Vacation rentals in Summit Point

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Top-rated vacation rentals in Summit Point

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Top guest favorite

A circular fire pit area is surrounded by gravel and rustic wooden benches. Tall trees provide natural privacy, and a two-story home is visible in the background, blending with the serene forest setting. Evening light enhances the peaceful ambiance of the space.

Home in Kearneysville

5 out of 5 average rating, 11 reviews

Creekside Pine Retreat

Escape to a serene two-acre retreat in a lush West Virginia pine forest. This modern, family-friendly home offers creek access stocked with trout and bass, and a cozy fire pit for evening gatherings. Enjoy both seclusion and proximity to top attractions: Summit Point Motorsports Park (15 mins), Hollywood Casino (20 mins), and Harpers Ferry and Shepherdstown (30 mins). Perfect for guests seeking comfort, adventure, and relaxation. Basement arcade/game room and RV parking available w/50 Amp hookup

Top guest favorite

The exterior of the historic home features white siding and a metal roof. A welcoming entrance is flanked by plants, and a spacious porch is visible. Surrounding landscaping includes a well-maintained garden, with colorful trees in the background indicating seasonal changes.

Home in Summit Point

5 out of 5 average rating, 21 reviews

Summit Point Historic "1850's House"

Set in Jefferson County, WV, this historic home built in 1850 has been transformed into a modern, bright and serene home away from home. The home is close to Winchester & Berryville, VA, & the historic West Virginia towns of Charles Town, Harpers Ferry and Shepherdstown. Whether you are here for the Summit Point races or the Charles Town Casino, or in town for a tour of our historic towns, hiking or tubing on the C&O and Potomac rivers we know you will have an amazing stay! NO PARTIES ALLOWED

Top guest favorite

A cozy tiny home is surrounded by lush greenery. Outdoor seating is provided with a small table and chairs, while planters filled with flowers enhance the space. A soaking tub is visible on the patio, adding to the charm of the outdoor area.

Tiny home in Harpers Ferry

4.98 out of 5 average rating, 133 reviews

Enchanting PET FREE W/Amazing ViewHot Tub Overlook

Enjoy majestic views of the Shenandoah River in our tiny home centrally located just 5 mins from AppalachianTrail, 6 mins from the rivers, 12 mins from Old Town Harpers Ferry. Featuring large patio, outdoor dining area, courtyard, firepit, hammock, outdoor 2 person soaking tub. The outdoor space provides private vistas of Shenandoah, moonlit nights, star gazing, "Mind Blowing" outdoor soaking tub or taking in the beautiful scenery while enjoying a relaxing shower in our all cedar shower room.

Top guest favorite

The exterior of a one-story home is showcased, featuring red shutters and a white front door. A well-maintained lawn surrounds the house, with a prominent tree and colorful flowerbeds adding to the inviting curb appeal.

Home in Inwood

4.95 out of 5 average rating, 158 reviews

Lindas Country Cottage

Come and relax in our Little County Charmer If needed for extended t. Under 2 miles from Interstate. 15 min from Charlestown Casino and horse racing. JD’s Fun Center with pool for children. ..2 hrs from Massanuttan . Take a ride to Historic Berkley Springs Or Harpers ferry.. Home is in a quite neighborhood. Tv Wi-Fi. Home is close to dining and fast foods delivery. So if you wanna feel right at home while visiting or town stop by and pay a visit at our small home with a little country charm

Top guest favorite

A cozy corner features a cushioned armchair adorned with decorative pillows, next to a small dark wood table with a lamp. A decorative bookshelf holds various books, with warm sunlight illuminating the space. A wooden staircase leads to the upper level.

Home in Winchester

4.98 out of 5 average rating, 200 reviews

Cameron Charmer pristine w/double master suites

Take a step into pure luxury in this newly renovated 1930's charmer in up and coming downtown area of Winchester. Owners have spared no expense to make this the kind of place where guests can come & forget about the rest of the world ! Incredible top of the line centralized dine in kitchen, wide open & inviting living areas, two master suites each with walk in closets & baths up lovely custom pine staircase. Come spoil yourself a bit at the Cameron Charmer, you are sure to enjoy your stay !

Top guest favorite

The exterior of the home is showcased at dusk, highlighting its wooden façade and large windows. Warm outdoor lights create a welcoming atmosphere. A spacious deck with steps leads to the entrance, surrounded by wooded terrain, indicating a private and serene location.

Guest suite in Harpers Ferry

4.98 out of 5 average rating, 121 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!

