Vacation Rentals By Owner In Oxford, MD

Beautiful waterfront home - well furnished large open house, great amenities including pool, game room and gym, Sonos sound system, spacious covered porch overlooking water, and outdoor pool with beautiful patio. Walking distance to quaint town of Oxford. Come make memories in this special oasis.

Gorgeous Waterfront

Oxford, Maryland, United States

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Bath

Sleeps

$509.76

In-town cottage with loads of charm and easy walking to parks and restaurantsbrTucked away in the quaint, historic town of Oxford, Pride and Joy is a terrific spot for those looking to step back in time--when you could walk to the corner store for milk and ice cream, meander up the street to the local produce stand, or simply sit on the front porch and sip a lemonade while enjoying the scenery. The old fashioned charm and white picket fence are a warm welcome to visitors who want to slow it down a bit. Pride and Joy's cheerful interior contributes to the allure and comfort you'll experience while delighting in its modern amenities. This is a perfect cottage for those wanting to enjoy nothing more than some peace and quiet and the respite that Oxford is known for.brbrProperty Information & Notes:brWiFi: Please note that the rural nature of the area limits the data access and some properties can experience slow speeds, or access limited to e-mail and web browsing and not streamingbrPet Policy: This property is dog-friendly for up to two dogs at no additional chargebrGrill: This property has a propane grill. Propane is providedbrOn-site parking is limited to one car. Public parking is available within walking distancebrBed Sizes:brBedroom 1 - QueenbrBedroom 2 - QueenbrBedroom 3 - 2 Sets of Bunk BedsbrLiving Room - Double Sleep SofabrPlease Note:brAll ESVR properties include bed and bath linens, beds made prior to your arrival, and a starter supply of toilet paper, bathroom soap, paper towels, and dishwater detergent. Please be sure to add these items to your grocery list for the duration of your stay.brbrOur properties do not allow group rentals to guests under the age of 25. Therefore, online bookings for group rentals will not be honored.brbrWeddings and special events of any kind are not permitted at our vacation rental properties due to local zoning ordinances and our homeowner agreements.brbrEvery effort has been made to ensure the accuracy of the images, descriptions, and amenities shown above. Although they are deemed reliable, they cannot be guaranteed.

Downtown Oxford | Charming | Pet Friendly

Oxford, Maryland, United States

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Bath

Sleeps

$1027.52

Luxury awaits at The Beach House, a stunning 4-bedroom, 4.5-bathroom vacation extravaganza in the vibrant Oxford neighborhood! This meticulously renovated home features a modern, open floor plan ideal for entertaining and relaxing after a day of exploring. Boasting a private beach, private pool, dock for fishing/crabbing and panoramic Choptank River views, you'll find endless opportunities for fun and relaxation.brbrPerfectly located within walking distance of top-rated waterfront restaurants, charming cafes, and marinas, and just a short drive to St. Michaels, Easton, and Tilghman Island, The Beach House is ideal for discovering the best of the Eastern Shore. Kayaking, sailing, biking, and exploring – the possibilities are endless! Secure the vacation you deserve – book The Beach House Today!brbrPROPERTY FEATURES:brbrWaterfront: Tred Avon RiverbrDock: Shared dock. Fishing Only. No electricity and no boats allowed to be tied up.brPool: 7’ x 40’ built-in saltwater swimming pool. Guests swim in the pool at their own risk.brGrill: Propane grill. Propane is provided.brWiFi: Available for guest use.brbrBED SIZES:brbrQueen - 1 / Queen - 1 / Queen - 1 / Queen - 2 / Twin - 1 /

