Winchester Holiday Rentals

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Winchester holiday rentals

Outdoor dining
Dreamtime - Modern A-frame Cabin w/ Hot tub

Cabin in Berkeley Springs

Dreamtime - Modern A-frame Cabin w/ Hot tub
10.0 out of 10, Exceptional, (51)
"Excellent stay! Great space, privacy, clean. "
United States
Erin B.
Dreamtime - Modern A-frame Cabin w/ Hot tub
Outdoor spa tub
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

Cabin in Rileyville

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
10.0 out of 10, Exceptional, (350)
"We had a great time and can't wait to return"
United States
Jacqueline B.
The price is HK$965
HK$1,740 total
includes taxes & fees
15 Dec - 16 Dec
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Property grounds
Cabin w New Hot Tub, River/Kayak, WiFi, & Fire Pit

Cabin in Great Cacapon

Cabin w New Hot Tub, River/Kayak, WiFi, & Fire Pit
9.4 out of 10, Exceptional, (192)
"Overall a decent cabin. Think it’s probably best if you have a group or family of 6 looking for something economical. Seems like the cabin could use an overall refresh. Wish the hot tub was on the enclosed patio. "
United States
Brian
Cabin w New Hot Tub, River/Kayak, WiFi, & Fire Pit
Property grounds
Hidden Gem in the woods with hot tub

Cabin in Berkeley Springs

Hidden Gem in the woods with hot tub
9.6 out of 10, Exceptional, (88)
"The cabin was very clean, well equipped, and the amenities were plentiful. It was also private and was everything I was expecting based on the property's description. I would rent it again."
United States
Juan
Hidden Gem in the woods with hot tub
Pool
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Cabin in Rileyville

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
10.0 out of 10, Exceptional, (340)
"Excellent experience! The cabin was great, the location was great, the sights and people were great!"
United States
Tom A.
The price is HK$965
HK$1,740 total
includes taxes & fees
15 Dec - 16 Dec
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Exterior
Amazing Grace log cabin home with 3 bedrooms, WiFi and AC in breathtaking Luray

Cabin in Luray

Amazing Grace log cabin home with 3 bedrooms, WiFi and AC in breathtaking Luray
2.0 star property
10.0 out of 10, Exceptional, (47)
"Great stay! "
United States
Kristen F.
The price is HK$2,451
HK$4,449 total
includes taxes & fees
15 Dec - 16 Dec
Amazing Grace log cabin home with 3 bedrooms, WiFi and AC in breathtaking Luray
Outdoor spa tub
Lookout Cabin in the mountains, Amazing Views!

Cabin in Page County

Lookout Cabin in the mountains, Amazing Views!
10.0 out of 10, Exceptional, (31)
"We did a short stay here on our way to Virginia Beach and it was everything that it was advertised to be! The beds were comfy. The view was breathtaking! Have fun driving up and down the mountain to get to it!"
United States
Jennifer W.
The price is HK$1,391
HK$2,898 total
includes taxes & fees
14 Dec - 15 Dec
Lookout Cabin in the mountains, Amazing Views!
Exterior
A Cozy Bear Cottage! A Beautiful Escape!

Cabin in Luray

A Cozy Bear Cottage! A Beautiful Escape!
10.0 out of 10, Exceptional, (80)
"If you want a cozy cabin feel, this is the place for you. It was so cute inside and the beds were very comfortable. The house was clean and they had everything you needed for your stay, including cups, utensils, trash bags, soap/shampoo, a hairdryer and even a baby crib. Will definitely be staying here again. "
United States
Alysha
A Cozy Bear Cottage! A Beautiful Escape!
Exterior
Enjoy Secluded Starry Nights! Near Luray, HotTub, FastWiFi, Handicap, Fireplace

Cabin in Rileyville

Enjoy Secluded Starry Nights! Near Luray, HotTub, FastWiFi, Handicap, Fireplace
10.0 out of 10, Exceptional, (208)
"This was one of the most peaceful getaways I’ve had in a longtime. Very Nice, well maintained cabin. Very private and the hot tub was great!"
United States
Chris H.
Enjoy Secluded Starry Nights! Near Luray, HotTub, FastWiFi, Handicap, Fireplace
1 bedroom, iron/ironing board, free WiFi, bed sheets
Wild And Wonderful Silos

Cabin in Harpers Ferry

Wild And Wonderful Silos
9.2 out of 10, Wonderful, (9)
"Very charming and spacious silo! Very quiet and comfortable. Highly recommend and would definitely stay again!"
United States
Lauren M.
The price is HK$1,365
HK$2,324 total
includes taxes & fees
15 Dec - 16 Dec
Wild And Wonderful Silos
Outdoor dining
Outdoor Theatre | Hot Tub | Fire Pit | Dogs

