Holiday rentals in Round Top

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Top-rated holiday rentals in Round Top

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A charming cabin is set beside a serene pond, featuring a colorful fountain that lights up the water. Soft string lights illuminate the outdoor space, creating a cozy atmosphere amidst the surrounding trees.
Cabin in Wrightsville
4.98 out of 5 average rating, 239 reviews

The Roundtop Chalet (romantic couples retreat)

Indulge in a getaway to our charming cabin, the perfect retreat for all your special celebrations - be it anniversaries, birthdays, or simply a much-needed escape from routine. Perfectly designed for romantic getaways, this cabin seamlessly blends rustic charm with modern comforts. Savour the warmth of a cozy fireplace, unwinding in a hot tub,and indulge with unlimited lattes, crafted by our Breville Touch Espresso Machine. Embrace serenity at its finest and make memories that will last forever

Guest favourite
A comfortable living area is presented, featuring a light-colored sofa with a decorative pillow. Two dark armchairs flank a rustic wooden coffee table, and a vintage rug adds warmth to the wood flooring. A framed photo and a door provide additional detail.
Flat in Gettysburg
4.94 out of 5 average rating, 158 reviews

A Hub for History Buffs!

A very private, brand new apartment all for you! New furnishings make it comfortable, antique pieces make it quaint! Both will make your stay with us enjoyable and peaceful. A kid and adult friendly space. Enjoy the deck in the morning and the electric fireplace in the evening. A quiet home-base for your visit to historic Gettysburg! We are a HUB for HISTORY BUFFS and more! Entrance is no longer through the garage! PS: In the winter, we are 15 min from Ski Liberty and have garage storage!

Top guest favourite
A single-story cottage features a red metal roof and a welcoming porch with seating. Lush greenery surrounds the property, and an American flag is displayed near the entrance. A gravel driveway leads up to the house, adding to the tranquil rural setting.
Cottage in Gettysburg
4.98 out of 5 average rating, 142 reviews

Country Cottage Nestled on a 20 acre Horse Farm

Relax with the whole family at this peaceful cottage nestled on a horse farm. Enjoy roasting marshmallows in the outdoor firepit or sit back on the porch to watch the wildlife. We are located only minutes from the battlefields and town center. Enjoy local restaurants, breweries, specialty shops, & wineries. Liberty Mountain Ski Resort is only a 20 minute drive. Take advantage of nearby golfing, scenic views, historical sites, ghost tours, museums, or take a guided bus tour of the battlefields.

Top guest favourite
A cottage exterior is presented, featuring blue siding and white trim. Decorative window boxes hold greenery beneath two gabled windows. A welcoming front porch is adorned with American flags. Lush grass and shrubs surround the home, contributing to its inviting appearance.
Cottage in Gettysburg
5 out of 5 average rating, 409 reviews

Serene 3BR Cottage with Creekside View Gettysburg

Voted #1 rental 2021–2025, & in the top 1% of AirBnb’s, Blue Coat Cottage is nestled between 2 picturesque farms directly across from Marsh Creek in historic Gettysburg. It perfectly blends battlefield access with peaceful country living. This home away from home is ideal for families & friends. Enjoy a fully equipped home with thoughtfully designed spaces, hidden kids’ nook, scenic views, a hammock, chiminea, front porch overlooking the creek, and a private backyard for relaxing & unwinding.

Top guest favourite
The image captures a charming Federal-style brick home with a series of large windows framed by black shutters. A small set of stairs leads to the entrance, while decorative elements evoke a sense of historical significance. Nearby buildings reflect the same architectural style, enhancing the neighborhood's character.
Home in Gettysburg
4.97 out of 5 average rating, 250 reviews

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.

Top guest favourite
The treehouse is perched among tall trees, featuring a wooden deck that wraps around its structure. A gentle staircase leads to the entrance. In the foreground, purple flowers bloom beside a rock outcropping, enhancing the natural landscape under a bright blue sky.
Treehouse in Shepherdstown
4.97 out of 5 average rating, 416 reviews

Cozy West Virginia Treehouse

Thanks for checking out our treehouse! It’s 4 minutes from downtown Shepherdstown and 15 minutes from downtown Harpers Ferry. We are excited to share it with other fun-loving folks! The treehouse has heat and AC, a tiny kitchen with a mini fridge, stove top, toaster oven, gravity-fed sink and kitchenware. There’s a bathhouse built on the back of the host’s home with a conventional toilet and shower. There’s also an outhouse with a light and essentials. We provide wood for the fire pit also.

