Hilltop Retreat w/ Pool, Games & Sunroom

Woodlawn, Maryland
$1036 avg/night
Minimum Stay 1 Nights
Bed 5

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 15

Max Sleeps

Night 1 nights

Min Stay

Welcome to your elevated escape — literally. Nestled atop a peaceful hill, this spacious 5-bedroom, 3-bathroom home offers a cozy, restful stay for families, groups, or anyone craving comfort with a splash of fun. From our midcentury-modern touches to our backyard poolside vibes, this retreat was designed with both connection and relaxation in mind.

The Space
Step inside and feel instantly at home. With enough room to sleep , this house balances space and intimacy across 5 thoughtfully designed bedrooms and a cozy futon sofa in the living room for extra flexibility.

Wake up slowly with your morning coffee in the sun-kissed sunroom, complete with rocking chairs and gentle views—a favorite spot to start the day. When it’s time to unwind or entertain, take your pick:

- Challenge friends to a game of foosball or darts, or pull out a classic board game for a cozy evening in.

- Stream your favorite shows on any of the 3 smart TVs (including two in the bedrooms for private viewing).

- Head outside to the beautiful backyard, where sun loungers, a picnic table, and a beautiful swimming pool await. With a fun collection of floaties and pool games, it's summer fun at its finest.

Sleeping Arrangements:
• Bedroom 1 – 1 King Bed (+ 1 Crib if needed)
• Bedroom 2 – 1 King Bed
• Bedroom 3 – 2 Queen Beds
• Bedroom 4 – 2 Queen Beds
• Bedroom 5 – 1 Queen Bed
• Living Room – 1 Convertible Futon Sofa

Additional Highlights:
• Three full bathrooms for easy group coordination
• Easy access via stone steps or driveway parking behind the house
• Fast, reliable WiFi
• Washer, dryer & iron on site for your convenience

Whether you're floating in the pool under the sun, gathered around a board game, or simply enjoying a slow morning in the sunroom, this home was made for memories.

Prime Location & Nearby Attractions

20 minutes from BWI Airport – ideal for smooth arrival and departure.

50 minutes to the White House in Washington, DC – perfect for a day in the capital.

16 minutes to Baltimore’s Inner Harbor (~8 mi away) – your gateway to charm and entertainment .


Explore Baltimore’s Highlights:
Just a short drive brings you to these local gems:

National Aquarium (Inner Harbor) – world-class marine exhibits

Maryland Science Center – family-friendly hands-on science fun

Historic Ships & Museums at the harbor – including the USS Constellation

Walters Art Museum – fine arts collection in Mount Vernon

Baltimore Museum of Art – modern and classical art on the north side

American Visionary Art Museum – unique outsider art near the harbor

We look forward to hosting you.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    2 Total (up To 50 Lbs Per Pet) Pet Friendly Service Animals Exempt From Fees Welcoming Cats And Dogs Only
  • BEACH

    Beach Sun Loungers Beach Towels
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    5 Bedrooms
  • GENERAL

    Unit Size: 2000 Sq Ft (186 Sq M) Uses Some LED Lighting
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Paper Towels Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi, With Speed Of 500+ Mbps (good For 6+ People Or 10+ Devices)
  • OUTDOORS

    Garden Outdoor Furniture Patio
  • POOL/SPA

    Outdoor Pool
  • BATHROOMS

    3 Bathrooms Bathtub Or Shower Hair Dryer Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk Desk Chair
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Water Sports Equipment
  • ENTERTAINMENT

    Foosball Table Games Smart TV
  • LIVING SPACES

    Dining Room Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Highchair Travel Crib
  • SERVICES AND CONVENIENCES

    Change Of Bedsheets (on Request) Change Of Towels (on Request) Housekeeping (on Request) Iron/ironing Board Safe
  • SUITABILITY/ACCESSIBILITY

    If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevators Smoke-free Property Upper Floors Accessible By Stairs Only

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 15

Map Map

School District Availability

Review Review

  • Curtis G.

    Submitted May 8, 2026

    Stayed Apr 24, 2026

    Yes yes yes it was Amazing

  • Michele W.

