Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Winchester vacation rentals

House (3 Bedrooms) | Interior
9 Mi to The Gorge: Updated Retreat w/ Yard!

Cottage in George

9 Mi to The Gorge: Updated Retreat w/ Yard!
3.0 star property
8.0 out of 10, Very Good, (1)
"The Home was very adequate for the 3 of us. Would like to have had an outside light"
United States
DEBRA
$327 nightly
The price is $361
Dec 21 - Dec 22
Total with taxes and fees
9 Mi to The Gorge: Updated Retreat w/ Yard!
Pool
Crescent Bar Condo

Condo in Crescent Bar

Crescent Bar Condo
10.0 out of 10, Exceptional, (17)
"Great place to stay in Cresent bar. The condo was clean and very nice. Complex is great with the pool in the middle. "
United States
Sigurros
$342 nightly
The price is $365
Dec 15 - Dec 16
Total with taxes and fees
Crescent Bar Condo
Terrace/patio
Suite Home @ Cave B - 2BR - Walk to the Gorge

Vacation Home in Quincy

Suite Home @ Cave B - 2BR - Walk to the Gorge
10.0 out of 10, Exceptional, (6)
"Gorgeous place and location. Super easy check in and out with clear instructions as well as well stocked with everything we needed for the weekend. "
United States
Jennifer M.
$445 nightly
The price is $486
Dec 12 - Dec 13
Total with taxes and fees
Suite Home @ Cave B - 2BR - Walk to the Gorge
Fridge, microwave, oven, stovetop
Cozy 1-bed condo at Cave B Winery with WiFi, AC & 10 mins to Gorge Ampitheatre

Condo in Quincy

Cozy 1-bed condo at Cave B Winery with WiFi, AC & 10 mins to Gorge Ampitheatre
10.0 out of 10, Exceptional, (2)
"Always a great getaway "
United States
Ryan D.
$391 nightly
The price is $426
Dec 18 - Dec 19
Total with taxes and fees
Cozy 1-bed condo at Cave B Winery with WiFi, AC & 10 mins to Gorge Ampitheatre
Fridge, microwave, oven, stovetop
Crescent Bar Condo near The Gorge, Boating & Golf. Sleeps 8. AMAZING Pool.

Condo in Quincy

Crescent Bar Condo near The Gorge, Boating & Golf. Sleeps 8. AMAZING Pool.
9.4 out of 10, Exceptional, (19)
"Great place for a family!"
United States
kailee p.
$426 nightly
The price is $464
Dec 14 - Dec 15
Total with taxes and fees
Crescent Bar Condo near The Gorge, Boating & Golf. Sleeps 8. AMAZING Pool.
Fridge, oven, stovetop, dishwasher
Moses Lake Golf Retreat @Moses Pointe Golf Course Hot Tub Sauna Pizza Oven

Vacation Home in Moses Lake

Moses Lake Golf Retreat @Moses Pointe Golf Course Hot Tub Sauna Pizza Oven
9.6 out of 10, Exceptional, (5)
"Great house, great Location, easy check in, very clean, and very nice ammenities."
United States
Scott T.
$607 nightly
The price is $662
Dec 12 - Dec 13
Total with taxes and fees
Moses Lake Golf Retreat @Moses Pointe Golf Course Hot Tub Sauna Pizza Oven
Exterior
10 mins from the Gorge Amphitheater, nestled in on the beautiful Columbia River

Apartment in Sunland Estates

10 mins from the Gorge Amphitheater, nestled in on the beautiful Columbia River
9.4 out of 10, Exceptional, (19)
"This was a perfect place for me to stay when I was going to concerts at the Gorge. Host’s were so nice!! The place was very clean and the views and area were fabulous! "
United States
christy f.
$366 nightly
The price is $399
Dec 12 - Dec 13
Total with taxes and fees
10 mins from the Gorge Amphitheater, nestled in on the beautiful Columbia River
Terrace/patio
2-bedroom condo at Cave B Winery with WiFi, AC~Adjacent to Gorge Ampitheatre

Condo in Quincy

2-bedroom condo at Cave B Winery with WiFi, AC~Adjacent to Gorge Ampitheatre
10.0 out of 10, Exceptional, (1)
"Very modern, clean, beautiful. Great throughout the entire space."
United States
Melanie C.
$494 nightly
The price is $538
Dec 15 - Dec 16
Total with taxes and fees
2-bedroom condo at Cave B Winery with WiFi, AC~Adjacent to Gorge Ampitheatre
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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Top Winchester Hotel Reviews

Soap Lake Natural Spa & Resort

Soap Lake Natural Spa & Resort

10/10 Excellent
"The kitchen wasn't what I was expecting. The overall room wasn't how it appeared in the photos. I was disappointed. The Woman who checked us in was an absolute sweetheart. We were there in November so it was only us out there. We had the whole area all to ourselves and that was awesome. I would recommend this place for sure. Just don't expect the pics to be a good representation because it's an older place. "
Kelly 1-night trip
Posted 4 days ago
Soap Lake Natural Spa & Resort

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $361 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Winchester?

Yes, we have vacation rentals near popular local attractions in Winchester, or you can go with a secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Winchester?

Endless views with easy access concerts at Gorge, Cave B Winery and SageCliffe: This vacation home rental outside of Winchester offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a hot tub.

What can I see and do in Winchester?

While exploring the area, visit family-friendly sights like Quincy Aquatic Center, or get outside and enjoy nature at Soap Lake. Moses Lake and Soap Lake Public Library are a couple of places you'll find in the larger area.

What are vacation rentals like in Winchester?

Vacation rentals are privately owned accommodations you can reserve for a couple days or more in Winchester. Vacation rentals provide amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a small group gathering.