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Winchester Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

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 HK$1,372
HK$4,597 total
includes taxes & fees
31 Aug - 1 Sept
NEW Luxe Decor + Foosball + Air Hockey | Sleeps 10
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, (22 reviews)
"Check in was easy and smooth."
United States
Melissa C.
The price is HK$1,568
HK$2,851 total
includes taxes & fees
23 Aug - 24 Aug
Crescent Bar Condo
A modern living room with a leather sofa, a coffee table, and a kitchen area with white cabinets and stainless steel appliances.

3. 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
The price is HK$1,373
HK$4,576 total
includes taxes & fees
1 Sept - 2 Sept
NEW Ivy Streat Retreat in Ephrata, Sleeps 10, EV Charger + Foosball + Air Hockey
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)
"Darcy was a fantastic host! We would definitely recommend this place to any of our family or friends. The home was beautifully stocked and provided such great amendities!"
United States
Vi P.
The price is HK$2,315
HK$4,348 total
includes taxes & fees
9 Sept - 10 Sept
Crescent Bar Condo near The Gorge, Boating & Golf. Sleeps 8. AMAZING Pool.
A house with a gravel driveway and a view of a lake and mountains.

5. 10 mins from the Gorge Amphitheater, nestled in on the beautiful Columbia River

10 mins from the Gorge Amphitheater, nestled in on the beautiful Columbia River
Sunland Estates
9.6 out of 10, Exceptional, (22 reviews)
"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.
The price is HK$2,117
HK$3,126 total
includes taxes & fees
22 Aug - 23 Aug
10 mins from the Gorge Amphitheater, nestled in on the beautiful Columbia River
A modern building with large windows and a covered outdoor seating area.

6. Suite Home @ Cave B - 2BR - Walk to the Gorge

Suite Home @ Cave B - 2BR - Walk to the Gorge
Quincy
9.8 out of 10, Exceptional, (7 reviews)
"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.
The price is HK$1,569
HK$3,904 total
includes taxes & fees
23 Aug - 24 Aug
Suite Home @ Cave B - 2BR - Walk to the Gorge
A circular island with modern buildings, a swimming pool, and a vineyard in the background.

7. `Encore at the Gorge` - Hot Tub, Views, Concerts!

`Encore at the Gorge` - Hot Tub, Views, Concerts!
Quincy
10.0 out of 10, Exceptional, (1 review)
"great that the property was pet friendly."
United States
Paul M.
The price is HK$2,113
HK$4,641 total
includes taxes & fees
23 Aug - 24 Aug
`Encore at the Gorge` - Hot Tub, Views, Concerts!
A modern waterfront property with a reflective pool, a covered patio, and a small outdoor seating area.

8. Columbia River Retreat Lakehouse

Columbia River Retreat Lakehouse
Quincy
10.0 out of 10, Exceptional, (1 review)
The price is HK$2,113
HK$4,641 total
includes taxes & fees
23 Aug - 24 Aug
Columbia River Retreat Lakehouse
A stone building with a balcony, a greenhouse, and a vineyard in the background.

9. `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 HK$1,380
HK$3,065 total
includes taxes & fees
30 Aug - 31 Aug
`The Wine Box` at Cave B Ridge - Wine Relax Enjoy
A modern living room with a sofa, a coffee table, and a view of a patio area with a chair and a small structure.

10. 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 HK$1,380
HK$3,065 total
includes taxes & fees
23 Aug - 24 Aug
Setlist Suite - 5A Cave B Ridge Condo at the Gorge
A modern living room with a sectional sofa, a coffee table, and a fireplace.

11. The Lazy Vine Lakehouse at the Gorge

The Lazy Vine Lakehouse at the Gorge
Quincy
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at the Lazy Vine Lakehouse. It was comfy & clean. We loved how convenient it was to walk to our concert at The Gorge!"
United States
Lani K.
The price is HK$2,113
HK$4,649 total
includes taxes & fees
30 Aug - 31 Aug
The Lazy Vine Lakehouse at the Gorge
A modern outdoor seating area with a built-in fire feature, overlooking a vineyard landscape.

