
House holiday rentals in Cumberland
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Top-rated house rentals in Cumberland
Guests agree: These houses are highly rated for location, cleanliness and more.

Cabin in the Woods - Weekday Specials!
Welcome to our log cabin! This three bedroom, two bath, all-wood home is set on five wooded acres less than a mile from the main highway. There is easy access to historic Frederick and Gettysburg. Surrounded by beautiful National and State Parks and only 20 minutes from Ski Liberty. Enjoy a relaxing time surrounded by trees or take a walk along the neighborhood orchards. Sit on the covered porch, relax by the fire-pit and eat on the back patio – or if it’s cold outside, enjoy the wood stove!
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*Pre-Civil War & Downtown~The Garlach House~c.1830
At this pre-Civil War home, you will find yourself within walking distance of restaurants, ice cream parlors, shops, museums & battlefields. Feel comfort in our home as you will be able to step back in time, but with modern day amenities. Enjoy our private fenced in backyard with a cup of coffee in the morning & a glass of wine in the evening as it is dimly lit, you can still see the stars! Take a short drive to local wineries, golf courses & Ski Liberty to enjoy skiing/snowboarding/tubing!
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4BR Historic Home-Walk to Square & Culp's Hill
Superior location in downtown Gettysburg historic district. Located on a quiet street two blocks from Lincoln Square, you can watch the sunset over the battlefield from the spacious backyard of this historic property. You will find comfort for your family with four bedrooms and two full bathrooms. We offer private off-street parking for up to three cars. (Special Winter Note: We are a easy and quick drive to Ski Liberty. Come stay with us and experience all that Ski Liberty has to offer!)
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Old Orchard House in Historic Gettysburg
Welcome to the Old Orchard House in Historic Gettysburg. This lovely Federal-style home was built in 1866 and maintains the charm of that era while offering modern conveniences to guests. With 3 bedrooms, a fully-equipped kitchen, and a backyard garden, this location is the perfect place to vacation with family or friends. Walk to the civil war battlefields, Gettysburg College, museums, shops, and restaurants. Take a short drive through the countryside to visit local wineries or Ski Liberty.
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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.
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Beautiful 3-bedroom home near downtown Gettysburg
Relax with the whole family and enjoy all Gettysburg has to offer in this quaint three-bedroom house. Located about 1.7 miles from the center of Gettysburg, this home boasts three bedrooms and two full baths. Full kitchen, dining room, and living room available as well as a spacious deck for sitting and garage area for enjoying time as well. You can enjoy all Gettysburg has to offer with this perfectly located home. Older house with some modern charm that will suit all your needs.
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Liberty Valley View - near ski slopes and golf
Relax in this completely renovated 3 bedroom home. Enjoy the peaceful quiet country scenery. Sleeps 6 people. Perfect for families or 3 couples. Enjoy the spectacular mountain and valley views from within the home and covered deck. Less than 2 miles from Liberty Mountain Resort with views of the back ski slopes. Multiple golf courses within a 15 minute drive. Approximately 8 miles from the Gettysburg National Park. Roku TV's in all bedrooms and family room ready for your apps.
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Historic Downtown Home. Haunted, Maybe?
Consistently rated among the top Airbnb stays in Gettysburg with 190+ five-star reviews. Stay in the heart of historic downtown, walking distance to Lincoln Square, restaurants, shops, Gettysburg College, and museums. After a day exploring the battlefield, relax in this beautifully updated home that sleeps 8, featuring a first-floor king suite, spacious gathering areas, fast Wi-Fi, streaming TV capability, a private fenced backyard, and free off-street parking for two vehicles.
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Simple Farmhouse~Goats~Near Mountains & Golf
A refuge from the everyday. Winter skiing at Liberty, visiting the Gettysburg Battlefield, hiking the state parks, golfing at Gettysburg National, or just sharing with family; Cornerstone Simplicity is a 5 bedroom, 4 1/2 bath, spacious, stone farmhouse available as a vacation home rental. With an office, large lawn, swing set, and a propane grill; there is plenty of space to enjoy life in historic Adams County. Enjoy a long weekend or longer in this home away from home.
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"The Historic Rowe House" Circa 1819
This charming, battle-scarred home sits in the heart of Gettysburg’s historic downtown, just a short walk from unique shops and the main square. Nearby, you’ll find popular spots like the Dobbin House, Garryowen, and Blue & Gray Grille, along with attractions such as the newly restored Lincoln Train Station, battlefield tours, museums, and more. Don’t miss the chance to stay in a witness house that stood right in the middle of the Confederate battle line.
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Relax near Gettysburg ski/wineries/fire pit!
Slow down and settle into this peaceful countryside retreat! A newly renovated spacious home that offers comfort and calmness. Whether you're gathering with loved ones or simply seeking a quiet place to rest, this space is designed to help unwind. We have everything that you need! Tucked near Liberty Mountain Resort and surrounded by wineries, breweries, and scenic trails. It's a gentle escape just 11 miles from the historic charm of downtown Gettysburg.
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The Enchanting Lavender House
The Lavender House is an enchanting pre-Civil War farmhouse nestled in the middle of a working 600 acre farm. It was remodeled with love 18 years ago and became a cozy family home, where children grew and memories were created. Full of charm, The Lavender House boasts hand chosen antiques, beautiful wood beams, original hard wood flooring and a wood burning fireplace to warm your winter nights. We hope you enjoy your stay at The Lavender House!
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Popular amenities for Cumberland house rentals
House rentals with a pool

