Cottage holiday rentals in Winchester

Our stay was exceptional and exactly what we were looking for. The breathtaking view of the mountains in the background was truly stunning. The home felt peaceful, warm, and very clean—perfect for a relaxing getaway. It was also conveniently located close to the main road. We had everything we needed in this charming, well-equipped home. We’ll definitely be returning!

We had a great stay at Heather Mary's place! The location is phenomenal for exploring everything Berkeley Springs has to offer - we were able to leave our car in the driveway and walk to everything. The house has everything you could possibly need, was incredibly well organized, and was spacious enough for our party of 5 (1 grandma, 2 parents, and 2 kids). Our kids already keep asking when we can "go back to the cottage"!

This house is a gem! The location allows for privacy and great hikes while still being close enough to Luray and Sperryville for restaurants and activities. I’d absolutely return. The house was clean and as advertised. The hosts were very responsive! The creek on the property was such a lovely feature. The only note I’d like to make is the area must have had a lot of rain right before our visit. To access the house, you drive over a very small concrete bridge over the creek. When we arrived the water was over the bridge, and probably 5 or so inches at its deepest. We had a sedan and weren’t comfortable driving over. Jerry quickly gave us alternate directions, so all in all in worked out and provided some excitement :). But if there’s been a lot of rain and you have a low car, be aware!

A very nice place in a private setting. Had all the essentials. The pool and hot tub were especially nice. Loved the wine at the winery also🍷 Andrea was helpful and responsive with all questions. Highly recommend staying!

Beautiful location, very peaceful, and very responsive owners! I highly recommend this location! Very easy access to Gettysburg and surrounding attractions. This unit exceeded expectations.

A quirky and fun experience. James home gives you an updated kitchen and bathroom with a quaint old house feel. The beds are comfortable and clean. We enjoyed the hot tub in the evenings and the short walk to town. The driveway was steep and we appreciated the ability to park in the lower spot also available. The little details like a HDMI in a basket and all the cleaning supplies was great. Having three small bedrooms for our group at this price was perfect.

This was our third visit and we have loved being there every time. We travel from Florida to Pennsylvania in the spring and fall and this is the only place we stay two overnights because it’s such a lovely place to be. Chris is as nice and welcoming as anyone could possibly be. Everything you need is there. The pool and hot tub are amazing. The gardens and bird life are like nowhere else. The Graves Mill Trail, about 25 minutes away is a beautiful place to hike. And Chris introduced us last year to old house Vineyards where you can have amazing brick oven pizza on Mondays. We will return again and again!

Amazing, immaculate property, peaceful setting, thoughtful hosts! The mountain cottage exceeded our expectations. The home looks exactly like the photos and has all of the amenities. No surprises, no builders grade junky stuff - granite countertops, new appliances, upgraded cabinetry with soft close drawers, large tiled shower with built in bench seat, lighted closets, working blinds, no step access into and through out the home. You walk in to find a welcome basket of water and snacks with a card from hosts. There are books for appliances if needed and a book that provides needed information and options for dining and recreation. Feels private! We had beautiful bird song in the mornings, saw a deer at the end of the driveway and many deer on the roads to the cottage. There is a fishing pond within a half mile and the North fork of the Shenandoah is close by. We enjoyed the peace, nature, cruising Skyline Drive and time with our family. Koren & Bill were super & provided tons of extra

This amazingly cozy farmhouse was just the vibe we were looking for. Beautiful outdoor seating (screened-in porch, deck overlooking the vineyards, and lounge chair by the pool) made it easy to breathe in the fresh air. Beds were comfortable and water pressure was great! The outside deck with Solostove was perfect for the chilly evenings. We enjoyed light snacks and wine at Muse Vineyards, which was lovely and got to meet Sally! We ventured into town for some local eats. Can’t say enough good things about Woodstock Cafe’s breakfast. We enjoyed a sweet treat at Sugar Creek and had a lovely walk down the street at Seven Bends. If you’re looking for a place to unwind, look no further!

Patti’s cottage is a lovely, affordable, quiet place near some great American historical sites. We wish we had had more time to spend there!

