
Hotels in Winchester
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Top-rated hotels in Winchester
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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!

Paw Paw 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 Paw Paw Suite is an inviting space with a queen size bed, double shower bathroom, and kitchenette. Located in the heart of Capon Bridge, you'll find it easy to walk to everything. For a relaxing stay in a friendly, artsy community, this is a great place to enjoy.

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 Football - 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!

Golden Room - Loudoun Valley Manor
Golden room is one of the several cozy bedrooms that Loudoun Valley Manor (Bed and Breakfast) offers for guests in a luxurious house conveniently located a quarter mile off Route 9. My place is close to Leesburg and Purcellville, VA. Over 20 wineries around. 50-minute drive from Washington, DC. 25 miles to Dulles airport. Restaurants, malls, Casino. Lots of space! Internet and cable TV. My place is good for couples and business travelers.

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!

A Redbud Room
Exposed brickwork (ca 1790) creates a charming alcove for the queen-sized bed and chairs by the (seasonal) gas-log fireplace. A separate dressing room is found beside the updated bathroom with a soaking tub and separate shower. The 15-inch interior brick walls ensure a cozy, quiet and private stay! This room is located on the second floor.

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.

Edison Room - GAP Trail Hotel at Morguen Toole Co
*Book direct & save* We understand that sometimes, efficiency is key. The Edison Room is perfect for a single traveler or a couple just looking for somewhere to rest their head for the night and be on their way the next morning. This room features a full bed and shares a communal bath in our hotel.

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

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 One at 351, Bedroom 3

The Knolls Serenity Room 7

Minutes to D.C. | Indoor Pool. Gym. On‑Site Dining
Hotels with a pool

Modern Hotel with Small Town Charm

1 BR-Massanutten Eagle Trace Mountain Resort

Wingate Chantilly | King Bed | Near Dulles

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

The Cozy Suite

The Ridge 03 Visit Harrisonburg-King bed

Guest suite - Breakfast, Pool table and Bar

The Chelf Room, Culpeper VA

Fun in Massanutten

Getaway in Virginia for up to 8!
Quick stats about hotels in Winchester

Total holiday rentals
Explore 30 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at € 61 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
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