Cabin in Luray

Outdoor Theatre | Hot Tub | Fire Pit | Dogs
9.8 out of 10, Exceptional, (58)
"Great place to stay for a quiet getaway in the mountains! Beautiful property"
United States
Lee S.
The price is HK$770
HK$2,296 total
includes taxes & fees
15 Dec - 16 Dec
Outdoor Theatre | Hot Tub | Fire Pit | Dogs
Outdoor spa tub
Adorable river front cabin ,with hot tub on the River

Cabin in Luray

Adorable river front cabin ,with hot tub on the River
9.2 out of 10, Wonderful, (12)
"Nice, clean little cabins with lots of amenities. Just a heads up, there's no cell service, so make sure you write down the code for the lockbox before you arrive. "
United States
Tabatha d.
Adorable river front cabin ,with hot tub on the River
Outdoor dining
Spectacular couples retreat, private wooded location, pet friendly, WiFi

Cabin in Berkeley Springs

Spectacular couples retreat, private wooded location, pet friendly, WiFi
10.0 out of 10, Exceptional, (160)
"The cabin was perfect, so quiet and peaceful. We thoroughly enjoyed our time there."
United States
Jesse C.
Spectacular couples retreat, private wooded location, pet friendly, WiFi
Property grounds
❤️ Secluded 1940s Romantic Tiny House on the River

Cabin in Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River
9.8 out of 10, Exceptional, (65)
"We truly loved this location and definitely will be back!"
United States
Astrid
The price is HK$315
HK$823 total
includes taxes & fees
21 Dec - 22 Dec
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

Holiday Home in Rileyville

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
9.4 out of 10, Exceptional, (205)
"Property is beautiful with private and secluded access to the river. Inside of the house was clean and comfortable. Would definitely come here again!"
United States
Tyler O.
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
Outdoor dining
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

Cabin in Luray

Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities
9.6 out of 10, Exceptional, (70)
"Check in was easy and I loved that they used my last four of my phone as the door code- made it easy to remember!"
United States
Kathy M.
The price is HK$1,021
HK$2,440 total
includes taxes & fees
12 Dec - 13 Dec
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities
Terrace/patio
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

Cabin in Berkeley Springs

Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
9.8 out of 10, Exceptional, (294)
"Secluded and peaceful, exactly what we were looking for. Loved this cabin!"
United States
John V.
The price is HK$685
HK$2,354 total
includes taxes & fees
22 Dec - 23 Dec
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Indoor spa tub
Hot Tub, Screened Porch, Grill, WiFi - Huge Cabin!

Cabin in Berkeley Springs

Hot Tub, Screened Porch, Grill, WiFi - Huge Cabin!
9.0 out of 10, Wonderful, (8)
"Great cabin "
United States
Linda C.
Hot Tub, Screened Porch, Grill, WiFi - Huge Cabin!
Terrace/patio
RIVERKEEPER INN, Waterfront Property on the Potomac River

Cottage in Harper's Ferry

RIVERKEEPER INN, Waterfront Property on the Potomac River
9.4 out of 10, Exceptional, (131)
"Beautiful location right on the Potomac River."
United States
Diane
RIVERKEEPER INN, Waterfront Property on the Potomac River
Outdoor spa tub
Huge Cabin w Hot Tub, Deck, Grill & WiFi

Cabin in Berkeley Springs

Huge Cabin w Hot Tub, Deck, Grill & WiFi
9.6 out of 10, Exceptional, (31)
"The house was great for our family to gather together in and everyone had a great time. Tony was hyper responsive and it was a great stay. "
United States
David W.
Huge Cabin w Hot Tub, Deck, Grill & WiFi
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

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

10/10 Excellent
"The staff were friendly and knowledgeable . Clean room and breakfast was excellent. Hotel close to restaurants and stores. "
Yolanda 3-night trip
Posted 2 days ago
SpringHill Suites by Marriott 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
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  • 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?

✨Luxurious Mountaintop Lodge🏔️WOW Scenic Views🫧Hot Tub under the BIG SKY STARS 🌟: This holiday home rental outside of Winchester is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals will I find in Winchester?

Choose from 17 Expedia holiday rentals in Winchester for a memorable holiday.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Rocking S Ranch are a couple of the family-friendly sights, whereas cultural attractions include Bright Box Theater and Museum of the Shenandoah Valley. Other places in town to visit include Apple Blossom Mall and Rock Harbor Golf Course.

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.