Downtown Oxford | Private Beach | Private Pool | Luxury

Oxford, Maryland, United States

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Bath

Sleeps

$800.77

Summary:brbrStep into history without sacrificing modern comforts. Combsberry is a 1730 waterfront estate nestled on 30 private acres at the northern headwaters of Island Creek. Featuring five beautifully appointed bedrooms, a gourmet kitchen, a heated pool, and serene walking grounds, it’s the ultimate retreat for family gatherings, romantic escapes, or peaceful solo getaways—especially during Maryland’s spectacular fall season.brbrbrbrTalbot County Licensure: STRN-25-43brbrbrbrThe Space:brbrDiscover Combsberry, a historic Maryland waterfront estate perfect for your fall getaway. Nestled on 30 acres along Island Creek near St. Michaels, this 1730 property offers five bedrooms, a heated pool, a gourmet kitchen, and stunning autumn foliage. Ideal for family vacations, couples’ retreats, or pet-friendly escapes, Combsberry blends timeless elegance with modern comfort.brbrbrbrWhat you'll love:brbr- Unmatched Privacy: 30 acres of tranquil waterfront with no neighbors in sight.brbr- Historic Beauty: Original architectural details paired with high-end updates.brbr- Luxury Amenities: Heated waterfront pool, coffee bar, and gourmet kitchen.brbr- Pet-Friendly: Bring your furry friend along ($200 pet fee).brbr- Fall Magic: Crisp air, colorful foliage, and cozy evenings by the fireplace.brbrbrbrCurated by Flaneur, this experience is designed in the spirit of slow travel — where comfort is intentional, beauty surrounds you, and every moment is yours to truly savor. Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your waterfront hosts.brbrbrbrGuest Access:brbrThis property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.brbrbrbrThe Neighborhood:brbrPrivate, serene waterfront location — yet close to St. Michaels, Easton and Oxford and seasonal events.brbrbrbrOther Things to Note:brbrProfessional caretakers maintain the estate year-round, ensuring your stay is private, seamless, and unforgettable. Pets welcome with a $200 non-refundable fee. Starter paper goods provided; please bring any additional supplies you may need.

Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways

Oxford, Maryland, United States

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Bath

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$246.75

Enjoy a delightful stay in a recently renovated, newly furnished guest cottage with water views in charming Oxford, Maryland. The house is in a quiet neighborhood with a beautiful view of Town Creek. Take a short walk or bike ride to town where you can enjoy fine dining and shopping. The house is equipped with TV, Wifi, AC to make your stay comfortable. There is reserved parking in front of the house and enjoy dining on the outside porch.br• No parties or events allowed.br• No smoking allowed. br• No pets allowed.br• No unregistered guests allowed. br• Please don’t eat or drink in the bedrooms. br• Please respect the noise curfew. No loud, unnecessary or disturbing noise especially from 10pm to 7am.br• No illegal substances allowed on the premises.br• Please respect check-in and check-out times. br• Please take care of the furnishings. You must pay for damages that exceed the security deposit. br• Please don’t rearrange the furniture.br• Please put your dishes in the dishwasher and start the dishwasher as you leave.br• Please take the trash out before you leave to the shed in back.br• Suitable for toddlers and children under 12.

Guest House

Newly Renovated Guest House located in Oxford MD

Oxford, Maryland, United States

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Bath

Sleeps

$393.49

Old School Charm Meets New School Living!brbrThis charming 3BR, 2BA duplex vacation home within walking distance from Downtown Oxford is designed with your comfort in mind. The character-filled interior is complemented by a first-floor bedroom and bathroom, relaxed living space and plenty of natural light.brbrThe professionally landscaped outdoors offers a large outdoor deck, screened porch and sprawling lawn. A great spot for enjoying a morning cup of coffee, family crab feast or evening cocktail with great conversation.brbrPerfectly positioned in historic Oxford and only minutes from the Play Ball Dog Park, Towne Park and Towne Beach. Don’t feel like cooking on your vacation Breakfast, lunch, dinner and dessert is just a short walk to Doc’s Sunset Grille, Anthony’s Italian Restaurant, Pope’s Tavern, Capsize OXMD, Salter’s Tap Room and Tavern and the famous Scottish Highland Creamery.brbrExperience the best rural vacation living available. Don't miss out on this fabulous rental. Book your getaway today.brbrPROPERTY FEATURES:brbrLand Toys: 2 adults bikes are available for guest use.brGrill: Propane grill. Propane is provided.brPet Friendly: This is a pet friendly rental.brWiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.brbrBED SIZES:brbrQueen - 1 / Queen - 1 / Bunk Bed - Twin over Full - 1 /

