Vacation rentals in Berryville

4.96 out of 5 average rating, 24 reviews

A charming exterior view of the recently renovated house showcases its distinctive blue wooden siding and pitched roof. Lush flower beds filled with yellow and white blooms surround the entryway, while the well-maintained garden adds vibrant color to the setting.

Guesthouse in Berryville

1800s Cozy Kitchen House

This award winning whimsical 1800s kitchen house that served the main house is walking distance to all town businesses and great for history and art lovers. Located on historic South Church Street, the property backs to Rose Hill Park, The Barns of Rose Hill music/art venue and the town government center/ library. Everything was chosen piece by piece with respect to the structure’s history with the addition of modern conveniences. Original steep and narrow steps may be difficult for some guests.

LocationFamilyAmenities

4.96 out of 5 average rating, 157 reviews

A cozy fire pit is surrounded by six white Adirondack chairs, creating an inviting gathering space. Soft lighting is provided by lanterns, while the cottage can be seen in the background, framed by trees under a dusky sky.

Cottage in Boyce

Pets? YES! Hot Tub | Fast Wi-Fi | Fire Pit

Moonflower Cottage is a historical farmhouse nestled on two rolling acres in Virginia's wine country. Visit the area's top vineyards, dining, and antique shops. Float down the Shenandoah River. Cap your day sipping cabernet as the sun sets and the cottage blooms like the moonflowers that grow wildly. Bathe in the warm glow of string lights under the grapevine arbor or enjoy a relaxing soak in the spa. Young or old, you are sure to find the vintage that you are looking for at Moonflower Cottage.

ValueFamilyBackyard

A comfortable living area is furnished with a sectional sofa and a classic armchair, complemented by an area rug. Decorative artwork adorns the shelves, and natural light fills the space through large windows, creating a welcoming environment for relaxation.

4.93 out of 5 average rating, 29 reviews

Purple Iris 3b 2b private oasis nr river/mountain

Come get away and relax in this stunningly decorated one level light-filled home on its own private oasis. “Purple Iris” is a magical place with an artistic feel & several modern amenities. Perfect location for visiting local wineries, taking a hike & going to small town shops & restaurants in downtown Berryville. Awesome fully stocked kitchen & outdoor deck with grill! You will LOVE it! Skyline Drive - 20 min Harpers Ferry- 20 min Shenandoah River - 5 min DC - 1.5 hr. Pets are welcome!

FamilyLocationHospitality

The entrance features a double door adorned with vibrant artwork. One side displays a rabbit amidst greenery, while the other showcases an abstract, colorful design. A vintage-style lamp stands beside the doors, adding character to the welcoming entryway.

4.87 out of 5 average rating, 68 reviews

Vidalia House in Berryville, The Whole Onion

This unique home is in town, close to everything, making it easy to plan your visit to Berryville. This listing is for private use of the entire house as a 4 BR (there are also separate listings for some individual rooms, sharing common spaces). Walking distance to dining, shops, Rosemont Manor and Barns of Rose Hill, this house was fully renovated and furnished with all the amenities you'll need for your group. Enjoy the local river, AT, Parks, wineries, breweries, music and festival events.

FamilyValueAmenities

4.99 out of 5 average rating, 164 reviews

A well-appointed kitchen features a central island with a marble countertop, surrounded by wooden cabinets and modern appliances. Natural light floods in through large windows, illuminating the dining area with a small table and four chairs. A patterned rug adds warmth to the wooden flooring.

Cottage in Berryville

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.

FamilyValueAmenities

A stone house with a metal roof is highlighted, surrounded by green trees and a grassy area. A covered porch extends along the front, supported by white columns. A paved pathway leads to the entrance, emphasizing the house's rustic charm in a serene rural setting.

4.98 out of 5 average rating, 82 reviews

The Hill House at Stubblefield

Enjoy spectacular views of the Blue Ridge from this meticulously crafted stone house. The Hill House is situated on 40 acres in beautiful Clarke County, Virginia, and offers easy access to any outdoor activity your heart desires. This getaway is 2 miles from a public boat landing, and is surrounded by pastoral views and country roads in all directions. The Hill House is on Stubblefield Farm, which has its origins dating back to 1792. Come enjoy local wineries, breweries, and antique shops.

LocationValueComfort

4.98 out of 5 average rating, 225 reviews

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

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 !

ValueFamilyGetting around

4.97 out of 5 average rating, 359 reviews

A spacious dining area features a wooden table with woven placemats, surrounded by upholstered chairs. Natural light fills the room through the windows. A comfortable seating arrangement with a sofa is visible in the background, complemented by a television on a console.

