Vacation rentals in Pikesville

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Top-rated vacation rentals in Pikesville

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

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Top guest favourite
Guest suite in Woodstock
4.98 out of 5 average rating, 207 reviews

Our Retreat -in a peaceful setting.

Private- apartment in the lower level of our house. House in a rural setting- you may spot white tail deer or other wildlife.Enjoy the peaceful tranquil setting.We are within 5 minutes by car to Rte 70 and shopping centers. 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. Non smoking. We aren't set up for heavy cooking. No stove.

Guest favourite
A well-lit hallway is lined with wooden doors leading to private spaces. The floor features dark tiles, while light walls enhance the brightness. At the far end, a glimpse of a serene bedroom is visible, highlighted by soft bedding and a wooden accent wall.
Guest suite in Mt. Washington
4.93 out of 5 average rating, 174 reviews

Our House Suite

Our House Suite is in our home, yet separate from us. *It is safe. *Private entrance, living room, dining area, bathroom & bedroom *Located in the peaceful residential neighborhood of Mt Washington *Equipped with refrig, freezer, micro & coffee maker *Sinai Hospital 3 min drive *Pimlico Race Course 10 minute walk(.7 mile) *Convention Center, Harborplace, Aquarium, The Gallery, Harbor East, M&T Bank Stadium, Oriole Park and hundreds of magnificent restaurants & shops downtown,15 min drive

Top guest favourite
The open-concept living space features a combination of comfortable furniture, including two green chairs and a gray sofa. A wooden coffee table occupies the center of the room, surrounded by an area rug. A fireplace and bookshelves add warmth and character to the setting.
Apartment in Sykesville
4.95 out of 5 average rating, 224 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.

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.
Guesthouse in Woodberry
4.89 out of 5 average rating, 247 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.

Guest favourite
A spacious living area is furnished with a plush grey couch and armchairs, centered around a round coffee table. Natural light fills the room, showcasing the open layout that connects to a modern kitchen in the background. A ceiling fan is visible above for comfort.
Bungalow in Timonium
4.85 out of 5 average rating, 396 reviews

* Stunning Bungalow Perfect for Everyone *

You'll love your stay at this charming and cozy 1 level bungalow!! It offers a brand new high quality renovation convenient to all the Baltimore hot spots. The open layout coupled with stylish finishes and decor will make you feel right at home. It's fully stocked with almost every possible thing you could imagine for your use! Really no need to bring anything but yourself and clothes. The 3 bedrooms with a movable foldaway queen sofabed can sleep 8 comfortably. Plenty of parking available.

Top guest favourite
A classic two-story house features a welcoming front porch with plants and seating. Soft lights illuminate the windows, and a blue door adds a charming detail. Lush greenery frames the home, enhancing its inviting presence in the evening light.
Home in Owings Mills
4.93 out of 5 average rating, 105 reviews

Garden Cottage: Dogs welcome | primary on main

Spring at Grandma’s House: a nostalgic storybook home in Owings Mills. Enjoy blooming dogwoods, a fenced yard for pups, and nightly deer sightings on our 1/2 acre. Ideal for sports families (near Ravens), medical travel (Primary on Main for easy access), and graduation season. Features a private upstairs bonus wing, fully stocked kitchen, fast Wi-Fi, and heritage charm 30 mins from Baltimore. Wegmans nearby. Restorative, cozy, dog-friendly. Full AC, laundry & parking. Permit: RHR-2026-00248

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.
Apartment in Baltimore
4.99 out of 5 average rating, 118 reviews

Private Serene Suite with Jacuzzi- Non Smoking

Escape to this serene in-law 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.

Guest favourite
An open-concept living area features a cozy seating arrangement with a light-colored sofa and patterned accent chairs. A sleek coffee table sits atop a patterned rug. The kitchen is visible in the background, showcasing rich wooden cabinetry and modern appliances.
Apartment in Timonium
4.91 out of 5 average rating, 110 reviews

Home Sweet Home Apartment in a beautiful home

Come to your home away from home! Beautiful and comfy apartment unit in a luxury home in the heart of the Historic Lutherville neighborhood. Walking distance to restaurants, shops, coffee shops, Mom's Organic Market and most importantly you can walk to light rails and bus stops that takes you to the airport, Baltimore city harbor, Camden yards, university of Maryland and downtown Baltimore City. Close to GBMC, St. Joseph's hospital, Towson University, Hunt Valley and Towson Mall.

Guest favourite
A modern living area is highlighted by a curved black sofa and a white armchair, complemented by a round glass coffee table atop a textured area rug. Natural light filters through large windows, illuminating the space, while decorative plants add a touch of greenery.
Home in Baltimore
4.93 out of 5 average rating, 160 reviews

Stunning 7BR Lux House in Baltimore

We've taken our 18 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!

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.
Guesthouse in Towson
4.99 out of 5 average rating, 290 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
The exterior of a mid-century modern home showcases a stone facade with multiple balconies and large windows. Surrounding greenery includes a well-maintained lawn and trees. A stone wall and grassy area enhance the inviting atmosphere of the property.
Guest suite in Baltimore
4.97 out of 5 average rating, 122 reviews

Gorgeous Mid-Century Gem near Lake Roland

We are located in a breathtaking park-like setting in stunning Lake Manor, near North Roland Park, and one block from Lake Roland Park. The space is a two bedroom, 2 bath apartment on ground floor with a large great room/living space, separate kitchen and private entrance, in a large beautifully preserved mid-century modern home. The owners live upstairs, but the spaces are distinct, private and separated by a heavy curtain. Very little noise bleeds through.

Guest favourite
A historic two-story house is presented, featuring a charming wooden porch and large windows. A unique metal sculpture resembling a rooster stands in the foreground, complemented by lush greenery and stone landscaping. The house's brick facade reflects its 200-year history.
Home in Monkton
4.93 out of 5 average rating, 114 reviews

Cozy up in the restored 1820s Miller's House!

The Miller's House is a quaint and beautiful, newly restored two-bedroom house that sits on a small river and is also a national historic landmark. The house has been painstakingly restored over the last 18 months, with modern amenities you'd expect such as all-new appliances and high speed WiFi. Proximity to the Gunpowder Falls for fishing or tubing, the NCR trail (less than .2 mile away) and endless roads to bike on make it a great escape.

Popular amenities for Pikesville vacation rentals

When is the best time to visit Pikesville?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Pikesville?

    Pikesville has more than 20 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 Pikesville?

    Experience the best of Pikesville 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 Pikesville?

    Four-legged friends are welcome in Pikesville. Choose from more than 20 vacation rentals for guests traveling with pets.

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

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

  • Where should I stay in Pikesville?

    Make yourself at home in Pikesville by choosing from our most frequently booked neighborhoods. We have over 250 vacation rentals in Cheswolde, over 250 vacation rentals in Glen, and over 250 vacation rentals in Mount Washington.

  • Do apartment rentals in Pikesville have air conditioning?

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

  • Do apartment rentals in Pikesville have a kitchen?

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

  • Do house rentals in Pikesville have wifi?

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

  • Do house rentals in Pikesville have free parking?

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

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

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

Quick stats about vacation rentals in Pikesville

  • Total vacation rentals

    Explore 60 vacation rentals in Pikesville

  • Nightly prices starting at

    Pikesville vacation rentals start at $42 CAD per night before taxes and fees

  • Verified guest reviews

    Over 2,340 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    60 of Pikesville vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Pikesville rentals

  • 4.8 Average rating

    Pikesville stays are highly rated by guests—averaging 4.8 out of 5!

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