Downtown Oxford | Outdoor Dining | Character Filled

Oxford, Maryland, United States

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Bath

Sleeps

$514.35

Summary:brDiscover the charm of Maryland’s Eastern Shore at our cozy cottage nestled in the heart of Oxford. Just steps from the water and a short stroll to restaurants, shops, and the ferry, this peaceful escape blends small-town charm with all the comforts of home.brbrThe Space:brWelcome to your perfect Shore retreat, thoughtfully curated 3-bedroom home tucked along a quiet street in the heart of Oxford. Just a short stroll from the town’s waterfront, local shops, and beloved restaurants, this is the kind of place where time slows down and simple pleasures take center stage. Inside, you’ll find sunlit living spaces, cozy furnishings, and all the comforts of home—from a fully stocked kitchen perfect for slow breakfasts, to high-speed WiFi and a comfortable space to work (if you must). Each bedroom offers a peaceful place to rest, and the two full bathrooms make group stays a breeze. Step outside into your own private yard—ideal for unwinding in the shade or sipping a glass of wine under the stars.brbrWith thoughtful touches throughout, the home is warm, welcoming, and designed to help you reconnect—with loved ones, with nature, and with yourself. Whether you're here for a weekend getaway, a family gathering, or just some much-needed stillness, this is your place to land softly. Come experience Oxford the Flaneur way—beautifully curated, effortlessly easy, and always unforgettable.brbrGuest Access:brThis property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.brbrThe Neighborhood:brQuiet residential neighborhood walkable to local dining and townbrbrOther Things to Note:brA starter supply of toilet paper and paper towel will be on hand but guest will need to purchase or bring additional with them.

Walk to Waterfront • Cozy Oxford Cottage

Oxford, Maryland, United States

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Bath

Sleeps

$458.97

Ahoy there, mateys! brbrPrepare to be captivated by this newly renovated 3-bedroom, 2-bathroom vacation rental in Oxford, a true treasure chest of comfort and relaxation. Picture yourself in a character-filled interior with a free-flowing floor plan and a generous dining room, perfect for sharing tales of your Eastern Shore adventures. brbrThe well-equipped and beautifully maintained kitchen boasts ample counter space and cupboards, making meal prep a breeze. Step outside to discover a professionally landscaped oasis with vibrant gardens and a spacious front porch – the ideal spot to savor your morning brew or toast the setting sun with a refreshing cocktail. brbrNestled in a tranquil Oxford neighborhood, this gem is perfectly positioned for exploring the Eastern Shore's delights. A leisurely stroll leads you to charming waterfront restaurants with breathtaking sunset views, delightful ice cream parlors, cozy coffee shops, bustling marinas, and picturesque waterfront parks. Embrace the outdoor life with endless opportunities for walking, biking, kayaking, and sailing, all just minutes away. And for even more adventure, St. Michaels and Tilghman Island are a short drive away. brbrDon't delay, book your Oxford getaway today and shiver me timbers with excitement!brbrPROPERTY FEATURES:brbrWiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.brbrBED SIZES:brbrQueen - 1 / Twin - 2 / Daybed with Trundle Bed - Twin Sized - 1 /

