Vacation rentals in Summit Point

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Top-rated vacation rentals in Summit Point

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Guest favorite

A cozy living area features a spacious gray sectional sofa adorned with patterned throw pillows in yellow and black. An accompanying ottoman sits nearby. A wall with a piece of artwork depicting an owl provides visual interest, complemented by a small table in the background.

Apartment in Winchester

4.83 out of 5 average rating, 136 reviews

The Comfortable In-Towner

A cute one bedroom apartment located on lower level of a historic 1840s home. This half basement has windows to let in natural light, a full-size kitchen with dishwasher, fridge, big closets, Queen size Tuft & Needle premium mattress and a private screened patio open to our courtyard with friendly neighbors and management on site. Window ac units, fans & radiators Quiet neighborhood in Old Town Winchester, Va, two short blocks from pedestrian mall with restaurants, shops cafes & entertainment.

Guest favorite

The interior of the tiny home features warm wooden walls and a skylight, providing natural light. A compact kitchenette is visible, along with a seating area that includes two metal chairs. A sliding door offers a view into the outdoor space.

Home in Harpers Ferry

4.93 out of 5 average rating, 120 reviews

Spectacular View, PET FREE, Skylight and Hot Tub

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, "Mind Blowing" outdoor 2 person soaking tub. The outdoor space provides private vistas of Shenandoah, moonlit nights, star gazing, or taking in the beautiful scenery while enjoying a relaxing shower in our cedar outdoor shower under the sun or stars

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, 164 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

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, 124 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

A comfortable seating area features a gray sofa positioned against exposed brick walls. A tan upholstered bench serves as a coffee table in front of the couch, while a light accent lamp provides illumination. Hardwood floors add warmth to the space.

Apartment in Winchester

5 out of 5 average rating, 224 reviews

Old Town Loft In Highly Desirable Area Downtown

Location, Location! A completely renovated apartment in the highly desirable center 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 reclaimed wood and quartz counters, coffee nook with Keurig, large tile shower with glass doors, hardwood floors, queen memory foam mattress, high speed Wi-Fi, 50’ smart TV, Xfinity HDTV with voice remote control, AC/Heat, Washer/Dryer, and dishwasher.

Top guest favorite

A small table with two chairs is set on a wooden deck, showcasing a bouquet of sunflowers and two glasses of red wine. Lush greenery surrounds the area, with glimpses of open lawn and trees in the background under a bright blue sky.

Loft in Charles Town

4.98 out of 5 average rating, 64 reviews

Walnut Glen - Quaint 1 Bedroom Country Get-A-Way

Quaint and cozy studio apartment nestled on a quiet country lane just outside of Charles Town. Relax with a glass of wine on the private deck, enjoy a s'more at your personal fire pit or cool off in the built-in swimming pool. Keep an eye out for the deer that come to graze early morning and evening on the 3 acre property. Close to all area attractions without all the crowds. The loft apartment is in a separate building from our home, above my stained glass shop.

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, 173 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.

Top 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, 259 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, 519 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.

Guest favorite

A rustic cottage features weathered wood siding and a welcoming front door. Two chairs sit on a circular brick patio, surrounded by colorful potted plants and neatly trimmed hedges. Lush greenery is visible in the background, enhancing the tranquil setting.

Cottage in Martinsburg

4.98 out of 5 average rating, 435 reviews

Last Rodeo Cottage

Our cottage is private where guest can relax; Looking to spend some quiet time out of the city. Close to D.C.and the Historic site of surrounding areas. Close to Charlestown Casinos. Our home is right off I- 81 This cottage is Handicap accessible from private parking to shower and amenities. Lovely park like setting shared with our family pets.

Top guest favorite

The wooden deck offers a serene view of the calm river, reflecting the warm hues of the trees lining the opposite bank. Bare branches create a gentle frame around the water, enhancing the tranquil atmosphere of the natural setting.

Cabin in Charles Town

4.94 out of 5 average rating, 116 reviews

The River House

Come unplug at this adorable, spacious cabin on the bank of the Shenandoah river. Enjoy peaceful dinners amongst the trees on a two tiered deck. Fall asleep to the rhythmic sounds of nature waking to coffee in sunroom. If you prefer social nightlife, you’re just 10 minutes from the casino, bars and restaurants

Guest favorite

Home in Kearneysville

5 out of 5 average rating, 24 reviews

WV Cozy Cabin Summit Point Races

Set in the foothills of WV, this cozy cabin on 2 acres is a haven to get away from it all. Bright and clean and an easy drive set in a central location from Summit Point & Charles Town Race Tracks and the historic towns of Harpers Ferry and Shepherdstown, WV. Ample space for your race car or horse trailers!