Holiday rentals in Woodlawn

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Top-rated holiday rentals in Woodlawn

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

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Top guest favourite
The historic row home showcases an elegant brick facade featuring multiple large windows that illuminate the interior. A welcoming entrance is complemented by light-colored trim. Surrounding trees outline the building, adding to the charming appeal of the neighborhood.
Flat in Washington Hill
4.98 out of 5 average rating, 419 reviews

Stunning 1BR Apt. in Historic Row Home w/ Parking

Just steps from Baltimore’s Inner Harbor, Fells Point, Little Italy, and John’s Hopkins Hospital, this fully equipped one bedroom apartment has everything you need! This modern and contemporary unit inside one of Baltimore’s historic row homes (built 1850) features tall ceilings and beautiful floor to ceiling windows. Apartment includes a full kitchen, full bathroom, one bedroom with office space, living room with HD TV and sofa bed, and a washer/dryer in unit. A bike is also available for use!

Guest favourite
An open floor plan showcases a spacious living area with two gray sofas and a brown chair placed on a dark area rug. A kitchenette is visible in the background, complemented by bar stools. Natural light enters through multiple windows, illuminating the space.
Guest house in Woodberry
4.88 out of 5 average rating, 241 reviews

Woodberry Studio Retreat

This newly constructed 600 sq. ft. studio loft features a contemporary open floor plan, full kitchen (new appliances), walk-in shower, yoga floor, big screen smart TV, queen bed, tons of morning and evening light, and is located in Historic Woodberry. This home is very private, safe, and fully equipped for short or long term stays. Walk to light rail station, JHU, Kennedy Krieger Institute, and the Hampden Avenue. Five star dining experience available just two blocks away, at Woodberry Kitchen.

Top guest favourite
The historic building features a distinctive red brick façade, complemented by large windows and decorative trim. Lush green trees provide shade in front, while parked vehicles line the street, enhancing the inviting urban atmosphere.
Flat in Butchers Hill
4.99 out of 5 average rating, 472 reviews

Butchershill- Clean, Fireplace, King Bed, Parking!

My name is John S Marsiglia. Always clean, very comfortable new King Mattress, Warm & Cozy Fireplace, Self checkin , Historic 2207 E Baltimore St. Search online. 900 Sq Ft. 12 ft ceilings,Fully equipped kitchen/kitchenette,Coffee,Tea,Cream,Brita filtered water pitcher,50" 4K smart TV, streaming only, Free Netflix, Prime,top speed WiFi, surround sound, comfortable clean furniture, antiques, oriental rugs, workspace w/desk, modern beautiful bathroom, dual shower heads&seats, private full size W&D

Guest favourite
An eclectic studio apartment displays a spacious bed and a patterned throw atop it. Sunlight filters through tall windows, reflecting off decorative wall art. A piano and a book-filled shelving unit add character, while plants bring life to the room's corners.
Flat in Union Square
4.91 out of 5 average rating, 835 reviews

South-Facing Studio Overlooking Union Square Park

Pick out tunes on the refurbished 1910 piano or classical guitar of this eclectically furnished studio apartment, elegantly lit by tall windows under high ceilings overlooking lovely Union Square Park in downtown Baltimore. The residential area is a mile from the inner harbor/ stadium and street parking is easy. Nearby, enjoy walking in the park, dinner at Rooted or even see a puppet show. A well-stocked library offers great reading and the kitchenette has coffee, tea, and a light breakfast.

Guest favourite
The spacious living area features a comfortable sectional sofa and a decorative area rug set on hardwood flooring. A TV unit is positioned next to the sofa, while a dining table with chairs is visible in the background, and natural light filters in through multiple windows.
Flat in Woodlawn
4.89 out of 5 average rating, 46 reviews

Home Away From Home

Welcome to our ground-level condo located in quiet neighborhood! - Great location - this hidden gem is only 1-min. from Patapsco State Park to hike, picnic, or relax by the water - Situated between Baltimore and Washington, DC - 2 Bedrooms / 4 Beds Total: 1 Queen Bed, 2 Full Beds, 1 Twin Hide-A-Way Bed. 2 Bathrooms, Laundry Room, Open Living Room & Dining Area, Fully-Equipped Kitchen, Study, and Patio - Smart TV, Wi-Fi, Board Games - Self Check-In - Free Parking Relax and enjoy your stay :)

Guest favourite
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 Lutherville
4.9 out of 5 average rating, 473 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 favourite
A classic brick Colonial house is surrounded by well-maintained gardens and lush greenery. Large trees provide shade over the front lawn, which features manicured bushes and young saplings, contributing to the inviting exterior of the home.
Guest suite in Catonsville
4.94 out of 5 average rating, 555 reviews

Rollingside: Two-Room Guest Suite

Two-room guest suite with private entrance located in picturesque Catonsville, MD on a pre-Colonial road originally used for rolling tobacco to the harbor. Downtown Baltimore is 20 minutes away, BWI airport and Amtrak station 15 minutes, and our street is located on a bus route. Beautiful 3.5 mile walk to historic Ellicott City and an hour from Washington, D.C. Individuals and families with children are welcome, but the Airbnb member renting the property must be over the age of 25.

