Cottage vacation rentals in Winchester

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Popular amenities for Winchester cottage rentals

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, 184 reviews

Wild & Cozy | Harpers Ferry Mountain Escape

KevinRating, 5 stars1 week ago
Good quiet place to stay near Harper’s Ferry. Place was clean, hot tub was nice we were able to watch deer next door and across the street hang out and graze. Everything was in place and clean. Beds were soft and comfortable. The only issue that I have is the rocks that line the driveway especially when turning out of the driveway will catch lower vehicles and cars it caused a little damage to my wife’s car and be careful where you park there is an oak tree with dead and rotting limbs that need to be trimmed that are right above the area where cars would park if you have more than one car. If I were to ever come back to Harper’s Ferry I would definitely stay there again.
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, 369 reviews

Holly Tree Retreat Located In Beautiful Luray, VA.

MatthewRating, 5 stars4 days ago
From the first step inside, felt right at home. Fully stocked kitchen and the place was spotless. Definitely a 10 out of 10. Was a bonus having such an amazing view of the mountains and cows. Do yourself a favor and book this location!
Top guest favorite
The exterior of a charming cottage is framed by a picket fence, lush greenery, and flowering plants. The soft colors of the house complement its quaint architecture, and a pathway leads to the entrance. Sunlight filters through the trees, creating a warm ambiance.
Cottage in Berkeley Springs
4.95 out of 5 average rating, 144 reviews

Cozy Cottage in the heart of Berkeley Springs WV

GabriellaRating, 5 stars2 weeks ago
I can’t say enough good things about this place. It’s walkable distance to downtown. The backyard is amazing and huge. Hot tub was great. The way she catered to the dogs was actually what won us over… a dog bed, towels, little treats. As dog lovers, you don’t see that much anymore with Airbnb but this place had it all don’t hesitate! There’s nowhere where we’re staying other than this when we come to Berkeley ❤️
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, 102 reviews

Creekside Cottage at Shenandoah

LuciaRating, 5 stars1 month ago
The place was cute, well decorated and spacious. The hot tub was wonderful after many strenuous hikes in Shenandoah. Kids enjoyed the foosball and air hockey, and s'mores over the solo stove. Beds were comfy.
Guest favorite
An inviting outdoor deck features a luxurious hot tub surrounded by trees, creating a serene retreat. Inside, a vibrant bathroom showcases floral wallpaper and elegant fixtures. A cozy bedroom is highlighted by bright orange walls, while the living area features a comfortable blue couch and greenery.
Cottage in Stanley
4.87 out of 5 average rating, 142 reviews

Vibrant Cottage | Hot Tub | Pets | Shenandoah NP

KelseyRating, 5 stars3 days ago
We had a great stay! Olivia was an excellent host. The place had the perfect vibe for a girls weekend and birthday celebration. The only issue we had was needing to catch 2 wasps that were in the house, but we were able to take care of that without issue. It was so nice to have so many towels and amenities that you don’t normally have in an Airbnb. Thanks again!
Guest favorite
A hot tub is positioned under a covered porch, featuring bubbling water and a soothing green light. In the background, the tranquil Cacapon River is visible, surrounded by autumn foliage. A fire pit can be seen nearby, contributing to the relaxing outdoor ambiance.
Cottage in Capon Bridge
4.97 out of 5 average rating, 181 reviews

The 3R's River, Relaxation, Retreat + hot tub

SantiagoRating, 5 stars3 days ago
Darrel went above and beyond in making sure we had a great stay! He was kind, responsive and overall a superstar. We had an incredibly relaxing time and enjoyed the peace his listing had to offer. An EXCELLENT way to spend some time away from the city. I hope to come back soon! Couldn't be happier with Darrel's service!
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, 442 reviews

Hidden Hill - Cozy Downtown Cottage with Hot Tub!!

MicheleRating, 5 stars1 week ago
So comfy and clean! Stayed for a few nights with some friends to forget about life for awhile. Easy walk to town, awesome hot tub on the deck and the grill works great. We left recharged and will def be back!
Top guest favorite
A hot tub is situated in the foreground, filled with clear blue water. Nearby, two wine glasses sit beside a bottle of white wine, with a soft glow from string lights illuminating the grapevine arbor in the background. The scene captures an inviting outdoor atmosphere.
Cottage in Boyce
4.98 out of 5 average rating, 106 reviews

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

MorganRating, 5 stars1 month ago
Had a lovely weekend in VA at Dollys place, and at a really great price. The house was very charming, though very clearly older, but everything about it was within what I consider normal expectations with an older home out in this area. We really enjoyed spending time in the backyard, which was fenced in and had a charming fire pit and table. Our dogs and kids alike took advantage of the ample room for activities back there! Dolly and her husband were very responsive and easy to reach and talk to. Would recommend for a weekend getaway!

