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
A spacious living area features large windows that allow natural light to fill the space, showcasing views of the surrounding greenery. Comfortable seating is arranged around a low table, with a television mounted on the wall, and decorative shelves filled with various items.
Cottage in Annapolis
4.96 out of 5 average rating, 453 reviews

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

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
4.98 out of 5 average rating, 515 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
The exterior of a renovated historic church features a striking red door and intricate Gothic-style windows. The building is set against a twilight sky, highlighting the brick facade and architectural details. The surrounding area is paved and there are hints of greenery.
Religious building in Washington Hill
4.97 out of 5 average rating, 404 reviews

Gorgeous Studio Apt. In Historic Chapel w/ Parking

This stunning private studio rivals Baltimore’s top hotels and is packed with premium amenities most Airbnbs don’t offer. Once a mystery church set for demolition, it’s now a fully renovated mid-century modern gem with private access, a fully stocked kitchenette, new hardwood floors, and a luxe stone tile rain shower. Sleep soundly with down feather bedding, enjoy luxury toiletries, a 55” smart TV, and courtyard views through gorgeous French doors—all in a prime location with easy, free parking

Top guest favourite
Guest house in Ellicott City
4.92 out of 5 average rating, 100 reviews

Cozy Historic Guest House

Located in the heart of Old Ellicott City! This studio is warm, cozy and decorated with almost all vintage furnishings to pay tribute to the 1800s home. The space offers a well stocked bedroom, full bathroom and kitchenette. Relax on the patio or walk to the many cafes and shops on Main Street. Parking is included. The home is built into a hill so you will need to walk up a series of steps & stoned in the back from the parking area to enter. Due to this our home may not be ideal for everyone.

Superhost
A single-story house features a welcoming entrance with a front door framed by simple step railings. A spacious driveway leads to the home, and a newly fenced backyard is visible to the left, surrounded by well-maintained grass and brick pathways.
Home in Catonsville
4.85 out of 5 average rating, 156 reviews

Delightful 4-Bed Whole House with Easy Parking

Newly relisted! Centrally located next to route 40 & 695 Beltway. House newly furnished. Huge park & soccer field within 5 mins, for dogs & to play. 5 mins drive to Starbucks, Chick-fil-A, Walmart, Applebees, Safeway, Enterprise, Lotte, Home Depot, Lowe's. Plenty of local restaurants & bars on Frederick Rd. Easy commute to BWI, B'moreCity, Hopkins, Ellicot & Columbia. Train for DC commute is 10 mins drive to Halethorpe. Previously only basement listed, guests loved it, now listing whole house.

Top guest favourite
A living area features a light grey sofa facing a large window that invites natural light. Two woven chairs are positioned nearby, and a stone fireplace adds a touch of warmth to the space. Modern light fixtures are installed on the walls.
Home in Catonsville
4.95 out of 5 average rating, 152 reviews

Tudor Home

Enjoy your stay in this cozy, newly remodeled Tudor home in a historic and architecturally eclectic neighborhood in Catonsville, MD! You’ll be close to everything but far enough to enjoy a relaxing trip. The home features Four bedrooms, two full baths, a fully stocked kitchen, a full basement, and 18ft ceilings on the main level. You will enjoy 65, 42, and 32-inch smart TV's throughout the home. In addition, a private upstairs main suite with King size bed, sofa seating area, and workstation.

Top guest favourite
A light-filled living room showcases a cozy sofa adorned with decorative pillows and a round mirror reflecting natural light. Two elegant armchairs and a small coffee table complement the space, inviting relaxation. A patterned rug adds texture to the hardwood floor.
Home in Catonsville
4.95 out of 5 average rating, 178 reviews

Mid Century Ridge

This house is a fully renovated 1920’s single family home with high ceilings, gorgeous natural light, and original hardwood floors. Decorated with style and comfort in mind, you will find it has everything to suit your travel needs while still feeling homey. Enjoy a large, fully-stocked kitchen, dining for 8, and comfortable living room with a TV. With a covered patio perfect for relaxing and a backyard for your pets, kids, or entertaining, you have everything you need for a wonderful stay!

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, 562 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.

Top guest favourite
A spacious bedroom features a wooden bed frame with a light-colored mattress, flanked by two minimalist wall sconces. Soft blue throws are neatly arranged on the bed. A large window allows natural light, complemented by warm wood flooring. A wooden console table displays modern amenities.
Flat in Baltimore
4.99 out of 5 average rating, 128 reviews

Private Serene Hideaway Suite with Jacuzzi

Escape to this serene suite, an extension of the main house, in Baltimore’s safest & quietest area. Ideal for couples, it offers a private Jacuzzi, California king bed, large modern TV, and dedicated HVAC for comfort. The spacious sitting area and luxurious shower create a peaceful retreat. Walk to nearby shops and parks for added convenience. A Tesla charger is available upon request, ensuring convenience for electric vehicle owners. Perfect for a relaxing getaway or city visit.

Top guest favourite
The bedroom features a spacious bed with a navy blue comforter. A sliding glass door opens to a wooden deck, framed by sheer curtains. Adjacent, two decorative vases with yellow flowers are positioned next to a textured wall. Warm wooden flooring enhances the inviting atmosphere.
Townhouse in Washington Village - Pigtown
4.98 out of 5 average rating, 210 reviews

Unique 2bd townhouse quietly located in the city.

Our peaceful and unique townhome is located in historic Pigtown. It is centrally located to many things the city has to offer. Just 1.5 miles from INNER HARBOR/AQUARIUM, 0.5 miles from the M & T Bank stadium, 0.7 miles from Top Golf, and the University of Maryland, 0.9 miles from the Horseshoe Casino, all within walking . Although downtown, the home offers a quiet and serene feeling, with the true literal meaning of your home away from home!

Top guest favourite
A wooden pier stretches into the water, flanked by lush greenery. A rainbow arcs above the serene landscape, with gentle waves lapping at the edge of the sandy shore. Trees and homes line the distant banks, completing the tranquil waterfront scene.
Place to stay in Glen Burnie
4.93 out of 5 average rating, 390 reviews

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

Top guest favourite
A bright living area is presented, featuring a grey sofa adjacent to a rich brown ottoman. A small kitchenette is visible with a stove and refrigerator, complemented by open shelving. Natural light enters through a skylight and windows adorned with blinds. A doorway leads to a bathroom.
Guest house in Owings Mills
4.96 out of 5 average rating, 139 reviews

The Garden Studio

Thoughtfully appointed 1 bedroom guesthouse in beautiful Greenspring Valley. Enjoy quiet quarters on an acre of private residential property within 5 minutes of the Baltimore beltway & restaurants, grocers, gas, and services. Close to Stevenson University (2 mi), Towson University (7 mi), convenient to other colleges & universities in the area; and 11 mi to the Inner Harbor. Host available in main house as needed.

Popular amenities for Woodlawn holiday rentals

When is the best time to visit Woodlawn?

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Frequently Asked Questions

  • 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.

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

    Experience the best of Woodlawn with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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.

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

    Yes! Work meets play with ease at over 10 house rentals in Woodlawn featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • 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 520 vacation rentals in Catonsville Manor, and over 70 vacation rentals in Westview Park.

  • Do apartment rentals in Woodlawn have air conditioning?

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

  • 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.

  • Do house rentals in Woodlawn have wifi?

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

  • Do house rentals in Woodlawn have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Woodlawn. Enjoy a tailored experience with all the comforts you desire.

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

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a kitchen, over 20 homes with air conditioning, over 30 homes with wifi, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

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 700 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

    30 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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