Winchester Vacation Packages

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Your Winchester Vacation

History, cuisine, art and more … There's so much to experience with a Winchester vacation package. And with the ability to customize your city getaway, you know it'll be one that's tough to forget. Want to explore? Winchester Speedway, Winchester Golf Club and Historic Shopping & Dining District of Winchester, Indiana are among the leading places to visit during your trip to Winchester. Expedia has what you need to escape your routine. Tailor your vacation to Winchester to suit your style of travel, whatever that may look like.

Top Winchester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sonesta Select Indianapolis Carmel

Sonesta Select Indianapolis Carmel

3 out of 5
per person
Jul. 31 - Aug. 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Indianapolis (IND)
8.2/10 Very Good! (1,000 reviews)
Was a bit dirty, but not the worst I’ve seen. Was happy they had a pool that was open late. Staff was not very friendly but got the job done. The patio doors lock was broken, so we couldn’t lock the door. Also, screen doors screen was popped out and door itself was broken off the track. Couldn’t use patio at all.

Reviewed on May 27, 2024

Ironworks Hotel Indy

Ironworks Hotel Indy

4 out of 5
Save 100% on your flight
per person
Jul. 17 - Jul. 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Indianapolis (IND)
9.8/10 Exceptional! (1,132 reviews)
Love the style and design of this place - it's quite unique. My friends and I make an annual trip to Indy, and we have found our newest favorite place. Will definitely be back!

Reviewed on May 26, 2024

Baymont by Wyndham Indianapolis

Baymont by Wyndham Indianapolis

2.5 out of 5
per person
Jul. 31 - Aug. 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Indianapolis (IND)
7.8/10 Good! (1,000 reviews)
The rooms were clean and neat. Staff was very helpful friendly and professional. The breakfast was hot and very clean eating area The pool was inside and they let my grandkids bring in the paddle toys to the pool. The hot tub was HOT but nice and relaxing.

Reviewed on May 23, 2024

Wingate by Wyndham Indianapolis Airport-Rockville Rd.

Wingate by Wyndham Indianapolis Airport-Rockville Rd.

2.5 out of 5
Wayne
per person
Jul. 31 - Aug. 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Indianapolis (IND)
7.8/10 Good! (1,001 reviews)
Staff was very friendly, they are in a remodel and the room upgrades are fantastic

Reviewed on May 6, 2024

Wingate by Wyndham Indianapolis Airport Plainfield

Wingate by Wyndham Indianapolis Airport Plainfield

2.5 out of 5
per person
Jul. 31 - Aug. 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Indianapolis (IND)
8/10 Very Good! (562 reviews)
Only issue we had were ants in room.

Reviewed on May 26, 2024

Winchester Hotel Deals

Randolph Inn and Suites
Randolph Inn and Suites
2.5 out of 5
890 E Washington, Winchester, IN
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (183 reviews)
"Super friendly and clean!!!"

Reviewed on Apr. 21, 2024

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Randolph Inn and Suites
Baymont by Wyndham Richmond I-70
Baymont by Wyndham Richmond I-70
2.5 out of 5
912 Mendleson Dr, Richmond, IN
Fully refundableReserve now, pay when you stay
8/10 Very Good! (896 reviews)
No Issues
"Stayed here several times over the last 5 years. Have never had any issues."

Reviewed on May 23, 2024

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Baymont by Wyndham Richmond I-70
Comfort Suites
Comfort Suites
2.5 out of 5
421 Commerce Road, Richmond, IN
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (237 reviews)
"New property, big rooms"

Reviewed on May 25, 2024

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Comfort Suites
See all 108 properties in Winchester
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Winchester vacation package cost?
Custom build your Winchester package from an affordable CA $1,102. Pick from any combination of flights, hotels and rental cars to create the escape you’ve been dreaming about for ages. Don’t forget to add on a few experiences or activities!
How do I get a cheap travel package to Winchester?
If you love amazing deals, bundle your bookings into a Winchester vacation package. Whether you’re looking for flights, hotels, rental cars or activities, you can book everything in one place. You’ll have a wealth of choice at your fingertips too. Expedia has more than 550 air carriers and 1,000,000 properties around the globe to choose from. Fly with who you want, stay wherever you like and save precious money — now that’s the ideal vacation!
Where should I stay in Winchester?
Stay where the action is. Many visitors book hotels within easy reach of popular sights, such as Winchester Speedway, Winchester Golf Club and Historic Shopping & Dining District of Winchester, Indiana.
What are the top hotels in Winchester?
If it’s comfort and convenience you’re after, look no further than Randolph Inn and Suites. Spend your evenings kicking back here and your days checking out Winchester’s best attractions.
How far in advance should I book my Winchester vacation?
It all depends on the airline, but you can generally compare international airfares on Expedia up to a year in advance. While it’s a good idea to book ahead of time, lucky travelers will sometimes score a cheaper ticket just weeks before departure dates.
What does an Expedia Winchester travel package include?
Travel packages include rental cars, flights and hotels, but you can mix and match them to create your ideal Winchester trip. You can also add on fun stuff like activities and tours once you’ve made your booking. You’re the boss! When you bundle your bookings with Expedia, you’ll enjoy deals you won’t find elsewhere.
What should I know before booking a Winchester travel package?
When you book your flights, hotels and car rentals together, you’ll land awesome discounts. Whether you’re organizing an outdoor getaway in a chalet or would rather stay in a convenient hotel in the city, Expedia can make it happen for less.
Can I choose my airline with a Winchester Expedia vacation package?
With a vacation package, you’re the one in charge. Whether you’re eager to fly to Winchester in coach or first class, simply pick from the available airline options. Expedia has access to over 550 airline partners globally.
If I'm not able to travel, can I cancel my Winchester vacation package?
If your vacation plans in Winchester have changed, it’s a relief to know that you can amend or cancel your booking. If your booking was made less than 24 hours ago, you may be eligible for a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may charge a fee. For more information, visit our Customer Service Portal.

Discover the most popular places to visit in Winchester

Image for Winchester Speedway

Winchester Speedway

5/5(1 review)

Catch an event at Winchester Speedway during your trip to Winchester.

Winchester Speedway
Image for Winchester Golf Club

Winchester Golf Club

Enjoy a round of golf in Winchester at Winchester Golf Club.

Winchester Golf Club
Image for Historic Shopping & Dining District of Winchester, Indiana

Historic Shopping & Dining District of Winchester, Indiana

You can find out about the history of Winchester with a trip to Historic Shopping & Dining District of Winchester, Indiana.

Historic Shopping & Dining District of Winchester, Indiana

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.