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Vacation rentals in Fairfield

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Top-rated vacation rentals in Fairfield

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A charming cabin is nestled among lush greenery, featuring a large covered porch that extends along the front. The surrounding area includes well-maintained grass and several trees, creating a serene outdoor environment that invites relaxation.

Cabin in Myersville

4.96 out of 5 average rating, 315 reviews

Cabin on Middle Creek - Myersville MD - Middletown

Park the car & walk across the creek on the foot bridge to serenity along Middle Creek. Nestled between South Mountain State Park & Gambrill State Park, lies a beautiful & relaxed 9-acre private cabin retreat. Great place to unwind & de-stress. Let the sound of the creek or rain on the tin porch roof put you to sleep at night. It has all the essentials of home. Enjoy the fire pit on cool evenings or take a dip in the stream on a warm day. The cabin offers a perfect peaceful or romantic setting

A charming cottage exterior features a gray metal roof and a welcoming entry with blue trim. A covered porch invites relaxation, while two wooden chairs and a small table provide a cozy outdoor seating area. Lush green grass surrounds the property.

Cottage in Orrtanna

4.9 out of 5 average rating, 129 reviews

Sweet Gettysburg Area Cottage Close to Outdoor Fun

Off the beaten path but close to it all, including historic Gettysburg, the Appalachian Trail, Caledonia State Park, and Michaux State Forest. Relax on a large screened-in porch, in the shade of our pines or on the banks of a mountain creek. Access your own streaming accounts through our TV/wifi. Great restaurants are nearby, or make use of our original 1950s efficiency kitchen and dine al fresco. You’re surrounded by wineries, farm markets and even a candy store. Central location to do it all!

Top guest favorite

A sleeping area is presented with a spacious bed, dressed in a light quilt. A dark armchair is positioned nearby. Natural light enters through a window, complemented by green walls and a decorative wall art piece depicting a forest scene.

Guest suite in Orrtanna

4.97 out of 5 average rating, 173 reviews

Cold Spring Hill

Cold Spring Hill is a studio apartment located in the back of our detached garage. This is a rural setting just minutes away from Michaux State Forest. We are approximately 10 miles from the center of Gettysburg and 8 miles from Liberty Mountain Resort. Whether you are visiting the battlefield, Ski Liberty or hiking the trails, this space offers a relaxing feel after a busy day. Sit back and enjoy the views of wildlife out the windows that over look an apple orchard. We do not allow pets.

A decorative wreath is displayed on a door, featuring an assortment of flowers and foliage in warm hues. The background consists of a textured glass door, allowing soft light to filter through, and the words 'WELCOME to The LOFT' are prominently featured.

Guest suite in Fairfield

4.88 out of 5 average rating, 216 reviews

Gettysburg-Ski-Golf-AT Hikes-RoseSniffers LOFT

Calling all RoseSniffers!! Stop and Smell the Roses in this stylish boutique studio with private entrance and free parking. Although you will wake up to a bird's eye view of mountains and farms, you will be close to four-season adventures: Skiing, Antiquing, Vineyards, History, Gettysburg Military Park, 5-Star Golfing, Performing Arts, and Dining are all minutes away! 4 mi to GBurg Battlefield 2 mi to Liberty Mtn 8 miles to 5+ AT access points Across street to GBurg National Golf Course

Top guest favorite

The charming A-frame structure is surrounded by lush greenery, blending seamlessly with the wooded environment. Large windows provide a view into the inviting interior, while a stone pathway leads to the entrance, accentuated by decorative elements and natural landscaping.

Place to stay in Shippensburg

5 out of 5 average rating, 396 reviews

The Frame ~ Charming Nature Escape ~ Hot Tub ~ BBQ

Escape to the charming 2BR 1Bath A-frame on a secluded wooded property just 10 mins away from Shippensburg, PA. Whether you're looking to savor nature‘s tranquility from the luxurious hot tub, share stories around the fire pit, or explore picturesque Cumberland Valley, this will be the ideal starting point for your adventures! *2 Comfortable BRs *Open Design Living *Full Kitchen *Smart TV *Backyard (Hot Tub, Sauna, Fire Pit, BBQ, Outdoor shower) *High-Speed Wi-Fi *Free Parking *EV charger

Top guest favorite

The exterior of a two-story house is surrounded by trees, with warm lights framing the balconies. Large glass windows provide visibility into the interior. A deck with a railing is seen above, and decorative elements are positioned outside the entrance.

Guest suite in Smithsburg

4.98 out of 5 average rating, 291 reviews

Creekside Retreat at the Jewel Vinsota

Relax in a quiet, curated, pet-friendly art exhibit. Live with paintings & sculptures that are for sale. This garden apartment is tucked into a hillside above a creek, along the Jewel Vinsota Sculpture Trail. Your host/gallery curators live upstairs. The “Artist’s Guesthouse” is next door. The private entrance is down a stone-stepped path. Perfect for 2 w/ the queen bed but room for 3 w/ the living room futon. Fully equipped kitchen. Private charcoal grill and fire pit next to the creek.

