Winchester Vacation Rentals

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Vacation Rentals in Winchester

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Property grounds
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, (190)
"Overall we enjoyed our stay. A couple things of note: Bringing black out shades is super helpful! The closet in the bedroom is big enough for a portable crib. Be sure to bring toilet paper. We only had one full and one partial roll between the two bathrooms(and they were paper thin). Because there isn’t anywhere super close, it’s nice to know to pack some ahead of time :) The road is so peaceful and we went on the trail quite a few times. It was a bit wet, so we didn’t make it all the way...
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Dreamtime - Modern A-frame Cabin w/ Hot tub
Property grounds
Dreamtime - Modern A-frame Cabin w/ Hot tub
10.0 out of 10, Exceptional, (26)
"Cabin was amazing. Definitely would go back!"
The price is $375
$475 total
includes taxes & fees
Jul 6 - Jul 7
Dreamtime - Modern A-frame Cabin w/ Hot tub
Hidden Gem in the woods with hot tub
Property grounds
Hidden Gem in the woods with hot tub
9.6 out of 10, Exceptional, (51)
"We had a great time. Cabin was clean, spacious and well maintained. The fire pit and hot tub were what we looked forward to the most... We were not disappointed."
Hidden Gem in the woods with hot tub
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Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
TV, fireplace, books, stereo
Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
9.4 out of 10, Exceptional, (9)
"I would consider changing carpet to vinyl flooring. Good location if you love to golf."
The price is $116
$290 total
includes taxes & fees
Jun 25 - Jun 26
Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
Cottage w Hot Tub, Pond & Kayaks, Fire Pit, & WiFi
Property grounds
Cottage w Hot Tub, Pond & Kayaks, Fire Pit, & WiFi
8.8 out of 10, Excellent, (15)
"Me and my friends had a great get away and loved the hot tub!"
The price is $151
$324 total
includes taxes & fees
Jul 9 - Jul 10
Cottage w Hot Tub, Pond & Kayaks, Fire Pit, & WiFi
Star view cabin-Riverfront
Property grounds
Star view cabin-Riverfront
9.8 out of 10, Exceptional, (278)
"I have to say the last two reviews made us a bit nervous but those people must have been self-proclaimed critics because we had a truly exceptional experience. Everything was perfect - the hot tub, the river access point, the fire pit(s). A dream come true. We will absolutely be back. Nina’s friendliness and attention to detail made this truly a one of a kind experience. Can’t wait to bring our whole family back!!"
Star view cabin-Riverfront
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Exterior
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
9.8 out of 10, Exceptional, (245)
"Perfect for a quiet getaway. Complete relaxation"
The price is $100
$316 total
includes taxes & fees
Jun 17 - Jun 18
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Escape to the Woods & stay in this gorgeous 4 bdr, 3 bth, Mountain cabin
Fridge, microwave, oven, stovetop
Escape to the Woods & stay in this gorgeous 4 bdr, 3 bth, Mountain cabin
8.2 out of 10, Very Good, (10)
"This was an excellent cabin for the price, if you are looking for something close to Berkeley Springs"
The price is $130
$473 total
includes taxes & fees
Jun 17 - Jun 18
Escape to the Woods & stay in this gorgeous 4 bdr, 3 bth, Mountain cabin
Riverside cottage, minutes from historic Harpers Ferry; private river access!
Property grounds
Riverside cottage, minutes from historic Harpers Ferry; private river access!
9.8 out of 10, Exceptional, (60)
"We enjoyed our stay! The location was perfect for us and the house worked well for young kids. Thank you!"
The price is $145
$223 total
includes taxes & fees
Jul 1 - Jul 2
Riverside cottage, minutes from historic Harpers Ferry; private river access!
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
Smart TV, DVD player, books, video library
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
10.0 out of 10, Exceptional, (30)
"Very clean. Crisp, clean linens. Gorgeous views and surroundings. Extremely responsive. Highly recommend!!"
The price is $145
$330 total
includes taxes & fees
Jun 19 - Jun 20
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI
Property grounds
Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI
9.6 out of 10, Exceptional, (152)
"Nice older cabin with very quiet, country location. Lots of privacy and walk to river. Dog friendly too! Bring coffee grounds for the coffee maker. Will definitely be back!"
Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI
Romantic, rustic, private A-frame chalet tucked in the woods - 4 miles to town!
Exterior
Romantic, rustic, private A-frame chalet tucked in the woods - 4 miles to town!
8.4 out of 10, Very Good, (27)
"This Coolfont cabin was the perfect weekend home for our family of four (and our dog). Friendly staff at the lodge welcomed us with giant smiles and answered all our of questions. The cabin was cozy and warm with ample space. Large, clean bathrooms. Especially loved the wood stove. We enjoyed the hiking and biking trails nearby, as well as the on-site restaurant, on-site pool and brew pub just across the street. Will definitely be back!"
Romantic, rustic, private A-frame chalet tucked in the woods - 4 miles to town!
Secluded Pet-Friendly High-Tech Log Cabin in the Woods
Fridge, microwave, oven, stovetop
Secluded Pet-Friendly High-Tech Log Cabin in the Woods
9.6 out of 10, Exceptional, (150)
"Most of our stay was on the property. The amenities were great. The game room was nice. The town was very nice and friendly. The food was good."
Secluded Pet-Friendly High-Tech Log Cabin in the Woods
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
Property grounds
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
10.0 out of 10, Exceptional, (334)
"We enjoyed our stay"
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
2 bedrooms, WiFi, bed sheets
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
9.4 out of 10, Exceptional, (299)
"Loved the cabin. Very cozy. Beautiful views from the deck. Upkeep was great. We really enjoyed the stay and plan to stay again in the future."
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
Beautiful Cottage At 'the Woods' Resort, Golf, Spa, Swimming & Resort Amenities
Interior detail
Beautiful Cottage At 'the Woods' Resort, Golf, Spa, Swimming & Resort Amenities
9.8 out of 10, Exceptional, (208)
"Had a great time at this property and were able to take advantage of the screened in porch and fireplace. Neighborhood was very nice and checkin was easy. They were very accommodating for the three dogs that also visited the property with us."
Beautiful Cottage At 'the Woods' Resort, Golf, Spa, Swimming & Resort Amenities
Breathtaking views with an indoor private pool, come escape with us
Exterior
Breathtaking views with an indoor private pool, come escape with us
9.8 out of 10, Exceptional, (229)
"Loved the view, the pool, brewery and the 3 floors of spaces to sleep worked perfect for our group."
Breathtaking views with an indoor private pool, come escape with us
Bear Valley- Riverfront with hot tub!
Outdoor dining
Bear Valley- Riverfront with hot tub!
9.8 out of 10, Exceptional, (101)
"We had a great time spending a long holiday weekend here. It was relaxing and peaceful and perfect for what we needed. However I would say the place needs some work and the owner should put some money back into it. The directv barely works and the internet is non existent but we made due without it. Cosmetically it needs some love. If it got some love we’d probably visit frequently however next time we’ll probably look for a more put together place. Location is fantastic so if you’re cool with...
Bear Valley- Riverfront with hot tub!
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
2 bedrooms, WiFi, bed sheets
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
9.8 out of 10, Exceptional, (269)
"This cabin reminded me of my grandpas cabin in the Big Horn Mountains. It's rustic and has that old cabin scent. We enjoyed watching the sunset from the back deck. I recommend bringing your own blankets if you get chilly in the evening. The kitchen has everything you need for preparing meals and the outdoor fire place is great for making smore's."
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
Charming mountaintop cabin with hot tub, pool table, and breathtaking views
Property grounds
Charming mountaintop cabin with hot tub, pool table, and breathtaking views
9.8 out of 10, Exceptional, (172)
"Beautiful house and setting in nature. A wonderful relaxing couple of days."
Charming mountaintop cabin with hot tub, pool table, and breathtaking views
Don't see what you're looking for?
See all available properties in Winchester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Winchester you may be interested in

