Holiday rentals in Gerrardstown

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Top-rated holiday rentals in Gerrardstown

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Guest favourite

Guest suite in Summit Point

4.97 out of 5 average rating, 132 reviews

The Big Room - Historic Schoolhouse

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. There are even a couple sidewalks ;) We have 3 churches and a post office. 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!

Superhost

Cabin in Gerrardstown

4.88 out of 5 average rating, 185 reviews

Modern Treetop Cabin with Views and Nearby Creek

Our cabin in the treetops is the perfect place to rest, work remotely, or use as a basecamp for exploring the surrounding area. Our aesthetic is modern eclectic. We do our best to use only chemical/cruelty free products that are ethically and sustainably sourced. The cabin has many modern conveniences including an eco-friendly hot tub with epic views, high speed internet and chromecast for streaming your connected devices. Hot tub is available year round. Pellet stove is available Oct-March.

Superhost

Cabin in Berkeley Springs

4.87 out of 5 average rating, 135 reviews

Magical quiet cabin nestled in the woods

Lovely cabin tucked into the woods where you can relax in nature with complete privacy/seclusion while still close to downtown. 2 bedrooms - the second bedroom is part of a partially open loft. Fully equipped, AC, elec heat, deck, gas grill & view, wifi, DVD player and desk/work area. Loads of amenities and fun things for kids to explore around the property. 10 minutes to downtown Berkeley Springs, near Cacapon Park - for golf, beach/lake access, many fun day trips. 50 minutes to wineries.

Guest favourite

Cottage in Winchester

4.9 out of 5 average rating, 101 reviews

Lockley Cottage at Historic Perry Farm

Peace and tranquility await you at a quaint cottage on historic Perry Farm, where the original 19th century farmhouse still stands today. Stroll several acres of land and enjoy pastoral views while you unwind at this peaceful historic property in the hills of northern Shenandoah Valley. This rural retreat is easily accessed from I-81 and located a short 10-minute drive from historic downtown Winchester. Enjoy local wineries, breweries, farm markets, and the renowned Apple Blossom Festival.

Guest favourite

Home in Inwood

4.89 out of 5 average rating, 558 reviews

Arden House, Inwood WV

Ground level studio apartment. No steps. Completely separate entrance from main house. Private entrance and parking. There is an entrance room with a double bed, twin bed and sofa. In a separate living area, there is a queen bed, TV, private bath, desk, table, microwave, convection oven, air fryer, refrigerator Outside there is a large area to use outdoor gas grill, picnic table and fire pit. Dogs allowed and must be kept on a leash when outside. Please NO CATS. The owner is allergic.

Guest favourite

Flat in Winchester

4.94 out of 5 average rating, 273 reviews

Downtown 1920's Gas Station

Luxury 1920’s Refurbished Gas Station repurposed into a beautiful apartment. Private off-street parking/EV car charging station, full kitchen, custom shower with rain system, super high speed wifi, smart TV & Blu-Ray. Plenty of light with frosted garaged doors. AC/Heat, Washer/Dryer, Dish Washer, coffee nook, and open living design. Be a part of Old Town Winchester in this unique fun space in walking distance to breweries, neighborhood Pizzoco Pizza parlor and the downtown walking mall.

Guest favourite

Cabin in Paw Paw

4.96 out of 5 average rating, 178 reviews

Easygoing

Tired of the chaos and need a place to unwind and relax ? We have the perfect place for you! A quaint, quiet cabin to let you clear your mind and spirit after a day of hiking, biking or kayaking since we are only five miles from both the Paw Paw tunnel and the Potomac river. The cabin is equipped with electric, heating, stove top, microwave, large deck, hammock chairs, horseshoe pit, 2 double size futons with lots more room to spare, indoor toilet but BEST of all is showering outside!

Guest favourite

Cottage in Winchester

4.97 out of 5 average rating, 425 reviews

Emma's Stone Cottage

Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 beautiful acres. In addition, it is located only 2.5 miles from I-81 and 14 minutes from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage is fully furnished with all the comforts of home. From the full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more. It has everything you need for a peaceful and enjoyable stay.

Guest favourite

Townhouse in Winchester

4.95 out of 5 average rating, 173 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.

Guest favourite

Farm stay in Romney

4.98 out of 5 average rating, 292 reviews

Potomac Hills B&B on 15 Acre Farm with a View

Escape to where beauty and serenity abound in a brand NEW guest house on a 15 acre farm in the Potomac Highlands. Just 2 hours from DC, this accessible, yet peaceful escape provides options for relaxation and outdoor adventure. Located 10 minutes from Romney, WV, this spot is convenient to hiking, river activities, hunting/fishing, and skiing. Explore or simply relax and enjoy life on the farm.

Superhost

Loft in Martinsburg

4.9 out of 5 average rating, 113 reviews

The Penthouse-Cool Vibes

Imagine being downtown near the restaurants, bars, and shopping. Go up 2 flights of stairs and you've arrived in heaven. The breathtaking views from the top floor is memorable. You'll love the light that spreads out through the huge windows! Enjoy the huge king size bed or just hang out in the comfy living room. You are going to make your friends so jealous when they see your pictures!

Guest favourite

Cottage in Shepherdstown

4.96 out of 5 average rating, 187 reviews

The GW Hollida Cottage of Shepherdstown

Let time slow just a bit at this unique and tranquil getaway! This recently renovated cottage is situated just behind the GW Hollida house, circa early 1800s. Whether taking a few extra breaths of fresh air on the deck, taking a stroll through the 5 acres of serenity, or kicking back to enjoy some peace and quiet, we are confident you'll love this place as much as we do!