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Winchester Vacation 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 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.
The price is AED 643
AED 2,044 total
includes taxes & fees
1 Oct - 2 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 AED 588
AED 1,979 total
includes taxes & fees
5 Oct - 6 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 AED 367
AED 846 total
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 AED 820
AED 1,698 total
includes taxes & fees
1 Oct - 2 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 AED 505
AED 979 total
includes taxes & fees
6 Oct - 7 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 AED 505
AED 979 total
includes taxes & fees
6 Oct - 7 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, (3 reviews)
"Great place to stay at Cbar. Clean and cozy with everything we needed."
United States
John W.
The price is AED 1,488
AED 2,680 total
includes taxes & fees
1 Oct - 2 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. 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 AED 720
AED 1,356 total
includes taxes & fees
20 Oct - 21 Oct
Outdoor Grill | Fast WIFI | 1 BR | Sleeps 4
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.
The price is AED 1,469
AED 1,828 total
includes taxes & fees
31 Oct - 1 Nov
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 AED 606
AED 1,311 total
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 AED 606
AED 1,311 total
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 AED 514
AED 640 total
includes taxes & fees
1 Oct - 2 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 AED 606
AED 1,311 total
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 AED 606
AED 1,384 total
includes taxes & fees
6 Oct - 7 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 AED 606
AED 1,311 total
includes taxes & fees
6 Oct - 7 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 AED 606
AED 1,311 total
includes taxes & fees
6 Oct - 7 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 AED 909
AED 1,971 total
includes taxes & fees
1 Oct - 2 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 AED 606
AED 1,311 total
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 AED 606
AED 1,384 total
includes taxes & fees
12 Oct - 13 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 AED 909
AED 1,971 total
includes taxes & fees
1 Oct - 2 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

Microtel Inn & Suites by Wyndham Ephrata

Microtel Inn & Suites by Wyndham Ephrata

10/10 Excellent
"Nice property, enjoyed our stay there. Will definitely stay there again."
Janet 2-night trip
Posted 1 hour ago
Microtel Inn & Suites by Wyndham Ephrata

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.