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
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.

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 Baltimore
4.93 out of 5 average rating, 176 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
An open living space features high ceilings with exposed beams and a neutral color palette. A comfortable sectional sofa, two accent chairs, and a coffee table are arranged over a decorative area rug. Natural light filters through the large windows, highlighting a media console and decorative baskets.
Home in Timonium
4.95 out of 5 average rating, 294 reviews

* Gorgeous House w/ Luxury, Charm, & Comfort *

Imagine having your entire family or friends together all under the same roof enjoying a beautifully decorated, renovated house with loads of amenities. Well, imagine no more!!!! This home has it all – 4 beds (3 king / 1 queen) with plush mattresses & high end bedding & 2 baths, 3 smart TVs, washer/dryer closet, open living space w/ 20 ft ceilings leading to farmhouse style kitchen full of functionality & style, and awesome deck w/ sectional couch, mounted TV, montrous picnic table, & 2 heaters.

Top 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 Baltimore
4.89 out of 5 average rating, 255 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.

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.
Apartment in Baltimore
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

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 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, 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.

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, 164 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, 300 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.

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, 119 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 recently, 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.

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.
Guesthouse 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 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 10 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 30 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 260 vacation rentals in Cheswolde, over 260 vacation rentals in Glen, and over 260 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 apartment rentals in Pikesville have wifi?

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

  • Do apartment rentals in Pikesville have free parking?

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

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

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with free parking, over 10 homes with wifi, over 10 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 $41 CAD per night before taxes and fees

  • Verified guest reviews

    Over 2,460 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 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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