
Hotels in Winchester
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Top-rated hotels in Winchester
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Deluxe King Suite in Boutique Hotel
SCH is Fredericksburg’s newest luxury boutique hotel offering the comfort of a First Class hotel with the ease of a fully automated check-in experience. Perfect for those guests needing an Extended Stay in the Fredericksburg area as every guest suite is a welcoming residential style retreat featuring a spacious living room - a separate well appointed bedroom - full kitchen equipped with Whirlpool appliances including a full size refrigerator - range - dishwasher - microwave - as well as a washer and dryer. At SCH our guests have exclusive access to our 16000 square foot Clubhouse offering complimentary daily continental breakfast and shared coworking spaces equipped with all the essentials you will need for on-the-road productivity. Our Clubhouse access includes state-of-the-art fitness center - resort style pool - game room - spa area with steam and sauna as well as a massage room. Amenity offerings can change due to the COVID19- pandemic.

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!

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 12 Travel JMU Harrisonburg - Queen Bed
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.

Wayside Inn (Room # 19) Massanutten Guest Room
Room 19 ~ The Massanutten Guest Room has a double bed and a full bath with a standard tub. This origin of the name for this room has a couple of versions. One is that it was named by the local Native Americans. "Massa" which means ground and "Nutten" means potato. Another version is that the Native Americans named it the Great Lookout Mountain. This room is one of three rooms on the first floor in the south wing. Check-in time begins at 3 pm, check-out time is at 11 am.

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!

Door-to-door shuttle service to/from Dulles
Hyatt Regency Dulles features 316 spacious rooms and suites designed for you to relax and stay productive. Our fresh, contemporary style blends perfectly with our premium travel amenities, including plush beds, 55" HDTV, Pharmacopia bath amenities, free Wi-Fi and oversize work desk. Upgrade to one of our suites and enjoy extra perks like separate bedroom and living areas, conference table, second TV and beautiful views.

Magnolia Cottage
Come relax in this private cottage nestled in the Shenandoah Valley. This quaint setting is perfect for a relaxing getaway from your busy life. The cottage has a king size bed, whirlpool tub and shower, kitchenette with complimentary coffee, tea, and snack items. We are minutes away from JMU, EMU, Bridgewater College, local restaurants and breweries. You won't want to leave this charming, one-of-a-kind place.

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.

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

Zen Suite at White Lotus Eco Spa Retreat

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

The Knolls The Paddock. Room 8

Botanical

Shepherdstown

Room 3 - Rustic, modern motel room with two twin beds.

The Cozy Suite

Bliss Point Farm and B&B, Blue Heaven Room
Hotels with a pool

Modern Hotel with Small Town Charm

1 BR-Massanutten Eagle Trace Mountain Resort

Accessible King Suite in Boutique Hotel

Suite In Manassas

Casa Om Potomac Room 1

Accessible King Rm w/ Sofa Bed + Outdoor Area

George Washington l Double Room l Great for 4

Massanutten Woodstone Casa K Condo
Hotels with a patio

Joshua Wilton House - Room 2: The Den

Historic Romantic Equestrian Luxury Harpers Ferry

Renovated Hotel By Historic Park

Relaxing 1 Bed/1 Bath/Half-Kitch

The Ridge 03 Visit Harrisonburg-King bed

Guest suite - Breakfast, Pool table and Bar

The Chelf Room, Culpeper VA

Fun in Massanutten
Quick stats about hotels in Winchester

Total holiday rentals
Explore 30 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $107 AUD 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

Wi-Fi availability
30 of Winchester holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Winchester rentals

4.7 Average rating
Winchester stays receive an average rating of 4.7 out of 5 from guests
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- Rentals with a patio Winchester
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- Rentals with outdoor seating Winchester
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- Luray Caverns
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