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 favorite
The historic brick building features a classic architectural style, with several evenly spaced windows and two prominent blue doors at the entrance. A pathway leads to the doorway, with a flag displayed on the left side. Lush greenery surrounds the property, creating a serene outdoor setting.
Apartment in Monkton
4.95 out of 5 average rating, 184 reviews

The Fisherman's Lodge at the 1858 Monkton Hotel

Love the outdoors? Love to fish, hike, bike, kayak? All of the above? The Monkton Hotel is a registered landmark that sits on the NCR trail, which runs along the Gunpowder River, home for some of the best trout fly fishing in the country. This fully renovated apartment, themed the "Fisherman's Lodge", is on the second floor and has the latest amenities. Nothing in the area matches the charm, convenience and history. An electric bike store, tube rental and great cafe are all in the same building.

Top guest favorite
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, 456 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 favorite
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 favorite
Apartment in Baltimore
4.98 out of 5 average rating, 521 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 favorite
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, 133 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 favorite
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, 167 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 favorite
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, 303 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 favorite
Guesthouse in Owings Mills
4.94 out of 5 average rating, 17 reviews

Private Suite w/ Kitchen, Bath, Separate Entrance

Escape to a peaceful private suite designed for comfort and relaxation. Enjoy your own entrance, a full kitchen stocked with essentials, and a private bathroom for complete convenience. The cozy queen-size bed and smart TV make it easy to unwind after a long day. Whether you're visiting for work or leisure, you’ll have everything you need in this quiet, self-contained space, modern amenities, privacy, and a calm atmosphere that feels like your own home away from home.

Guest favorite
A bright and inviting living room features a light gray sofa adorned with various decorative cushions in warm tones. A round glass coffee table with a gold base sits at the center, complemented by a floral arrangement. Soft carpet underfoot and a lamp provide additional warmth.
Home in Randallstown
4.88 out of 5 average rating, 17 reviews

Charming Randallstown townhome

Stay in this stylish 3 bedroom, 2.5 bathroom townhouse in Baltimore County, Randallstown. Beautiful living room and dining room. You can enjoy a meal in this fully equipped chef’s kitchen. Soak up some sun on the huge deck. Relax in one of the comfortable bedrooms with televisions in all rooms. 5 minutes from the beltway - 695, you can be downtown Baltimore in 20 minutes. Lots of dining, shopping and markets close by.

Top guest favorite
Guesthouse in Owings Mills
4.96 out of 5 average rating, 140 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.

Top guest favorite
A spacious master suite features a king-size bed with a decorative canopy, flanked by nightstands. Two armchairs provide seating, and a woven area rug adds warmth. A mural depicting nature adorns the wall, while large windows allow natural light. An accessible doorway leads to the bathroom.
Farm stay in Cockeysville
4.95 out of 5 average rating, 129 reviews

Master's Suite · 1920s Tudor Estate, Hunt Valley

A king-size suite in the gatehouse of a 1920s English Tudor estate, deep in Maryland’s horse country — peaceful and private, but an easy drive from the city. • King bed, vaulted ceilings, hand-painted mural • Carrara marble bath with a clawfoot soaking tub • Private sun porch over open farmland • Pool, tennis & miles of farmland to wander • Hunt Valley 10 min · Towson 15 · Baltimore 25 · Ellicott City/Columbia ~35

Superhost
A two-story home built into the hillside is framed by lush greenery. A wooden porch, supported by stone pillars, features a railing and an American flag. The exterior showcases a mix of siding and stone, with large front windows allowing natural light into the interior.
Home in Ellicott City
4.82 out of 5 average rating, 144 reviews

Mello-Ray River House

PETS STAY FREE!! At our Historic 3BR, 2BA colonial on Frederick Rd—once the main route from Baltimore to Ellicott City. Built on a foundation dating to the late 1700s, the current structure has stood since 1875. Overlooks the Patapsco River and the B&O Railroad, the first in the nation. Features hardwood floors, modern kitchen, central air, and fenced patio. Walk to shops, parks, and the historic district.

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 house rentals in Pikesville have a kitchen?

    Absolutely! We offer over 20 house 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 Apartment Rentals in Pikesville?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with free parking, 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 €26 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 & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Pikesville vacation rentals include wi-fi 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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