Downtown Oxford | Character Filled

Oxford, Maryland, United States

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Bath

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$488.0

This bright and airy 3BR, 2BA cape cod vacation home in Oxford is designed with your comfort in mind. The free-flowing floor plan features a character-filled interior and large dining room.brbrOverflowing with counter space and cupboards, this well-equipped, beautifully maintained kitchen includes sliding doors that lead to a large deck with oversized picnic table and benches for outdoor entertainment. The professionally landscaped outdoors offers gardens and a beautifully manicured lawn. A great spot for enjoying a morning cup of coffee or an evening cocktail.brbrLocated in a peaceful Oxford neighborhood and perfectly positioned to take advantage of all the Eastern Shore has to offer. An easy walk to great waterfront restaurants with magnificent sunsets, ice cream parlors, coffee shops, marinas and waterfront parks. Enjoy an abundance of outdoor activities like walking, biking, kayaking and sailing all minutes away. Just a short drive to St. Michaels and Tilghman Island. All this and so much more make Willows Dream your perfect vacation destination. Don’t miss out on staying at this fabulous rental. Book your getaway today.brbrPROPERTY FEATURES:brbrGrill: Propane grill. Propane is provided.brWiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.brbrBED SIZES:brbrQueen - 1 / Queen - 1 / Sleeper Sofa - Queen /

Downtown Oxford | Outdoor Dining | Character Filled

Oxford, Maryland, United States

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Bath

Sleeps

$1007.0

Bonfield Manor is located at the entrance of Oxford, a half-mile walk or bike ride to restaurants, shops and the Riverview Ave beach. The waterfront property offers a 12-acre park-like setting, fabulous views, and access to Boone Creek and the Choptank at its confluence into the Chesapeake Bay. Bonfield Manor and its plantation buildings were established in 1771-73. The original Georgian manor burnt down in 1927 and was replaced by an elegant lodge built on the original mound (and colonial basement kitchen). brWith two master bedrooms with ensuite bathrooms on the ground floor, two queen size bedrooms and 2 bedrooms with 2 twin beds each on the second floor, and 3 additional shared bathrooms Bonfield Manor can accommodate up to12 people. There is an additional pull-out sofa in one of the twin bedrooms upstairs and a kids' bed that can be set up as additional beds upon demand. The 12-acre property with its shaded outdoor patio, swimming pool, large dock, and extensive grounds provides both privacy, time to relax and an extensive playground for young and old. Fishing, crabbing, canoeing, and swimming are at your fingertips as are games, TV, WI-Fi, piano, and books for indoor entertainment. You are at the entrance of Oxford with everything in walking distance, St Michaels a ferry trip away, and Easton a 15 minutes drive.

Historic Oxford Waterfront Estate

Oxford, Maryland, United States

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Bath

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$854.18

Spectacular new waterfront home in beautiful historic Oxford, comfortably sleeps 10 with perfect set up for 2 families. Enjoy Town Creek and Tred Avon water views from every room and angle. Gorgeous sunsets from the wraparound porch, stargazing and fishing from the dock. Walk to Morris Street for a relaxed coffee, stroll through Town Park, or take the Ferry to St. Michaels.brbrStep into the living room with stunning water views and large fireplace, connected to open kitchen and dining room with French doors onto wrap around screened in porch with exterior fireplace for cozy fall/winter evenings. 5 bedrooms, 4.5 baths, including 2 master suites, 2 kids' rooms with bunk bed and shared bath, and additional guest room with adjacent bath.brbrThe Town of Oxford has issued short term rental license #STR25-06 for this property. Due to the residential neighborhood of our property, we are unfortunately unable to accommodate groups of young adults under 25 years of age.

Stunning Chesapeake Waterfront Home

Oxford, Maryland, United States

5

Bed

4

Bath

10

Sleeps

$454.28

Newly renovated charming house in the middle of town. 1 block from the Chesapeake Bay, across the street from park/ playground. 3 bedrooms on second floor with 2 full baths. Extra half bath downstairs. Front screened in porch with rocking chairs. Outdoor grill. Front & Back stairways. Dog friendly town. 1 block from ferry to St Michaels by bike or car. 3 restaurants in Oxford. Many more in nearby towns. Kitchen includes refrigerator, dishwasher, microwave, wine cooler. Master bedroom has king bed. 2 guest rooms have twin beds. Living room and front room have seating. Dining table for 6. Nice yard for outdoor entertaining or children to play. Available June 16-July 11 ; 7-night min. OR July 29-Aug 15.