12. 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
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.

13. Vista & Vine Lakehouse

Vista & Vine Lakehouse
Quincy
The price is HK$1,941
HK$4,428 total
includes taxes & fees
23 Aug - 24 Aug
Vista & Vine Lakehouse
A modern building with a flat roof, large glass windows, and outdoor seating.

14. DeWine Sundowners Lakehouse at the Gorge

DeWine Sundowners Lakehouse at the Gorge
Quincy
The price is HK$1,941
HK$4,428 total
includes taxes & fees
23 Aug - 24 Aug
DeWine Sundowners Lakehouse at the Gorge
A room with a large window offering a view of a vineyard and distant hills.

15. Sage & Saddle Retreat~Wine~Gorge Ampitheatre

Sage & Saddle Retreat~Wine~Gorge Ampitheatre
Quincy
10.0 out of 10, Exceptional, (3 reviews)
"Always a great getaway "
United States
Ryan D.
The price is HK$3,234
HK$5,000 total
includes taxes & fees
19 Sept - 20 Sept
Sage & Saddle Retreat~Wine~Gorge Ampitheatre
A modern building with large glass windows offering expansive views of a desert landscape.

16. `The Backstage Pass` at Cave B Ridge Condos 2D

`The Backstage Pass` at Cave B Ridge Condos 2D
Quincy
The price is HK$1,596
HK$3,334 total
includes taxes & fees
31 Aug - 1 Sept
`The Backstage Pass` at Cave B Ridge Condos 2D
A modern house with a large outdoor area, including a pool and seating.

17. Rustic Elegance at the Gorge

Rustic Elegance at the Gorge
Quincy
The price is HK$1,941
HK$4,436 total
includes taxes & fees
24 Aug - 25 Aug
Rustic Elegance at the Gorge
A vineyard with rows of grapevines, a building with a curved roof, and a distant view of hills.

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

The Starlight Lounge Cave B Ridge - Escape & Wine
Quincy
The price is HK$1,380
HK$3,065 total
includes taxes & fees
23 Aug - 24 Aug
The Starlight Lounge Cave B Ridge - Escape & Wine
A modern, single-story building with a patio area featuring outdoor furniture.

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

Champagne Lounge 11D Cave B Ridge, Views & Wine
Quincy
The price is HK$1,380
HK$3,065 total
includes taxes & fees
23 Aug - 24 Aug
Champagne Lounge 11D Cave B Ridge, Views & Wine
A modern, glass-enclosed building with a patio area featuring outdoor furniture.

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

Cave B Ridge - Sound Stage 11A Views, Wine, Gorge
Quincy
The price is HK$1,380
HK$3,065 total
includes taxes & fees
24 Aug - 25 Aug
Cave B Ridge - Sound Stage 11A Views, Wine, 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

Endless views with easy access concerts at Gorge, Cave B Winery and SageCliffe

Endless views with easy access concerts at Gorge, Cave B Winery and SageCliffe

10/10 Excellent
"The property was beautiful with stunning views. The hosts thoughtfully provided every amenity we needed, even arranging to add a travel crib at our request (along with new crib sheets and an adorable stuffy). They were responsive to our questions. Do understand that if you're visiting on a concert/festival weekend, you can hear all the noise from the venue as well as any late night concertgoers returning and carrying on some after parties. We absolutely loved being so close to all the action, but if you have light sleepers in your party, don't forgetful your ear plugs! Will definitely be returning for our next Gorge adventure!"
Tracy C. 4-night trip
Posted 3 hours ago
Endless views with easy access concerts at Gorge, Cave B Winery and SageCliffe

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 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?

Charming 3-Bedroom Townhouse Located in Crescent Bar, WA with Spectacular Views!: This holiday home rental outside of Winchester offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 East Beach Park. Soap Lake and Moses 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.