 average rating, 202 reviews

Eastern Shore Charm on Winchester Creek

Aug 21 – 28

$116 per night
Guest favorite

Home in Woolford

4.93 out of 5 average rating, 117 reviews

Waterfront Getaway with Dock

Aug 20 – 27

$198 per night
Guest favorite

Cottage in California

4.97 out of 5 average rating, 190 reviews

Cozy Little Cottage

Apr 30 – May 7

$76 per night

Other great vacation rentals in Oxford

Guest favorite

Guesthouse in Oxford

4.99 out of 5 average rating, 81 reviews

The Nichols House Cottage

Jul 25 – Aug 1

$122 per night
Guest favorite

Cottage in Oxford

5.0 out of 5 average rating, 17 reviews

Historic Home in Heart of Oxford, MD

Jul 16 – 23

$209 per night
Guest favorite

Home in Oxford

5.0 out of 5 average rating, 22 reviews

Stewart Ave Retreat

Jan 29 – Feb 5

$266 per night
Guest favorite

Cottage in Oxford

4.97 out of 5 average rating, 65 reviews

Tilghman Cottage II

Apr 18 – 25

$300 per night
Guest favorite

Home in Oxford

5.0 out of 5 average rating, 37 reviews

Stunning Chesapeake waterfront home

Jan 21 – 28

$489 per night
Guest favorite

Guesthouse in Cambridge

5.0 out of 5 average rating, 12 reviews

Camelot Cottage

Jun 10 – 17

$82 per night
Guest favorite

Guesthouse in Oxford

4.89 out of 5 average rating, 19 reviews

Newly Renovated Guest House

Feb 19 – 26

$203 per night
Guest favorite

Home in Cambridge

4.92 out of 5 average rating, 48 reviews

Osprey's Retreat - Waterfront with private beach!

Sep 10 – 15

$389 per night
Guest favorite

Cottage in Easton

5.0 out of 5 average rating, 83 reviews

Cottage on Solitude Creek, Hot Tub & Firepit

Nov 4 – 11

$333 per night
Guest favorite

Guesthouse in Cambridge

4.96 out of 5 average rating, 72 reviews

Charming Guesthouse w/ Pool in Historic Cambridge

Mar 15 – 22

$127 per night
Guest favorite

Home in Saint Michaels

4.98 out of 5 average rating, 81 reviews

SM’s Premier Rental Heated Pool opens 4/12

Nov 2 – 9

$681 per night
Guest favorite

Home in Cambridge

5.0 out of 5 average rating, 29 reviews

Small, peaceful getaway

Feb 10 – 17

$158 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

$120 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 air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Oxford. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

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