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Cottage vacation rentals in Winchester

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Winchester cottage rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Cottage rentals with a hot tub

Top guest favorite
A single-story cottage features a red metal roof and light-colored exterior. Situated on a spacious lawn, the front porch is accessorized with white railings. The backdrop showcases rolling green hills and a distant mountain under a clear sky.
Cottage in Luray
4.97 out of 5 average rating, 381 reviews

Holly Tree Retreat Located In Beautiful Luray, VA.

Top guest favorite
The living room features a dark blue accent wall, a lighted ceiling fan, and a white-brick fireplace as a focal point. Two sofas are arranged for comfort, complemented by decorative pillows. Natural light streams through multiple windows, enhancing the open and inviting space.
Cottage in Berkeley Springs
4.96 out of 5 average rating, 179 reviews

Cozy Cottage in the heart of Berkeley Springs WV

Superhost
A serene view of the cottage set beside a gently flowing creek. Lush greenery surrounds the property, with a large tree in the foreground. The home is partially visible, featuring a star decoration on the facade and a covered porch overlooking the landscape.
Cottage in Luray
4.84 out of 5 average rating, 118 reviews

Creekside Cottage at Shenandoah

Top guest favorite
The exterior of a single-story cottage showcases a welcoming entrance with a wooden ramp leading to the front door. Lush green grass and light landscaping surround the home, which is framed by tall trees. A covered area is visible at the side of the structure.
Cottage in Fairfield
4.97 out of 5 average rating, 119 reviews

Mom's Cottage

Superhost
The exterior of a charming brown cottage is surrounded by lush green foliage. A spacious wooden deck with railing leads to the entrance, which is framed by white French doors. A red shade sail is positioned above the deck, adding a pop of color.
Cottage in Berkeley Springs
4.95 out of 5 average rating, 458 reviews

Hidden Hill - Cozy Downtown Cottage with Hot Tub!!

Superhost
The exterior of the house showcases a modern design with a red facade and multiple levels. Spacious decks are present, providing areas to relax and enjoy nature. Large windows reflect the surrounding greenery, while trees create a tranquil environment.
Cottage in Front Royal
4.94 out of 5 average rating, 100 reviews

Country Elegance overlooking the Shenandoah River

Top guest favorite
A fire pit surrounded by multiple Adirondack chairs sits on a gravel surface. The backyard vegetation includes trees and shrubs, while a grey house with lit windows is visible in the background, complementing the serene outdoor setting.
Cottage in Wardensville
4.99 out of 5 average rating, 127 reviews

Cottage at Lost River Ridge

Guest favorite
A hot tub is positioned at the edge of the deck, with gentle water cascading over its sides. Purple lights illuminate the water, creating a tranquil ambiance. The backdrop features trees and distant mountains against a softly lit sky, suggesting a peaceful evening landscape.
Cottage in Luray
4.99 out of 5 average rating, 195 reviews

Mountain Meadow Cottage w/ Hot tub & Mt Views

Pet-friendly cottage rentals

Guest favorite
The image presents a bird's-eye view of a bungalow surrounded by lush greenery and vibrant flowering trees. A well-maintained driveway leads to the home, enhancing the peaceful setting in a wooded area. The property is situated amidst rolling hills, offering a serene atmosphere.
Cottage in Leesburg
4.97 out of 5 average rating, 103 reviews

Hilltop Cottage @ Shiloh

Guest favorite
The exterior of the cottage is captured from an angle, showcasing its charming two-story structure with a sloped metal roof. Lush green hills rise in the background, while a grassy area with trees surrounds the property, providing a serene natural setting.
Cottage in Mathias
4.93 out of 5 average rating, 197 reviews

Lost River Dog/Bike friendly 3BR/2BA-large deck

Superhost
An inviting front porch features comfortable seating arrangements alongside potted plants. A walkway made of stone leads to the entrance, framed by lush greenery and decorative elements. The soft lighting creates a welcoming atmosphere for relaxation.
Cottage in Marshall
4.89 out of 5 average rating, 109 reviews

Garden Oasis outdoor entertainment at FrogPointe.

