
Cottage vacation rentals in Winchester
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Top-rated cottage rentals in Winchester
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Popular amenities for Winchester cottage rentals
Cottage rentals with a hot tub

Wild & Cozy | Harpers Ferry Mountain Escape
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.

Holly Tree Retreat Located In Beautiful Luray, VA.
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!

Cozy Cottage in the heart of Berkeley Springs WV
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 ❤️

Creekside Cottage at Shenandoah
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.

Vibrant Cottage | Hot Tub | Pets | Shenandoah NP
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!

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

Hidden Hill - Cozy Downtown Cottage with Hot Tub!!
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!

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

Cozytown Cottage/Whitetail Ski Resort/Hagerstown
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.

Robins Nest
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!

The willow tree house
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!

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

Sweet Scenes Cottage
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.

Lockley Cottage at Historic Perry Farm
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.

Amy's Place
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.

Stone School House - Minutes from Harper's Ferry
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

Charming riverside cottage-firepit, yard, Pets
Everything was perfect. Would definitely stay again!

Cottage w/EV Charger + Trout Stream
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.

Purple Kangaroo Cottages
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.

Snickers Gap Cottage
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!

Spectacular Mountain Retreat
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!

NEW * The Getaway Cottage at Rocky Marsh Farm
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!

Wheatland Spring Farm + Brewery Cottage House
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.

Milton Valley Cottage on Historic Estate Farm
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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