Vacation rentals with a pool in Gettysburg

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Top-rated rentals with a pool in Gettysburg

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

A historic stone farmhouse from 1861 is set on a well-maintained lawn, surrounded by green shrubbery and trees. The two-story structure features red shutters on the windows and a welcoming front porch that invites relaxation.

Home in Gettysburg

Civil War Farm House w/Heated (seasonal) Pool

Welcome to this historical Civil War Farm House. This stone home built in 1861 by Christian Shriver and was actively used as a field hospital during the war. Mrs Shriver prepared General Reynolds his breakfast on the first day of the battle (which he was killed). The Durboraw's moved here in the early 1890's and have remained here on the farm ever since. Please note, pool is open seasonally mid-May through mid- Sept. Please inquire to its opening/closing if booking around these times.

5.0 out of 5 average rating, 320 reviews

Guest favorite

Home in Waynesboro

Beautiful 5 star Mansion, Pool, Home Theater

Nestled on 3 beautifully landscaped acres, this 7-bedroom, 5.5-bath mansion offers the utmost privacy and modern comfort, sleeping up to 32 guests. With over 5,000sf of space, +2500sf enjoy one or two full kitchens (depending on group size, additional charge applies) home theater with Bose surround sound, and a lush backyard with a swimming pool, gazebo, and scenic pond. Additional amenities include an indoor pool table, outdoor dining area with a propane gas grill, and dedicated workspace.

4.85 out of 5 average rating, 193 reviews

Guest favorite

A wooden deck extends from the cabin, surrounded by lush green trees. A striped awning provides shade over a picnic table, creating a space for outdoor dining or relaxation. The natural ambiance enhances the secluded feel of the property.

Cabin in Keedysville

Quiet Antietam Cabin

This quiet cabin is located between Boonsboro and Sharpsburg in Keedysville, MD. It is surrounded by tall oaks and pines. A wide path leads to Antietam Creek, popular for fishing, kayaking, and tubing. 45-min drive to Whitetail Ski Resort (30 miles); 1-hr to Gettysburg, PA; Close to Antietam Battlefield, Shepherdstown, Harpers Ferry, Hagerstown, Frederick, Washington, D.C., C&O canal bike trail and Appalachian Trail. Minimum age to rent is 25 yrs. Families with children are welcome.

4.82 out of 5 average rating, 129 reviews

Guest favorite

A heated pool is surrounded by a stone wall and lush greenery, offering a serene atmosphere. The lodge features large windows and a balcony overlooking the pool area, seamlessly connecting indoor and outdoor spaces.

Guest suite in Myersville

Harmony Lodge nestled in wooded tranquility!

Tranquil lodge nestled on 3 wooded acres in Myersville, MD. Relax by the heated pool, enjoy the warmth of the fire pit, or receive a massage in the studio. Minutes away from downtown Frederick and Middletown restaurants, shops, and parks. Visit the local wineries and festivals. Tour historic battlefields. Go antiquing. Take in a round of golf, bike the C&O canal, hike the Appalachian trail, boat on the Potomac River, or go skiing. Bring your fur baby with you to enjoy the activities!

4.92 out of 5 average rating, 345 reviews

Guest favorite

A spacious backyard features a large in-ground pool with two fountains, surrounded by a concrete deck. Lounge chairs are positioned around the pool, and vibrant flowers add color. A screened gazebo is visible in the background, providing shaded seating for relaxation.

Home in Mechanicsburg

POOL & Lrg Private Yard, Gazebo, Outdoor Kit/Bath!

Hershey, Gettysburg, and the Dutch Country are at your fingertips, yet you'll enter your own private retreat in this comfortable home on a large corner lot with mature trees in a peaceful neighborhood. Newly remodeled kitchen! Conveniently located to all the attractions of Central PA, with Hershey 30 minutes to the east, Gettysburg 30 minutes west, and the Amish Country 45 minutes South. Ski Roundtop is only 9 miles from the house! Easy access to PA Interstates and the PA Turnpike!

