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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Winchester vacation rentals

A modern living room with a leather sofa, a coffee table, and a kitchen area with white cabinets and stainless steel appliances.

1. 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.
The price is ￥25,309
￥89,812 total
includes taxes & fees
Oct 11 - Oct 12
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.

2. Crescent Bar Condo

Crescent Bar Condo
Crescent Bar
9.8 out of 10, Exceptional, (26 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.
The price is ￥15,818
￥37,694 total
includes taxes & fees
Oct 8 - Oct 9
Crescent Bar Condo
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

3. 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.
The price is ￥27,682
￥92,751 total
includes taxes & fees
Oct 8 - Oct 9
NEW Luxe Decor + Foosball + Air Hockey | Sleeps 10
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 place, clean and owner communicates quickly!"
United States
Jamie N.
The price is ￥35,306
￥73,121 total
includes taxes & fees
Oct 8 - Oct 9
Crescent Bar Condo near The Gorge, Boating & Golf. Sleeps 8. AMAZING Pool.
A modern building with a glass entrance, a visible living area with a sofa and table, and a kitchen area.

5. Serenity Suite 4B- Amphitheater, Winery & Spa

Serenity Suite 4B- Amphitheater, Winery & Spa
Quincy
The price is ￥26,055
￥59,505 total
includes taxes & fees
Oct 8 - Oct 9
Serenity Suite 4B- Amphitheater, Winery & Spa
A tennis court with a net, surrounded by a fence, and residential buildings in the background.

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, (3 reviews)
"Great place to stay at Cbar. Clean and cozy with everything we needed."
United States
John W.
The price is ￥64,063
￥121,919 total
includes taxes & fees
Oct 8 - Oct 9
Sun-kissed at Sunserra in Crescent Bar on River, Golf, Wineries, Gorge Concerts
A stone building with a balcony, a greenhouse, and a vineyard in the background.

7. `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.
The price is ￥26,055
￥59,505 total
includes taxes & fees
Oct 11 - Oct 12
`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.

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

Cave B Ridge - Desert Stage - Views, Wine & Gorge
Quincy
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful views, great setup. Nice place. Would stay there again."
United States
Melody M.
The price is ￥26,100
￥59,607 total
includes taxes & fees
Oct 15 - Oct 16
Cave B Ridge - Desert Stage - Views, Wine & Gorge
A modern outdoor seating area with a built-in fire feature, overlooking a vineyard landscape.

9. 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
The price is ￥26,100
￥59,607 total
includes taxes & fees
Oct 11 - Oct 12
Cave B Ridge - The Sky View Lounge 5C
A patio with a chair and table, overlooking a vineyard and a canyon with a river.

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

Verse & Vine Retreat – 5B Cave B Ridge Condo
Quincy
The price is ￥26,055
￥59,505 total
includes taxes & fees
Oct 14 - Oct 15
Verse & Vine Retreat – 5B Cave B Ridge Condo
A modern, single-story building with a patio area featuring outdoor furniture.

11. Champagne Lounge 11D Cave B Ridge, Views & Wine

Champagne Lounge 11D Cave B Ridge, Views & Wine
Quincy
The price is ￥26,055
￥59,505 total
includes taxes & fees
Oct 8 - Oct 9
Champagne Lounge 11D Cave B Ridge, Views & 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.

12. 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.
The price is ￥26,055
￥59,505 total
includes taxes & fees
Oct 13 - Oct 14
Setlist Suite - 5A Cave B Ridge Condo at the Gorge
A modern house with a glass-enclosed patio, a dining area, and a living room with a sofa and chairs.

13. Vineyard River Vista 4D at Cave B Ridge

Vineyard River Vista 4D at Cave B Ridge
Quincy
10.0 out of 10, Exceptional, (1 review)
"Very clean! We loved it. Amazing view! Would love to come again"
United States
Kendall S.
The price is ￥26,100
￥59,607 total
includes taxes & fees
Oct 20 - Oct 21
Vineyard River Vista 4D at Cave B Ridge
A modern, single-story building with a wooden ceiling and large glass windows, featuring a patio with outdoor seating.

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

`Tumbleweed Corner 1C` at Cave B Ridge Condos
Quincy
10.0 out of 10, Exceptional, (1 review)
The price is ￥26,100
￥59,607 total
includes taxes & fees
Oct 8 - Oct 9
`Tumbleweed Corner 1C` at Cave B Ridge Condos
A modern interior with large glass windows, a leather sofa, and a dining area with outdoor seating.

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

Unplug - Views! Cave B Ridge 2B Winery Spa Gorge
Quincy
The price is ￥26,100
￥59,607 total
includes taxes & fees
Oct 20 - Oct 21
Unplug - Views! Cave B Ridge 2B Winery Spa Gorge
A room with a large window offering a view of a vineyard and distant hills.

16. Outdoor Grill | Fast WIFI | 1 BR | Sleeps 4

Outdoor Grill | Fast WIFI | 1 BR | Sleeps 4
Quincy
10.0 out of 10, Exceptional, (6 reviews)
"It was a beautiful and cozy home! The view was incredible!"
United States
Yvette
The price is ￥30,560
￥57,751 total
includes taxes & fees
Oct 8 - Oct 9
Outdoor Grill | Fast WIFI | 1 BR | Sleeps 4
A modern, glass-enclosed building with a patio area featuring outdoor furniture.

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

Cave B Ridge - Sound Stage 11A Views, Wine, Gorge
Quincy
The price is ￥26,100
￥59,607 total
includes taxes & fees
Oct 8 - Oct 9
Cave B Ridge - Sound Stage 11A Views, Wine, Gorge
A stone building with a balcony, a greenhouse, and a view of a vineyard.

18. Sunset Splendor - Relax & UnWine 3B

Sunset Splendor - Relax & UnWine 3B
Quincy
The price is ￥26,055
￥59,505 total
includes taxes & fees
Oct 8 - Oct 9
Sunset Splendor - Relax & UnWine 3B
A modern building with a covered outdoor seating area, large windows, and a sandy landscape.

19. Wine Down in 3C at Cave B Ridge

Wine Down in 3C at Cave B Ridge
Quincy
The price is ￥26,055
￥59,505 total
includes taxes & fees
Oct 18 - Oct 19
Wine Down in 3C at Cave B Ridge
A vineyard with rows of grapevines, a building with a curved roof, and a distant view of hills.

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

The Starlight Lounge Cave B Ridge - Escape & Wine
Quincy
The price is ￥26,100
￥59,607 total
includes taxes & fees
Oct 8 - Oct 9
The Starlight Lounge Cave B Ridge - Escape & Wine
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

Lakeside Oasis the Gorge Amphitheatre and Cave B Winery - Ancient Lakes Retreat

Lakeside Oasis the Gorge Amphitheatre and Cave B Winery - Ancient Lakes Retreat

10/10 Excellent
"We loved our stay at Hunter’s place! It was clean, comfy, and perfect for our group. Excellent location with Cave B winery and the Gorge Amphitheater right next door! We would definitely stay again in the future!"
Ally K. 3-night trip
Posted 2 days ago
Lakeside Oasis the Gorge Amphitheatre and Cave B Winery - Ancient Lakes Retreat

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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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?

The Sunland Hideaway -Spacious 4-bedroom house in tranquil Sunland Estates.: This vacation home rental outside of Winchester is located next to a golf course and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Make the most of the selection of games in this rental home to help you unwind.

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.