Hotels in Winchester

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Top-rated hotels in Winchester

Guests agree: these hotels are highly rated for location, cleanliness, and more.

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Guest favorite
A cozy room features a spacious bed with plush pillows and soft linens. A comfortable chair is positioned nearby, with art pieces adorning the walls. Natural light filters through sheer curtains, and an air conditioning unit is visible beside the window.
Hotel room in Martinsburg
4.87 out of 5 average rating, 23 reviews

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!

A well-appointed bedroom features a spacious bed covered with a light-colored quilt and decorative pillow. A bedside lamp emits a soft glow. Light teal curtains with floral patterns frame a window, and a landscape painting hangs above the headboard.
Hotel room in Sterling

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.

Hotel room in Massanutten
New place to stay

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.

Superhost
Hotel room in Harrisonburg
5 out of 5 average rating, 3 reviews

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.

Hotel room in Herndon
4.71 out of 5 average rating, 157 reviews

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.

Hotel room in Frederick

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.

Hotel room in Frostburg
New place to 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.

Guest favorite
The guest room features a queen bed with a carved wooden headboard, complemented by antique furnishings. A small television is positioned on a wooden stand. Natural light enters through a window adorned with floral curtains, enhancing the warm wooden flooring and decorative wall trim.
Hotel room in Middletown
4.75 out of 5 average rating, 16 reviews

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.

A cozy guest room features a full-size bed with white linens, situated beneath a softly glowing ceiling light. A tall dresser stands adjacent to the bed, and a mirror reflects part of the room. A small wastebasket is placed in the corner along with a door leading to the bathroom.
Hotel room in Petersburgh
5 out of 5 average rating, 5 reviews

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.

Superhost
Hotel room in Ashburn
4.79 out of 5 average rating, 100 reviews

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.

A spacious room features a double bed dressed in a striped blanket, complemented by a wooden nightstand and a lamp. A mini fridge is situated nearby, and light from a window brightens the space. Wall art adds subtle decoration above the bed.
Hotel room in Frostburg
4.43 out of 5 average rating, 28 reviews

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.​

Hotel room in Winchester

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

Quick stats about hotels in Winchester

  • Total vacation rentals

    Explore 20 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at ﺩ.ﺇ441 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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