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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Winchester vacation rentals

A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

1. NEW Luxe Decor + Foosball + Air Hockey | Sleeps 10

NEW Luxe Decor + Foosball + Air Hockey | Sleeps 10
Ephrata
9.4 out of 10, Exceptional, (3 reviews)
"The host was friendly and helpful during the check-in process. They were also flexible regarding a last-minute additional guest reservation."
United States
Chalky M.
$537 nightly
The price is $586
Sep 9 - Sep 10
Total with taxes and fees
NEW Luxe Decor + Foosball + Air Hockey | Sleeps 10
A modern living room with a leather sofa, a coffee table, and a kitchen area with white cabinets and stainless steel appliances.

2. NEW Ivy Streat Retreat in Ephrata, Sleeps 10, EV Charger + Foosball + Air Hockey

NEW Ivy Streat Retreat in Ephrata, Sleeps 10, EV Charger + Foosball + Air Hockey
Ephrata
10.0 out of 10, Exceptional, (1 review)
"Amazing !!!!!"
United States
peter f.
$520 nightly
The price is $568
Sep 24 - Sep 25
Total with taxes and fees
NEW Ivy Streat Retreat in Ephrata, Sleeps 10, EV Charger + Foosball + Air Hockey
A swimming pool with lounge chairs and umbrellas, surrounded by buildings with red roofs and a mountainous backdrop.

3. Crescent Bar Condo

Crescent Bar Condo
Crescent Bar
9.6 out of 10, Exceptional, (24 reviews)
"The place was immaculate & everything we needed for our 5 day stay.The Crescent Bar staff were friendly, pool & hot tub an absolute gem.We can't wait to book our next trip."
United States
Kim E.
$342 nightly
The price is $365
Sep 9 - Sep 10
Total with taxes and fees
Crescent Bar Condo
A hotel with a well-lit outdoor area, a tree, and a view of the night sky with the aurora borealis.

4. Crescent Bar Condo near The Gorge, Boating & Golf. Sleeps 8. AMAZING Pool.

Crescent Bar Condo near The Gorge, Boating & Golf. Sleeps 8. AMAZING Pool.
Quincy
9.6 out of 10, Exceptional, (25 reviews)
"Great location, condo and host! Thank you"
United States
Brieanne S.
$426 nightly
The price is $464
Sep 28 - Sep 29
Total with taxes and fees
Crescent Bar Condo near The Gorge, Boating & Golf. Sleeps 8. AMAZING Pool.
A yurt with a table and chairs, a red curtain, and a patterned rug.

5. Yurt #3 - Glamping by the Gorge & Cave B

Yurt #3 - Glamping by the Gorge & Cave B
Quincy
$265 nightly
The price is $279
Sep 9 - Sep 10
Total with taxes and fees
Yurt #3 - Glamping by the Gorge & Cave B
A pool area with lounge chairs, a water slide, and a clear sky.

6. Sun-kissed at Sunserra in Crescent Bar on River, Golf, Wineries, Gorge Concerts

Sun-kissed at Sunserra in Crescent Bar on River, Golf, Wineries, Gorge Concerts
Quincy
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay at Cbar. Clean and cozy with everything we needed."
United States
John W.
$714 nightly
The price is $778
Sep 9 - Sep 10
Total with taxes and fees
Sun-kissed at Sunserra in Crescent Bar on River, Golf, Wineries, Gorge Concerts
A residential area with houses, a swimming pool, and a lake.

7. Condo in Crescent Bar Resort—20 minutes from the Gorge amphitheater.

Condo in Crescent Bar Resort—20 minutes from the Gorge amphitheater.
Quincy
9.0 out of 10, Wonderful, (12 reviews)
"Would definitely stay again. "
United States
kailee p.
$457 nightly
The price is $498
Sep 30 - Oct 1
Total with taxes and fees
Condo in Crescent Bar Resort—20 minutes from the Gorge amphitheater.
A patio with a chair and table, overlooking a vineyard and a canyon with a river.

8. Verse & Vine Retreat – 5B Cave B Ridge Condo

Verse & Vine Retreat – 5B Cave B Ridge Condo
Quincy
$360 nightly
The price is $377
Oct 6 - Oct 7
Total with taxes and fees
Verse & Vine Retreat – 5B Cave B Ridge Condo
A modern house with a glass-enclosed patio, a dining area, and a living room with a sofa and chairs.

9. Vineyard River Vista 4D at Cave B Ridge

Vineyard River Vista 4D at Cave B Ridge
Quincy
$360 nightly
The price is $377
Oct 6 - Oct 7
Total with taxes and fees
Vineyard River Vista 4D at Cave B Ridge
A yurt with a table and chairs, a red chair, a potted plant, and a view through a window.

10. Yurt #1 - Glamp by the Gorge & Cave B

Yurt #1 - Glamp by the Gorge & Cave B
Quincy
$265 nightly
The price is $279
Sep 9 - Sep 10
Total with taxes and fees
Yurt #1 - Glamp by the Gorge & Cave B
A stone building with a balcony, a greenhouse, and a vineyard in the background.

