Search Winchester Cottage 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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Cottages in Winchester

Our top choices for Winchester cottages

Homey Luray Cabin w/ Fire Pit & Deck!
Interior

Homey Luray Cabin w/ Fire Pit & Deck!

3.0 star property
9.0 out of 10, Wonderful, (2)
"The downstairs area would not get warm enough to stay downstairs, the wood for the back porch was rotting too underneath so we stayed off that, and I’m not sure if it was someone who stayed before left a box of beer by the jacuzzi. Overall we had a good time. "
Homey Luray Cabin w/ Fire Pit & Deck!
Riversong Cabin w/ Fire Pit on North River
Interior

Riversong Cabin w/ Fire Pit on North River

3.0 star property
Riversong Cabin w/ Fire Pit on North River
Cozy Winter Retreat: Great Location & Pet Friendly
Interior

Cozy Winter Retreat: Great Location & Pet Friendly

3.0 star property
10.0 out of 10, Exceptional, (1)
Cozy Winter Retreat: Great Location & Pet Friendly
Mountain Town Adventures Home w/ Fire Pit!
Interior

Mountain Town Adventures Home w/ Fire Pit!

3.0 star property
10.0 out of 10, Exceptional, (1)
"It was fantastic"
Mountain Town Adventures Home w/ Fire Pit!
Front Royal Retreat ~ 1 Mi to National Park!
Interior

Front Royal Retreat ~ 1 Mi to National Park!

3.0 star property
Front Royal Retreat ~ 1 Mi to National Park!
Peaceful Luray Cabin w/ Hot Tub, Deck & Fire Pit!
Interior

Peaceful Luray Cabin w/ Hot Tub, Deck & Fire Pit!

2.0 star property
10.0 out of 10, Exceptional, (1)
Peaceful Luray Cabin w/ Hot Tub, Deck & Fire Pit!
Charming Hedgesville Retreat w/ Deck + Fireplace!
TV, fireplace

Charming Hedgesville Retreat w/ Deck + Fireplace!

3.0 star property
10.0 out of 10, Exceptional, (3)
Charming Hedgesville Retreat w/ Deck + Fireplace!
Walk to Stores: Home in Historic Shepherdstown!
Interior

Walk to Stores: Home in Historic Shepherdstown!

3.0 star property
Walk to Stores: Home in Historic Shepherdstown!
Sunny Front Royal Vacation Rental w/ Hot Tub!
Interior

Sunny Front Royal Vacation Rental w/ Hot Tub!

3.0 star property
Sunny Front Royal Vacation Rental w/ Hot Tub!
Secluded Berkeley Springs Home w/ Fire Pit + Deck!
Interior

Secluded Berkeley Springs Home w/ Fire Pit + Deck!

3.0 star property
Secluded Berkeley Springs Home w/ Fire Pit + Deck!
Charming Home With Yard Near Shenandoah River!
Interior

Charming Home With Yard Near Shenandoah River!

3.0 star property
10.0 out of 10, Exceptional, (3)
"Cozy house nestled in the mountains of West Virginia. Well-maintained, clean, great yard for pets and/or kids! Lovely grilling and fire pit area. We throughly enjoyed our stay!"
Charming Home With Yard Near Shenandoah River!
Chic Front Royal Retreat Near Shenandoah River!
Interior

Chic Front Royal Retreat Near Shenandoah River!

3.0 star property
10.0 out of 10, Exceptional, (5)
"Nice place near skyline drive"
Chic Front Royal Retreat Near Shenandoah River!
Home w/ Hot Tub Near Shenandoah Nat'l Park!
Interior

Home w/ Hot Tub Near Shenandoah Nat'l Park!

3.0 star property
Home w/ Hot Tub Near Shenandoah Nat'l Park!
Cozy Cabin With Sunroom & Cacapon River Access!
Interior

Cozy Cabin With Sunroom & Cacapon River Access!

3.0 star property
10.0 out of 10, Exceptional, (2)
"We had a fantastic family trip. This was a great landing point to amazing outdoor adventures in the area. "
Cozy Cabin With Sunroom & Cacapon River Access!
Modern Mountain Retreat w/ Deck + Hot Tub!
Private kitchen

Modern Mountain Retreat w/ Deck + Hot Tub!

3.0 star property
Modern Mountain Retreat w/ Deck + Hot Tub!
Lush, Modern Farmhouse w/ Mtn Views & Sunroom
Interior

Lush, Modern Farmhouse w/ Mtn Views & Sunroom

3.0 star property
Lush, Modern Farmhouse w/ Mtn Views & Sunroom
Renovated WV Schoolhouse: History Buffs Heaven!
Interior

Renovated WV Schoolhouse: History Buffs Heaven!

3.0 star property
10.0 out of 10, Exceptional, (2)
"The school house is amazing. Clean, comfortable, quiet. I would definitely stay there again if I am in the area"
Renovated WV Schoolhouse: History Buffs Heaven!
Front Royal Hilltop Cabin w/ Panoramic Views!
Outdoor spa tub

Front Royal Hilltop Cabin w/ Panoramic Views!

3.0 star property
Front Royal Hilltop Cabin w/ Panoramic Views!
Spacious Virginia Retreat w/ Deck & Scenic Views!
Interior

Spacious Virginia Retreat w/ Deck & Scenic Views!

3.0 star property
10.0 out of 10, Exceptional, (1)
"So I had to book a place big enough for a large family last minute and found this property and let me tell you this property was spacious and breathtaking! Had a everything we needed for a home away from home! The fridge and stove were a dream! The plus was having washer/dryer access, hot tub and a massage chair! Oh and the tower!! The view from the deck was beautiful but from the tower was just amazing! Will definitely be coming back especially once the pool is built!"
Spacious Virginia Retreat w/ Deck & Scenic Views!
Pet-friendly Basye Vacation Rental w/ Fireplace!
Interior

Pet-friendly Basye Vacation Rental w/ Fireplace!

3.0 star property
10.0 out of 10, Exceptional, (3)
"The house was perfect! It was exactly as described. Sparkling clean, comfortable beds and linens. Lots of extras that made our stay comfy like game boards, puzzles, snacks, coffee and creamer. Thank you for sharing your beautiful home. "
Pet-friendly Basye Vacation Rental w/ Fireplace!
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
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Motel 6 Winchester, VA

Motel 6 Winchester, VA

10/10 Excellent
"Pleasant staff, good stay. Repeat visitor. "
JOHN 1-night trip
Posted 2 hours ago
Motel 6 Winchester, VA

Frequently asked questions

Why book your cottage in Winchester with Expedia?
We think that holidays should be simple, so if you're in search of cottages in Winchester at a competitive price, Expedia has got your back. Keep costs down and check in to a cheap option far away from the city rush, or splurge on an upmarket cottage to spoil your favourite people.
How can I find cheap cottages in Winchester?
The easiest way to locate cheap cottages in Winchester is with Expedia's useful filter tool. Narrow your search results by star rating, amenities and budget to snag awesome prices in just a few keystrokes.
What is there to do in Winchester near my cottage?
Winchester has enough activities and sights to keep you on the hop for weeks, starting with Rock Harbour Golf Course. The Kernstown Battlefield, Museum of the Shenandoah Valley and Apple Blossom Mall are other fantastic attractions. If you're in town a while, Jim Barnett Park and Handley Regional Library are nice final touches to your itinerary.