
Hotels in Winchester
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Top-rated hotels in Winchester
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Prime Spot! Pet-friendly Property, Free Breakfast!
See a vacation through the eyes of one of our visitors! The National Firearms Museum and Fair Oaks Park are just a few of the city's many cultural attractions. Learn the true meaning of travel and how much fun you can have by staying at this first-rate hotel. The location of the property puts public parks and shopping malls within easy walking distance. It offers a variety of recreational activities, including golf and wine tasting. By living here, you experience the wonders of this amazing city

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!

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.

Wayside Inn (Room #7) Jefferson Guest Room
Room 7 ~ The Jefferson Guest Room has a full/double bed with a full bathroom. It is located up the main staircase on the 3rd floor. This room also connects to the Taylor Guest Room # 8. (If you are traveling with family, this set of rooms is a great option!) The room was named after Thomas Jefferson, the 3rd president of the United States. Thomas Jefferson was one of the U.S. presidents born in Virginia. Check-in time begins at 3 pm, and check-out time is at 11am.

Boutique Motel in Fairfield
Kick back and relax, Stay a little longer at Fairfield Extended Stay. These rooms are designed with the furnishings of a well-appointed home, featuring mini fridge and microwave, full baths, and a comfortable living area. Our extended stay motel near Fairfield, PA is ideal for corporate relocation, extended work engagements, vacationing in Gettysburg and other short or long term lodging needs. this calm, stylish space.

Close to Quantico Marine Corps Base
A quite, secure setting just outside the Marine Corp Base Quantico and the Marine Corp National Museum. Only 35 miles to Washington DC and close to historic Fredericksburg VA. This one bedroom unit has a fully equipped kitchen and flat screen TVs in the living room and the bedroom. Pets (dogs only) are allowed with a fee. Please contact host for details on pet policies and fees.

Prime Downtown Location+Celebrity Chef 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 312
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.

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.

King Room l George Washington l Downtown Charm
Experience the rich heritage of downtown Winchester while enjoying upscale amenities like a Roman-style indoor pool and live music lounge. This king room offers plush bedding, a workspace, and refined comfort. Ideal for business trips or weekend getaways.
Popular amenities for Winchester hotels
Family-friendly hotels

Wayside Inn (Room #4) Wilkenson Guest Room

Wayside Inn (Room #8) Taylor Guest Room

Wayside Inn (Room # 19) Massanutten Guest Room

Wayside Inn (Room #20) Rutherford Stateroom

Welcome To Tysons Corner Suites

Wayside Inn (Room #21) Hite Guest Room

Wayside Inn (Room #1) Jubal Early State Room

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

Vacation in Virginia for 4!

Modern Hotel with Small Town Charm

Luxury 2 Bed & 2 Bath Unit with Full Amenities

Deluxe King | Wingate Chantilly | Free Breakfast

Signature Aloft chill vibe and grab-n-go eats

Serene Hideaway Perfect for a Relaxing Countryside

House shuttle zips you to/from the airport gratis

Suite In Manassas
Hotels with a patio

The Ridge 01 Explore Shenandoah-JMU-Queen bed

The Ridge 11 Travel JMU Harrisonburg- Queen bed

The Ridge 12 Travel JMU Harrisonburg - Queen Bed

The Ridge 08 - Explore Harrisonburg/JMU

The Ridge 03 Visit Harrisonburg-King bed

The Ridge 07 JMU Queen Bed

The Ridge 10 Visit Harrisonburg JMU -King Bed

The Ridge 09 JMU /Business Travel - King
Quick stats about hotels in Winchester

Total holiday rentals
Explore 20 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $155 SGD 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
20 of Winchester holiday rentals include wifi 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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