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Vacation rentals in Woodlawn

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Top-rated vacation rentals in Woodlawn

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

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Rental unit in Sykesville

4.97 out of 5 average rating, 165 reviews

Hickory Haven •1B King •Bsmt Apt •Clean •LG

Walk into a generously spacious, open-concept apt. The comfortable furnishings in this home blend authentic styles with modern design. Start your mornings w/ a meticulously clean bathroom. Enjoy movie night in the large living room, or lay on the comfortable king-sized bed. Read through the night by a warm stove fire. Stay in the backyard and enjoy the serenity of Sykesville! Enjoy the high-speed internet and the large space for your work-at-home needs. Stay-a-while and make the place your home.

Guesthouse in Baltimore

4.87 out of 5 average rating, 202 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.

Rental unit in Sykesville

4.97 out of 5 average rating, 307 reviews

Heart of Sykesville! 2 Bedroom Suite! Walk to town

Located in the heart of Sykesville, Linden, a two bedroom basement suite, welcomes you to relax and rewind! We have designed our space to feel like your home away from home.The kitchenette includes a full refrigerator, microwave, slow cooker, Instapot, and a hot plate for meal prep. An easy stroll to Main Street will give your car a rest as you enjoy dining and shopping, live music from May/Oct and a wonderful Splash Park from May/Sept. Private guest patio with small gas grill. Dogs considered.

Guesthouse in Glenwood

4.95 out of 5 average rating, 177 reviews

The Caretaker's Cottage-Historic Roundabout Hills

The Caretaker's Cottage was built in the 1770s by Ruben Merriwether, and sits near the manor house where he and his ancestors lived at Roundabout Hills. An exceptional space with a fabulous full kitchen perfect for those who like to cook, it is truly a one of a kind place to stay. The house, where John and Fiona live, and the cottage are secluded and private, but close to all of the art, culture, restaurants and dining in the nearby towns of Frederick, Columbia, Baltimore, and Washington, DC.

Rental unit in Baltimore

4.82 out of 5 average rating, 102 reviews

1BR Apartment with Private Entrance | Guest Suite

Discover your Baltimore Oasis! Immerse yourself in our charming, fully-equipped basement apartment. Enjoy complete privacy with separate indoor spaces for the 1BR, a well-appointed kitchenette, a cozy living room, and a dining area. Your getaway offers quick access to a variety of attractions, all within a 5-mile radius. From golf courses and parks to museums, the iconic Baltimore Harbor, shopping malls, zoos, aquariums, stadiums, and the renowned Johns Hopkins Hospital, your adventure awaits.

Guest suite in Woodstock

4.99 out of 5 average rating, 165 reviews

Our Retreat -in a country setting.

Private- apartment in the lower level of our house. House is in a rural setting- you may spot a few white tail deer or other wildlife. Come here and enjoy the peaceful tranquil setting. We are within 5 minutes to Rte 70 and shopping centers. Over 1800 sq. our space isn't childproof. Workout equipment available for use at your own risk. We control the HVAC and will adjust as requested. May not be suitable for those with mobility issues due to the walk to the entrance. We don't allow smoking.

Home in Catonsville

4.91 out of 5 average rating, 120 reviews

Cozy Catonsville Home

No cleaning fees, no charge for additional guests. NOTE: We are doing construction next to our house but no work will take place on days that are open for guests to stay. Everyone is welcome to rent this entire house and relax with the family. Great for friends getaways and family outings. Located within 20 minutes of BWI, 23 minutes to the Inner Harbor in Baltimore, and 60 minutes from the National Mall in Washington DC. One mile from historic Ellicott City and from downtown Catonsville.

Guest suite in Catonsville

4.94 out of 5 average rating, 502 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.

Guest suite in Randallstown

4.99 out of 5 average rating, 130 reviews

Private Efficiency Suite ~ King Bed ~ Baltimore Co

Welcome to Hickory Roots Hideaway! A cozy yet spacious 750 sq ft efficiency guest suite situated on our picturesque 4 acre homestead! Great Wi-Fi and amenities make this a perfect getaway even if work and virtual school must continue. Enjoy a relaxing stay - you are welcome to explore our garden, shoot some hoops in our basketball court, or get to know our adorable farm animals. We are conveniently located with easy access to I-70, I-795, and just 30 minutes from downtown Baltimore!

Home in Baltimore

4.94 out of 5 average rating, 125 reviews

Stunning 7BR Lux House in Baltimore

We've taken our 17 years of travel and love for creating memorable moments and developed the perfect stay for you. A hidden gem, nestled in the heart of Baltimore, this gorgeous newly-remodeled 7 BR, 4 Bath House has been updated with amenities such as a Built-in Bluetooth theater speaker system, a master suite with dual showers and freestanding tub, and plenty of natural lighting in our charming sunroom. Elevate your time away with a massage therapist, or special event!

Guesthouse in Towson

4.99 out of 5 average rating, 210 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.

Townhouse in Hampden

4.95 out of 5 average rating, 406 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.

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Popular amenities for Woodlawn vacation rentals

Free parking on premises

Air conditioning

Stay near Woodlawn's top sights

Patapsco Valley State Park55 locals recommend

Giant Food18 locals recommend

Pho Saigon5 locals recommend

Hip Hop Fish and Chicken5 locals recommend

H Mart Catonsville5 locals recommend

Security Square Mall station4 locals recommend

Other great vacation rentals in Woodlawn

Rental unit in Mt. Washington

4.94 out of 5 average rating, 69 reviews

Mother-in-law suite with yard

Guest suite in Baltimore

5 out of 5 average rating, 20 reviews

Baltimore Luxury Apartment Near Mt. Washington

Home in Catonsville

5 out of 5 average rating, 11 reviews

Hillside Hideaway

Home in Owings Mills

5 out of 5 average rating, 33 reviews

Lovely furnished basement w private entrance

Home in Catonsville

5 out of 5 average rating, 22 reviews

Charm County Retreat

Rental unit in Ellicott City

4.88 out of 5 average rating, 57 reviews

Tiny Studio Apartment Off Main

Rental unit in Pikesville

4.88 out of 5 average rating, 8 reviews

Solase Luxury Apartment Retreat

Rental unit in Baltimore

5 out of 5 average rating, 24 reviews

Hidden Gem

Quick stats about vacation rentals in Woodlawn

Total rentals
40 properties
Total number of reviews
430 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi

Frequently Asked Questions

Do house rentals in Woodlawn have wifi?
Absolutely! We offer over 20 house 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 20 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 30 vacation rentals in Woodlawn featuring dedicated workspaces. Stay connected and productive in your home away from home.
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 free parking, over 20 homes with air conditioning, over 20 homes with wifi, 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 170 vacation rentals in Chadwick Manor, over 70 vacation rentals in Westview Park, and over 490 vacation rentals in Catonsville Manor.
Do house rentals in Woodlawn have a kitchen?
Absolutely! We offer over 20 house 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.

Destinations to explore