Vacation rentals in Cockeysville

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Top-rated vacation rentals in Cockeysville

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Top guest favorite

The historic brick building features a classic architectural style, with several evenly spaced windows and two prominent blue doors at the entrance. A pathway leads to the doorway, with a flag displayed on the left side. Lush greenery surrounds the property, creating a serene outdoor setting.

Apartment in Monkton

4.95 out of 5 average rating, 167 reviews

The Fisherman's Lodge at the 1858 Monkton Hotel

Love the outdoors? Love to fish, hike, bike, kayak? All of the above? The Monkton Hotel is a registered landmark that sits on the NCR trail, which runs along the Gunpowder River, home for some of the best trout fly fishing in the country. This fully renovated apartment, themed the "Fisherman's Lodge", is on the second floor and has the latest amenities. Nothing in the area matches the charm, convenience and history. An electric bike store, tube rental and great cafe are all in the same building.

Superhost

A two-story house with a light beige exterior, featuring green shutters on the windows. The front porch is accessed by a small set of stairs and is flanked by manicured shrubs. A spacious lawn surrounds the property, integrating natural greenery into the setting.

Home in Monkton

4.83 out of 5 average rating, 71 reviews

Charming 3-bedroom in Historic Monkton Village

Whether you are coming for the world renowned trout fishing on the Gunpowder River, the excitement of steeplechase racing or just to relax in the country, you are only 30 minutes from Baltimore Walk just 300 feet to fish or float on the river Enjoy 3 local farm to table breweries Listen to live music at 2 exceptional wineries Experience the famed Manor Tavern Walk through the historic Ladew Gardens Or Enjoy a local polo match Whatever you choose, my house is your house. See guidebook for details

Guest favorite

A spacious living area is furnished with a large black sofa, a small wooden coffee table, and a TV mounted on a stand. Natural light enters from a nearby window, and decorative shelving adds depth to the room. A lamp provides additional lighting.

Apartment in Timonium

4.88 out of 5 average rating, 16 reviews

Home away from home! Near city, parks, colleges.

Easy access to everything from this centrally located neighborhood! Relax with your coffee on the deck overlooking the quiet back yard. Minutes to the city, hiking, shopping, colleges, everything you need is close by. The apartment has a toaster oven, microwave, refrigerator and coffee maker and washer and dryer. Large black sofa has 4 recliners! It is a private area closed off from the rest of the house. Weekly housekeeping can be arranged for an added fee. I look forward to hosting you!

Guest favorite

A welcoming porch area features two black rocking chairs positioned near a decorative door with glass panels. A vintage-looking milk can adds rustic charm, while a warm light fixture illuminates the entryway. The surroundings include trees and green space visible in the background.

Guest suite in Parkton

4.93 out of 5 average rating, 59 reviews

Bull House Winery Private Farmhouse Suite

Make some memories at this unique and family-friendly place. This one bedroom with pull out queen sleeper sofa is a great place to visit. The space is located on the same property as the farm winery, adjacent to trails along Gunpowder River, known for fly fishing, swimming, tubing and hiking opportunities. Join us for peaceful sunrises, beautiful sunsets and starry skies. We are close to the NCR, Big Truck Brewery, Inverness Brewery, the Farmyard, historic Manor Mill and other local interests.

Top guest favorite

A modern bedroom is highlighted by a spacious bed dressed in white linens. Two abstract paintings adorn the walls. A workspace with a desk and chair is positioned nearby, with light provided by a lamp on a side table. The room is complemented by soft lighting and stylish window treatments.

Guest suite in Towson

5 out of 5 average rating, 65 reviews

Towson Retreat: Fully Equipped w/ Garden View

Get cozy in this lovingly-renovated home away from home. Our guest suite features a private entrance, full kitchen, in-unit washer/dryer, and unique design touches. Enjoy the surrounding greenery on the patio or stroll around the corner to Towson Town Center. Visiting a college student? We're walking distance from Goucher College, 1.5 miles from Towson University, and just 20-minutes north of Baltimore City. Love the great outdoors? Checkout nearby Loch Raven Reservoir or Boordy Vineyards.

Top guest favorite

The charming two-story home features a light blue exterior with white trim and a welcoming porch supported by classic columns. A well-maintained yard showcases lush greenery and flowering plants. An American flag is displayed prominently, adding to the home's inviting presence.

Guest suite in Monkton

4.96 out of 5 average rating, 178 reviews

Private Garden Apartment in Historic District

Our 1919 charming home, surrounded by 50 acres of preserved land, is in an historic district and a stone's throw from the NCR hike/bike trail. We have tubes to float down the Gunpowder River which winds around our property and is accessible by foot. The bike path is lovely! Inverness Brewery is located 5 minutes away, Starbright farm is a glorious lavender farm 15 minutes north, Boordy Vineyards, a family run winery, is 20 minutes east, and Ladew Toipiary Gardens is another gem to behold!

