Winchester Holiday Rentals

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Check prices for these dates

Tonight
1 Sept - 2 Sept
Tomorrow
2 Sept - 3 Sept
This weekend
5 Sept - 7 Sept
Next weekend
12 Sept - 14 Sept

Holiday Rentals in Winchester

Our top choices for Winchester holiday rentals

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Outdoor dining

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (92)
"This beautiful cabin has everything you need for a wonderful stay. My husband and I stayed here for our 44th anniversary while visiting local wineries. It was a perfect location."
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Pool

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

10.0 out of 10, Exceptional, (327)
"Loved the privacy "
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
Miscellaneous

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

10.0 out of 10, Exceptional, (382)
"What a wonderful property! Our stay was restful and quiet, and we were even treated to visiting deer! This lovely home made our visit to the area very special."
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
Falling Leaf Cabin - Rustic Charm With Modern Decor!
Exterior

Falling Leaf Cabin - Rustic Charm With Modern Decor!

9.8 out of 10, Exceptional, (294)
"20th Anniversary weekend getaway. Perfect setting, quiet and peaceful. Luray had enough to do, food, entertainment etc. Wonderful weekend. "
Falling Leaf Cabin - Rustic Charm With Modern Decor!
Private, light filled retreat space... with your own pickleball court!
Smart TV, fireplace

Private, light filled retreat space... with your own pickleball court!

10.0 out of 10, Exceptional, (44)
"Everything about this day was great. Everything was explained as far as remotes and use of technology. It was comfy, cozy and beautiful."
Private, light filled retreat space... with your own pickleball court!
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
Property grounds

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

9.6 out of 10, Exceptional, (190)
"We had a great time sitting on the porch relaxing. "
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
Family Farmhouse Inn
Garden

Family Farmhouse Inn

3.0 star property
9.6 out of 10, Exceptional, (36)
"Great place to stay! It’s clean cozy and quiet! I would definitely stay again in the future!"
The price is HK$1,006
HK$1,129 total
includes taxes & fees
2 Sept - 3 Sept
Family Farmhouse Inn
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, (279)
"Very nice stay. We used the fire pit and hot tub and enjoyed both. Excellent location close to cacapon, we ended up hiking and doing the clay shooting. The cabin itself was very nice, cozy, and clean. "
The price is HK$702
HK$2,385 total
includes taxes & fees
2 Sept - 3 Sept
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Secluded River Cabin Getaway (Masten Cabin)
Fridge, microwave, oven, stovetop

Secluded River Cabin Getaway (Masten Cabin)

9.8 out of 10, Exceptional, (160)
"A beautiful home and property. This is a wonderful weekend getaway home. Modern and comfortable, but especially quiet!"
Secluded River Cabin Getaway (Masten Cabin)
Private Log Cabin - Hot Tub, NEW SatelliteWi-Fi, Fireplace, Sm Pet Considered
Exterior

Private Log Cabin - Hot Tub, NEW SatelliteWi-Fi, Fireplace, Sm Pet Considered

9.8 out of 10, Exceptional, (123)
"Peaceful, quiet, remote retreat. Enjoyed the hot tub and the beds were comfy. Walked around town and bought some treasures from the antique stores. Would recommend and will stay again."
Private Log Cabin - Hot Tub, NEW SatelliteWi-Fi, Fireplace, Sm Pet Considered
Dreamtime - Modern A-frame Cabin w/ Hot tub
Outdoor dining

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (46)
"We stayed here for our anniversary and had a great time. Hosts were very responsive when we had a question about the hot tub, "
The price is HK$2,331
HK$2,949 total
includes taxes & fees
18 Sept - 19 Sept
Dreamtime - Modern A-frame Cabin w/ Hot tub
Charming Cabin in the Woods with River Access
Exterior

Charming Cabin in the Woods with River Access

9.8 out of 10, Exceptional, (31)
"Very nice rest time…"
The price is HK$1,271
HK$2,293 total
includes taxes & fees
28 Sept - 29 Sept
Charming Cabin in the Woods with River Access
Star view cabin-Riverfront
Property grounds

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (326)
"Great location, great views, "
Star view cabin-Riverfront
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Exterior detail

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

10.0 out of 10, Exceptional, (129)
"Place was nice and clean. Location was good. We enjoyed the quiet. Had a blast!"
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Grill, Fire Pit, WiFi, Deck, Hammock, Games & Dogs
TV, offices

Grill, Fire Pit, WiFi, Deck, Hammock, Games & Dogs

8.8 out of 10, Excellent, (6)
"Found this cabin to be cute and comfortable. Nice surroundings with deer, turtles, birds and squirrel. Would return again! "
The price is HK$1,234
HK$2,568 total
includes taxes & fees
2 Sept - 3 Sept
Grill, Fire Pit, WiFi, Deck, Hammock, Games & Dogs
Blue Ridge Getaway - Sunset Views, A.T. Access
Exterior

Blue Ridge Getaway - Sunset Views, A.T. Access

10.0 out of 10, Exceptional, (57)
"My girlfriend and I had a wonderful weekend escaping the hustle and bustle of the city. The view was spectacular and the property was perfect!"
The price is HK$780
HK$2,796 total
includes taxes & fees
11 Sept - 12 Sept
Blue Ridge Getaway - Sunset Views, A.T. Access
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Interior

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

10.0 out of 10, Exceptional, (64)
"We had a great time exploring Harper’s Ferry and loved having this as our home base!"
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Smart TV, books

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

10.0 out of 10, Exceptional, (72)
"Perfect for hiking trails along Skyline Drive. Luray is a cute town with plenty to do nearby."
The price is HK$1,123
HK$2,400 total
includes taxes & fees
2 Sept - 3 Sept
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Breathtaking View with an Indoor Pool
Outdoor dining

Breathtaking View with an Indoor Pool

9.8 out of 10, Exceptional, (258)
"Great Property"
Breathtaking View with an Indoor Pool
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
Terrace/patio

Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks

10.0 out of 10, Exceptional, (10)
"2 night stay celebrating our 21 year anniversary! Host was attentive & communicated through text daily to check how our stay was going! Unique property grounds & highly enjoyable!"
The price is HK$1,303
HK$2,118 total
includes taxes & fees
2 Sept - 3 Sept
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
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.
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Top Winchester Hotel Reviews

Find out more about Winchester

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Shenandoah Valley Discovery Museum, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theatre scene while you're visiting.

What are some of the best holiday rentals that Winchester has to offer?

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub: This holiday home rental outside of Winchester is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Winchester?

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

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Nalls Farm Market are a couple of the family-friendly sights, whereas cultural attractions include Bright Box Theater and Winchester Little Theater. Other places in town to visit include Patsy Cline Historic House and Museum of the Shenandoah Valley.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family getaway.