Winchester Holiday Rentals

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Check prices for these dates

In two weeks
19 Sept - 21 Sept
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
In four months
26 Dec - 28 Dec

Holiday Rentals in Winchester

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$1,130 total
includes taxes & fees
8 Sept - 9 Sept
Family Farmhouse Inn
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 "
The price is HK$1,186
HK$2,078 total
includes taxes & fees
9 Sept - 10 Sept
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Interior

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

10.0 out of 10, Exceptional, (66)
"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.
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
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, "
Dreamtime - Modern A-frame Cabin w/ 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, (296)
"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 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$2,386 total
includes taxes & fees
9 Sept - 10 Sept
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
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, (191)
"We had a great time sitting on the porch relaxing. "
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities
Outdoor dining

Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

9.6 out of 10, Exceptional, (60)
"Family and I loved our stay at Whistling Woods Retreat! Relax by the fire and take in the blue ridge mountains! Short drive to luray and Shenandoah national park. Tons of games and places to explore on the property for the kids. Definitely Recommend ! "
The price is HK$1,106
HK$2,548 total
includes taxes & fees
8 Sept - 9 Sept
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities
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
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!
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$781
HK$2,809 total
includes taxes & fees
11 Sept - 12 Sept
Blue Ridge Getaway - Sunset Views, A.T. Access
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$1,235
HK$2,529 total
includes taxes & fees
21 Sept - 22 Sept
Grill, Fire Pit, WiFi, Deck, Hammock, Games & Dogs
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$2,402 total
includes taxes & fees
11 Sept - 12 Sept
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Hot Tub, FirePit, Large Yard, Screened Porch, WiFi
Terrace/patio

Hot Tub, FirePit, Large Yard, Screened Porch, WiFi

9.6 out of 10, Exceptional, (21)
"We had a great time relaxing in the hot tub. We had so many adventures in the area we didn't have time for the fire pit. The place was gorgeous. "
The price is HK$1,149
HK$2,155 total
includes taxes & fees
9 Sept - 10 Sept
Hot Tub, FirePit, Large Yard, Screened Porch, WiFi
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Outdoor spa tub

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

10.0 out of 10, Exceptional, (335)
"we were looking for a quiet get away, loved having our 16YO boy more interested in fishing and hiking then sitting on his Xbox! We all really loved how quiet and calm it was, definitely plan on going back"
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Canal Cabins
1 bedroom, pillow-top beds, free WiFi, bed sheets

Canal Cabins

3.0 star property
9.6 out of 10, Exceptional, (8)
"Very nice "
The price is HK$926
HK$1,047 total
includes taxes & fees
5 Sept - 6 Sept
Canal Cabins
Cabin near River, Firepit, Family-friendly, WiFi, Great Location, Veteran owned!
Exterior

Cabin near River, Firepit, Family-friendly, WiFi, Great Location, Veteran owned!

9.8 out of 10, Exceptional, (38)
"Very nice location, would stay here again. Had everything we needed."
Cabin near River, Firepit, Family-friendly, WiFi, Great Location, Veteran owned!
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.