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Browse for Winchester Boutique Hotels from $76

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Featured Winchester Boutique Hotels

The George Washington Hotel, A Wyndham Grand Hotel
3.5 out of 5
103 E Piccadilly St, Winchester, VA
Free CancellationReserve now, pay when you stay
per night
Dec 15 - Dec 16
4.7/5Exceptional! (1,104 reviews)

"This is a very elegant, beautifully maintained historic hotel. Our room was pretty and generously sized with a very comfortable bed. The linens were crisp and absolutely spotless. Overall cleanliness of the room and the hotel is very high. We enjoyed our visit and would stay again at this hotel. ..."…"

Reviewed on Dec 6, 2019

The George Washington Hotel, A Wyndham Grand Hotel
La Quinta Inn & Suites by Wyndham Winchester
3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Free CancellationReserve now, pay when you stay
per night
Dec 22 - Dec 23
4.3/5Excellent! (1,663 reviews)

"Brand new hotel. Great rooms. Good sized fitness facility."…"

Reviewed on Dec 2, 2019

La Quinta Inn & Suites by Wyndham Winchester
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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.

Where Should I Stay in Winchester?

Searching for a stylish accommodation for your visit to Winchester? A boutique hotel may be exactly what you're looking for if you enjoy smaller hotels with personalized service and a cool atmosphere. Winchester has 2 boutique-style accommodations that characterize the local flavor of this destination.

Travelers say they enjoy these boutique hotels in Winchester:

La Quinta Inn & Suites Winchester: 3-star hotel with 99 guestrooms. Enjoy the indoor pool, free breakfast, and free parking. Popular with our guests for its comfortable rooms and overall value.

The George Washington Hotel, A Wyndham Grand Hotel: 3.5-star hotel with 90 guestrooms. This property offers 2 restaurants, a bar, and a full-service spa. Expedia travelers like its walkable location and guestroom size.

What Should I See and Do in Winchester?

Once you've decided where you'll stay in lively Winchester, consider what to do for fun during your trip. Visitors speak positively about this destination's major shopping centers, scenic landscape, and interesting historical sites.

Winchester is also known for its:
  • Skyscrapers
  • Restaurants
  • Cafés
  • Theater
  • Entertainment

Activities and attractions to experience around Winchester include Bright Box Theater, Winchester Little Theater, and Wayside Theater. You might also want to consider exploring Old Court House Civil War Museum, Shenandoah Valley Discovery Museum, and George Washington's Office while you're here.

When Should I Plan a Trip to Winchester?

If you're curious about the local weather, use this info to plan your escape to Winchester:

  • Hottest months: July, June, August, and September, with an average temperature of 84°F
  • Coldest months: January, February, December, and March, with an average temperature of 25°F
  • Driest months: February, January, December, and October, with an average rainfall of 2.63 inches
  • Rainiest months: May, September, June, and July, with an average rainfall of 3.69 inches

Getting Around Winchester

The nearest major airport is in Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) from the heart of the city. If you'd like to explore around the area, consider renting a car to take in more sights.

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What is the definition of a boutique hotel?


Winchester boutique hotels pride themselves on being unique. They are typically small properties that are independently run or part of a small chain, with a strong personality and attention to detail, creating a more immersive and memorable experience for guests than the average hotel.

Size: Boutique hotels usually have less than 100 rooms. Sometimes as few as 10. Due to the small size, guests tend to get more attentive service and flexibility with special requests.

Guestrooms: Often fitted with luxury bedding, upscale bathrooms, premium toiletries and added unique touches. It’s common to find each room in a boutique hotel looks different.

Ambience: You’ll find distinctive decor and luxury artwork in every space from the lobby, to restaurants to guestrooms, often influenced by the local community or made by local artisans. There’s likely to be several welcoming communal spaces.

Food: Some boutique hotels have a gourmet restaurant or cafe. In-room amenities may include a good coffee machine and interesting minibar selection.

Local community: Many boutique hotels support local businesses and involve the local community. Some boutique hotels are heritage hotels that preserve a cultural significance.


How many rooms does a Winchester boutique hotel have?


Small and stylish is the general rule. Boutique hotels tend to have between 10 - 100 rooms and suites.

Many boutique hotels will feature guest rooms with individual decor or themes, meaning each room looks different.


What is the difference between a Winchester boutique hotel and a regular hotel?


The main differences come from size, design and individuality.

Additionally, boutique hotels tend to incorporate Intricate designs, standout art pieces, involvement with the local community, and more inviting communal spaces free of crowds. All of these together with more flexible and attentive service, creates a more memorable experience for guests than a regular hotel affords.

Size and Identity: Winchester boutique hotels are smaller, often with less than a hundred guestrooms. Most are independently owned, which gives them the freedom to express a strong unique character -- often chic and luxurious, sometimes quirky or historic. The unique decor and attention to upscale details features centrally in boutique hotels, whereas regular hotels might be more focused on function to cater to more guests.

Design and Individuality: Every space in a Winchester boutique hotel is often designed to be not only beautiful, but interesting and engaging for guests. No generic hotel art in sight. Where large chain hotels tend to have similar decor across their properties, boutique hotels are more likely to go for one-of-a-kind effect. They may even incorporate local influences or craftsmanship. It’s also common for each guestroom to lookompletely different look than the next.

Experience: The smaller size and independence of a Winchester boutique hotel allows staff to offer a more personal experience to guests compared to most other hotels. Larger hotels have to cater widely to many guests spread across a bigger property; hotel chains need to be consistent, sensible and similar across all properties in the brand; other small hotels aren’t necessarily concerned with all the frills and luxury facilities. In contrast, at boutique hotels are able to focus on a small number of guests and offer fresh 4-star and 5-star amenities.


Is a boutique hotel the same as a luxury hotel?


No. Some boutique hotels are classed as luxury hotels, while others are not.

A boutique hotel must be small, whereas luxury hotels can be of any size. They are usually much larger, with hundreds of rooms. Boutique hotels are often independently-run or part of small boutique chain. Majority of luxury hotels are part of large international hotel chains. There are many luxury hotels that are not boutiques.

Not all boutique hotels are luxury hotels, but many are. A luxury Winchester boutique hotel will likely be fitted with luxury amenities like premium bedding, artisan toiletries and in-room conveniences, upscale decor and expensive furniture. It may also have a gourmet restaurant on-site.


Are Winchester boutique hotels expensive?


Not necessarily. The price of boutique hotels varies. Some boutique hotels are expensive to stay in, but others are not.

Most Winchester boutique hotels are independent and have upscale amenities. They are also committed to high-quality, attentive guest services. Together, this creates a luxury experience. Therefore it's not uncommon to find boutique hotels classed as luxury hotels with higher rates.

However, there are often affordable boutique hotels too. Especially when they are located outside the tourist hotspots and away from the hotel chains, you might find beautiful boutique hotels that are cheaper. Hotel chains also mean a consistent level of service and guests pay for that brand experience. Boutique hotels are independent and may in fact be cheaper. So it really depends on the hotel and the destination.