Top guest favorite

The living area features a spacious sectional sofa positioned around a round coffee table. A soft area rug lies beneath. Natural light filters through multiple windows with blinds, illuminating the hardwood floors. A decorative plant adds a touch of greenery, while a lamp provides warm lighting.

Apartment in Winchester

4.98 out of 5 average rating, 110 reviews

Old Town Loft Modern Oasis In Downtown Winchester

Location, Location! A completely renovated, 2 bed/1 bath, 1100 sq. ft. apt in the highly desirable center of Winchester. You’ll still be able to see some of its original character throughout this historic building. The apartment has a fully stocked custom kitchen with quartz counters, coffee nook with Keurig, large tile shower with glass doors, hardwood floors, memory foam mattresses, high speed Wi-Fi, 60’ smart TV, Xfinity HDTV, AC/Heat, Washer/Dryer, dishwasher and 2 free parking spaces.

Top guest favorite

A spacious living area features vaulted ceilings with large windows allowing natural light to fill the room. A comfortable sofa faces a central coffee table, with a dining area containing a round table and chairs nearby. Shelving units display books and decorative items, enhancing the inviting space.

Cabin in Gerrardstown

4.98 out of 5 average rating, 159 reviews

The Nest: Cozy Chalet w/Wi-Fi, Deck & Grill

The Nest is a chalet-style cabin tucked into the tree-lined mountains of Berkeley County, WV. It offers adventure, a quiet retreat & good family fun. With 5-acres in the countryside, you'll enjoy star studded skies on clear nights & wake up to birds singing & deer wandering, with mountain views through vaulted windows. The Nest is near Martinsburg, Berkeley Springs, Harpers Ferry, Shepherdstown, Charles Town & Cacapon State Park, among other go-to destinations on the Eastern Panhandle.

Top guest favorite

A charming Craftsman-style home is seen, featuring a welcoming front porch with a bright yellow door. The neatly landscaped yard is surrounded by a wooden fence, with stone pathways leading through the lush green grass.

Home in Charles Town

4.94 out of 5 average rating, 17 reviews

Beautiful Happer Ferry

visitors drawn to the nearby Hollywood Casino, historic downtown, and local attractions. Freshly Updated Throughout — New luxury vinyl plank flooring, fresh paint, a stunning kitchen with shaker-style cabinets, quartz countertops, and stainless-steel appliances. ✨ Charming Sunroom & fully fence Private Backyard Retreat — . ✨ Prime Location — Just minutes to the Casino, downtown Charles Town, local parks, shops, and dining — and an easy commute to Northern Virginia andDC.

Top guest favorite

The exterior of a renovated red brick building is displayed, featuring large windows and a prominent entrance. A decorative cupola is positioned at the roof's peak. Surrounding landscaping includes a small garden area. A sign indicates late checkout time on Sundays.

Guest suite in Summit Point

4.98 out of 5 average rating, 171 reviews

The Big Room - Historic Schoolhouse

Checkout as late as 8pm on Sundays! Located one mile from the racetrack in the little village of Summit Point. This is a large renovated former classroom with 13' ceilings in the old Elementary School. Summit Point is a quiet place where you can take a leisurely stroll. The Railside Market serves food and sundries one block away. (currently has limited hours) Multiple food options are available in nearby Charles Town and lots more in Winchester Virginia.

Guest favorite

An open-concept kitchen and living area is presented, featuring modern cabinetry and stainless steel appliances. A cozy armchair with a blue cushion sits beside a small table, while barstools line the kitchen counter. A patterned table adds a splash of color to the space.

Townhouse in Winchester

4.93 out of 5 average rating, 252 reviews

Modern Elegance in Historic Old Town Winchester

Just a block and a half from the Old Town Winchester pedestrian mall, this historic beauty with modern elegance is sure to please. You are within walking distance of quaint shops, great restaurants, The Brightbox Theater, and The Shenendoah Discovery Museum. Spend the day touring the areas great wineries or enjoying Skyline Drive, and then return to enjoy a great night out, or an evening at home making dinner in the spacious modern kitchen.

Top guest favorite

A charming stone cottage with a wooden front porch features a sloped roof and a brick chimney. Surrounded by trees, the cottage is set on a grassy area, providing a sense of seclusion. Large windows and a welcoming entrance enhance the exterior appeal.

Cottage in Winchester

4.97 out of 5 average rating, 506 reviews

Emma's Stone Cottage

Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 acres. In addition, it is located only 2.5 miles from I-81 and approx 10 miles from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage has everything you need for a peaceful and enjoyable stay including full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more.