4.89 out of 5 average rating, 103 reviews

Top guest favorite

A covered porch is supported by rustic wooden beams, featuring two green adirondack chairs and a circular coffee table. A hanging fern adds a touch of greenery above. Stone flooring complements the natural surroundings, which include lush shrubs and plants just beyond the porch.

Home in Fairfield

Brent Road Retreat

Rustic post and beam home rich with character. Five bedrooms and 2 full bath 2200 s/f sleeps up to 13. Cozy wood stove for heat with propane backup; a/c. House enjoys large yard and mature woodland surroundings. Relax on covered porch or large shaded deck and enjoy the biodiversity of your secluded surroundings. Five minutes to Liberty Resorts skiing and golf; 15 minutes to Gettysburg. Property features artwork from various local renowned artists. Two night minimum on weekends.

4.93 out of 5 average rating, 273 reviews

Guest favorite

Home in New Market

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.

4.92 out of 5 average rating, 165 reviews

Top guest favorite

A saltwater pool is surrounded by tall, lush trees, offering a sense of privacy. The clear blue water reflects the sky, while a spacious deck provides ample room for relaxation. Greenery and landscaping are visible in the background, enhancing the tranquil outdoor setting.

Home in Gettysburg

Gettysburg Farm Stay w/ Pool & Barnyard Animals

Get comfortable and enjoy plenty of extra room at this spacious place. Our rental is sparkling clean and tastefully decorated to ensure you have a relaxing stay. The main floor has a kitchen equipped for your basic cooking and baking needs, a dining room with seating for six, a living room, and one full bathroom. Upstairs, you will find four bedrooms and one full bathroom. One bedroom has a king-sized bed, and the other three have queen-sized beds. Pool will close 10/8/26

4.96 out of 5 average rating, 84 reviews

Top guest favorite

A charming A-Frame cabin is surrounded by trees, featuring a stone exterior and a spacious deck. Soft lighting illuminates the entryway, while wildlife such as a deer and birds are present nearby. A wooden pathway leads from the cabin into the natural landscape.

Cabin in Goldsboro

Star Gazer Luxury A-Frame Wood Cabin. Near Harrisb

Escape to our charming A-Frame cabin nestled amidst 16 acres of breathtaking woodland, offering an unmatched retreat for nature enthusiasts. Immerse yourself in the awe-inspiring vistas, relish the cozy interiors, unwind in the indulgent hot tub, and gather around the inviting fire pit. Discover unparalleled comfort, tranquility, and natural beauty that will leave you rejuvenated. Don't miss out on this extraordinary experience; secure your reservation now!

5.0 out of 5 average rating, 108 reviews

Top guest favorite

A tranquil pool area is showcased at dusk, with soft purple lighting illuminating the water. Lounge chairs line the poolside, and trees surround the space, creating a calm and serene environment. The moon is visible in the clear sky, enhancing the peaceful ambiance.

Tent in Westminster

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!

4.97 out of 5 average rating, 115 reviews

Top guest favorite

A spacious mountain home is set against a backdrop of trees, with a gently sloping field leading to a small pond in the foreground. A wooden fence encircles the property, highlighting the serene outdoor environment that encompasses the house.

Home in Sabillasville

Stoney Spring Overlook

This beautiful mountain home offers breathtaking views of the surrounding Catoctin Mountains. The area is rich with outdoor adventures and attractions. Though it feels like a peaceful retreat tucked away in the mountains, it’s only 30 minutes from Frederick, MD, historic Gettysburg, PA, and about an hour from the Washington, D.C. area. Whether you’re seeking a quiet escape or hoping to explore more of the Frederick County.

4.95 out of 5 average rating, 156 reviews

Top guest favorite

Farm stay in Cockeysville

The Master's Suite · King Suite, 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

4.95 out of 5 average rating, 147 reviews