We have stayed at this home many times because- a.) They have a fenced-in backyard so it is nice to be able to let out our dogs without worrying about them running away and b.) we love hiking at Lost River State Park which is just a short 12 minute ride to from the house, and c. It is a beautiful quaint home- very peaceful and has all the amenities we need.

This place is very quiet and peaceful and the access to the river is wonderful. The porch is great for relaxing! Me and my dogs had a wonderful time. It is not close to just run out for food or things you forgot, but that was what I was looking for. I would definitely stay again! It is obvious that Valerie is doing this because she wants to (not just for the money). She provides plenty of amenities and supplies and thinks about the little things that make a difference. She was also very reasonable and friendly. The cottage is lovely!

Thoroughly enjoyed the stay! The house was very clean, nicely decorated, and well stocked with plenty of cookware, games, books, and extra linens and blankets. The area was so beautiful, with rolling hills, mountain views, farm scenery, fragrant fresh air, and spectacular star views at night. My city dog absolutely loved getting to run and play in the well maintained large fenced in yard! Billy and Margit provided dog treats, yard toys, extra leash, water/food bowls, dog towels, pet proof trash lids, and sofa cover indicating that dogs are allowed on the sofa. My dog was so welcomed! Billy and Margit provided whole bean coffee that they freshly roasted, and a bean grinder. The coffee was amazing! Really enjoyed drinking the coffee in the mornings while listening to the chorus of birds chirping. Hiked at Whiteoak Canyon Falls, less than 20 minutes from Amy's place. The early check in and late check out times were another generous touch that was enjoyed. Would love to stay again!

The cottage was amazing, communication and cleanliness was top notch from the host as well. It was a lovely time, and if I find myself in the area again I would love to stay here yet again. No complaints, perfect experience. Thank you :)

Loved having our son at Sandi’s for our special family weekend

I think I am officially a regular at this Cottage LOL Everytime I am looking for somewhere to relax and unwind this is the place that immediately comes to mind. It is beautiful and the host always makes everything so easy. It is always stress-free from the moment I book through when I checkout. I am already thinking about when I can get there again :) If you want privacy, the beauty of nature, and a all out relaxing experience, I would give this place a try. 5 stars all day !!

This was a great, peaceful place to stay and Morgan was a great host. The location is nice and quiet, with an amazing bakery and a couple restaurants around the corner, and walkable to town. Morgan was a great host, went the extra mile to make sure we were right at home and gave lots of great recommendations.

We had a great time. The cottage is lovely, very well decorated, comfortable, it felt like home. We enjoyed the deck and the bonfire by the water. We would have loved to use the kayak and canoe but the weather was not amenable to it unfortunately. Julie was proactive and shared detailed instructions and local recommendations. She was responsive when I asked questions ahead of our arrival. I would totally recommend for a couple or family and would definitely come back.

No surprises as the home matched the pictures & description quite well. Driveway was easy to find but a bit tricky entering & exiting but offering plenty of parking & privacy too. Outside setting offers plenty of opportunity for cooking, recreation & relaxation too.

This cottage was a solid spot to stay while traveling through the area. Bonnie is a kind & responsive host. Recommended!

Super cute place to stay. Had everything we needed. The host was communicative and prepared!

40 South Parrish Lane is a beautiful old two-story house on a secluded street within walking distance to the best that Winchester has to offer. My Winchester host pointed out to me that the house right across from the front door on Wolfe Street was built from the remnants of a colonial fort, so you have history right out the front door, which is nice. Wendy made everything as easy as possible to move in and the house included all the necessary amenities for a comfortable stay, including a dedicated parking space. This is our second stay here and I look forward to more!

Only needs a weekend spot to attend a wedding in Winchester. The house is way up on the mountain, so going in/out was a bear. Pretty much get what you need before heading up. The morning view across the valley is beautiful. The house had everything I needed. Bring bug spray if you’re going to go walk around.

10/10 stay. It exceeded our expectations and was even more charming than the photos. The space was exceptionally clean, spacious, and beautifully maintained. The location was ideal—right down the road from Stone Tower Winery and close to downtown Leesburg. The only minor suggestion would be to provide a few hangers for added convenience.