Vacation rentals in Round Top

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Round Top

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

0 of 0 items showing

1 of 3 pages

Guest favorite

A calm lake reflects surrounding greenery and a picturesque landscape. Trees line the banks, with a hill visible in the background. Nearby, a house is set back from the water, surrounded by open spaces, creating a peaceful natural setting.

Chalet in Mercersburg

4.94 out of 5 average rating, 112 reviews

Amazing Whitetail Ski Holiday and Mountain Retreat

Welcome to our beloved Mountain home. Located at Whitetail resort you can walk to the slopes and enjoy the après ski in our beautiful cozy house with cabin feel. Perfect ski holiday, weekend getaway, or place to work remotely with high-speed internet. Only 1.5 hours from DC & Baltimore. This is the perfect place to escape the city, connect with nature and recharge. A place to build up fond memories. All season adventures, enjoy skiing, swimming, hiking, golfing, fishing, lakes and local farms.

Guest favorite

Cottage in Middletown

4.9 out of 5 average rating, 271 reviews

Charming "Cream of the Crop" Cape ~❤️of Middletown

Cozy cape in the ❤️ of Middletown, MD. Walking distance (1/2 mile)to quaint Middletown restaurants, shops, & parks. Set your sights on adventure within a short drive. Enjoy downtown Frederick restaurants, shops, parks, & nightlife.Visit the local wineries, breweries & festivals. Hike the Appalachian trail. Float the Potomac River. Bike the C&O Canal. Ski the slopes @ area ski resorts. Golf 18 holes @ the championship golf course. Visit wedding venues. Go antiquing. Tour quaint nearby towns. Etc

Guest favorite

A charming stone cottage is set against a backdrop of lush trees and open sky. A gravel path leads to the entrance, with two chairs positioned on the grassy area, offering a serene view of the surrounding nature.

Cottage in Leesburg

4.92 out of 5 average rating, 401 reviews

Romantic Stone Cottage Circa 1869-75 acres to Hike

Plan a getaway in our newly renovated Stone Cottage nestled on hilltop just 15 minutes from Leesburg & less than 90 minutes from DC. The property adjoins next to a hidden state park, not on the map with gentle hiking trails. Secluded location however 10 min to some of the areas finest wineries & breweries. Custom-made king-size bed and fresh interior, are sure to impress . So whether you are visiting for a wedding, exploring wine country or in need of a quiet setting, we invite you to enjoy!

Top guest favorite

Guest suite in Harpers Ferry

4.98 out of 5 average rating, 108 reviews

Tequila Sunset, Harpers Ferry. Entire first floor!

Welcome to Tequila Sunset in Harpers Ferry, WV! This beautiful, secluded home has stunning sunset views, you'll truly feel on top of the world! 100 mile vista of the gorgeous Blue Ridge Mountains. Entire first floor is yours, no shared spaces! Over 1200 SF of room to unplug & relax. King size Nectar bed, cozy indoor wood burning fireplace, outdoor firepit, 84" TV, & a private deck to enjoy the natural surroundings. Just 2 miles from the renowned Mountain Lake Club and the Appalachian Trail!

Guest favorite

An aerial view of the great room reveals a cozy seating area with an orange sectional sofa and a coffee table, situated around a gas fireplace. High ceilings and large windows fill the space with natural light, and a dining table for six complements the open layout.

Cabin in Hedgesville

4.94 out of 5 average rating, 140 reviews

Starcatcher Chalet, The Woods Resort

Enjoy a fun, relaxing stay at our completely renovated chalet in The Woods Resort in beautiful Berkeley County, WV--a 90-minute drive from the Washington DC-Baltimore Metro Area. You'll be in the heart of the WV Eastern panhandle, close to Sleepy Creek, Berkeley Springs, Cacapon State Park, Antietam National Battlefield, and more. The Woods Resort amenities (fees apply) include a spa, restaurant, and two golf courses, three swimming pools, tennis, pickleball, fitness, and a playground.

Guest favorite

A new wood pier extends over still waters towards a green, tree-lined shore. The pier is flanked by posts, leading to a rocky bank, with a clear view of a nearby cottage among the trees. Sunshine reflects gently off the water.

Cottage in Pasadena

4.97 out of 5 average rating, 172 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

Superhost

A cozy fire pit is surrounded by Adirondack chairs, set on a gravel area amidst tall trees. A wooden deck leads to a cabin with warm lights glowing from the windows, providing a welcoming ambiance in a forested setting.

