
Hotels in Winchester
Find and book unique hotels on Airbnb
Top-rated hotels in Winchester
Guests agree: these hotels are highly rated for location, cleanliness and more.

The Knolls Town & Country Room 9
This vintage motel has been updated to provide charming efficiency rooms. Each room has a kitchenette, private bath, 55” smart tv, & Wi-Fi. The Knolls is located steps from the VA, minutes from Martinsburg & Charles Town, & close to Charles Town Casino as well as many other local attractions. Parking is directly in front of your door. Each room is equipped with a smart lock on the door. Room #9 is comfortably designed with luxury linens, memory foam mattress, and so much more. Come stay with us!

Historic Cashtown Inn General Lee Suite
Stand on the front porch of the Cashtown Inn, let your eyes roam among the gentle grade of Old Chambersburg Pike. It rises past apple orchards and open fields towards the wooded slope of Cashtown Gap in South Mountain. If these hills could talk of the stories of bygone days, we would hear of weary travelers looking for a meal, lodging for the night. Or of brave soldiers passing on their way to battle to the sound of marching bands. Cashtown Inn was built circa 1797, 8 miles West of Gettysburg.

Redbud Suite ~ 1 of 5 Unique Stays at Basswood
For those seeking to step away from the bustle of the city and slow down in a friendly, charming town. Basswood is a historic home that has been lovingly remodeled to include five private suites each with their own unique style. The Redbud Suite is a cozy space with a kitchenette, queen bed and private bathroom down the hall. Located in the heart of Capon Bridge, you'll find it easy to walk to local restaurants and entertainment, while enjoy being perched above the beautiful Cacapon River.

Herring Suite, in the historic Inn at Thomas House
The Herring Suite is a 2nd floor, private queen bedroom with en suite bath, in the Inn at Thomas House, in Historic Dayton, VA This is the main bedroom in the Inn, named for the original owners, Alexander and Abigail Herring, who built the Thomas House in 1818. Guests enter the Inn from Main street, a quiet street, lined with quaint shops, where its common to see horse-drawn buggies traveling by. The Thomas House restaurant, is on-site, and open Tuesday - Saturday for breakfast and lunch.

The Ridge 06 JMU/Business Travel - Queen
Centrally located in the heart of the Friendly City, this stylish rental is minutes from the lively downtown of Harrisonburg. Perfect for a weekend of exploring the Valley or visiting JMU, it provides comfortable, clean, and newly remodeled rooms. Rooms are located in a central building that includes shared hallway, laundry, common area with microwave, coffee station (supplies included) and outdoor seating area with fire ring. Downtown sport delicious cuisine for your enjoyment.

Joshua Wilton House - Room 1: The Study
This stunning Victorian bedroom overlooks our private patio and garden. Tall ceilings, exposed brick, and red walls give this spacious room a warm, cozy feel. Enjoy the king-sized bed, antique writing desk, and browse our book collection at your leisure. The bathroom features a shower/bathtub combination, one of only two bathtubs in the home. This is one of the largest out of our five rooms, so if you're looking for room to stretch out, look no further!

Near Potomac Mills Mall + Breakfast. Kitchen. Pool
Stay close to Potomac Mills Mall and just minutes from Quantico at this hotel in Woodbridge. Perfect for families, groups, and business travelers, every spacious suite includes a full kitchen, free Wi-Fi, and separate spaces to work and relax. Fuel up with free hot breakfast, swim year-round in the indoor pool, and stay on track with the fitness center. Paid on-site parking and a prime I-95 location make getting around easy.

Mountain Laurel Studio
The Mountain Laurel Studio of Spring Water Cottage This Suite which provides a cozy sitting room includes a wet bar, electric fireplace, Roku TV, basic cable, small fridge/freezer combo, microwave, glassware and utensils. French doors from the bedroom lead to your private balcony. The bathroom features a large shower “room” equipped with multiple jets, a rain shower and a wand.