3-bedroom historic vacation home newly renovated in the middle of Oxford MD.

Oxford, Maryland, United States

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Bath

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$507.7

Charming Cottage in the heart of Oxford, within walking distance to all our favorite Oxford things!brWe call this circa 1900 cottage gem Memory Lane for the wonderful memories you will create during your vacation. As self-proclaimed Scottish Creamery Fanatics, the cottage's close walk to Talbot County's best ice cream store wins first bragging rights. But walking to the ice cream store is only the beginning. You are one simple block to Oxford Beach called The Strand where you can bring your kayaks, paddleboards or simply a towel and a chair to lie on the beach, soak in the afternoon sun and search for sea glass. Memory Lane's in-town location means never having to get in the car during your vacation - bike or walk to The Oxford Market, Wednesday's Farmer's Market, Capsize waterfront restaurant, the expansive waterfront shaded park or Salter's Tavern at the Robert Morris Inn. This cottage's tranquil water-oriented decorating could be straight from an HGTV show - think updated design comfortably mingling with the Bay and its historic Oxford location. Additional touches such as a wet bar; board games and kids' toys make this vacation property home to all ages and are particularly child-friendly. Memory Lane is just like our favorite ice cream flavors - you can never get enough!brbrProperty Information & Notes:brBicycles: Three (3) adult bikes and 1 tyke bike. Helmets not provided. Please bring your own or we can recommend a rental agency.brFireplaces: One gas, one wood burning. Firewood is not providedbrFirepit: Firewood is not providedbrWiFi: Please note that the rural nature of the area limits the data access and some properties can experience slow speeds, or access limited to e-mail and web browsing and not streaming.brPet Policy: This property is dog-friendly for up to two dogs at no additional charge.brGrill: This property has a propane grill. Propane is providedbrTelevision is Roku only; no cablebrRenovated Garage Rec Room with ceiling fansbrWalk to town Beach, Restaurants, Parks and ShopsbrBed Sizes:brBedroom 1 - KingbrBedroom 2 - QueenbrBedroom 3 - QueenbrBedroom 4 - 2 SinglesbrPlease Note:brAll ESVR properties include bed and bath linens, beds made prior to your arrival, and a starter supply of toilet paper, bathroom soap, paper towels, and dishwater detergent. Please be sure to add these items to your grocery list for the duration of your stay.brbrOur properties do not allow group rentals to guests under the age of 25. Therefore, online bookings for group rentals will not be honored.brbrWeddings and special events of any kind are not permitted at our vacation rental properties due to local zoning ordinances and our homeowner agreements.brbrEvery effort has been made to ensure the accuracy of the images, descriptions, and amenities shown above. Although they are deemed reliable, they cannot be guaranteed.

