Holiday rentals in Berryville

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Top-rated holiday rentals in Berryville

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Guest favourite

Guest suite in Summit Point

4.97 out of 5 average rating, 128 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!

21–28 Dec

₹10,652 per night

Guest favourite

Cottage in Berryville

4.98 out of 5 average rating, 115 reviews

Guest Cottage on Historic Estate & Cattle Farm

Fully restored c.1900 farm house on 190 acre estate, ~1 hr from D.C. Cottage is situated at end of a farm road (past the main house and barns), very private w/ creek and cows right outside. Enjoy walks on the farm, local hikes, breweries & wineries, pick-your-own fruit farms, tubing on the Shenandoah, restaurants, antique shops, and more. 1 queen bdrm and bath on 1st flr, 2nd queen bdrm & loft with twin beds on 2nd flr. wifi, fire pit, small grill. Over 25 only, Max 4 adults. 1 SMALL DOG ONLY.

30 Apr – 7 May

₹21,676 per night

Guest favourite

Cottage in Bluemont

4.95 out of 5 average rating, 169 reviews

The Cottage at Stonecroft

Nestled at the foot of the Blue Ridge Mountains among beautiful rolling hills, on a working horse farm outside the village of Bluemont. This circa 1902 Cottage will put you in touch with the history of the area, antique shops, wineries/breweries and nearby hiking. 2 bedrooms and bath upstairs; sitting/living room , dining table and full kitchen on main level. Wifi, fire pit and small charcoal grill. Over 21 only. Absolutely no pets/animals. For your safety property has video security system.

21–28 Nov

₹11,998 per night

Guest favourite

Flat in Winchester

5.0 out of 5 average rating, 137 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.

4–11 Oct

₹13,806 per night

Guest favourite

Flat in Winchester

4.94 out of 5 average rating, 270 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.

18–25 Aug

₹12,691 per night

Guest favourite

Home in Winchester

4.98 out of 5 average rating, 151 reviews

Colonial Getaway Near Old Town Historic Winchester

Colonial style home- enjoy a spacious home with large living room, dining room, kitchen, 3 bedrooms and 2.5 bathrooms. Perfect for a family or a longer stay. Just a few miles drive to Old Town Winchester which includes numerous restaurants, bars, shopping and some kind of event... like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. Near by to other scenic attractions as well- Shenandoah National Park, Luray Caverns, and Harper's Ferry!

18–25 Dec

₹12,818 per night

Guest favourite

Home in Bluemont

4.93 out of 5 average rating, 202 reviews

The Country French Cottage at High Meadows Estate

Come visit the alluring wine country of Bluemont Virginia, and stay in a beautifully appointed country French cottage on the 50 acre circa 1896 High Meadows Estate atop the Blueridge Mountains. Just 50 minutes west of Washington DC, this stunning country retreat is just 5 minute from the vineyards of Bluemont, the Shenandoah River, the Appalachian Trail, Hiking, Canoeing, Kayaking, Farmers Markets, the the cute villages or Berryville, Harpers Ferry, Luckettes, Middleburg and many more.

7–14 Dec

₹12,622 per night

Guest favourite

Cottage in Winchester

4.97 out of 5 average rating, 421 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.

24–31 Oct

₹10,264 per night

Guest favourite

Townhouse in Winchester

4.95 out of 5 average rating, 169 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.

2–9 Jan

₹9,352 per night

Guest favourite

Loft in Purcellville

4.99 out of 5 average rating, 286 reviews

"When Pigs Fly" Airbnb Most Hospitable Host in VA

Located between Middleburg, VA and Purcellville, VA, our loft is just about 15 minutes away from restaurants, wineries, breweries and many local points of interest. You will have views from every window in addition to all of the amenities you will need for a pleasant stay. We welcome your dogs while you visit. The only thing we ask is that you keep them off the couch, pick up their "business" and crate them if they are left alone.

12–19 Nov

₹9,230 per night

Guest favourite

Home in Berryville

4.95 out of 5 average rating, 189 reviews

Riverfront Getaway w/ Breathtaking Views!

Welcome to the Shenandoah Valley! Expect a private, serene, and relaxing experience! Our newly renovated home has great deck space and beautiful views right on the Shenandoah River! Enjoy river tubing, fishing, kayaking, reading a book by the fire, or drinking coffee on the porch while watching a breathtaking sunrise! Conveniently located an hour west of DC and 25 minutes east of Winchester.

6–13 Sep

₹25,932 per night

Guest favourite

Guest house in Round Hill

4.98 out of 5 average rating, 373 reviews

Private Carriage House

A recently renovated carriage house by an interior designer situated on a treed and private property conveniently located for exploring wineries, breweries, horse events or civil war sites in Middleburg, Purcellville, Leesburg, Bluemont or Round HIill. Enjoy the sounds and sights of nature and fresh air. Recharge in a peaceful setting. Adults only. No pets, children or infants.

25 Jun – 2 Jul

₹10,626 per night