Winchester Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Winchester Vacation

Our Winchester vacation packages provide countless opportunities to discover new sights, sounds and experiences. And with all of the travel arrangements worked out, you can relax and enjoy your city adventure without a worry in the world. Can't wait to do some sightseeing but don't know where to begin? Any trip to Winchester should include Quincy Aquatic Center. Stop dreaming and start adventuring. Explore the broad range of options on Expedia today and put your Winchester vacation plans into action!

Top Winchester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Microtel Inn & Suites by Wyndham Ephrata

Microtel Inn & Suites by Wyndham Ephrata

2.5 out of 5
Price was CA $1,881, price is now CA $1,724 per person
CA $1,724
per person
Sep 4 - Sep 7
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Wenatchee (EAT)
8.6/10 Excellent! (23 reviews)
Would stay again

Reviewed on Jul 19, 2026

River Road Lodge 7 Bedroom Lodge by NW Comfy Cabins by RedAwning

River Road Lodge 7 Bedroom Lodge by NW Comfy Cabins by RedAwning

3.5 out of 5
Price was CA $12,469, price is now CA $11,327 per person
CA $11,327
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Regina (YQR) to Wenatchee (EAT)
No reviews

All Seasons River Inn

All Seasons River Inn

2 out of 5
Price was CA $2,545, price is now CA $2,316 per person
CA $2,316
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Regina (YQR) to Wenatchee (EAT)
9.8/10 Exceptional! (91 reviews)
Good location and very clean, but I feel that the price was high for what you get.

Reviewed on Jul 20, 2026

Icicle Village Resort

Icicle Village Resort

3.5 out of 5
Price was CA $2,537, price is now CA $2,315 per person
CA $2,315
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Regina (YQR) to Wenatchee (EAT)
9.4/10 Exceptional! (1,493 reviews)

Sleeping Lady Mountain Resort & Spa

Sleeping Lady Mountain Resort & Spa

4 out of 5
Price was CA $2,433, price is now CA $2,229 per person
CA $2,229
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Regina (YQR) to Wenatchee (EAT)
9/10 Wonderful! (460 reviews)
Great time at Sleeping Lady -highly recommend. Wonderful get away! Great cabins, beautiful spot, very quiet, lovely pool, very nice dining room. And don't miss the s'mores!

Reviewed on Jul 20, 2026

Ready to book your vacation to Winchester?

 

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Winchester Hotel Deals

Soap Lake Resort, a Dazzler Select by Wyndham

Soap Lake Resort, a Dazzler Select by Wyndham

3.5 out of 5
236 Main Avenue East Soap Lake WA
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Aug 5 to Aug 6
CA $168
CA $185 total
Aug 5 - Aug 6
includes taxes & fees
Soap Lake Resort, a Dazzler Select by Wyndham
Microtel Inn & Suites by Wyndham Ephrata

Microtel Inn & Suites by Wyndham Ephrata

2.5 out of 5
405 DIAMOND DR. Ephrata WA
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Aug 20 to Aug 21
CA $154
CA $170 total
Aug 20 - Aug 21
includes taxes & fees
8.6/10 Excellent! (26 reviews)
"Would stay again"

Reviewed on Jul 19, 2026

Microtel Inn & Suites by Wyndham Ephrata
Holiday Inn Express & Suites George Quincy South by IHG

Holiday Inn Express & Suites George Quincy South by IHG

3 out of 5
224 Bing Ave George WA
Fully refundable
The price is CA $126 per night from Aug 5 to Aug 6
CA $126
CA $139 total
Aug 5 - Aug 6
includes taxes & fees
9/10 Wonderful! (537 reviews)
"I don’t know if they change bed since they are now a Hilton. When they were George Microtel, the beds were comfortable. Last time we stayed since the change, the beds were horrible. We won’t go back."

Reviewed on Jul 9, 2026

Holiday Inn Express & Suites George Quincy South by IHG
See all 230 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.
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Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from CA $1,724 on Expedia for your Winchester break. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Winchester costs.
What are the cheapest months to go to Winchester?
January, February and October are the best times to search for cheap Winchester vacation packages. Travelling in less busy months means you can typically find reduced prices on accommodations and flights.
How many days is enough for Winchester?
The ideal duration for your Winchester vacation depends on what you'd like to do. Generally, a few days to a week will give you enough time to hit all the leading sights and discover some hidden treasures along the way.
How to find the best Winchester package deals?
Start your search for a Winchester package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Winchester package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Winchester escape underway.
Is it cheaper to book a Winchester vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component separately. And you'll still get the freedom to create a customized Winchester vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Winchester?
If you're considering a spur-of-the-moment Winchester getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Winchester?

  1. Choose when to go: Check your diary and pack your bags. Your preferred time of year and the available activities will also help you decide when to vacation in Winchester.
  2. Set your budget: Consider expenses like transportation, flights and meals when working out how much to save for your trip to Winchester. Then, select a property that suits your budget, whether that's a wallet-friendly option or a high-end retreat.
  3. Determine how many days away: Start by making a list of all the activities and attractions you want to get to in Winchester. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customized Winchester vacation package.

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