Find Extended Stay Hotels in Winchester, VA

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Top Winchester Extended Stay Hotels | Reserve now, pay later

Hampton Inn Front Royal

2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1001)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
$107 nightly
The price is $119
Dec 14 - Dec 15
Total with taxes and fees
Hampton Inn Front Royal

TownePlace Suites by Marriott Winchester

3.0 star property
Winchester
8.8 out of 10, Excellent, (478)
"Nice place to stay. Great staff and breakfast."
United States
Stormy
$107 nightly
The price is $117
Dec 7 - Dec 8
Total with taxes and fees
TownePlace Suites by Marriott Winchester

Sauna, theatre, game room, gym, EV charger hot tub, firepit ,baby accommodations

2.0 star property
Toms Brook
10.0 out of 10, Exceptional, (2)
"Host was very responsive and helpful! The VRBO was beautiful and well taken care of. The mountain view was awesome. Our group of 11 stayed very comfortably! The hot tub and sauna were clean and easy to use. Additionally, our host provided a loaf of sourdough bread and muffins from a local bakery which were delicious. We would definitely stay here again. Thank you!"
United States
Paulina G.
$623 nightly
The price is $687
Dec 8 - Dec 9
Total with taxes and fees
Sauna, theatre, game room, gym, EV charger hot tub, firepit ,baby accommodations

The Vue - Mountain top hot tub overlooking the Shenandoah River

2.0 star property
Front Royal
9.8 out of 10, Exceptional, (10)
"Love the view and beautiful appointed decor throughout the home…"
United States
Lynn M.
$355 nightly
The price is $392
Dec 22 - Dec 23
Total with taxes and fees
The Vue - Mountain top hot tub overlooking the Shenandoah River

Skyland Hideaway • Relaxing Cabin w/ Hot Tub, Deck, Grill, & Fire table

Linden
10.0 out of 10, Exceptional, (15)
"Quiet with amenities to support R&R, enjoying nature, and togetherness."
United States
Patricia B.
$332 nightly
The price is $366
Dec 9 - Dec 10
Total with taxes and fees
Skyland Hideaway • Relaxing Cabin w/ Hot Tub, Deck, Grill, & Fire table

Rosamond nice downtown studio apt

Winchester Historic District
8.0 out of 10, Very Good, (2)
"Small but appropriately priced."
United States
John M.
$170 nightly
The price is $193
Dec 7 - Dec 8
Total with taxes and fees
Rosamond nice downtown studio apt

The Juniper Cabin • Private Hideaway w/ Hot Tub, Grill & Screened Porch

Linden
10.0 out of 10, Exceptional, (22)
"We had a fantastic time staying at this property for the weekend."
United States
Colin N.
$291 nightly
The price is $321
Dec 7 - Dec 8
Total with taxes and fees
The Juniper Cabin • Private Hideaway w/ Hot Tub, Grill & Screened Porch

The Foxwood Cabin: Cozy Retreat w/ Hot Tub, Screened Porch, Firepit & Grill

Front Royal
10.0 out of 10, Exceptional, (5)
"Beautiful, quiet place to stay. Beds are very comfortable. Every room was very clean. "
United States
Alex H.
$342 nightly
The price is $377
Dec 7 - Dec 8
Total with taxes and fees
The Foxwood Cabin: Cozy Retreat w/ Hot Tub, Screened Porch, Firepit & Grill

Guest House at Mt Independence

2.0 star property
Delaplane
10.0 out of 10, Exceptional, (4)
"Great property, conveniently located to attractions. Host was extremely responsive and friendly. Home and surrounding property was immaculate. We will be staying here again when back in the area. "
United States
Scott S.
$355 nightly
The price is $367
Dec 8 - Dec 9
Total with taxes and fees
Guest House at Mt Independence
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find out more about Winchester

Discover top Winchester attractions

Winchester, Virginia, is a captivating blend of history and outdoor adventure, perfect for travelers seeking quality experiences. Begin your journey at the historic Old Town, where cobblestone streets are lined with charming boutiques, art galleries, and inviting restaurants. Be sure to visit the Museum of the Shenandoah Valley, which not only showcases regional art but also boasts stunning gardens that are perfect for a leisurely stroll. For a taste of local history, the Stonewall Jackson's Headquarters Museum offers a glimpse into Civil War life with fascinating exhibits. Nature enthusiasts will love the nearby Shenandoah National Park, where family-friendly hiking trails reveal breathtaking views of the Blue Ridge Mountains. After a day of exploration, unwind in the Winchester area, where you can find upscale accommodations that cater to your every need, featuring amenities like fine dining, luxurious spa services, and attentive staff ready to ensure a memorable stay. The combination of rich history, outdoor activities, and quality lodging makes Winchester a remarkable choice for your next family getaway.

Find the best extended stay hotels in Winchester

Travelers seeking a comfortable stay with convenient kitchen amenities in Winchester, Virginia will find these top hotels to be excellent choices. Each hotel is equipped to make meal preparation easy and enjoyable during your visit.