11. `The Wine Box` at Cave B Ridge - Wine Relax Enjoy

`The Wine Box` at Cave B Ridge - Wine Relax Enjoy
Quincy
10.0 out of 10, Exceptional, (1 review)
"Very clean and cozy. The perfect weekend getaway for two."
United States
Brit F.
$360 nightly
The price is $377
Oct 6 - Oct 7
Total with taxes and fees
`The Wine Box` at Cave B Ridge - Wine Relax Enjoy
A modern living room with large glass windows, a wooden ceiling, and a view of vineyards.

12. Cave B Ridge - Desert Stage - Views, Wine & Gorge

Cave B Ridge - Desert Stage - Views, Wine & Gorge
Quincy
10.0 out of 10, Exceptional, (1 review)
"Wonderful spot. Thank you"
United States
Amy S.
$360 nightly
The price is $377
Oct 6 - Oct 7
Total with taxes and fees
Cave B Ridge - Desert Stage - Views, Wine & Gorge
A modern interior with large glass windows, a leather sofa, and a dining area with outdoor seating.

13. Unplug - Views! Cave B Ridge 2B Winery Spa Gorge

Unplug - Views! Cave B Ridge 2B Winery Spa Gorge
Quincy
$360 nightly
The price is $377
Oct 6 - Oct 7
Total with taxes and fees
Unplug - Views! Cave B Ridge 2B Winery Spa Gorge
A modern, glass-enclosed building with a patio area featuring outdoor furniture.

14. Cave B Ridge - Sound Stage 11A Views, Wine, Gorge

Cave B Ridge - Sound Stage 11A Views, Wine, Gorge
Quincy
$360 nightly
The price is $377
Oct 6 - Oct 7
Total with taxes and fees
Cave B Ridge - Sound Stage 11A Views, Wine, Gorge
A vineyard with rows of grapevines, a building with a curved roof, and a distant view of hills.

15. The Starlight Lounge Cave B Ridge - Escape & Wine

The Starlight Lounge Cave B Ridge - Escape & Wine
Quincy
$360 nightly
The price is $377
Oct 6 - Oct 7
Total with taxes and fees
The Starlight Lounge Cave B Ridge - Escape & Wine
A modern living room with a sofa, a coffee table, and a view of a patio area with a chair and a small structure.

16. Setlist Suite - 5A Cave B Ridge Condo at the Gorge

Setlist Suite - 5A Cave B Ridge Condo at the Gorge
Quincy
10.0 out of 10, Exceptional, (1 review)
"It was clean and cooled when we arrived. We will absolutely be staying here again!"
United States
Scotland S.
$360 nightly
The price is $377
Oct 6 - Oct 7
Total with taxes and fees
Setlist Suite - 5A Cave B Ridge Condo at the Gorge
A modern living room with a large glass door leading to an outdoor patio, a white sofa, leather armchairs, and abstract wall art.

17. Cave B Ridge River View Retreat 3D - Wine & Relax

Cave B Ridge River View Retreat 3D - Wine & Relax
Quincy
$360 nightly
The price is $377
Oct 6 - Oct 7
Total with taxes and fees
Cave B Ridge River View Retreat 3D - Wine & Relax
A modern, single-story building with a wooden ceiling and large glass windows, featuring a patio with outdoor seating.

18. `Tumbleweed Corner 1C` at Cave B Ridge Condos

`Tumbleweed Corner 1C` at Cave B Ridge Condos
Quincy
$360 nightly
The price is $377
Oct 6 - Oct 7
Total with taxes and fees
`Tumbleweed Corner 1C` at Cave B Ridge Condos
A modern outdoor seating area with a built-in fire feature, overlooking a vineyard landscape.

19. Cave B Ridge - The Sky View Lounge 5C

Cave B Ridge - The Sky View Lounge 5C
Quincy
10.0 out of 10, Exceptional, (1 review)
"Had the best time at this condo that had beautiful scenic views from the outdoor patio and big bonus that it was walking distance to The Gorge. Very clean and has everything you need for a great weekend. Will definitely be coming back!"
United States
Whitney
$360 nightly
The price is $377
Oct 6 - Oct 7
Total with taxes and fees
Cave B Ridge - The Sky View Lounge 5C
A modern kitchen with a large island, bar stools, pendant lighting, and a view of the outdoors.

20. Vista & Vine Lakehouse

Vista & Vine Lakehouse
Quincy
$537 nightly
The price is $562
Sep 9 - Sep 10
Total with taxes and fees
Vista & Vine Lakehouse
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

Quincy INN and Suites

Quincy INN and Suites

10/10 Excellent
"Quincy Inn was perfect for our trip to The Gorge for "Labor Dave weekend". Super clean rooms, very comfortable beds, within walking distance to coffee and delicious food spots. Highly recommend!"
Wendy 3-night trip
Posted less than an hour ago
Quincy INN and Suites

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 $365 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.

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?

Sun-kissed at Sunserra in Crescent Bar on River, Golf, Wineries, Gorge Concerts: This vacation home rental outside of Winchester offers an outdoor pool, a balcony, and air-conditioning to help you feel perfectly comfortable in your new surroundings. You can relax into your vacation with a garden and 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 Park. Colockum Ridge Golf Course and Soap Lake 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.