Top guest favorite

A spacious home is set on a green lawn, surrounded by tall trees. Mountain and valley views stretch in the background, capturing the serene countryside atmosphere. The home's exterior features a combination of siding and a metal roof, lending a rustic charm.

Home in Fairfield

4.99 out of 5 average rating, 129 reviews

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.

Top guest favorite

The exterior of the cabin is shown, featuring a raised deck with a black railing. Large windows allow light to enter the interior. Green plantings and landscaping are present at the base, complementing the natural surroundings.

Cabin in Biglerville

4.98 out of 5 average rating, 166 reviews

Charlie’s Place-Beautiful, quiet 2-bedroom cabin.

Our cabin is located on a private stoned road. Very quiet and remote location. Keep this in mind when booking. 25 minute drive to downtown Gettysburg, 40 minutes to Carlisle Fairgrounds. Near Michaux State Forest, Pine Grove Furnace State Park and Caledonia State Park; many hiking, ATV and snow mobile trails. For those that enjoy skiing we are 30 minutes to Liberty Mountain in Fairfield and 50 minutes to Roundtop Mountain in Lewisberry.

Top guest favorite

The exterior of a single-story cottage showcases a welcoming entrance with a wooden ramp leading to the front door. Lush green grass and light landscaping surround the home, which is framed by tall trees. A covered area is visible at the side of the structure.

Cottage in Fairfield

4.97 out of 5 average rating, 119 reviews

Mom's Cottage

Mom's Cottage sits on the shore of Lake Kay in the shadow of Liberty Mountain. Gettysburg battlefield is ten miles away and two golf courses are nearby. Jacks Mountain Road covered bridge, Michaux State Forest, including the Appalachian Trail, Pine Grove Furnace, and Caledonia SP are nearby. Other local features include Mount St. Mary's, Cunningham Falls SP, and Catoctin Mountain Park. A paddle boat and two kayaks are available.

Top guest favorite

The exterior of a colonial era spring house showcases a natural stone base supporting a wooden structure. A spacious balcony with wooden railings extends from the second floor. Brightly colored hanging flower pots add a touch of greenery to the inviting façade.

Home in Blue Ridge Summit

4.99 out of 5 average rating, 584 reviews

Colonial Era Spring House

A unique and private mountain top colonial era spring house, with two springs flowing thru the basement. Originally the site of a tannery in the 1700s. Here you can relax, recharge, and rejuvenate. We celebrate all four seasons where you can enjoy Mother Nature's ever changing scenery at 1300' above sea level with fresh mountain air. Our area offers many things to do, or you may choose to stay in and do nothing at all.

Top guest favorite

A charming guesthouse is set within a lush garden, featuring colorful flowers, greenery, and a variety of plants. A large evergreen tree provides shade in front of the house, which includes a covered porch and picnic table, inviting relaxation among the natural surroundings.

Guesthouse in Gettysburg

4.99 out of 5 average rating, 446 reviews

The Cock and Feather Guesthouse

PLEASE READ ALL OF THE HOUSE RULES BEFORE BOOKING YOUR RESERVATION. OUR CALENDAR IS CURRENTLY OPEN THROUGH DECEMBER 13. WE WILL BE CLOSED FOR THE WINTER SEASON FROM DECEMBER 14 UNTIL MARCH 31. PLEASE CHECK BACK IN MID-FEBRUARY FOR AVAILABILITY BEGINNING APRIL 1, 2026.

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Popular amenities for Fairfield vacation rentals

Laptop-friendly workspace

Air conditioning

Ski-in/ski-out vacation rentals in Fairfield

Top guest favorite

An outdoor pool area is presented, featuring a clear, inviting swimming pool surrounded by lounge chairs. Two cabanas are visible, providing shaded seating areas. The poolside is bordered by a smooth concrete surface, complemented by greenery in the background.

Condo in Mercersburg

5 out of 5 average rating, 22 reviews

SlopeSide

The exterior of the vacation home is shown, featuring a combination of brick and siding. Lush greenery surrounds the property, with a well-maintained lawn and shaded areas created by mature trees. The design includes multiple large windows, enhancing natural light.

Home in Mercersburg

5 out of 5 average rating, 6 reviews

Ski-in ski-out Renovated Townhouse-Pool/Hottub.

A covered outdoor patio is presented, featuring a small round table surrounded by two chairs. Decorative string lights are hung above, and a view of snow-capped hills is visible in the background, providing a scenic backdrop for outdoor relaxation.