Pet-friendly cottage rentals

Top guest favorite
Cottage in Greencastle
4.96 out of 5 average rating, 102 reviews

Cozytown Cottage/Whitetail Ski Resort/Hagerstown

PaulaRating, 5 stars5 months ago
I love the peace and tranquillity at Jens place! I brought my teenage grandson along for a trip to the country and some time for us to connect away from it all. We spent time doing one of the puzzles at the house and relaxing. It was amazing to see him let down the “teenage edge” in the cozy atmosphere her cottage provides. While out and about one evening we stumbled upon what is an annual Christmas Tree lighting in the town square of Greencastle. What an experience! If you need to unwind and let go of the crazy world, look no further. Jen is an excellent host and her getaway will remain at the top of my list.
Superhost
Cottage in Hamilton
4.87 out of 5 average rating, 397 reviews

Robins Nest

JordanRating, 5 stars4 days ago
We had a wonderful stay! The property was a great deal and exactly what we were looking for — peaceful, private, and secluded without being too far from everything. The location was perfect for a relaxing getaway. The host was incredibly friendly, responsive, and proactive, which made the whole experience even better. The listing description was accurate, everything was spotlessly clean, the AC worked perfectly, and check-in was super easy. We would absolutely stay here again and highly recommend it to anyone looking for a quiet, comfortable place to stay!
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
4.95 out of 5 average rating, 131 reviews

The willow tree house

GenineRating, 5 stars1 week ago
Susan’s place was full of thoughtful touches like wireless phone chargers, a basket of various charging cables and even some Easter treats and a smores “kit” to use at the fire pit. Perfectly situated for a visit to Luray Caverns and Shenandoah National Park. Great hot showers, fluffy towels and comfy beds. Well equipped kitchen and outdoor deck area for outside dining, with gas grill were appreciated. We thoroughly enjoyed our stay!
Top guest favorite
Cottage in Mathias
4.93 out of 5 average rating, 190 reviews

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

ChrisRating, 5 stars1 month ago
The cottage/house was as described and wonderful. The location was perfect to explore the many nearby hiking and outdoors options. The property itself has an excellent view. The fenced in yard was convenient for our dog. Inside everything was clean and well-maintained. There were a number of nice touches to make you feel at home. There was everything one would need and more. I needed to work remotely one day and the WiFi was very reliable. Great stay!
Guest favorite
Cottage in Luray
4.94 out of 5 average rating, 110 reviews

Sweet Scenes Cottage

TaylorRating, 5 stars3 days ago
We had a great stay! This is the CLEANEST Airbnb I’ve ever been to. Very beautiful area and scenery, and perfect distance from Luray Caverns and Shenandoah National Park. Valerie was very responsive and helpful when needed. The only suggestion would be to take a car that can handle a somewhat steep and rocky driveway.
Top guest favorite
The cottage is nestled among greenery, with trees lining a gentle slope leading to the entrance. A gravel driveway is visible, leading up to the building, which features a white exterior and a steep roof. The surrounding area appears calm and spacious.
Cottage in Winchester
4.92 out of 5 average rating, 150 reviews

Lockley Cottage at Historic Perry Farm

John ArthurRating, 5 stars3 days ago
It was a very nice place. The fire pit was great. We got to sit around the first night. A cottage was very quaint and clean. Will use it again and lots of extra things for us to use when we ran out of like the water thank you, Michael.
Top guest favorite
A modern cottage is enveloped in a blanket of fresh snow, with a red and cream exterior. The front porch features steps leading to the entrance. Surrounding trees and shrubs are covered in white snow, creating a serene winter landscape.
Cottage in Etlan
4.98 out of 5 average rating, 183 reviews

Amy's Place

DixieRating, 5 stars3 days ago
This was our third time staying here and it is always wonderful. The property itself is beautiful and peaceful. Our dog loves the fenced in yard and dog amenities (water bowl, poop bags). The coffee that Billy provides is so good and much appreciated. Phone coverage can be spotty (the provide wifi works great), so the recommendations and directions provided in the Welcome binder are very useful. Love it here & hoping we will be able to visit again soon.
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
4.83 out of 5 average rating, 209 reviews

Stone School House - Minutes from Harper's Ferry

KatieRating, 5 stars2 weeks ago
Mark’s place was perfect! It was just what our family of four needed for a last-minute getaway. The house is beautiful and unique and we appreciated the basket of goodies. Location’s convenient to Harper’s Ferry, Charles Town, Frederick, Shepherdstown. My husband loved the sauna! Mark was super kind and responsive. We had a wonderful stay!