Hampton Inn Winchester N/Conference Center, VA

  • Why it's great for an extended stay: The Hampton Inn Winchester N/Conference Center is perfect for travelers who appreciate the convenience of in-room kitchen facilities, featuring a fully-equipped kitchen that includes a refrigerator and microwave. With a fantastic guest review rating of 9.2, it promises a comfortable and enjoyable stay. Guests can also indulge in a complimentary breakfast to start their day on a delicious note.
  • Other amenities: Beyond the kitchen amenities, this hotel offers a range of features to enhance guests' experiences, including a lovely terrace, ample free self-parking, and daily housekeeping. The location is ideal for exploring the historical district nearby, and outdoor enthusiasts will appreciate the access to hiking and biking trails. Additional comforts include premium bedding, a deep soaking bathtub, and a separate living room for added space.
  • Nearby attractions: Eastgate Plaza Shopping Center - 0.09 miles, Nalls Farm Market - 0.28 miles, Mt Hebron Cemetery - 1.36 miles

Candlewood Suites Winchester by IHG

  • Why it's great for an extended stay: The Candlewood Suites Winchester by IHG provides an exceptional experience for travelers who value having their own cooking space. With a full-size kitchen complete with a stovetop, dishwasher, and refrigerator, guests can easily prepare meals at their convenience. The hotel boasts a solid review rating of 9.0, ensuring a satisfying stay for all visitors.
  • Other amenities: Guests can enjoy a range of additional features, including free self-parking and early check-in options. The hotel is pet-friendly, accommodating furry companions with ease. Daily housekeeping ensures a clean and fresh environment, while the grocery and convenience store on-site adds to the convenience of meal planning. Fitness facilities are also available for those looking to maintain their workout routine during their stay, and the air conditioning provides a comfortable atmosphere year-round.
  • Nearby attractions: Valley Health - 0.93 miles, Shenandoah University - 0.43 miles, Jim Barnett Park - 0.92 miles

TownePlace Suites by Marriott Winchester

  • Why it's great for an extended stay: TownePlace Suites by Marriott Winchester is tailored for travelers who value the comforts of home, offering a well-equipped kitchen with a stovetop, dishwasher, and microwave. With an excellent guest review rating of 8.8, this hotel ensures a cozy and practical stay for its guests.
  • Other amenities: In addition to the kitchen facilities, guests can enjoy a refreshing outdoor pool and a roof garden for relaxation. The hotel provides complimentary breakfast options, including a continental spread, making mornings straightforward. With accessible parking and fitness center facilities, this hotel caters to both convenience and comfort. Housekeeping services are provided daily, and the presence of a snack bar adds a nice touch for those late-night cravings.
  • Nearby attractions: Eastgate Plaza Shopping Center - 0.82 miles, Nalls Farm Market - 1.01 miles, Mt Hebron Cemetery - 2.09 miles

Expand your search

Most booked related extended stays in Winchester in 2026

Frequently asked questions

What are the best extended stay hotels in Winchester?
Discover Winchester from one of the 31 long-term rentals waiting to be booked. Featuring useful amenities including kitchens, pots and pans and tableware, you can enjoy the hotel lifestyle — but with the extra comforts of home. Recharge after a busy day of exploring at Wingate by Wyndham Winchester. Cook your own meals and take advantage of a picnic area and a free continental breakfast here. Hilton Garden Inn Winchester is another excellent choice. It comes with fitness facilities and a conference center as well as a kitchen. Want to know what Expedia travelers think of our long-term rentals in Winchester? They've given them a total average guest review score of 9.6.
Are there any cheap extended stay hotels in Winchester?
An extended stay in Winchester doesn't have to cost a pretty penny. Look up Clarion Inn & Conference Center, an inexpensive option roughly 1.0 mi from the downtown area. It offers a range of conveniences including vending machines and a business center. Or, put down your bags at TownePlace Suites by Marriott Winchester. This low-cost property features laundry facilities and a free continental breakfast and is about 2.0 mi from the center. With extended stay hotels in Winchester starting at just $85 a night, you're in for an affordable treat!*There are plenty of fabulous free attractions around Winchester if you'd love to sightsee cheaply too. Shenandoah University and Winchester Medical Center are just the start.*These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the top pet-friendly extended stay hotels in Winchester?
Clarion Inn & Conference Center rolls out the welcome mat for the entire family, including your best pal. This pet-friendly retreat includes pet-friendly services and laundry facilities and is a popular choice for an extended stay in Winchester. Dogs and their owners are also well looked after at TownePlace Suites by Marriott Winchester. This long-term stay offers pet-friendly services, a cafe and more.
What are the best extended stay hotels with kitchens in Winchester?
If you're on the road with the kids, dining out doesn't have to swallow a huge chunk of your travel budget. Save on takeout and restaurant bills at Candlewood Suites Winchester, an IHG Hotel. Offering a kitchen, pet-friendly facilities and housekeeping services, this hotel is a top pick for traveling families. You can also cook your own meals at ANS Inn has clean, spacious rooms located on 5 acres with little traffic.. Pet-friendly facilities and a king bed help make this option one of our most in-demand long-term stays in Winchester.
Why book an extended stay hotel in Winchester through Expedia?
Reserve your extended stay hotel in Winchester with Expedia and get set to save. Along with our competitive offers and reward programs, we make finding the ideal long-term stay a piece of cake. Use the filters to search for properties according to location, family-friendly amenities, price range and more. Some long-term rentals may offer weekly rates so you have cash left over for the fun stuff. Usually equipped with homey amenities like a kitchen and laundry, your next extended stay in Winchester is only a couple of clicks away!
What can I expect from an extended stay hotel?
Book an extended stay hotel in Winchester and take as much time as you need discovering this exciting destination. Along with being able to stay a couple of weeks or more, these types of properties come with features designed to make your visit easier. Kitchens, laundries and dining areas are just the start. To find the perfect extended stay hotel, use Expedia's filters to search for properties based on amenities, price range and more. Often offering competitive weekly rates, extended stay hotels can be more affordable than your standard hotel.

Top Winchester Hotel Reviews

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