
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.

Waterfront Gem with Free Parking
Larger groups should consider our Deluxe Upgrade: https://www.airbnb.com/rooms/29510842 Watch boats cruise along the Harbor, enjoy a quaint interior courtyard oasis, or socialize in the sun-drenched, open concept living room surrounded by vaulted ceilings and local artwork. Waterfront Gem has a fully equipped kitchen, big screen Smart TV with cable channels, high-speed WiFi, and so much more. This historic, award-winning property can be your home away from home. Award-winning property with gorgeous interior architecture. Highlights include: (1) Huge waterfront balcony- perfect for people watching (2) Interior courtyard garden- amazing for morning coffee (3) 2 large bedrooms on separate floors for privacy (4) Each bedroom has private bathroom away from living area (5) Open kitchen/living space with lots of seating for "together" time (6) Fully equipped kitchen for cooking (7) 65-inch TV, Fast WiFi, Keurig for coffee, washer/dryer, dishwasher, and lots of other amenities and extras. Exclusive access to the waterfront balcony, interior courtyard, and all areas of the house which are for you and you only! You'll have access to the entire condo which occupies the entire 3rd and most of the 2nd floor (there is a women's fashion boutique on the 1st floor and a small studio apartment with separate entrance on the 2nd floor). Tenants of the store and studio apartment do not have access to your space. The property has "Smart Locks" which allow guests to enter with a custom pass code I set (and remove upon checkout) for each guest. Different guests want different things, so I'll try my best to accommodate you in the way you'll most appreciate. If you prefer privacy, you'll have as much as you want, and I've included lots of local tips and recommendations in our House Guide for you to explore on your own. If you're looking for opinions, input, ideas, etc... then I'm more than happy to be a resource for you! I grew up in the area, live just a few blocks away, and am often out and about in the neighborhood, enjoying all that Fells Point has to offer. Located in the heart of Baltimore's most charming neighborhood: Fell's Point! Conveniently located nearby Johns Hopkins Medical Center (1 mile). Great for walking: you can follow the waterfront promenade all the way from Fells Point, through the Inner Harbor, up to Federal Hill Park. Or stick around the neighborhood, window shop, and check out quirky stores and restaurants. Water Taxi is 100 feet away and has 10+ stops to bring you to all the top tourist destinations by scenic boat ride. Uber/Lyft are the best methods to get around quickly and often are only 1 or 2 minutes away. Parking is tricky, but if you're coming into town with a car, I can help you coordinate valet service with the hotel directly across the street, direct you to a nearby parking garage, or suggest free street parking a few blocks away. Parking directly outside of the property is hourly during the day (because of the prime location).

Private suite Catonsville/Baltimore Near Airport
Relax with the family at this peaceful place to stay. You can explore the Suburbs outside the city of Baltimore. Charming Basement Apartment. Fully Furnished with 2bed and 1 bedroom, Air bed if needed. full bath -Kitchenet with microwave, fridge, toaster and coffee maker is available for guests. -Dining area and living room with TV. -There are amazing restaurants, cafes and bars near -The Patapsco River is one of the most important destinations for saltwater fishing Flowing from the western MD

Apt 15 min from StAgnes/SSA/Sinai/UMBC
Fully furnished basement apartment - less than 5 minutes from 695/70, Social Security Administration, Baltimore Gas & Electric, Centers for Medicare & Medicaid Services, Lockheed Martin, Northrop Grumman, FBI Baltimore Field Office and University of Maryland of Rehabilitation & Orthopaedic Institute (formerly Kernan Hospital). Also within 15 minutes of Northwest & Sinai. We're in the middle of everything - within 15 minutes there are 6 hospitals, 4 colleges, & 3 malls. Tesla charging available

Urban 1-Bedrm. Apt. Overlooking Union Square Park
The south-facing, 2nd floor 1-bedroom apartment of an owner-occupied historic townhouse overlooks historic Union Square Park in Baltimore City. Located 2 doors from the author, H.L. Mencken's home place, the neighborhood is primarily residential , but very convenient to the Inner Harbor. The apartment has a full kitchen (with light breakfast items), historic details & eclectic furnishings. Street parking is easy. The space is good for couples and solo adventurers, and business travelers.