    Submitted Apr 7, 2026

    Stayed Apr 3, 2026

    Hilltop Retreat had everything we needed to accommodate my family traveling to Maryland. The house is spacious and parking was available. The driveway is on a steep hill and there are lots of steps, so be prepared. I did reach out about the temperature in the house, which is controlled remotely and ot was adjusted. I would love to stay again during pool season to enjoy that amenity!

  • Margaret M.

    Submitted Dec 14, 2025

    Stayed Dec 12, 2025

    It was a perfect fit for our trip.The five bedrooms were spacous and the house was spotless! Highly recommend

  • Aracely A.

    Submitted Nov 4, 2025

    Stayed Oct 31, 2025

    They host were so nice & helpful. When we asked about parking and how to turn on the outside lights they came back to the house to show us. Usually hosts would delay on a response but they were really fast and accommodating with what we had questions for. The house itself was beyond what we thought i’d be, it’s so beautiful inside and out. Very spacious & most of all I loved how it was on a hill really have the whole place character. I would definitely book here again for the summer.

  • John H.

    Submitted Oct 30, 2025

    Stayed Oct 23, 2025

    The host is very responsive, which everyone in our group appreciated.This older house has been nicely remodeled and has all modern amenities. Our group of thirteen (including six children) was very comfortable. A baby crib was also present (but bring your own baby high-chair). All rooms are spacious and brightly lit. There is plenty of closet space, and it was VERY nice to have three full bathrooms (one on each level), plus a fully-supplied laundry room.The thermostat is controlled from a remote-location, but the owner quickly adjusted it.The outdoor grounds are well-kept, and we enjoyed the nearby park. Two of us jogged 5K in the neighborhood, which felt perfectly safe.The driveway is VERY steep, but we parked two cars at the top, and there is sufficient room on the street for 2-3 additional cars. The house is close to a busy thoroughfare, but noise is not a problem because the house is high above the road.We came in October, so the swimming pool was closed. But I imagine this would be a nice retreat in the summer.

  • Submitted Oct 15, 2025

    Stayed Sep 20, 2025

    For the most part the property was clean.

  • Lauren S.

    Submitted Aug 27, 2025

    Stayed Aug 9, 2025

    This stay looks good on paper but the hosts have work to do in terms of communication and guest experience.We booked this stay in large part for the pool however the evening we checked in the pool was completely cloudy. I had to ask multiple times for pool to be treated so it would be safe for us to use with my daughter. I felt like my concerns were not taken seriously by the owners in how they communicated. One of the owners also showed up at the property during our stay without notice cleaning the yard because previous guest left lots of trash from a party. I have never had this happen at a Vrbo rental and it made us kind of uncomfortable. Considering this is a newer listing I think the owners need to work on communication with guest in preparation for their stay. There were very limited instructions given and when problems arose I did not feel like I was treated with much respect or taken seriously. In general the house was nice and comfortable and kitchen had good amenities. If it had not been for the pool situation I would have given higher rating.

  • Alysia J.

    Submitted Jul 15, 2025

    Stayed Jun 28, 2025

    I did not enjoy my stay here. I initially booked for a graduation party. I arrived the day of the party and it was contractors working on the property due to a sewage pipe being replaced which was an eye sore when pulling up to the property. I observed the contractors placing their trash in the trash bins which prompted me to have to take my trash bags to a local dump after the party. The entire front of the property was dug up with mud and dirt was everywhere. The water in the home did not drain properly . I was charged after my stay additional fees as well. I would not book again.

  • Jasmin J.

    Submitted May 21, 2025

    Stayed May 15, 2025

    This property was amazing. I had 10 of my family members stay with me for my graduation and everyone was able to have their own bed and or space. No room felt too congested even when we all gathered in the living room. Everytime I called the host answered and got back to me in a timely fashion. After my graduation the host even allowed more of my out state family members to come over and enjoy dinner with no problems. This house is 100% a house you want to stay at!! The host provided the rooms with tv netflix and all access through the host.

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Total

Includes taxes and fees
$1,045+
View details