
Hotels in Winchester
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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!

Aria Hotel and Spa
Aria Hotel and Spa provides the ideal destination to escape the pressures of city life, whether for a weekend stay or a full week of rejuvenation. It is conveniently located one exit from Dulles Airport and within walking distance of Dulles Mall. Aria Guests have access to private spa areas, lounges, a sauna, steam, salt rooms, a beautiful guest dining room, and a cafe. Aria offers a wide selection of body treatments, massages, facials, aromatherapy, body scrub, wrap, and weight loss regimens.

Luxury 2 Bed & 2 Bath Unit with Full Amenities
For more than 45 years, Massanutten has offered an authentic mountain experience and endless outdoor adventures including ziplining, skiing, hiking, and mountain biking. Whether you seek relaxation, exploration, or inspiration, Massanutten is the perfect family destination. You will never run out of things to do and places to explore, with 12 on-site dining locations, escape rooms, a day spa, an award-winning indoor/outdoor water park, two 18-hole golf courses, and so much more.

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.

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.

Historic Downtown Location + Premium Restaurant
The Visitation Hotel Frederick offers an upscale, boutique experience, blending historic elegance with modern comforts. This landmark building, with a rich 200-year history, has been transformed into a premier hotel. Originally a monastery and later a well-known school, the Visitation Hotel now welcomes travelers seeking a peaceful and comfortable stay.

Historic Hotel Gunter - Room 316
Step into the timeless elegance of the Hotel Gunter, the iconic five-story landmark that has graced Downtown Frostburg since 1897. Adorned with classic balconies, it remains a beloved gathering place. Nestled in the heart of the town, our historic hotel offers modern comfort alongside effortless access to the finest local shops and restaurants.

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.

The Hermitage Inn Full 1 Bed
Experience the charm of history while enjoying modern comforts in our beautifully restored historical suite located in the heart of Grant County. Includes a cozy full-size bed with premium linens for a restful night's sleep. Equipped with essential appliances and dining essentials for a home-away-from-home experience.

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.

Single (1 Full Bed)
One double bed with a microwave & mini fridge. The room has been updated with flat screen televisions, mini-fridges, microwaves, air-conditioning, and free wi-fi. Many of the rooms have been remodeled to update flooring, plumbing, electrical, and bathroom fixtures.

George Washington l Queen Bed l Historic Charm
Stay in the heart of Winchester’s walkable downtown, where fine dining and local history meet. This well-appointed queen room offers upscale finishes, elegant décor, and all the essentials for a restful night. A perfect fit for solo travelers or couples.
Popular amenities for Winchester hotels
Family-friendly hotels

Prime Spot! Pet-friendly Property, Free Breakfast!

Historic Hotel Gunter - Room 308

Pet-Friendly Stay Close to Fairfax Museum

Spacious Room Short Drive to EagleBank Arena

A Great Stay in Chambersburg with beautiful rooms!

Get an Overall Fantastic Stay! Free Breakfast!

Boutique Motel in Fairfield

Relax and Recharge! Pets Allowed, Free Breakfast
Hotels with a pool

King Room l George Washington l Downtown Charm

King Room l George Washington l Double Vanity

Deluxe King | Wingate Chantilly | Free Breakfast

Signature Aloft chill vibe and grab-n-go eats

2 Queen Beds | Wingate Chantilly | Park & Fly

Winchester Stay | 2 Units | Downtown Location

House shuttle zips you to/from the airport gratis

George Washington l King Bed l Vanity for Two
Hotels with a patio

The Ridge 01 Explore Shenandoah-JMU-Queen bed

The Ridge 11 Travel JMU Harrisonburg- Queen bed

The Ridge 14 Harrisonburg JMU- Queen Bed

The Ridge 06 JMU/Business Travel - Queen

The Ridge 08 Sweet Hearts Getaway!

The Ridge 03 Visit Harrisonburg-King bed

The Ridge 07 JMU Queen Bed

The Ridge 05 Explore Valentine's Day Retreat
Quick stats about hotels in Winchester

Total vacation rentals
Explore 20 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at G$25,089 GYD per night before taxes and fees

Verified guest reviews
Over 100 verified reviews to help you choose

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
20 of Winchester vacation rentals include wi-fi access

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

4.8 Average rating
Winchester stays are highly rated by guests—averaging 4.8 out of 5!
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- Family-friendly rentals Winchester
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- Hotel rooms Virginia
- Hotel rooms United States
- Whitetail Resort
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- Stone Tower Winery
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- Cunningham Falls State Park
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- South Mountain State Park
- Shenandoah River Outfitters
- Jiffy Lube Live
- Sky Meadows State Park
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- Big Cork Vineyards
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- Rock Gap State Park
- Old Town Winchester Walking Mall
- Bluemont Vineyard
- Reston Town Center
- Museum of the Shenandoah Valley
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