Default HTG hotel image

Search and Rent Winchester Condos

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 condo rentals

A swimming pool with lounge chairs and umbrellas, surrounded by buildings with red roofs and a mountainous backdrop.

1. 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.
$225 nightly
The price is $236
Oct 11 - Oct 12
Total with taxes and fees
Crescent Bar Condo
A modern building with a glass entrance, a visible living area with a sofa and table, and a kitchen area.

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

Serenity Suite 4B- Amphitheater, Winery & Spa
Quincy
$360 nightly
The price is $377
Oct 11 - Oct 12
Total with taxes and fees
Serenity Suite 4B- Amphitheater, Winery & Spa
A hotel with a well-lit outdoor area, a tree, and a view of the night sky with the aurora borealis.

3. 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.
$426 nightly
The price is $464
Oct 9 - Oct 10
Total with taxes and fees
Crescent Bar Condo near The Gorge, Boating & Golf. Sleeps 8. AMAZING Pool.
A stone building with a balcony, a greenhouse, and a view of a vineyard.

4. Sunset Splendor - Relax & UnWine 3B

Sunset Splendor - Relax & UnWine 3B
Quincy
$360 nightly
The price is $377
Oct 11 - Oct 12
Total with taxes and fees
Sunset Splendor - Relax & UnWine 3B
A patio with a chair and table, overlooking a vineyard and a canyon with a river.

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

Verse & Vine Retreat – 5B Cave B Ridge Condo
Quincy
$360 nightly
The price is $377
Oct 11 - Oct 12
Total with taxes and fees
Verse & Vine Retreat – 5B Cave B Ridge Condo
A stone building with a balcony, a greenhouse, and a vineyard in the background.

6. `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 11 - Oct 12
Total with taxes and fees
`The Wine Box` at Cave B Ridge - Wine Relax Enjoy
A modern building with large glass windows offering expansive views of a desert landscape.

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

`The Backstage Pass` at Cave B Ridge Condos 2D
Quincy
$360 nightly
The price is $377
Oct 11 - Oct 12
Total with taxes and fees
`The Backstage Pass` at Cave B Ridge Condos 2D
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.
$360 nightly
The price is $377
Oct 11 - Oct 12
Total with taxes and fees
Cave B Ridge - Desert Stage - Views, Wine & Gorge
A modern, single-story building with a patio area featuring outdoor furniture.

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

Champagne Lounge 11D Cave B Ridge, Views & Wine
Quincy
$360 nightly
The price is $377
Oct 11 - Oct 12
Total with taxes and fees
Champagne Lounge 11D Cave B Ridge, Views & Wine
A modern building with a covered outdoor seating area, large windows, and a sandy landscape.

10. Wine Down in 3C at Cave B Ridge

Wine Down in 3C at Cave B Ridge
Quincy
$360 nightly
The price is $377
Oct 11 - Oct 12
Total with taxes and fees
Wine Down in 3C at Cave B Ridge
A modern interior with large glass windows, a leather sofa, and a dining area with outdoor seating.

11. 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 11 - Oct 12
Total with taxes and fees
Unplug - Views! Cave B Ridge 2B Winery Spa Gorge
A room with a large window offering a view of a vineyard and distant hills.

12. 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
$335 nightly
The price is $365
Nov 3 - Nov 4
Total with taxes and fees
Outdoor Grill | Fast WIFI | 1 BR | Sleeps 4
A modern living room with a sofa, a coffee table, and a view of a patio area with a chair and a small structure.

13. 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 11 - Oct 12
Total with taxes and fees
Setlist Suite - 5A Cave B Ridge Condo at the 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
$360 nightly
The price is $377
Oct 11 - Oct 12
Total with taxes and fees
Cave B Ridge - The Sky View Lounge 5C
A modern, single-story building with a wooden ceiling and large glass windows, featuring a patio with outdoor seating.

15. `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)
$360 nightly
The price is $377
Oct 11 - Oct 12
Total with taxes and fees
`Tumbleweed Corner 1C` at Cave B Ridge Condos
A modern outdoor hot tub area with a covered seating space and a building with large windows.

16. Tesla Charger | Waffle Bar | Hot Tub | Sleeps 8

Tesla Charger | Waffle Bar | Hot Tub | Sleeps 8
Quincy
9.6 out of 10, Exceptional, (4 reviews)
"Such a beautiful home in a beautiful environment. Charlotte was an amazing host and we had an amazing stay. No issues that affected us and we would definitely return!"
United States
Nick L.
$568 nightly
The price is $618
Oct 14 - Oct 15
Total with taxes and fees
Tesla Charger | Waffle Bar | Hot Tub | Sleeps 8
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
$360 nightly
The price is $377
Oct 11 - Oct 12
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.

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

The Starlight Lounge Cave B Ridge - Escape & Wine
Quincy
$360 nightly
The price is $377
Oct 11 - Oct 12
Total with taxes and fees
The Starlight Lounge Cave B Ridge - Escape & Wine
A modern living room with a large glass door leading to an outdoor patio, a white sofa, leather armchairs, and abstract wall art.

19. 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 11 - Oct 12
Total with taxes and fees
Cave B Ridge River View Retreat 3D - Wine & Relax
A modern house with a glass-enclosed patio, a dining area, and a living room with a sofa and chairs.

20. 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.
$360 nightly
The price is $377
Oct 11 - Oct 12
Total with taxes and fees
Vineyard River Vista 4D at Cave B Ridge
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

Winchester Condo Rentals information

Number of reviews
35
Accommodation
98 Condo Rentals
Lowest Price
$236
Highest Price
$618

Explore a world of travel with Expedia