Stoney Spring Overlook
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Pool | Hot Tub | Pickleball|Game Room | Gettysburg
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POOL & Lrg Private Yard, Gazebo, Outdoor Kit/Bath!
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Historic Peace and Plenty Farm: Pool House
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Romantic Getaway-Heated Spa - Seasonal Pool!
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An Escape Bordering National Park land 1 mi to C&O
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The Historic Booth House at the Harpers Ferry KOA
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Gettysburg Farm Stay w/ Pool & Barnyard Animals
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Weekly house rentals

A "Suite" Place to Crash
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Brent Road Retreat
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*Fully Fenced* Minutes to Gettysburg & Liberty Mtn
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Spacious Home on Historic Land w/ Grill & Fire Pit
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Gettysburg 2 Easy Times
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The CORNER BRICK
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Colonial Era Spring House
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Historic Stone home in Downtown!
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Private house rentals

Homestead, a serene organic farm minutes off I81.
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Rustic-Modern Farmhouse Near PA's Top Attractions
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Walk to Gettysburg Battlefield Charming Brick Stay
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The Sunset House in Gettysburg
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Culp House Getaway - A Historic Gettysburg Stay
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Reynold's Retreat
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IDEAL location Families & groups! ADA approved
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Historic ADA Home | 2 Blocks to Square + Parking
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Destinations to explore
- New York Holiday rentals
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- Washington Holiday rentals
- Ocean City Holiday rentals
- Pittsburgh Holiday rentals
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- Virginia Beach Holiday rentals
- Niagara Falls Holiday rentals
- Raleigh Holiday rentals
- Jersey City Holiday rentals
- Mississauga Holiday rentals
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- Hersheypark
- M&T Bank Stadium
- Liberty Mountain Resort
- Johns Hopkins University
- Oriole Park at Camden Yards
- Federal Hill Park
- Hershey's Chocolate World
- CFG Bank Arena
- Baltimore Convention Center
- Spooky Nook Sports
- Harpers Ferry National Historical Park
- Roundtop Mountain Resort
- National Aquarium
- Cowans Gap State Park
- Cunningham Falls State Park
- South Mountain State Park
- Harbor East
- Caledonia State Park
- Baltimore Museum of Art
- Pennsylvania Farm Show Complex & Expo Center
- Greenbrier State Park
- Hersheypark Stadium
- Giant Center
- Broad Street Market





