Winchester Hotels

Find the best Winchester hotel for your dates, by price or preference

Compare hotel deals across hundreds of providers, all in one place

Look out for Winchester hotels with free cancellation or excellent ratings

Trusted Winchester hotel providers

See all hotels in Winchester

View more hotels

Hotels in Winchester rated best by other travelers

Rated by travelers as the best in the city, these stays all get 5 stars for cleanliness, customer service and location.
See more

Fast facts

Sleep easy, armed with the stuff that's good to know before you go.
Highest-rated hotelThe Sewanee Inn – 5
Cheapest month to bookApril

Your guide to finding the best hotels in Winchester, Tennessee

Enjoy your time in Winchester by staying at a hotel that matches your needs. We’ve created a list of some of Winchester's best hotels, from luxurious to more modest hotels.

Best time to visit Winchester

Winchester is an interesting travel destination year-round, but what you hope to do (or avoid) during your vacation should be considered before booking, such as weather and price. Low and high season in Winchester

Busiest month(s): June sees the largest number of tourists to Winchester, resulting in an average nightly rate of $164. If you are booking during this period, budget for relatively higher rates compared to the slower times of the year, where average prices drop to $117 per night.

Quietest month(s): You'll save on lodging and avoid peak season prices by travelling during July, when the average rate per night is $117.

June is the most expensive month to stay in Winchester, so plan accordingly. When prices peak, you can expect to spend an average of $164 per night on hotels. Prices are usually highest on Friday. No matter the time of year, Wednesday is often the cheapest day to book hotels.

Where to stay in Winchester, Tennessee

With Skyscanner, it's easy to find the best Winchester hotels at a rate you want.

Popular hotels in Winchester

These are some of the other most popular Winchester hotels you can book:

The 3-star Best Western Inn provides a relaxing stay in the heart of Winchester, where you can enjoy its swimming pool, hot tub, restaurant, and wi-Fi.

Things to do in Winchester

Many Winchester sites take you right to the city center, like the Tims Ford State Park. If you love food, you'll enjoy the authentic local cuisine, creative twists on classics, and flavors from around the world at Holt's Diner, Rafael's Pizzaria & Restaurant, Big Marvs BBQ, Scallywags Grill, and Margaritas.

Finding cheap hotels in Winchester: FAQs

You can always cancel or amend your hotel reservation if you need to, but look out for hotels in Winchester with free cancellation or flexible booking options if you want to protect your money. Some hotels allow you to cancel and get your money back if your plans change.
Of course, the cheapest hotel deal we found within the next seven days is C$137 per night. If you need somewhere in the next 24 hours, we've found you somewhere to stay for C$144 per night.
The average price of a hotel during the week is C$156 per night, and the average price on weekends is C$161. Overall, it looks like the cheapest day to stay in Winchester could be Monday.
We crunched some numbers on our calendar and found that Monday is the cheapest day to stay in Winchester, and the most expensive day seems to be Saturday.
Get your morning laps at Best Western Inn Winchester and Quality Inn.