Guest favorite

A spacious living area features a cozy sectional couch adorned with decorative pillows. Soft, warm lighting illuminates the room, complemented by a striped rug on the floor. Visible in the background is the open-plan kitchen and dining area, enhancing the sense of space.

Guest suite in Timonium

4.9 out of 5 average rating, 449 reviews

* Spacious Private Suite Full of Style & Comfort *

Welcoming recently updated private basement suite with trendy decor and style! The one bedroom spot offers so much more than just that. You will have full use of the open shelf kitchen, perfectly setup cozy living room, spacious full bathroom, breakfast nook, and laundry room if needed. Any couple, working professional, or small family / group of friends would love the stay here. Not to mention the great location convenient to all Baltimore attractions. Plenty of parking available.

Top guest favorite

An open-concept living area features a cozy seating arrangement with a light-colored sofa and patterned accent chairs. A sleek coffee table sits atop a patterned rug. The kitchen is visible in the background, showcasing rich wooden cabinetry and modern appliances.

Apartment in Timonium

4.91 out of 5 average rating, 104 reviews

Home Sweet Home Apartment in a beautiful home

Come to your home away from home! Beautiful and comfy apartment unit in a luxury home in the heart of the Historic Lutherville neighborhood. Walking distance to restaurants, shops, coffee shops, Mom's Organic Market and most importantly you can walk to light rails and bus stops that takes you to the airport, Baltimore city harbor, Camden yards, university of Maryland and downtown Baltimore City. Close to GBMC, St. Joseph's hospital, Towson University, Hunt Valley and Towson Mall.

Top guest favorite

A charming stone cottage features a red front door with black shutters framing the windows. A friendly dog stands on the stone path, surrounded by lush greenery. The staircase leading to the studio is visible on the right side, along with decorative elements of the owner's residence.

Guesthouse in Towson

4.99 out of 5 average rating, 258 reviews

Cute cottage studio with full kitchen and laundry

Warm and inviting private upstairs studio with off-street parking, full kitchen, laundry, electronic fireplace, rainhead shower and deck with tranquil garden in the Riderwood area of Towson. Studio is situated next to owner's stone cottage, and is tucked away at the back of 2.5 acres with private bridge and creek. Centrally located to shops, galleries, walking and biking trails, Lake Roland, Baltimore, DC and PA. Especially suitable for a restorative or romantic getaway.

Guest favorite

A well-equipped kitchenette is visible, featuring modern appliances, including a microwave and refrigerator, alongside ample storage and countertop space. A small dining area with a round white table and pink chairs is situated nearby, enhancing the inviting layout of the space.

Guest suite in Towson

4.91 out of 5 average rating, 141 reviews

Cozy Suite in Towson l Free Parking + Laundry

Welcome to your stylish, sun-filled, private basement apartment in Towson, MD! Unwind in a queen-sized bed, enjoy a spa-like rain shower, and cook meals in the fully equipped kitchenette with a microwave, Keurig, air fryer, and portable cooktop. Stream your favorite shows on the 43" Smart TV or work remotely with high-speed WiFi. Guests enjoy free street parking, private entrance, and a shared washer/dryer on-site, making it easy to settle in and feel right at home.

Top guest favorite

A modern living space is showcased with a light-colored sofa and two brown leather armchairs, inviting relaxation. A dark coffee table acts as a focal point on a textured area rug. Natural light streams in through large windows, enhancing the room's spacious feel.

Home in Timonium

5 out of 5 average rating, 30 reviews

Timeless Elegant Getaway

Welcome to our Timeless Elegant Getaway, a beautifully restored home that combines classic charm with modern comforts. Nestled in a tranquil neighborhood, this elegant retreat is perfect for those seeking a sophisticated and relaxing escape. Located in a peaceful and charming neighborhood, our home is just a short drive from local attractions, dining, and shopping. Enjoy a stroll through nearby parks or visit the city center for a variety of cultural experiences

Guest favorite

A spacious living area features a large sectional sofa with decorative cushions, positioned beside a contemporary coffee table. A flat-screen television is mounted on a sleek media console. Natural light filters through the oversized windows, illuminating the modern, minimalistic design.

Apartment in Towson

4.87 out of 5 average rating, 149 reviews

Towson Luxury Apartment

Welcome to our charming apartment in the heart of Towson, Maryland! This stylish and inviting retreat is the perfect home away from home, offering a delightful blend of comfort and convenience. House Rules: 🚫 No pets (If validated, a pet fee of $150 will apply). 🚭 No smoking (If validated, a smoking fee of $500 will apply). 🎉 No parties (If validated, a party fee of $1,000 will apply). Book your stay today and experience the best of Towson!