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Winchester Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winchester holiday 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.
The price is AU$829
includes taxes & fees
30 Sept - 1 Oct
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.
The price is AU$794
includes taxes & fees
6 Oct - 7 Oct
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
9.8 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 AU$340
includes taxes & fees
5 Oct - 6 Oct
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 place, clean and owner communicates quickly!"
United States
Jamie N.
The price is AU$644
includes taxes & fees
30 Sept - 1 Oct
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
The price is AU$398
includes taxes & fees
30 Sept - 1 Oct
Yurt #3 - Glamping by the Gorge & Cave B
A yurt with a table and chairs, a red chair, a potted plant, and a view through a window.

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

Yurt #1 - Glamp by the Gorge & Cave B
Quincy
The price is AU$395
includes taxes & fees
30 Sept - 1 Oct
Yurt #1 - Glamp by the Gorge & Cave B
A tennis court with a net, surrounded by a fence, and residential buildings in the background.

7. 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.
The price is AU$1,075
includes taxes & fees
8 Oct - 9 Oct
Sun-kissed at Sunserra in Crescent Bar on River, Golf, Wineries, Gorge Concerts
A room with a large window offering a view of a vineyard and distant hills.

8. Sage & Saddle Retreat~Wine~Gorge Ampitheatre

Sage & Saddle Retreat~Wine~Gorge Ampitheatre
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 AU$508
includes taxes & fees
25 Oct - 26 Oct
Sage & Saddle Retreat~Wine~Gorge Ampitheatre
A residential area with houses, a swimming pool, and a lake.

9. 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.
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.

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

Verse & Vine Retreat – 5B Cave B Ridge Condo
Quincy
The price is AU$524
includes taxes & fees
6 Oct - 7 Oct
Verse & Vine Retreat – 5B Cave B Ridge Condo
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.
The price is AU$524
includes taxes & fees
8 Oct - 9 Oct
`The Wine Box` at Cave B Ridge - Wine Relax Enjoy
A residential area with a gravel driveway, a wooden fence, and a small shed.

12. RV parking in Sunland, close to park and store. No bathroom. No septic dump.

RV parking in Sunland, close to park and store. No bathroom. No septic dump.
Sunland Estates
9.4 out of 10, Exceptional, (3 reviews)
"It was a great space and I have nothing but positives about the RV lot:)"
Canada
Shawn
The price is AU$251
includes taxes & fees
30 Sept - 1 Oct
RV parking in Sunland, close to park and store. No bathroom. No septic dump.
A modern living room with large glass windows, a wooden ceiling, and a view of vineyards.

13. 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 AU$524
includes taxes & fees
6 Oct - 7 Oct
Cave B Ridge - Desert Stage - Views, Wine & Gorge
A modern outdoor seating area with a built-in fire feature, overlooking a vineyard landscape.

14. 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 AU$530
includes taxes & fees
11 Oct - 12 Oct
Cave B Ridge - The Sky View Lounge 5C
A modern living room with a sofa, a coffee table, and a view of a patio area with a chair and a small structure.

15. 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 AU$530
includes taxes & fees
11 Oct - 12 Oct
Setlist Suite - 5A Cave B Ridge Condo at the Gorge
A modern, single-story building with a patio area featuring outdoor furniture.

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

Champagne Lounge 11D Cave B Ridge, Views & Wine
Quincy
The price is AU$524
includes taxes & fees
8 Oct - 9 Oct
Champagne Lounge 11D Cave B Ridge, Views & Wine
A modern kitchen with a large island, bar stools, pendant lighting, and a view of the outdoors.

17. Vista & Vine Lakehouse

Vista & Vine Lakehouse
Quincy
The price is AU$796
includes taxes & fees
11 Oct - 12 Oct
Vista & Vine Lakehouse
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
10.0 out of 10, Exceptional, (1 review)
The price is AU$524
includes taxes & fees
6 Oct - 7 Oct
`Tumbleweed Corner 1C` at Cave B Ridge Condos
A modern building with a glass entrance, a visible living area with a sofa and table, and a kitchen area.

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

Serenity Suite 4B- Amphitheater, Winery & Spa
Quincy
The price is AU$524
includes taxes & fees
7 Oct - 8 Oct
Serenity Suite 4B- Amphitheater, Winery & Spa
A modern building with a flat roof, large glass windows, and outdoor seating.

20. DeWine Sundowners Lakehouse at the Gorge

DeWine Sundowners Lakehouse at the Gorge
Quincy
The price is AU$796
includes taxes & fees
8 Oct - 9 Oct
DeWine Sundowners Lakehouse at the Gorge
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
"The room was clean, bed was comfortable and the staff was very friendly and helpful."
Kristen 1-night trip
Posted 9 hours ago
Quincy INN and Suites

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winchester holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as AU$340 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday 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 holiday.

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 holiday rental in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winchester has to offer?

The Sunland Hideaway -Spacious 4-bedroom house in tranquil Sunland Estates.: This holiday home rental outside of Winchester is located next to a golf course, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Make the most 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 wider area.

What are holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for family trips.