Condo in Mercersburg

4.82 out of 5 average rating, 67 reviews

Ski🎿 & hike from front steps—Mountainside getaway

Top guest favorite

The illuminated sign of Whitetail Resort is showcased against a winter backdrop, surrounded by snow-covered ground and barren trees. Stone pillars frame the sign, creating a welcoming entrance to the resort.

Condo in Mercersburg

4.92 out of 5 average rating, 48 reviews

Whitetail Resort Ski-in/Ski-out slope side condo.

A spacious living area features a light blue and teal striped accent wall. A contemporary grey sectional sofa is adorned with decorative pillows, and a cozy throw is casually draped over the arm. White doors lead to additional rooms, enhancing the open feel.

Home in Mercersburg

4.82 out of 5 average rating, 79 reviews

SKI YA LATER Whitetail

A living area is illuminated by a centrally placed chandelier, providing a warm glow. Two patterned armchairs and a cozy sofa adorned with colorful cushions are positioned around a decorative area rug. Tall windows allow natural light to fill the space, offering views of the outside.

Home in Mercersburg

4.67 out of 5 average rating, 3 reviews

Whitetail Ski Resort Ski In-Out, Mercersburg, PA

The exterior of a brick building is displayed, featuring multiple large windows and a covered entrance with steps. Landscaping includes neatly trimmed bushes and trees in the background, blending with a cloudy sky.

Condo in Mercersburg

4.84 out of 5 average rating, 49 reviews

Rockwell Suite #206 at the Inns of Whitetail

A scenic view of the chalet surrounded by vibrant autumn foliage. A large red tree stands in the foreground, with the sun shining through its leaves. The wooden exterior of the home is visible, complementing the green trees and clear blue sky.

Chalet in Mercersburg

4.93 out of 5 average rating, 117 reviews

Amazing Summer Holiday and Mountain Retreat

Other great vacation rentals in Fairfield

Top guest favorite

A large two-story home is bordered by a white picket fence and features a blue metal roof. A front porch with railings is visible, along with well-maintained landscaping and trees in the background. Clear blue skies complement the peaceful rural setting.

Apartment in Blue Ridge Summit

5 out of 5 average rating, 30 reviews

Mountain Top Suite Central location from MD/PA/WVA

Top guest favorite

A stone pathway is framed by lush greenery and shrubs, leading through a serene garden area. The surrounding trees provide shade, and a glimpse of colorful outdoor decor can be seen in the distance, inviting exploration in the tranquil outdoor setting.

Apartment in Fairfield

4.95 out of 5 average rating, 56 reviews

Still Waters on Lake Kay

A modern kitchen showcases sleek stainless steel appliances, including a refrigerator and a gas cooktop surface integrated into a large white island. White cabinetry and tiled backsplash provide a clean aesthetic, while two brown bar stools offer seating at the island.

Home in Fairfield

5 out of 5 average rating, 15 reviews

Cozy Mountain Retreat - Remodeled Near Ski Resort

Top guest favorite

A clear view of the backyard reveals a gathering area with several metal-framed chairs arranged around a round, metal table. The home’s exterior features a raised deck with a white railing, surrounded by lush greenery and trees, creating a serene outdoor space.

Home in Fairfield

5 out of 5 average rating, 39 reviews

*Hot Tub* @ Retreat by Gettysburg & Liberty Mtn

Top guest favorite

The exterior of the guest house presents a single-story structure with a light brown facade and maroon shutters framing multiple windows. A covered porch is visible, leading to the front door, while neatly trimmed shrubs enhance the landscape along the gravel pathway.

Home in Fairfield

5 out of 5 average rating, 31 reviews

Guest House - Twisted Creek Farm

Top guest favorite

The image shows a gravel pathway leading towards a two-story loft and an adjacent building with a rustic appearance. A pink flowering tree is present on the left, contrasting with the green lawn. The porch features a wooden railing, indicating outdoor seating.

Farm stay in Fairfield

4.94 out of 5 average rating, 84 reviews

Milkhouse Loft peaceful farm stay by Ski Liberty.

Top guest favorite

A spacious green lawn is framed by tall trees, providing shade. A distinctive log cabin is visible to the left, featuring a welcoming porch. The tranquil marsh creek flows gently beside the property, enhancing the serene outdoor setting.

Cabin in Gettysburg

5 out of 5 average rating, 40 reviews

Cabin On The Creek

Top guest favorite

A welcoming living room features a comfortable sofa and two accent chairs arranged around a coffee table. Large glass doors allow natural light to flood the space, offering access to a deck with views of the surrounding landscape. A ceiling fan adds to the airy feel.

Home in Fairfield

4.96 out of 5 average rating, 77 reviews

Tree Top Tranquility.

Destinations to explore