
House vacation rentals in Winchester
Find and book unique houses on Airbnb
Top-rated house rentals in Winchester
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester house rentals
House rentals with free parking

Opal house
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.

Grasshopper Cottage
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.

Home away from home
The pictures don’t do this place justice. Plenty of room for our family of 5.

Gift House: Quiet, self check in & free Parking
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.

Vintage Modern Rowhome – So Close to Everything!
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.

Arden House, Inwood WV
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!

Private Basement/Apartment with Separate Entry
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.

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

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

Mountain Retreat-Stunning Views/Pool/Hot tub
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.

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

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

Driftwood Cottage
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!

Brent Road Retreat
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.

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

Charming Cottage/Hot Tub, in a certified wildlife
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

Trevino’s Getaway
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!

Peacefield - Blue Ridge views near Culpeper
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.

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

Harpers Ferry Farmhouse, Heated Year Round Pool
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!

Cedar Creek Wayside Castle
It’s a private place to go and enjoy and famili kids are very happy with the pool and activities

Walnut Lane
Place was lovely and exactly as listed. Spacious , great views, clean and lots of DVDs and board games. Highly recommend staying here!

Relaxing Aldie Retreat, with Fireplaces and Pool
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

Stunning Riverfront Home w/ Pool, Hot Tub & Kayaks
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
Destinations to explore
- Rappahannock River Vacation rentals
- Outer Banks Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- Pocono Mountains Vacation rentals
- South Jersey Vacation rentals
- Jersey Shore Vacation rentals
- New York Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Plainview Vacation rentals
- Long Island Vacation rentals
- Cottage rentals Winchester
- Family-friendly rentals Winchester
- Pet-friendly rentals Winchester
- Rentals with a washer and dryer Winchester
- Apartment rentals Winchester
- Cabin rentals Winchester
- Condo rentals Winchester
- Rentals with outdoor seating Winchester
- Rentals with a patio Winchester
- House rentals Virginia
- House rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Bryce Resort
- Luray Caverns
- Whitetail Resort
- Cacapon Resort State Park
- Stone Tower Winery
- Gambrill State Park
- Cunningham Falls State Park
- South Mountain State Park
- Twin Lakes Golf Course
- Robert Trent Jones Golf Club
- Shenandoah Valley Golf Club
- Notaviva Vineyards
- Whiskey Creek Golf Club
- Bowling Green Country Club
- Reston National Golf Course
- Sly Fox Golf Club
- Creighton Farms
- River Creek Club
- Berkeley Springs State Park
- JayDee's Family Fun Center
- Car and Carriage Caravan Museum
- Hidden Creek Country Club
- Herndon Centennial Golf Course
- The Golf Club at Lansdowne