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Explore beach hotels in Winchester, KY from $99

Name: Best Western Winchester Hotel
Price range: $99 total
Rating: 8.4

Top Winchester Beach Resorts & Hotels

Best Western Winchester Hotel

1307 W Lexington Ave, Winchester, KY

Fully refundableReserve now, pay when you stay

$90 nightly

$99 total

Jun 3 - Jun 4

Total includes taxes and fees

This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express ...

8.4/10 Very Good! (921 reviews)

"Great experience with management at this location. Extremely helpful."

Reviewed on May 30, 2025

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.

Beach Condos in Winchester

The Gatsby Getaway, Downtown LEX

Lexington

$184 nightly

$211 total

Jun 8 - Jun 9

Total includes taxes and fees

9.8/10 Exceptional! (13 reviews)

Beach Villas in Winchester

12acre Villa right by Keeneland-Keene Creek Estate 10,000sqft

Lexington

Get rates

9.8/10 Exceptional! (35 reviews)

How to find the best Winchester beach hotels?

We have 921 honest, unfiltered reviews from genuine customers you can check out, with an average review rating of 8.4.

How can I find Winchester beach hotels with nice views?

Use our ocean view filter to see the Winchester beach hotels that offer spectacular views. From cliffside panoramas to beach view hotels with rooms overlooking the sand. Check out poolside and tranquil garden views, too.

How much does it cost to stay in a beach hotel in Winchester?

Currently, we have resorts and hotels in Winchester on the beach going from $99 a night to $244 for top-end luxury. Prices vary depending on your travel dates, amenities, and neighborhood.

How do I find Winchester beach hotels that are good for families?

Filter your search results by clicking on the family friendly filter to see kid-friendly amenities and activities. From beach resorts with kids’ clubs to beachfront hotels offering fun watersports—you have plenty of choice.

Why should I book my beach hotel in Winchester with Travelocity?

With great deals on a vast selection of Winchester beachfront hotels, 24/7 customer service, and the ability to bundle your hotel, flights, and car rental to save more—Travelocity makes it easy.

Do any beach hotels in Winchester have a pool?

Many Winchester hotels on the beach have pools. You can choose which amenities you want and use our pool filter to see the Winchester beach hotels that have pools on site.

When is the best time to stay in a beach hotel in Winchester?

The best time to visit Winchester for local events and activities is .

Are there cheap beach hotels in Winchester?

Prices for Winchester beach hotels currently start at just $99 a night. With 54 Winchester beach hotels to choose from, you have stacks of tempting options, whatever your budget.

What are some great things to do in Winchester by the beach?

Enjoy swimming, reading, and sunbathing on the beach in Winchester. There’s also action-packed beach fun and watersport adventures, too. Check each hotel’s information section to find out what’s available.

How can I find the best beach hotels deals in Winchester?

Pop in your travel dates and hit search and hunt though our fantastic deals on Winchester beach resorts and beachfront hotels. Download the free Travelocity appOpens in a new window for awesome member discounts.

Popular Beach Stays in Winchester

Top landmarks in Winchester

Kentucky Horse Park

4.5/5(328 reviews)

Explore Kentucky Horse Park, a favorite green space in Lexington, and also enjoy the area's horseback riding. Attend a sporting event or simply enjoy the lively bars while you're in the area.