Apartment in Winchester

Downtowner

No hassle parking on premises and a private entrance. The "Downtowner" is a 1920's era restored home in a quiet residential section of Winchester's Historic District and just a short stroll to the downtown "pedestrian only" walking mall with restaurants, cafes, and shops. Clean and spacious, the apartment is complete with bed linens, towels, etc. and stocked with water in the fridge as well as a Keurig with coffee options, tea, hot chocolate, etc...Xfinity HDTV with voice remote control.

LocationFamilyTV

4.74 out of 5 average rating, 740 reviews

Loft in Winchester

Immerse yourself in Old Town Winchester (Apt #4)

Our loft apartment is in the heart of Old Town Winchester on the Old Town Mall. Located off of a little alley, with security lighting and motion detectors you will be staying steps away from dining, shops, and everything our community has to offer. Yet, our apartments are quiet and secure. Our building is OLD & has all of the charm that goes along with it. If you are looking for a sparkly new place, you may want to stay elsewhere, If you want clean, funky, and awesome, we are your place!

ValueLocationParking

4.97 out of 5 average rating, 294 reviews

The front porch features two white rocking chairs with red cushions, positioned next to a welcoming red door adorned with a wreath. Lush flowers bloom in a garden bed below, adding color to the inviting entrance.

Home in Winchester

City Charmer minutes from Old Town

Renovated 1950's cottage style home. Enjoy a small house with a great front porch and large backyard with patio. Just minutes to drive and about 10-15 minutes to walk to Historic Old Town Winchester which includes numerous restaurants, bars, shopping, and often some kind of event like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. if you're looking for a day trip to the big city or just sit back and relax right here in our small town.

FamilyValueLong stay

4.93 out of 5 average rating, 322 reviews

The exterior of the townhouse features two large windows on the upper floor, a welcoming front door framed by a porch. A small patio area is furnished with a bistro table and two chairs, surrounded by neatly arranged landscaping and stone pathways.

Townhouse in Winchester

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.

LocationValueCleanliness

4.99 out of 5 average rating, 407 reviews

A hot tub is situated on a deck surrounded by trees, with sunlight filtering through the branches. A pink float is placed beside the tub. The calming water reflects the warm light, creating a serene atmosphere.

Guesthouse in Bluemont

Skyhorse Retreat Guest House

In the middle of VA wine country and only minutes to three Appalachian Trail trailheads. Located 45 miles west of Washington D.C., on a 10-acre property on top of the Blue Ridge Mountains. Private guesthouse (built Jan 2020) with a large deck overlooking trees. The Guest House sleeps 4, has a full kitchen, and access to a Hot Tub at the main house which is shared with our other guests. Breakfast items and snacks included.

ValueFamilyCleanliness

Popular amenities for Berryville vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Berryville

Superhost

A single-story brick house is framed by a well-maintained lawn featuring decorative white fencing. A front porch with white railings invites relaxation, while a path made of concrete leads towards the entrance. Lush greenery surrounds the home, enhancing the welcoming outdoor space.

4.92 out of 5 average rating, 39 reviews

Rustic chic 3 bedroom home with onsite parking.

LocationValueCondition

5.0 out of 5 average rating, 60 reviews

The exterior of Longview House reveals a modern two-story design, featuring large glass doors that open to a welcoming entryway. Stone steps lead up to the entrance, surrounded by lush greenery and natural landscaping.

Cottage in Bluemont

Designer Modern Mountain Escape (w/View & Hot Tub)

FamilyLocationView

Superhost

A long gravel driveway leads to a charming house framed by blooming trees and vibrant yellow bushes, showcasing the natural beauty of the surroundings. The home features a light-colored exterior with large front steps and a welcoming entrance, flanked by lush greenery.

5.0 out of 5 average rating, 4 reviews

Friends Getaway (maximum of four guests)

LocationAmenitiesBreakfast

4.9 out of 5 average rating, 31 reviews

Home in Winchester

Cozy 3BR Retreat w/ Patio, Fire Pit & Yard

ValueFamilyAccess

5.0 out of 5 average rating, 33 reviews

A fire pit constructed from natural stones rests on a grassy area surrounded by trees. Two wooden chairs are positioned beside the pit, offering a welcoming space for relaxation. Stacked logs are visible in the background, suggesting a rustic outdoor setting.

Home in Bluemont

Yellow House in Bluemont Village

ValueLocationOutdoor spaces

4.95 out of 5 average rating, 39 reviews

Home in Bluemont

Red Rooster Cottage with hot tub and seasonal pool

FamilyLocationHospitality

5.0 out of 5 average rating, 9 reviews

Home in Millwood

Peony Place renovated farmhouse in horse country

LocationGrillBackyard