House vacation rentals in Winchester

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Popular amenities for Winchester house rentals

House rentals with free parking

Guest favorite
Home in Warrenton
4.96 out of 5 average rating, 23 reviews

Opal house

DarrellRating, 5 stars3 weeks ago
This home worked perfectly for our companies 3 week stay while there for work. It was clean. AC and heat worked really well. Large washer and dryer for when laundry was needed.
Top guest favorite
Home in McGaheysville
4.97 out of 5 average rating, 198 reviews

Grasshopper Cottage

SethRating, 5 stars2 weeks ago
This was a great place for our family of 5. Plenty of living and sleeping space. Conveniently located to a lot of great places to explore.
Guest favorite
Home in Fredericksburg
4.88 out of 5 average rating, 357 reviews

Home away from home

ShaynaRating, 5 stars1 month ago
The pictures don’t do this place justice. Plenty of room for our family of 5.
Guest favorite
Home in Fredericksburg
4.9 out of 5 average rating, 124 reviews

Gift House: Quiet, self check in & free Parking

CarolRating, 5 stars1 month ago
Joseph's place, THE GIFT HOUSE, is conveniently located close to I-95, the shopping center, and the historic district. The house is very comfortable, located in the lovely neighborhood, and equipped with just about anything you could need! Joseph is a wonderful host! I enjoyed my return stay to the house.
Top guest favorite
Home in Downtown Frederick
4.99 out of 5 average rating, 115 reviews

Vintage Modern Rowhome – So Close to Everything!

JacksonRating, 5 stars1 week ago
We had a great time here! It’s a beautiful, well-appointed space and a perfect base for exploring Frederick and the surrounding area. Would definitely recommend and was perfect for our weekend getaway.
Guest favorite
Home in Inwood
4.88 out of 5 average rating, 633 reviews

Arden House, Inwood WV

JuliaRating, 5 stars1 week ago
Mary is an absolute wonderful host! Her space is full of everything you could want/need for an overnight stay! Mary communicated wonderfully and clear. The space was easy to find, with the clear directions and was in a peaceful area. For our little family of 3, traveling through on our spring vacation, Mary's space was perfect for us and the price point was a big part of that too! If you are debating on booking, you absolutely should!
Guest favorite
Home in Dumfries
4.7 out of 5 average rating, 118 reviews

Private Basement/Apartment with Separate Entry

JessicaRating, 5 stars2 weeks ago
Quiet neighborhood, beautiful area. It's in a community, not close to restaurant's or activities. It's a great place to relax at night. Beds were comfy, great shower and kitchen area. Very spacious. Truly appreciated the accommodations on our late check in Can hear the family upstairs as mentioned but Hashim and family were quick to quiet down the kids in the morning, so not a problem. Would happily stay here again.
Guest favorite
Home in Front Royal
4.96 out of 5 average rating, 114 reviews

Cozy house in Shenandoah N.P. City of Front Royal

CarolRating, 5 stars2 weeks ago
Kae's place was just as she described and very comfortable and clean. It was a great location - quiet neighborhood yet a short drive to shopping, restaurants and Shenandoah Park.

House rentals with a hot tub

Top guest favorite
Home in Berkeley Springs
4.98 out of 5 average rating, 329 reviews

Abby's Lookout - Raised Retreat w/Hot Tub & WiFi

ChrissyRating, 5 stars3 weeks ago
Everything was amazing! The home was clean and comfortable. Anything we could possibly need was provided. Gina was quick to respond to questions and the location was fabulous. We’ll absolutely be back!
Top guest favorite
Home in Lost City
5 out of 5 average rating, 132 reviews

Mountain Retreat-Stunning Views/Pool/Hot tub

YaelRating, 5 stars1 month ago
We had an incredibly relaxing, peaceful, quiet getaway. The house is more than enough space for 2 people, well stocked kitchen, amazing scenery. Beautiful Mountain View’s, screened in porch, super serene.
Guest favorite
Home in High View
4.95 out of 5 average rating, 131 reviews

Mtn. View~Cave Hot Tub~50 Ac~ATV Trails~Fishing

ChristinaRating, 5 stars3 weeks ago
It was a peaceful family get away. The house is well stocked with necessities. The animals were an adorable touch. I enjoyed feeding them more than the kids did. The trails are more for able bodied people. My clumsy 2 year old was not able to get very far. My kids and dogs loved playing in the mini beach. The cave hot tub unique but we were not able to use it. The peoperty itself is gorgeous. I would love to come back.
Top guest favorite
Home in Frederick
4.97 out of 5 average rating, 115 reviews

Hot Tub Time Machine-happy, charming, tidy, yard

BridgetRating, 5 stars4 days ago
Great time. Great location. This was our second leg of Easter break. Choose this novelty for its location and hot tub😀. We came into town early for College Rugby Nationals at Maryland SoccerPlex. My husband and I explored! Just a 35 minute drive to the fields and 35 minutes to mountain fun. Bonus!!! A great local town filled with history. Loved NOLA for breakfast and had amazing adult time at local winery BIG. Very dog friendly neighborhood and home. Loved all the games and comfortable dining area for family time. Recommend you bring a robe for hot tub! Everything else was provided in abundance.
Top guest favorite
Home in Fayetteville
4.98 out of 5 average rating, 105 reviews