Private cottage rentals

Top guest favorite
The tranquil river flows through a lush, green landscape, bordered by trees and shrubs. Smooth stones and fallen branches are visible in the water, reflecting the surrounding foliage. The scene captures a serene atmosphere, perfect for relaxation by the riverside.
Cottage in Bridgewater
5 out of 5 average rating, 18 reviews

Charming riverside cottage-firepit, yard, Pets

CoryRating, 5 stars2 weeks ago
Everything was perfect. Would definitely stay again!
Guest favorite
A firepit surrounded by black metal chairs is situated in a grassy area, with the cottage visible in the background. The home features a covered porch with multiple windows, and trees provide shade around the property, set against a backdrop of distant hills.
Cottage in Star Tannery
5 out of 5 average rating, 9 reviews

Cottage w/EV Charger + Trout Stream

BrianRating, 5 stars3 months ago
WE had a lovely weekend stay at Bret's place. It was a cold, snowy trip but we still took long walks up the road and watched the snow fall with a roaring fire. Bret did a good job reaching out to make sure everything went smoothly. The kitchen is quite small but has everything you need to cook some good meals. Would be a cool place to visit in warmer months with the lovely creek right outside the front door! Do note the water is pretty smelly so you can do everything with it but drink, but there is plenty of drinking water provided.
Top guest favorite
The cottage exterior features a charming design with a covered front porch supported by wooden pillars. Potted plants adorn the steps, while large windows provide glimpses of the inviting interior. A gravel driveway leads to the entrance, surrounded by greenery.
Cottage in Mercersburg
5 out of 5 average rating, 31 reviews

Purple Kangaroo Cottages

SamRating, 5 stars2 months ago
We had a lovely stay at this cottage. Very clean and nice amenities. 25 minutes from White tail and 15 minutes from downtown Mercersburg. Super friendly hosts.
Top guest favorite
A charming historic cottage is surrounded by lush greenery, featuring a welcoming deck with seating and a fire pit area. The soft hues of the house contrast with the natural landscape, enhancing the outdoor space's appeal. Large trees provide shade, creating a tranquil atmosphere.
Cottage in Bluemont
5 out of 5 average rating, 121 reviews

Snickers Gap Cottage

SuzanneRating, 5 stars3 days ago
I’d give it 6 stars if I could! Over the top wonderful weekend. The chocolate chip cookies were delicious! The charm of this cozy cottage was perfect. And no over the top rules! Everything made sense. Truly enjoyed our stay. And so many beautiful vineyards in the area!
Top guest favorite
A wooden dock extends over a serene pond, surrounded by lush greenery. A rustic bench crafted from logs is positioned beside the water. An outdoor fire pit with a metal frame is located nearby, offering a cozy spot for gatherings.
Cottage in Madison
4.94 out of 5 average rating, 87 reviews

Spectacular Mountain Retreat

BriannaRating, 5 stars1 month ago
This place was perfect for our weekend getaway. The cabin was spacious, clean and comfortable, plus close to so many hikes in Shenandoah national park. The hosts really thought of everything, from coffee to cookware and even having the fire pit filled with brush so we could easily have a fire. The location is nestled in the mountainside and is SO quiet, coffee overlooking the mountains and hills with nothing but the sounds of nature was therapeutic. We are already talking about planning our next trip back!
Top guest favorite
The exterior showcases a modern cottage with a stone facade and dark siding, framed by wood pillars. Two inviting entry doors provide access, with large windows above. Flanking the doors, two comfortable chairs are positioned, each accompanied by planters, adding a welcoming charm to the entrance.
Cottage in Shepherdstown
4.97 out of 5 average rating, 151 reviews

NEW * The Getaway Cottage at Rocky Marsh Farm

AverieRating, 5 stars1 week ago
The house and property were beautiful, the house was super clean and felt cozy even though it’s new! Check in was really easy and Zeb was quick to respond. Loved being able to sit outside at the fire pit! It was a 10 minute drive to Shepardstown and 30 minutes to Harper’s Ferry so we were able to explore and go to some of the places that Zeb recommended! Highly recommend!
Guest favorite
An aerial view showcases expansive green fields surrounding the cottage and farm. A red-roofed building is prominently featured, with outdoor seating visible nearby. The landscape includes trees and farm structures, with distant hills providing a scenic backdrop under a partly cloudy sky.
Cottage in Waterford
4.97 out of 5 average rating, 126 reviews

Wheatland Spring Farm + Brewery Cottage House

RachelRating, 5 stars2 weeks ago
My husband and I decided on a last-minute weekend getaway, and Bonnie was so accommodating with this gorgeous little cottage! The space was clean, comfortable, thoughtfully furnished, and the kitchen had everything we needed. The historical details were one-of-a-kind. Absolutely loved the quiet setting on the family farm and close proximity to the brewery, too! I would highly recommend this space - it's the perfect location for exploring wine country.
Top guest favorite
Cottage in Berryville
4.98 out of 5 average rating, 106 reviews

Milton Valley Cottage on Historic Estate Farm

LauraRating, 5 stars1 week ago
Kelly’s home was so charming and peaceful! We appreciated all the small touches you don’t find in your average bnb. We loved sitting on the porch and watching the cows over coffee. We liked being near to town but off the beaten path. Will return!

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