Downtown Oxford | Charming | Pet Friendly | Bikes

Oxford, Maryland, United States

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Select Dates for Price

Hotel

Upgraded King at Boutique Hotel, Private Beach, Walk to Restaurants & Shops

Oxford, Maryland, United States

Sandaway Suites & Beach is located in the historic district of Oxford, MD where you can walk to several restaurants and shops. With stunning views and a private sandy beach on the Eastern Shore of MD rests our boutique hotel. We invite you to stay in one of our beautifully restored upgraded king rooms. Experience in-room comforts and in-town conveniences. Take a day trip to St. Michaels, Easton, or Cambridge. At the end of the day, see an awesome sunset at Sandaway's private beach.brbrThis instant booking special guarantees an upgraded King room. The room may be 1st, 2nd, or 3rd floor inside Sandaway's Lodge or annex building. To bring you this special price, please note you are booking a category of room, and that your particular room assignment will be messaged to you before your arrival date. Pictures in the listing are samples of our rooms. Because we don't have elevators, please let us know if you need assistance with stairs.brbrSandaway Suites & Beach is an Adults only property, non-smoking, and pet free. Celebrating 53 years of quality romantic getaways! Book your Chesapeake Bay Getaway ™ brbrEnjoy all amenities at Sandaway Suites & Beach in Oxford, Maryland.brSpecializing in adults-only Chesapeake Bay getaways to help ensure peace and relaxation.brPrivate beach and waterfront lawn with lounge chairs.brIn-room coffeebrBagged Ice AvailablebrKayak & Bike rental delivery available.brCharge your Tesla or any electric car with our complimentary charging stations.brbrbrbrSpecializing in Chesapeake Bay getaways for peace and relaxation (Not suitable for children infant to 12 years). No lifeguard on duty.

1

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1

Bath

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STN-23-23 - First time offered waterfront located on Boone Creek between Oxford and Easton. Home features 5 bedrooms - 3 bedrooms with insuite bathrooms each with soaking tubs and shower. Enjoy wonderful art and unique antique finds throughout the home. Custom gourmet kitchen with everything you will need to test your culinary skills - flat top grill for the barbeque chef in you. Cycle to Oxford and the Bellevue ferry and continue to St. Michaels for a day of small town fun or kayak and explore the marvels of the Eastern shore. Perhaps you just want to sit by the pool and daydream,- it is your call. Come se for yourself

NEW Listing WATERFRONT sleeps 10 5 bedrooms 4 1/2 bths - dock & pool STN-23-23

Oxford, Maryland, United States

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$692.52

This charming 4-bedroom, 3.5-bathroom cottage in the historic town of Oxford was designed with your vacation in mind. This home offers the best of both worlds: the character of a nineteenth-century home that has been updated for modern living, with spacious living areas and generous amenities. A foodie's dream, the beautifully maintained kitchen is equipped with an oversized butcher block center island perfect for family meals and memorable conversations. br brThe beautifully landscaped backyard offers a private patio dining space for hosting the perfect cookout and is surrounded by gardens for you to enjoy as you unwind. Featuring just the rural vacation atmosphere you are looking for. br brWonderfully located in the heart of Oxford's quaint historic district, which was established in 1683. It’s within walking distance of a great park, beach, local shops and restaurants, as well as the oldest operating ferry in the country. This location is also an easy drive away from wineries, bars, grocery stores, farmer's markets, cafes and specialty stores. The town park and beach are perfect places for children to play or for relaxing by the water. All the perks of Talbot County living at your fingertips. br brDon't miss out on the memories you can create and the spectacular Oxford sunsets you can experience. We love this vacation home. You will too. Book your stay today!

Downtown Oxford | Charming | Outdoor Dining

Oxford, Maryland, United States

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Bath

Sleeps

$431.9

Make some memories at this unique and family-friendly 19th Century farmhouse. Relax, ride bikes a few short blocks to the historic downtown, beach, ferry to St. Michael's or local ice cream shop (voted best in Maryland). Grill, make s'mores and otherwise enjoy the serenity of a hand-hewn house with large yard in a charming town on the Eastern Shore.

Historic Renovated Jackrabbit Cottage

Oxford, Maryland, United States

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Bath

3 bedroom cottage/ 2 1/2 baths. Kitchen, living/ dining area. outdoor shower after coming from the beach 1 block away.Outdoor grill for cooking. Oxford is 1 1/2 hours from Wash DC or Baltimore, MD. it is a cute, historic town on the Chesapeake bay. great biking area. near St Michaels and Easton , MD . Boating. park across st great for children and picnics.

Sleeps

Select Dates for Price

Cottage

Cozy 3 bedroom historic cottgage in Oxford, MD avialable Aug 2024

Oxford, Maryland, United States

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Bath

Sleeps

$1096.04