La Quinta Inn & Suites by Wyndham Winchester
Exterior
La Quinta Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, (1386)
"Great value stay for an overnight on a road trip. New hotel with comfortable rooms, friendly service, and thoughtful amenities. Would choose again when I am in the area!"
The price is $103
$112 total
includes taxes & fees
Jun 17 - Jun 18
La Quinta Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester
Lobby
Microtel Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, (819)
"Staff was awesome! The room was very clean and the complimentary breakfast was way better than we expected! Would definitely stay there again!"
The price is $84
$92 total
includes taxes & fees
Jun 17 - Jun 18
Microtel Inn & Suites by Wyndham Winchester
Travelodge by Wyndham Winchester
Seasonal outdoor pool
Travelodge by Wyndham Winchester
2.5 star property
8.0 out of 10, Very Good, (1075)
"Older building but clean would stay again "
The price is $65
$71 total
includes taxes & fees
Jun 30 - Jul 1
Travelodge by Wyndham Winchester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $100 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we offer vacation rentals in Winchester near Shenandoah Valley Discovery Museum, or you can go with a secluded option if you want a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theater scene while you're visiting.

What are some of the best vacation home rentals in Winchester?

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails: This vacation home rental near Winchester is located in a rural location and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Winchester?

Choose from 15 Expedia vacation rentals in Winchester for a memorable vacation.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Nalls Farm Market are a couple of family-friendly sights, whereas cultural attractions include Museum of the Shenandoah Valley and Bright Box Theater. Other places in town to visit include Jim Barnett Park and Apple Blossom Mall.

What’s a vacation rental in Winchester like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Winchester. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for family trips.

Recent reviews of Winchester properties
Expedia verified reviews

Sleep Inn & Suites

Sleep Inn & Suites

5/5 Excellent
Sleep Inn is great for the price point
"Great place to stay for the price point. Staff were very friendly and helpful. The room and the building (interior and exterior) is in need of minor cosmetic attention like peeling wallpaper, water stains, fresh paint and caulking in the bathroom etc. "
A verified traveler stayed at Sleep Inn & Suites
Posted 2 days ago
Sleep Inn & Suites