Driftwood Cottage

NateRating, 5 stars6 months ago
My wife and I booked this airbnb to take some time to get away, and it was well worth the trip. Close to Gettysburg, and plenty to do at the property itself. We would gladly stay at this beautiful home again!
Guest favorite
Home in Fairfield
4.92 out of 5 average rating, 239 reviews

Brent Road Retreat

RobinRating, 5 stars2 weeks ago
The place is even more beautiful than I could have imagined! There was a crackling fire when we came in, there’s such a personal touch throughout the house and the surrounding nature is picturesque. One of the favorite places I’ve ever stayed. Our whole party raved about it.
Top guest favorite
Home in Sharpsburg
4.95 out of 5 average rating, 143 reviews

Steps to Winery & Battlefield-Pvt Acre w/ Hot Tub!

AliciaRating, 5 stars1 week ago
So happy we chose to stay here for a short family getaway - this was an amazing stay for our kids (11, 8, and 2) and us adults - we all thoroughly enjoyed. Jordan sets the bar for a thoughtful, responsive host, and the home was well-planned, stocked, and comfortable. We really loved the wood-burning fire pit to make s’mores, and I was impressed that Jordan even took the time to provide marshmallow sticks to make the experience perfect; the hot tub was lovely. Beautiful place to see the clear, star-filled night sky. The bathrooms and bedrooms had more than enough extra towels and bedding (and charging stations!) for our family, and the bedrooms/beds were super comfortable and quiet - we all slept like babies after touring Antietam Battlefield and the winery down the hill. Lots of food options close by (Easter Sunday/Monday there were some unposted closures so make sure to call), we visited Harper’s Ferry nearby afterwards. Can’t say enough good things; kids are already asking to return!
Superhost
Home in Sumerduck
4.79 out of 5 average rating, 38 reviews

Charming Cottage/Hot Tub, in a certified wildlife

StacyRating, 5 stars1 week ago
Such a beautiful house and easily the best location I have ever stayed at. The yard was immaculate. The hot tub was perfect, and the area was incredibly peaceful.

House rentals with a pool

Top guest favorite
Home in Massanutten
4.99 out of 5 average rating, 110 reviews

Trevino’s Getaway

JeanRating, 5 stars1 week ago
We really enjoyed our stay at Jonathan and Tyler’s place with its many amenities. The PS4 and table football were a huge hit! Thank you!
Guest favorite
Home in Boston
4.96 out of 5 average rating, 141 reviews

Peacefield - Blue Ridge views near Culpeper

AlanRating, 5 stars1 month ago
3 Nights was not enough for our 7 member family. We cooked, grilled, soaked in the hot and best of all had a delightful tour of Barbara's and Mike's Sheep Farm, all fit in around wedding events in Rixeyville. If life wouldn't have been in the way, 2 more days enjoying the massive deck and game room downstairs would have been perfection.
Guest favorite
Home in Big Pool
4.86 out of 5 average rating, 81 reviews

4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acr

KristinRating, 5 stars3 days ago
Gorgeous private property, surrounded by nature. Welcoming home with wonderful amenities. Instantly aware a great deal of thought was put into all aspects of this home, providing a seamless transition to vacation mode. Host was very communicative and helpful. Would highly recommend.
Top guest favorite
Home in Harpers Ferry
4.97 out of 5 average rating, 192 reviews

Harpers Ferry Farmhouse, Heated Year Round Pool

RachelRating, 5 stars1 month ago
Perfect location for a women’s wellness retreat! The ladies are already asking when we can come back. Plenty of spaces big and small to facilitate us, both as a group as well as individuals looking to relax and recharge. Having two kitchens was nice for feeding such a big group, and the heated saltwater pool was the cherry on top!
Superhost
Home in Strasburg
4.76 out of 5 average rating, 266 reviews

Cedar Creek Wayside Castle

RogeRating, 5 stars1 week ago
It’s a private place to go and enjoy and famili kids are very happy with the pool and activities
Top guest favorite
Home in Luray
4.98 out of 5 average rating, 100 reviews

Walnut Lane

AshleyRating, 5 stars5 months ago
Place was lovely and exactly as listed. Spacious , great views, clean and lots of DVDs and board games. Highly recommend staying here!
Superhost
Home in Aldie
4.75 out of 5 average rating, 8 reviews

Relaxing Aldie Retreat, with Fireplaces and Pool

DawnRating, 5 stars1 month ago
Absolute peaceful oasis. This home gives you every essence of Virginia Wine Country. The home was quaint and the deer came up every morning to greet us. I can’t wait to come back in the summer when the pool is open! Thanks again
Superhost
Home in Stafford
4.9 out of 5 average rating, 97 reviews

Stunning Riverfront Home w/ Pool, Hot Tub & Kayaks

EdwardRating, 5 stars3 months ago
Host was very friendly, very responsive and very helpful. Place had expansive windows with beautiful views of the Potomac river and it was very relaxing to be there. Only complaint would be that some of the place was a bit dated, but that did not significantly impact the overall positive experience for us.

Quick stats about house rentals in Winchester

  • Total rentals

    40 properties

  • Total number of reviews

    1.6K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 properties include access to wifi

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