Top guest favourite
Place to stay in Shippensburg
5 out of 5 average rating, 466 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 favourite
A well-appointed king bedroom features a tufted beige headboard and soft white bedding. Flanking the bed, two bedside tables with lamps provide illumination. A rounded ottoman sits at the foot of the bed, complemented by a light-colored area rug with subtle patterns.
Flat in Gettysburg
4.95 out of 5 average rating, 128 reviews

Heart of Gettysburg Walk to Everything!

Walking distance to shops, museums, restaurants, and the battlefield. Situated where federal troops were positioned on July 2-3, 1863 and steps from the site where Lincoln gave his immortal Gettysburg address. Parking for two vehicles on site. Amenities include: - King Bed - Wi-Fi - Off street parking for guests - Netflix - TV lots of channels - Shampoo and Conditioner - Body Wash - Keurig and Coffee Pods - Washer and Dryer - Pinball Machine (Fun!) - Refrigerator - Dishwasher

Top guest favourite
An expansive open-concept living area is highlighted by large windows, providing ample natural light and panoramic views of the surroundings. Comfortable seating areas are arranged around a central coffee table, while a cozy stone fireplace serves as a focal point against a feature wall.
Home in Smithsburg
4.96 out of 5 average rating, 216 reviews

The Great Escape Lodge ~ Exquisite Mountain Views

The Great Escape Lodge is a soaring A-frame offering luxury accommodations. Owner designed and custom built in 2022, this luxury getaway is nestled in the stunning Catoctin Mountains with views parallel to those seen on Paramount's hit series Yellowstone. This exquisite residence offers outstanding interior and exterior custom touches and amenities. From the open concept great room to the massive deck with rockers and hot tub, there are endless opportunities to enjoy the scenic views.

Top guest favourite
The entrance to The Crooked Cottage is framed by wooden planks and surrounded by greenery. Two windows offer glimpses into the inviting interior, while a gravel pathway leads up to the door, playfully adorned with a sign featuring the name of the cottage.
Home in Myersville
4.98 out of 5 average rating, 302 reviews

The Crooked Cottage: a Cozy, Curated Escape

You will instantly relax in this stylish, pet-friendly home only 8 mins from I-70, exit 42. Under a canopy of trees find a beautifully landscaped yard with decks and two fire pit areas. Enjoy the well-apportioned kitchen with organic, fair trade coffee. Relax with 2 Roku TVs, games and puzzles, bathe with soaking salts and Turkish towels. For outdoor enthusiasts, pitch your tents. Sit by the wood-stove in the winter, or lay in a hammock when it’s warm. Welcome to The Crooked Cottage!

Superhost
A cozy bedroom features a spacious bed complemented by a neutral-colored blanket. Wooden flooring and a rustic dresser add warmth, while an angled ceiling showcases natural wood panels. Soft light filters through the window, enhancing the tranquil atmosphere.
Flat in Gettysburg
4.86 out of 5 average rating, 109 reviews

Summer Kitchen

This renovated ‘summer kitchen’ is close to Gettysburg battle field and Gettysburg university. There are a set of fairly steep steps that lead to the bedroom, so please ensure that you are able to climb these (see pics). There is a small sitting room, bathroom and kitchenette on the first floor, and the bedroom is the only thing on the 2nd floor. There is plenty to do in historic Gettysburg, or if you like to ski or snowboard, Ski Liberty is only about 20 mins away!

Top guest favourite
The exterior of a private home is showcased, featuring a single-story structure set back from a paved driveway. Lush greenery surrounds the property, complemented by large trees flanking the entrance. A porch with railings is visible, adding to the welcoming appearance of the home.
Home in Gettysburg
4.98 out of 5 average rating, 257 reviews

Beautiful private home in the country

Beautiful private home in the country yet only 7 minutes to Gettysburg center square. Enjoy the privacy of this 4 bedroom 2 full bath home with a full kitchen, laundry, bbq grill, and fire pit in the 2 acre back yard! 3 queen beds and 1 single bed plus a twin pull out couch are available and every room has its own heating and air conditioning for everyone’s comfort! This home is pet friendly so feel free to bring your whole family!

Popular amenities for Round Top holiday rentals

  1. Airbnb
  2. United States
  3. Pennsylvania
  4. Adams County
  5. Round Top