Winchester Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Winchester

Juliana Spa Suite - Luxury Main Floor

9.4 out of 10, Exceptional, (3)
"It was close to everything great property "
The price is NZ$254
includes taxes & fees
21 July - 22 July
Juliana Spa Suite - Luxury Main Floor

Welcome to the Ladybug Retreat!

The price is NZ$627
includes taxes & fees
27 July - 28 July
Welcome to the Ladybug Retreat!

Newly renovated Farm cottage with Mountain views

10.0 out of 10, Exceptional, (32)
"The cottage was very charming and outfitted for maximum relaxation. We would definitely stay there again."
The price is NZ$549
includes taxes & fees
21 July - 22 July
Newly renovated Farm cottage with Mountain views

Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!

9.0 out of 10, Wonderful, (24)
"Everything was as described. We had a lovely weekend relaxing under the stars in the hot tub and spending time with family in the Shenandoah Valley. We can't wait to come back to this oasis!"
The price is NZ$507
includes taxes & fees
28 July - 29 July
Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!

Historic Bluemont Village Home

10.0 out of 10, Exceptional, (36)
"This was one of the best VRBO experiences I’ve had! Communication with the host was exceptional, and the home itself was gorgeous. It’s clear they have put a lot of thought into make this house a perfect getaway — it is beautifully decorated and has all the comforts of home. We will definitely stay here again!"
The price is NZ$718
includes taxes & fees
21 July - 22 July
Historic Bluemont Village Home

Cameron Charmer pristine downtown apt with double master suites

9.0 out of 10, Wonderful, (2)
"Property is freshly renovated, very clean, nicely appointed. There was a pervasive musty/mildewy smell throughout the unit, i expect there is a leak somewhere from the renovation. Also, while well appointed, there were no hospitality items...usually there is at least coffee/tea, especially at this price point. We enjoyed our stay and the location was convenient to the theater and the downtown area."
The price is NZ$585
includes taxes & fees
25 July - 26 July
Cameron Charmer pristine downtown apt with double master suites

Spring Retreat! Hot tub, Bar, Game room, Grill & 10 mins to Skyline Drive

9.8 out of 10, Exceptional, (32)
"This house was perfect for a family getaway! Tons of room for everyone and a whole game room to keep the kids occupied! "
Spring Retreat! Hot tub, Bar, Game room, Grill & 10 mins to Skyline Drive

Spacious home steps from Main St and Shenandoah NP with firepit & large backyard

10.0 out of 10, Exceptional, (13)
"We needed a place to stay for our golf foursome. Thisfour bedroom property met all of our needs."
The price is NZ$640
includes taxes & fees
21 July - 22 July
Spacious home steps from Main St and Shenandoah NP with firepit & large backyard

On the river ~ hot tub ~ serene river views ~ fire pit

10.0 out of 10, Exceptional, (15)
"We enjoyed our stay!"
On the river ~ hot tub ~ serene river views ~ fire pit

Cozy 2-bedroom condo in charming Stephens City

10.0 out of 10, Exceptional, (1)
"This was the perfect location for our little get away. We had Easter lunch, played games, and stayed in a very clean nice place!!"
The price is NZ$385
includes taxes & fees
12 Aug - 13 Aug
Cozy 2-bedroom condo in charming Stephens City

Sunset Haven - 10 min from Skyline Drive. Hot Tub

9.8 out of 10, Exceptional, (7)
"Really enjoyed our stay. The house was lovely with amazing views. The bar and game room were fun. Lots of detail and thought were put into making this house feel like home. We will definitely be back!"
The price is NZ$816
includes taxes & fees
21 July - 22 July
Sunset Haven - 10 min from Skyline Drive. Hot Tub

Cozy Luxury, Meet Not Your Typical Cuties Cabin, a Secluded Retreat in Linden VA

The price is NZ$868
includes taxes & fees
3 Aug - 4 Aug
Cozy Luxury, Meet Not Your Typical Cuties Cabin, a Secluded Retreat in Linden VA

Big Sunny Family House

10.0 out of 10, Exceptional, (35)
"The house was clean, the kitchen had sufficient utensils and supplies, the location was close to restaurants."
The price is NZ$831
includes taxes & fees
22 July - 23 July
Big Sunny Family House

Walk to Old Rag* hot tub* 360 mountain views

10.0 out of 10, Exceptional, (20)
"Nice, peaceful farmhouse with everything you need for a comfortable stay. Close to vineyards and quaint villages with great restaurants, however the best thing about it is its proximity to the Old Rag Mountain trailhead. If you're planning to do that hike, this home is just a short walk to the trailhead so you won't have to worry about the parking issues, and after the hike, the hot tub on the home's deck is heavenly! Wonderful place for a wonderful get away!"
The price is NZ$1,060
includes taxes & fees
21 July - 22 July
Walk to Old Rag* hot tub* 360 mountain views

Windy Knoll Adventure!

8.8 out of 10, Excellent, (3)
"Great stay and very accommodating for outings/get together with friends. We loved the fire pit area. Great views of the Shenandoah river as well."
The price is NZ$844
includes taxes & fees
6 Aug - 7 Aug
Windy Knoll Adventure!

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

10.0 out of 10, Exceptional, (14)
"View was great, was pretty isolated from other houses in the area, and cute decor. Very comfortable stay. "
The price is NZ$666
includes taxes & fees
19 Aug - 20 Aug
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

Timeless Elegance in Restored Suite – King Bed & Private Spa Bath

The price is NZ$1,078
includes taxes & fees
21 July - 22 July
Timeless Elegance in Restored Suite – King Bed & Private Spa Bath

Pirate's Cove River Front Oasis, Group Adventure

10.0 out of 10, Exceptional, (4)
"The place is amazing and the host was quick with the response! Me and my family had a great time and will be returning guests!!!"
The price is NZ$2,445
includes taxes & fees
21 July - 22 July
Pirate's Cove River Front Oasis, Group Adventure

Peaceful cottage in farmland - close to Luray, Shenandoah River & National Park

2.0 star property
10.0 out of 10, Exceptional, (9)
"This place was amazing and Ruth was so kind and amazing as well. Beautiful area and very peaceful. Will definitely be coming back again ! "
The price is NZ$382
includes taxes & fees
23 July - 24 July
Peaceful cottage in farmland - close to Luray, Shenandoah River & National Park

Peaceful Mountain Hideout | Luray Charm

2.0 star property
10.0 out of 10, Exceptional, (3)
"The stay was beautiful. Beautiful scenery and great for families with pets. Awesome rental property!"
The price is NZ$512
includes taxes & fees
22 July - 23 July
Peaceful Mountain Hideout | Luray Charm
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews

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?

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly: 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. Kitchen amenities include a dishwasher, a fridge and a stovetop. 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 19 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.