Cabin in Hedgesville

4.85 out of 5 average rating, 192 reviews

Stylish Retreat w Fireplace, Games & Pool Access

Experience a peaceful getaway at The Woods Resort. With an outdoor screened porch, a fire pit and a wood burning fireplace, you can comfortably enjoy this retreat in any season! Access to two outdoor pools, an indoor pool with hot tub, tennis and pickleball courts, a gym, and 36 holes of golf. Enjoy the indoors and outdoors in any season! The highlights: - Wood burning fireplace - Screened Porch with seating for the group - WiFi for streaming movies & remote work - Resort Amenities

Guest favorite

An enclosed porch features a swinging twin bed adorned with cozy pillows and blankets. Natural light enters through multiple windows, illuminating indoor greenery. A small table holds a drink and a lantern, enhancing the warm, rustic ambiance alongside wooden paneling and soft lighting.

Cabin in Harpers Ferry

4.97 out of 5 average rating, 156 reviews

Applemoon: Charming Log Cabin in a Mountain Lake Community

Applemoon is a dog-friendly 1960s log cabin nestled on an acre of the Blue Ridge Mountains. 2 bedrooms with Smart TVs, a porch with hanging daybed and bistro table, and a cozy game loft will give you plenty of space to relax. Outside, enjoy dinner on the huge deck or build a fire and don't forget to look up at the night sky! Applemoon strikes the perfect balance between rustic charm and comfort while maintaining your immersion in the peaceful mountain woodlands of Harpers Ferry.

Guest favorite

A game room features a variety of entertainment options, including arcade machines and a shuffleboard table. A vending machine is also present, providing snacks and drinks. The room is designed with colorful accents and a green carpet area, making it inviting for guests of all ages.

Home in Hummelstown

4.93 out of 5 average rating, 128 reviews

Small Town Sweets: Charming Home Near Hersheypark

Beautifully restored home(2019) in Hummelstown, PA, about 3 miles from Hersheypark. Walking distance to many local restaurants, bars, & shops. Game room on 1st level will keep kids and teens entertained. Three large BRs with Queen beds, and 1 Kids' bedroom that sleeps 4, all of which include a smart TV. Queen rooms include luggage bench, full length mirror, and USB charging ports. New appliances, furniture, and bedding throughout. Oversized living space and front porch.

Superhost

The cabin's living area features a warm wood interior with vaulted ceilings and large windows offering views of the lake. A comfortable brown leather sofa is positioned near a coffee table, complemented by two wooden armchairs. A cozy wood stove adds to the inviting atmosphere.

Cabin in Harpers Ferry

4.81 out of 5 average rating, 436 reviews

Cozy Cabin Hidden Away on a Lake!

MOUNTAIN MAMA VACATION HOMES The perfect getaway for any season! Enjoy the lake views inside next to a roaring fire, or in the summertime take the kids for a swim in the shallow water just off your private beach. Relax in the hot tub set in the back deck as the sun sets over the lake and the stars start to come out. Make every night movie night on the 50" 4k TV. Whether you want to stay in or see the area, this cabin has something for every member of the family!

Top guest favorite

Home in Sabillasville

4.93 out of 5 average rating, 114 reviews

Stoney Spring Overlook

This beautiful mountain farm home has breath taking scenic views of the surrounding Catoctin mountain. There are many nearby outdoor activities, including scenic hikes, mountain biking, Ski Liberty, wineries and the Catoctin zoo. While it is a peaceful get away in the mountains, it is just 30 minutes away from the Frederick, MD and historic Gettysburg, PA. Whether you want to get away from the city or explore more of Maryland, this is the perfect stay for you!

Top guest favorite

A quiet garden area features a stone pathway winding through vibrant greenery and blooming plants. The pathway is bordered by large shrubs and trees, creating a serene natural setting. A blue garden sign stands prominently among the foliage, adding a touch of color.

Guesthouse in Owings Mills

4.97 out of 5 average rating, 115 reviews

The Garden Studio

Thoughtfully appointed 1 bedroom guesthouse in beautiful Greenspring Valley. Enjoy quiet quarters on an acre of private residential property within 5 minutes of the Baltimore beltway & restaurants, grocers, gas, and services. Close to Stevenson University (2 mi), Towson University (7 mi), convenient to other colleges & universities in the area; and 11 mi to the Inner Harbor. Host available in main house as needed.