Holiday Homes in Winchester

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Next weekend
3 Oct - 5 Oct
In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov

Featured Holiday Homes in Winchester

Our top choices for Winchester holiday homes

Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub
Pool

Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub

10.0 out of 10, Exceptional, (98)
"Clean and nice place to stay to visit Shenandoah "
The price is AU$626
includes taxes & fees
28 Sept - 29 Sept
Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub
Cottage on King | Charming Historic Leesburg Home
Terrace/patio

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (58)
"Clean comfortable fully stocked within walking distance to everything Leesburg has to offer -a GREAT place to stay ... beds were so comfy and so was the sofa definitely would stay again ... totally loved it!! "
The price is AU$563
includes taxes & fees
13 Oct - 14 Oct
Cottage on King | Charming Historic Leesburg Home
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, (196)
"We loved everything about our stay. The views were spectacular and the setting was so tranquil. "
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Interior

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

10.0 out of 10, Exceptional, (68)
"The property was clean, quiet and the neighborhood was safe. We had a great time and tawny was a great host."
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Gorgeous getaway: 10 private acres w/ Hot Tub in GW forest near Shenandoah River
Dining

Gorgeous getaway: 10 private acres w/ Hot Tub in GW forest near Shenandoah River

9.8 out of 10, Exceptional, (31)
"The Chateau was fabulous! As described, private, zen-like, very comfortable with a great deck, views and large outback hot tub. "
Gorgeous getaway: 10 private acres w/ Hot Tub in GW forest near Shenandoah River
Cozy place near Shenandoah National Park, Luray Caverns & 30min to Massanutten!
Exterior

Cozy place near Shenandoah National Park, Luray Caverns & 30min to Massanutten!

9.8 out of 10, Exceptional, (31)
"Immaculate home and a few minutes from the Shanandoa Mts. Peaceful place!"
The price is AU$570
includes taxes & fees
24 Sept - 25 Sept
Cozy place near Shenandoah National Park, Luray Caverns & 30min to Massanutten!
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Outdoor dining

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

9.8 out of 10, Exceptional, (234)
"Wonderful location, beautiful as always. Looking forward to our next trip."
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
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, (132)
"The house was perfect, right in the middle of historic Harper’s Ferry. We all had the best time! "
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Outdoor dining

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

9.8 out of 10, Exceptional, (194)
"We love our time there. Cabin was amazing "
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Newly renovated Farm cottage with Mountain views
Outdoor dining

Newly renovated Farm cottage with Mountain views

10.0 out of 10, Exceptional, (35)
"The cottage is lovely, with modern kitchen and bath and charming furnishings throughout. Views are wonderful and the location is quiet, set well back from the road. The host is very prompt and courteous in communications. She went above and beyond the call of duty in helping us when I temporarily mislaid the key."
The price is AU$500
includes taxes & fees
28 Sept - 29 Sept
Newly renovated Farm cottage with Mountain views
Secluded River Cabin Getaway (Masten Cabin)
Fridge, microwave, oven, stovetop

Secluded River Cabin Getaway (Masten Cabin)

9.8 out of 10, Exceptional, (163)
"A beautiful home and property. This is a wonderful weekend getaway home. Modern and comfortable, but especially quiet!"
Secluded River Cabin Getaway (Masten Cabin)
Grand 9BR Provenance Manor Ideal for Weddings & Gatherings
Private kitchen

Grand 9BR Provenance Manor Ideal for Weddings & Gatherings

The price is AU$2,792
includes taxes & fees
1 Oct - 2 Oct
Grand 9BR Provenance Manor Ideal for Weddings & Gatherings
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Exterior

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

10.0 out of 10, Exceptional, (146)
"Wonderful house for a great weekend away"
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
The Outpost: A Rustic Respite in the Shenandoah Valley 4 Bikes For Use Tesla Ch
Outdoor dining

The Outpost: A Rustic Respite in the Shenandoah Valley 4 Bikes For Use Tesla Ch

8.8 out of 10, Excellent, (42)
"Great environment, lots to do within the area. Check in process is very convenient. Every room feels like a new adventure."
The Outpost: A Rustic Respite in the Shenandoah Valley 4 Bikes For Use Tesla Ch
River Woods Retreat:10min to River, L2 EV, Hikes, 2 Fireplaces, Hottub, SP 10mi
Smart TV, fireplace, DVD player

River Woods Retreat:10min to River, L2 EV, Hikes, 2 Fireplaces, Hottub, SP 10mi

10.0 out of 10, Exceptional, (55)
"A beautiful cabin far from the hustle and bustle. Great place to relax. "
The price is AU$611
includes taxes & fees
6 Oct - 7 Oct
River Woods Retreat:10min to River, L2 EV, Hikes, 2 Fireplaces, Hottub, SP 10mi
4 King Suites w/ Hot Tub, Fire Pit, Ping Pong, Arcade, Hi Speed Internet
Exterior

4 King Suites w/ Hot Tub, Fire Pit, Ping Pong, Arcade, Hi Speed Internet

10.0 out of 10, Exceptional, (19)
"We loved the night out at this property. A beautiful house in a great spot. The hosts were so accommodating and really friendly. "
4 King Suites w/ Hot Tub, Fire Pit, Ping Pong, Arcade, Hi Speed Internet
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
Luray farmhouse on the river
Exterior

Luray farmhouse on the river

9.4 out of 10, Exceptional, (37)
"We had a great time and PLENTY of space for our 3 families of all ages. It was off the beaten path but within 10 min to everything you could want. Home is so spacious and the owner was amazing to work with! She even left breakfast goodies. There are little bars but remember, you’re on the river so it’s expected and they communicated that. The water has a terrible smell at first because again, your on the water but once you run it a bit l, it cleared right up. We would absolutely reccomend this...
The price is AU$594
includes taxes & fees
30 Sept - 1 Oct
Luray farmhouse on the river
✨Luxurious Mountaintop Lodge🏔️ Scenic Views🫧Hot Tub under the BIG SKY STARS 🌟
Outdoor dining

✨Luxurious Mountaintop Lodge🏔️ Scenic Views🫧Hot Tub under the BIG SKY STARS 🌟

10.0 out of 10, Exceptional, (42)
"Our fall getaway to Berkeley Springs was all the more enjoyable for our family with the beautiful view, hot tub, and game room!!"
✨Luxurious Mountaintop Lodge🏔️ Scenic Views🫧Hot Tub under the BIG SKY STARS 🌟
Waterfront property in Harpers Ferry - Private River Access
Property grounds

Waterfront property in Harpers Ferry - Private River Access

10.0 out of 10, Exceptional, (32)
"Enjoyable stay, lovely location Clean comfortable home."
Waterfront property in Harpers Ferry - Private River Access
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

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester

10/10 Excellent
"A great stop for our family of four on a long drive home."
Sean 1-night trip
Posted 1 day ago
Hilton Garden Inn Winchester

Find out more about Winchester

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
1,802
Accommodation
685 Holiday Homes
Lowest Price
AU$500
Highest Price
AU$2,792