Superhost
A comfortable living area features a leather sofa and a coffee table atop a striped area rug. A large mirror and wall-mounted TV enhance the space, while natural light filters in through sheer curtains. A decorative fireplace adds warmth to the room.
Townhouse in Federal Hill - Montgomery
4.88 out of 5 average rating, 139 reviews

Fed Hill ☆ Parking ☆ Deck ☆ Walk Score 95 ☆ Harbor

Find yourself at peace with all the comforts of home in a uniquely renovated 2 bedroom, 1.5 bath rowhome in Federal Hill, in the heart of Charm City. You'll find secure gated parking for two compact cars, an outdoor fireplace, a laundry room, a second-story deck and more! Steps from the Inner Harbor, Downtown, Aquarium, Ravens & O's stadiums, Baltimore convention center and countless restaurants and shops. Leave the car parked and walk to all the best that the city has to offer!

Top guest favourite
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.
Guest house in Towson
4.99 out of 5 average rating, 277 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.

Top guest favourite
A comfortable living area features a light-colored sofa adorned with patterned cushions. Artwork is displayed on the walls, and a stylish lamp provides warm lighting. A wooden coffee table holds an assortment of magazines, while an armchair is positioned nearby, offering additional seating.
Townhouse in Hampden
4.95 out of 5 average rating, 471 reviews

Comfy Home in Charming Hampden

2 bedroom + den on cute street in Hampden/Wyman Pk. Quick walk to restaurants & shops on The Avenue as well as Hopkins University and The Baltimore Museum of Art. Minutes drive to downtown, train station. Front porch & back yard. Over a century old, with updates and character. Please note the 1/2 bath is located in the basement. Also, there is a 10 step flight of steps from the street to the main level and a flight of steps to main bath and bedrooms on the second floor.

Top guest favourite
A cozy sleeping area is featured with a spacious bed adorned with an abstract circular accent design. Soft blue pillows enhance the bedding, while warm orange walls add vibrancy. Soft lighting from two bedside lamps illuminates the space, complemented by a framed artwork and a small wardrobe.
Apartment in Hampden
4.94 out of 5 average rating, 195 reviews

Sun House in Hampden Private Apartment no stairs

Artists and creatives are welcomed! Stay at our 1920 rowhouse with its mix of 70's era textiles and contemporary style. Only two steps to a welcoming porch and keyless entry to our foyer/Shared hall. Straight ahead is Sun Apartment, private studio with stocked kitchen, comfiest 5 star bed, private bath, laundry and back yard access. Yoga room/ office located in shared hall. No need for a car in the heart of Hampden's Avenue just a block away. LGBTQ+ friendly

Top guest favourite
An outdoor seating area features two vibrant red chairs placed on a mulch bed. A small table stands between the chairs, surrounded by greenery and decorative plants. A bright red door provides an inviting entrance, while a vintage wrought iron fence encloses the area for privacy.
Guest house in Catonsville
4.96 out of 5 average rating, 305 reviews

Fox Cottage *Pet Friendly*

Fox Cottage is a modern addition to our 115 year old Victorian home. It’s a One Bedroom Queen size mattress & memory foam topper. There’s a Loft with a Full Size Memory Foam Mattress. The loft is a cozy space accessible by a vintage wooden ladder. It is not appropriate for people who cannot climb a ladder. There’s an outdoor seating area with a Chiminea to light a fire, enjoy a cup of coffee or wine, work or just listen to the birds.

Popular amenities for Woodlawn holiday rentals

When is the best time to visit Woodlawn?

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Frequently Asked Questions

  • How much does it cost to stay in apartment rentals in Woodlawn?

    Experience the best of Woodlawn with our apartment rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Woodlawn have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Woodlawn. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Woodlawn have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in Woodlawn. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Woodlawn?

    Yes! Work meets play with ease at over 40 vacation rentals in Woodlawn featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • What are the most popular amenities for Apartment Rentals in Woodlawn?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly vacation rentals in Woodlawn?

    Woodlawn has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Where should I stay in Woodlawn?

    Make yourself at home in Woodlawn by choosing from our most frequently booked neighborhoods. We have over 180 vacation rentals in Chadwick Manor, over 70 vacation rentals in Westview Park, and over 520 vacation rentals in Catonsville Manor.

  • Do apartment rentals in Woodlawn have a kitchen?

    Absolutely! We offer over 10 apartment rentals with a kitchen in Woodlawn. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Woodlawn?

    Four-legged friends are welcome in Woodlawn. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do apartment rentals in Woodlawn have free parking?

    Absolutely! We offer over 10 apartment rentals with free parking in Woodlawn. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Woodlawn

  • Total holiday rentals

    Explore 60 holiday rentals in Woodlawn

  • Nightly prices starting at

    Woodlawn holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 660 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    60 of Woodlawn holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Woodlawn rentals

  • 4.7 Average rating

    Woodlawn stays receive an average rating of 4.7 out of 5 from guests

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