Vacation rentals with a pool in Carroll County

NEW Family/Pet Friendly, fenced in yard with Pool!

Welcome to Amber Oasis, a serene luxury retreat in a quiet Reisterstown neighborhood- just minutes from Owings Mills and only 25 minutes from Baltimore’s Inner Harbor. Designed for comfort, connection, and unforgettable stays, this spacious home is perfect for families, groups, and extended visits. Designed with families and longer stays in mind, this spacious property offers privacy, comfort, and thoughtful amenities- including a private fenced yard with pool, generous indoor living space, etc.

Secluded Country Farm Estate

Take it easy at this unique and tranquil getaway. Sunrise to sunset, enjoy the 360-degree view of the peaceful natural wooded and pastoral setting with its own entrance. A large country kitchen, oak cabinets, a wood-burning fireplace, and ample room to relax. The upper level has a full bath, and 2 queen bedrooms, one with a walk-in closet and TV. For added relaxation, enjoy the light-filled sitting area/tower to read, watch TV, or pull out the trundle bed for additional sleeping accommodation.

Keymar Guest House

Escape to the country and enjoy the relaxation of scenic laid-back living. Our guest house is a private retreat attached to the main house on our 15 acre farmette. While the main house is over 100 years old, the guest house was added as an in-law suite in 2005. Enjoy the fresh indoor area, as well as the scenic outdoors with views of mountains, farms and open spaces. Centrally located to Frederick, Gettysburg and Westminster (30 minute drive) and Baltimore and Washington (60 minute drive).

Owings Mills Townhouse: 8 Mi to Liberty Reservoir!

Find your bliss at this suburban 3-bedroom, 2.5-bathroom, Owings Mills vacation rental, and enjoy a splendid home away from home. This peaceful townhome boasts a sun deck, a fenced backyard, designated workspaces, and access to a community pool. Its central location is just outside of Baltimore and a scenic drive to Soldiers Delight Overlook and Gunpowder Falls State Park. After a day of exploring, nestle in with your favorite movie on one of the 2 Smart TVs. Maryland is calling for you!

Chapelgate Refuge

Experience the architectural charm and modern luxury of "Chapelgate Refuge," a unique 4-bedroom home meticulously converted from a historic chapel and set on a peaceful, rural family farm in Randallstown. This sanctuary offers one-of-a-kind spaces and a massive, private backyard perfect for unwinding. Guests also enjoy access to a community swimming pool and tennis courts. Ideal for families, groups, or a peaceful corporate getaway, this property provides a truly unique escape.

Historic Peace and Plenty Farm: Pool House

Peace and Plenty Farm is a 40+ acre, stunning rural escape located in Frederick County, two miles from Historic New Market, 45 minutes from Gettysburg, and an hour from Baltimore or Washington D.C. Feel free to explore our farm’s trails and hidden gems, play yard games with the family, or swim in our lap pool (open from June through October). Our generous space is suitable for a couple's getaway, a weekend with friends, a family vacation, a working vacation, or a quiet retreat.

Cozy Suite/2 Large Bedroom 1 Full Bath/4ppl/pets

Welcome to your private getaway in Finksburg, MD just minutes from Baltimore! This serene 2-bedroom, 1 full bath suite features a private pool, firepit, and river access for peaceful mornings and scenic walks. Enjoy a fully stocked kitchen, comfortable living areas, and a dedicated workspace—perfect for remote work. Home is Pet-friendly! Whether you're looking to relax, explore nature, or work in a quiet setting, this home offers the perfect balance of comfort and tranquility.

Rustic Cabin, Modern Comforts, Resort Amenities

Fidler's Grove Cabin at Pearlstone is roomy and rustic with all the essentials for a comfortable stay for up to 8 guests. Guests have access to the Pearlstone Campus amenities including campfire pit, outdoor pools (seasonal), hiking trails, sports fields & courts. With sufficient advanced notice (subject to staff availability, additional fees apply), you can opt for additional activities such as High Ropes Adventure Course and other team building games, Zip Line, and more.

Rest and Recharge Retreat

We have a new larger tent for 2026! Queen size bed. We have also added a sauna to our retreat. Rest and recharge at this beautifully landscaped glamping retreat. Enjoy quiet moments of zen in the meditation garden, awake to the birds and butterflies, float the afternoon away in the pool or enjoy stargazing in the hot tub at night. We are set up for a quiet retreat for 2 people. Additional guests must be approved in advance. No parties!

Farm Stay + Pool | Animal Tour Included

Cozy, family-friendly farm stay with animals, a pool, and space to truly relax. Split-bedroom layout gives parents/ couples and kids their own privacy while still enjoying time together. Kids love watching the goats and chickens, and families enjoy a peaceful stay just minutes from local wineries and activities. This is a private lower-level suite with its own entrance, designed to feel open, cozy, and separate from the main home.

Cozy & inviting 2BD 2BTH Apt Home

“Relax, recharge, and live in style—your perfect 2BR Owings Mills escape awaits. Enjoy a modern, spacious 2BR/2BA with a private balcony, free parking, Smart TVs, and fast WiFi. Perfect for families, couples, and business travelers. Includes a fully equipped kitchen and 24-hour fitness center. Conveniently located near shopping, dining, and easy access to Baltimore.”

Backyard Oasis Swim Spa & Fire Pit Near Gettysburg

Private backyard oasis with swim spa, fire pit, and outdoor seating just minutes from downtown Westminster. Perfect for families, couples, and groups visiting Gettysburg, Baltimore, and DC. Enjoy a fully equipped home, fast WiFi, and a relaxing stay close to top attractions, dining, and shopping.