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Cottage vacation rentals in Winchester

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Vacation rentals for every style

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Popular amenities for Winchester cottage rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Cottage rentals with a hot tub

Superhost
The exterior of the cottage is surrounded by tall trees, featuring a spacious wooden deck illuminated by string lights. A jacuzzi is positioned on the right side, while outdoor seating areas are visible. The inviting atmosphere is complemented by the soothing natural surroundings.
Cottage in Harpers Ferry
4.85 out of 5 average rating, 192 reviews

Wild & Cozy | Harpers Ferry Mountain Escape

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, 376 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
4.95 out of 5 average rating, 161 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
4.86 out of 5 average rating, 112 reviews

Creekside Cottage at Shenandoah

Top guest favorite
A tranquil pool area is surrounded by lush greenery and vibrant flowers. The charming cottage, featuring a welcoming porch, is visible in the background under a bright blue sky. The clear water of the pool reflects the sunlight, inviting relaxation.
Cottage in Hamilton
4.95 out of 5 average rating, 385 reviews

*Cottage @ Firefly Cellars* VA Wine Country escape

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
4.98 out of 5 average rating, 105 reviews

Mom's Cottage

Guest favorite
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, 448 reviews

Hidden Hill - Cozy Downtown Cottage with Hot Tub!!

Top 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, 190 reviews

Mountain Meadow Cottage w/ Hot tub & Mt Views

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Pet-friendly cottage rentals

Top guest favorite
The exterior of the home is shown, featuring a modern design with a sloped roof and large windows. A wooden deck extends into the yard, framed by greenery. The area is well-maintained, with a lawn leading up to the house, providing a welcoming entrance.
Cottage in New Market
4.96 out of 5 average rating, 137 reviews

The willow tree house

Top 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, 193 reviews

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

Top guest favorite
A charming cottage features a red and yellow exterior with a welcoming front porch and steps leading to a bright red door. Vibrant yellow daffodils bloom in the foreground, adding a touch of spring to the serene country setting.
Cottage in Etlan
4.98 out of 5 average rating, 187 reviews

Amy's Place

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
4.94 out of 5 average rating, 119 reviews

Sweet Scenes Cottage

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, 216 reviews

Stone School House - Minutes from Harper's Ferry

Top guest favorite
A charming exterior of a yellow cottage is framed by lush greenery and colorful flower beds. The entrance features a decorative wrought iron gate adorned with a seasonal wreath, inviting guests into a serene country setting.
Cottage in Middleburg
4.94 out of 5 average rating, 135 reviews

English Cottage

Guest favorite
The cottage exterior features a light-colored facade complemented by dark trim. A flag gently waves in the breeze, and surrounding lush greenery contributes to the tranquil setting. A gravel pathway leads to the entrance, creating an inviting access point.
Cottage in Hyndman
4.99 out of 5 average rating, 108 reviews

Mountain Oasis Cottage

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, 283 reviews

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

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Private cottage rentals

Guest favorite
A quaint building with a light grey exterior is accented by turquoise trim and windows, showcasing a charming entryway with double doors. Lush greenery is positioned in front, complementing the urban streetscape. Nearby structures reflect the historic character of the area.
Cottage in Sperryville
4.96 out of 5 average rating, 393 reviews

The River Cottage: Main Street Sperryville, VA

Top guest favorite
The cottage is nestled among vibrant autumn foliage along the riverfront. A rock cliff rises behind it, while a winding path leads to the house, which is surrounded by a mix of colorful trees. The serene river can be seen nearby.
Cottage in Green Spring
4.98 out of 5 average rating, 97 reviews

The River House

Top guest favorite
A charming cottage is framed by a mature tree with autumn leaves. The exterior is painted in calming blue and white, featuring a welcoming porch supported by columns. A gravel path leads to the entrance, surrounded by vibrant greenery and fallen leaves.
Cottage in Aldie
4.97 out of 5 average rating, 117 reviews

Status House at the Little River Inn

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 cottage is framed by neatly trimmed hedges, leading to a welcoming front entrance. The light green exterior is complemented by white railings and a warm wooden door. A manicured lawn features round bushes, enhancing the quaint and charming appearance of the home.
Cottage in Harpers Ferry
4.93 out of 5 average rating, 382 reviews

Carrot Top Cottage surrounded by National Park

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
4.95 out of 5 average rating, 133 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, 194 reviews

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

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
4.9 out of 5 average rating, 29 reviews

Secluded Mountain Top Retreat | Stunning Views

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