* 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.

Charm City's Creative Escape in Reservoir Hill
Welcome to your creative one bedroom, one bath retreat in Reservoir Hill, designed for peaceful getaways, staycations, or work trips. This art filled space blends historic charm with modern comfort and features multiple standing and seated workstations. Enjoy a functional bedroom with a Murphy bed for added space, a fully stocked kitchen, formal dining area, bar cart with vinyl player, balcony views, and thoughtful details throughout, perfect for rest, creativity, and photo worthy moments.

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.

Cozy in Canton | Private Driveway | Pet Friendly
Enjoy your own private driveway with easy access to this thoughtfully renovated 1-bedroom suite in a finished basement of an owner-occupied home. No shared spaces. The suite features a brand-new kitchen, sleek appliances, and fresh flooring throughout. Elevate your stay with luxuries like a Dyson blow dryer and straightener, plus Ritz-Carlton hand soap, body wash, shampoo, and conditioner for a boutique hotel experience. Located near major highways and Canton bars and restaurants.

Baltimore Luxury Apartment Near Mt. Washington
Welcome to Baltimore's newest luxury apartment. This apt is located on the lower level of a new modern home. Apt. features 2 bedrooms, 1 spa bath, laundry room, luxury vinyl flooring & upgraded kitchenette with the finest appliances which include a full-size dishwasher, ninja foodie air fryer & oven, microwave & coffee maker. The apt is private & secure with its own designated entrance. You'll love the ample parking, nearby parks, easy access to I-83 & proximity to Sinai hospital.

Cozy 2BR Retreat in Baltimore
Welcome to Baltimore! This airy, stylish, and inviting 2-bedroom, 1-bath home is the perfect place to relax after a day of exploring. Located in the Beechfield neighborhood, you'll enjoy a quiet residential setting that reflects the beauty, resilience, and warmth of a true Baltimore community. If you're looking for comfortable stay in a genuine Baltimore neighborhood, this is your spot. If you prefer only glossy, picture-perfect surroundings, this may not be the best fit.

Private basement and entrance
Relax in this peaceful SUITE. The renovated basement SUITE has a private entrance and long-term stay facilities, including a free in-unit washer and dryer, refrigerator, and stove. Convenience stores are just a minute's walk away in a walkable neighborhood We are proud to provide 5-star services for our guests, ensuring they have the best time during their stay with us. Please note that: ==> ***We do not accommodate reservations for someone else*** <==

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
Other great holiday rentals in Woodlawn

Guest Room & Private Bth in Private Home

Comfy, Cozy, & Affordable Room #2

Cozy and Private Room

Cozy Room, Private, Smart TV, All Essentials (5)

The Pink Duchess, quiet and comfy queen room!

Simply Comfy-Your Best Stay!

Nice and clean airbnb room in a walkout basement

Welcome to Our Cozy home!
When is the best time to visit Woodlawn?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $95 SGD | $95 SGD | $76 SGD | $81 SGD | $91 SGD | $78 SGD | $72 SGD | $72 SGD | $76 SGD | $81 SGD | $82 SGD | $82 SGD |
| Avg. temp | 1°C | 3°C | 7°C | 13°C | 18°C | 23°C | 26°C | 25°C | 21°C | 14°C | 8°C | 4°C |
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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- Walter E Washington Convention Center
- Georgetown University
- National Mall
- M&T Bank Stadium
- Nationals Park
- The White House
- District Wharf
- Capital One Arena
- Liberty Mountain Resort
- National Museum of Natural History
- Baltimore Convention Center
- Oriole Park at Camden Yards
- Hampden
- National Museum of African American History and Culture
- Arlington National Cemetery
- Betterton Beach
- Sandy Point State Park
- Washington Monument
- Georgetown Waterfront Park
- Patterson Park
- National Harbor
- Cunningham Falls State Park
- Smithsonian American Art Museum
- Great Falls Park