Charming Mountain Apartment
Kick back and relax in this calm, stylish space; nested in a peaceful mountain community. Located 4.7 miles from downtown Harpers Ferry. The area has a lot to offer in every season: hiking in the Appalachian trail, snow tubing, breweries and wineries, kayaking/tubing and fishing. Come and enjoy breathtaking sunsets and lots of wildlife with us!

The Peaceful Suite
This private Suite is perfect for the seasoned traveler. The Suite Dreams on Water has all the amenities you need for a short or extended stay in Martinsburg. Lots of luxury touches await your stay in this space that shares only the living room, dining room, kitchen, gym, office, and laundry. Your suite has its own private bathroom.

Wayside Inn (Room #18 ) Shenandoah Guest
Room 18 - The Shenandoah Guest Room has a queen bed and a bath with a shower only (no tub). The Shenandoah Guest Room is in the South wing on the 1st floor. This guest room was named for the Shenandoah Valley. The history of Wayside Inn is very important to the Shenandoah Valley. Check-in begins at 3 pm, check-out time is at 11 am.

Easy access to DC & just 10 mins from the airport
The Aloft Guestroom at Aloft Dulles Airport North features a stylish 285 sq ft (26 sqm) layout equipped with a mini fridge and coffee/tea maker. Enjoy Aloft’s contemporary design, plus wireless internet access (for a fee), making this room a comfortable and convenient choice for any traveler.
Popular amenities for Winchester hotels
Family-friendly hotels

Immaculate Queen Bedroom in Home with Parking

Inn at Cemetery Hill 2nd FL Super Suite

Room 4 - Rustic, modern motel room with king bed.

Botanical

Welcome To Tysons Corner Suites

The One at 351, Bedroom 3

The Knolls Serenity Room 7

Trouvaille House Suite #1 “Provence Suite"
Hotels with a pool

Woodstone Massanutten 4 Bedrooms

Modern Hotel with Small Town Charm

1 BR-Massanutten Eagle Trace Mountain Resort

Suite In Manassas

Renovated Hotel By Historic Park

Casa Om Potomac Room 1

Accessible King Rm w/ Sofa Bed + Outdoor Area

Fun in Massanutten
Hotels with a patio

The Ridge 01 Explore Shenandoah-JMU-Queen bed

Joshua Wilton House - Room 2: The Den

Historic Romantic Equestrian Luxury Harpers Ferry

Relaxing 1 Bed/1 Bath/Half-Kitch

The Cozy Suite

The Ridge 08 JMU/Business travel -Queen Bed

The Ridge 03 Visit Harrisonburg-King bed

Guest suite - Breakfast, Pool table and Bar
Quick stats about hotels in Winchester

Total holiday rentals
Explore 30 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at € 60 per night before taxes and fees

Verified guest reviews
Over 100 verified reviews to help you choose

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Winchester holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winchester rentals

4.7 Average rating
Winchester stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- Outer Banks Holiday rentals
- Jersey City Holiday rentals
- Cabin rentals Winchester
- Rentals with a patio Winchester
- Apartment rentals Winchester
- Rentals with outdoor seating Winchester
- Pet-friendly rentals Winchester
- Fitness-friendly rentals Winchester
- House rentals Winchester
- Cottage rentals Winchester
- Rentals with a fireplace Winchester
- Family-friendly rentals Winchester
- Rentals with breakfast Winchester
- Rentals with pools Winchester
- Flat rentals Winchester
- Rentals with a washing machine and dryer Winchester
- Hotel rooms Virginia
- Hotel rooms United States
- Luray Caverns
- Stone Tower Winery
- Whitetail Resort
- Cunningham Falls State Park
- Shenandoah Valley Golf Club
- Berkeley Springs State Park
- Bryce Resort
- Gambrill State Park
- Cacapon Resort State Park
- Creighton Farms
- Robert Trent Jones Golf Club
- South Mountain State Park
- River Creek Club
- Notaviva Vineyards
- Sly Fox Golf Club
- Bowling Green Country Club
- Twin Lakes Golf Course
- Dinosaur Land
- JayDee's Family Fun Center
- Reston National Golf Course
- Warden Lake
- Herndon Centennial Golf Course
- The Golf Club at Lansdowne
- Big Cork Vineyards




