
Hotels in Winchester
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Quick stats about hotels in Winchester

Total holiday rentals
Explore 20 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $77 SGD per night before taxes and fees

Verified guest reviews
Over 110 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
Top-rated hotels in Winchester
Guests agree: these hotels are highly rated for location, cleanliness and more.

A Great Stay in Chambersburg with beautiful rooms!
You’ll love the stylish decor of this charming place to stay. Inviting hotel off I-81 close to historic Gettysburg Our welcoming Baymont by Wyndham Chambersburg hotel is situated in the Cumberland Valley, just 15 miles from the Pennsylvania-Maryland border. We’re located off I-81 at exit 14 and Wayne Ave., 25 miles west of historic Gettysburg and close to many restaurants and Amish farm markets. Lots of great local attractions too! Please contact the hotel for information on extended stay rates.

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.

Near Potomac Mills | Indoor Pool + On‑Site Dining
Enjoy a modern, convenient stay at Courtyard Potomac Mills Woodbridge, ideally located just off I-95 and minutes from Potomac Mills Outlet Mall. Perfect for business, weekend getaways, or family trips, the hotel offers newly updated rooms with plush bedding, HDTVs, and workspaces, plus great amenities like an indoor pool, restaurant, and 24-hour fitness center. Only 25 miles south of Washington, D.C., you’ll be close to shopping, dining, and top regional attractions.

Close to Rio Lakefront + Gym. Pool. Restaurant.
Check in, drop your bags, and explore Rio Lakefront or grab dinner near the water. At Hilton Garden Inn Rockville-Gaithersburg, you’re minutes from Rockville’s Tech Corridor, local trails, and Shady Grove Metro—but still tucked into a quiet spot with a pool, gym, and on-site bar. Fast Wi-Fi, and comfy rooms make it easy to unwind, whether you're visiting campus, exploring D.C., or working in the heart of Montgomery County’s innovation hub.

Near Potomac Mills Mall + Breakfast. Kitchen. Pool
Stay close to Potomac Mills Mall and just minutes from Quantico at Residence Inn Woodbridge Potomac Mills. Perfect for families, groups, and business travelers, every spacious suite includes a full kitchen, free Wi-Fi, and separate spaces to work and relax. Fuel up with free hot breakfast, swim year-round in the indoor pool, and stay on track with the fitness center. Paid on-site parking and a prime I-95 location make getting around easy.

Queen Studio w/ Kitchen + Free Breakfast & Pool
Welcome to Residence Inn by Marriott Gaithersburg Washingtonian Center, your extended-stay home in the heart of one of Gaithersburg’s most vibrant neighborhoods. Wake up to free hot breakfast daily, relax by the seasonal outdoor pool, and explore Rio Lakefront just steps away. Whether you're here for work or play, our spacious suites with full kitchens and thoughtful amenities are designed to make every stay effortless.

Near Wolf Trap National Park + Breakfast. Pool.
Spread out, sleep in, and sip free cocktails at this two-room suite stay near Tysons Corner. Wake up to made-to-order breakfast (hello, omelets), hop on the Metro to explore D.C., or chill by the indoor pool after a day of shopping or sightseeing. With on-site parking, and a separate living room in every suite, it’s the perfect mix of hotel perks and homey space—no tiny rooms or shared kitchens here.

Historic Hotel Gunter - Room 311
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.
Popular amenities for Winchester hotels
Family-friendly hotels

Upscale Extended Stay Suite w/ Free Hot Breakfast

Upscale Extended Stay Suite Hotel W/Free Breakfast

Walk to Rockville Metro Station + Dining & Pool

Wayside Inn (Room #7) Jefferson Guest Room

Wayside Inn (Room #22) Byrd Guest Room

Meeting House | Queen

The Ridge 13 Visit Harrisonburg

Rio Lakefront Close | On-Site Dining + Fitness
Hotels with a pool

2 Units | Queen Room | George Washington

Woodstone Massanutten 4 Bedrooms

Close to Potomac Mills Mall + Breakfast & Kitchen

Deluxe King | Wingate Chantilly | Free Breakfast

Serene Hideaway Perfect for a Relaxing Countryside

Suite In Manassas

Getaway in Virginia for 6!

George Washington l Double Room l Great for 4
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

Historic Hotel Gunter - Room 315

The Ridge 03 Visit Harrisonburg-King bed

Historic Hotel Gunter - Room 312

Tysons Corner Suites
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