Guest favorite
A spacious covered deck is depicted, featuring two lounge chairs and a small table. A long picnic table offers seating for multiple guests. Expansive views of a grassy area and trees can be seen beyond the railing, framed by scenic mountain hills in the background.
Cottage in Luray
4.93 out of 5 average rating, 132 reviews

Sweet Scenes Cottage

Top guest favorite
A sunny view of a quaint cottage with a red and green roof, surrounded by lush green fields. Neat rows of vegetables are visible in the foreground, with trees providing shade nearby. The scenic mountains form a backdrop, enhancing the rural charm of the property.
Cottage in Etlan
4.98 out of 5 average rating, 191 reviews

Amy's Place

Top guest favorite
A spacious room features a custom wood bed with light bedding and natural elements. The wooden ceiling beams provide an open feel, while soft light enters through multiple windows. A cozy sitting area includes a couch and side tables, enhancing the peaceful ambiance.
Cottage in Leesburg
4.92 out of 5 average rating, 442 reviews

Romantic Stone Cottage Circa 1869-75 acres to Hike

Guest favorite
An outdoor dining table is set with plates, glasses, and a bottle of wine. A vibrant fruit bowl is at the center, surrounded by colorful napkins. A black and white dog is resting beneath the table, while greenery and the stone cabin are visible in the background.
Cottage in Purcellville
4.84 out of 5 average rating, 221 reviews

Stone School House - Minutes from Harper's Ferry

Guest favorite
A charming cape-style home is set amidst lush greenery, featuring a welcoming porch with seating. The structure showcases a sloped roof and multiple windows, allowing natural light to fill the interior. A paved path leads to the front entrance, enhancing accessibility.
Cottage in Middletown
4.9 out of 5 average rating, 287 reviews

Charming "Cream of the Crop" Cape ~❤️of Middletown

Private cottage rentals

Guest favorite
A charming cottage exterior is showcased with two large, arch-top windows above a spacious garage. The garage doors feature red barn-style accents, framed by neatly landscaped gardens and gravel pathways. A wooden staircase leads to an upper-level entry, set against a backdrop of lush greenery.
Cottage in Round Hill Village
4.92 out of 5 average rating, 198 reviews

Best Countryside Retreat & No Cleaning Fees EVER

Guest favorite
A welcoming living area features a comfortable gray sofa with colorful cushions, accompanied by a plush armchair. Natural light filters through large windows, offering views of the river. A decorative rug adds warmth, while a coffee table and a cozy chair complete the space.
Cottage in Shepherdstown
4.91 out of 5 average rating, 285 reviews

Riverfront Cottage in Shepherdstown, WV

Guest favorite
The exterior of a two-story house is presented, featuring a light grey facade with detailed trim and a prominent chimney. An American flag is displayed on the porch, which includes decorative railings. A snow-covered yard surrounds the house, accentuated by mature trees.
Cottage in Winchester
4.95 out of 5 average rating, 37 reviews

Modern 3BR country farmhouse

Guest favorite
The kitchen features modern cabinetry and a central wooden island with high stools. A large window allows natural light to fill the space, complemented by stylish pendant lighting. Appliances include a black refrigerator, stove, and sink, creating a functional and inviting area for meal preparation.
Cottage in Madison
4.92 out of 5 average rating, 147 reviews

Creekside Cottage Near Hiking

Guest favorite
The cottage features a charming exterior with a red metal roof and a welcoming porch, supported by white columns. A large tree provides shade, and potted plants are positioned on the porch. The surrounding lawn is well-kept, adding to the inviting appearance of the home.
Cottage in Waterford
4.96 out of 5 average rating, 135 reviews

Wheatland Spring Farm + Brewery Cottage House

Top guest favorite
A charming roadside cottage is presented, featuring a stone exterior with large windows. The metal roof reflects natural light, while surrounding greenery complements the structure. A gravel area is visible in front, providing convenient access to the entrance and nearby steps.
Cottage in Elkton
4.9 out of 5 average rating, 202 reviews

Bridge House, 10 min to Shen. Nat'l. Park

Guest favorite
A cozy living area features a vibrant orange couch adorned with green and patterned pillows. A purple accent chair complements the space, which is illuminated by natural light from a window. A decorative lamp and wall clock add character, while a staircase leads to the upper level.
Cottage in Winchester
4.89 out of 5 average rating, 45 reviews

House/cottage 2bed, Private yard, walk to Oldtown

Superhost
A gravel road stretches through a forested area, bordered by trees displaying vibrant autumn foliage in shades of orange, red, and green. Telephone poles line the side of the road, adding an element of scale to the serene mountain landscape.
Cottage in Winchester
4.88 out of 5 average rating, 32 reviews

Secluded Mountain Top Retreat | Stunning Views

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