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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Winchester bed & breakfast

A residential property with a well-maintained garden, a stone staircase leading to the entrance, and string lights overhead.

1. Inn at Churon Winery

Inn at Churon Winery
4.0 star property
Valle De Los Caballos
9.8 out of 10, Exceptional, (1,002 reviews)
"Excellent location, gorgeous views. Love staying here."
United States
Ryan
$158 nightly
The price is $177
Dec 6 - Dec 7
Total with taxes and fees
Inn at Churon Winery
A building with white flowering vines hanging from the exterior.

2. Idyllwild Bunkhouse

Idyllwild Bunkhouse
3.0 star property
Idyllwild
8.6 out of 10, Excellent, (1,000 reviews)
"the cabin was as described with easy check in and good location close to the town centre"
United States
Tim Worthington
$82 nightly
The price is $90
Nov 12 - Nov 13
Total with taxes and fees
Idyllwild Bunkhouse
A large estate with a central building, surrounded by vineyards and cypress trees.

3. Domaine Chardonnay

Domaine Chardonnay
5.0 star property
Valle De Los Caballos
10.0 out of 10, Exceptional, (45 reviews)
"We had an amazing time at the property! Felt like home. Will definitely be a place to return :) thank you Laura and all the staff for your welcoming services!"
United States
Karen
$412 nightly
The price is $462
Nov 11 - Nov 12
Total with taxes and fees
Domaine Chardonnay
A stately house with a prominent black front door, a stone facade, and a well-maintained garden with a fountain.

4. Domaine Chardonnay, one of Temecula Wine Country's premier residential properties, is an exclusive, privately operating, winery estate Bed & Breakfast with 3 beautifully appointed, independent guest suites for overnight accommodations, each featuring

Domaine Chardonnay, one of Temecula Wine Country's premier residential properties, is an exclusive, privately operating, winery estate Bed & Breakfast with 3 beautifully appointed, independent guest suites for overnight accommodations, each featuring
Valle De Los Caballos
10.0 out of 10, Exceptional, (9 reviews)
"This property is a stunning first class experience for a person or couple that appreciates amazing Decour breathtaking views and fine linens it’s a very peaceful experience.. A special retreat and will be back again."
United States
HollyCollins
$433 nightly
The price is $482
Nov 10 - Nov 11
Total with taxes and fees
Domaine Chardonnay, one of Temecula Wine Country's premier residential properties, is an exclusive, privately operating, winery estate Bed & Breakfast with 3 beautifully appointed, independent guest suites for overnight accommodations, each featuring
A large stone building with a symmetrical facade, multiple chimneys, and a well-maintained garden with a fountain.

5. Domaine Chardonnay, one of Temecula Wine Country's premier residential properties, is an exclusive, privately operating, winery estate Bed & Breakfast with 3 beautifully appointed, independent guest suites for overnight accommodations, each featuring

Domaine Chardonnay, one of Temecula Wine Country's premier residential properties, is an exclusive, privately operating, winery estate Bed & Breakfast with 3 beautifully appointed, independent guest suites for overnight accommodations, each featuring
Valle De Los Caballos
10.0 out of 10, Exceptional, (6 reviews)
"Wonderful experience."
United States
tim c.
$488 nightly
The price is $543
Nov 10 - Nov 11
Total with taxes and fees
Domaine Chardonnay, one of Temecula Wine Country's premier residential properties, is an exclusive, privately operating, winery estate Bed & Breakfast with 3 beautifully appointed, independent guest suites for overnight accommodations, each featuring
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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Learn more about Winchester

Horseback riding trails wind through Winchester's Diamond Valley Lake Recreation Area, where you can also fish for bass and trout. Visit nearby Temecula for wine tasting tours or explore the Western Science Center in Hemet for fascinating Ice Age fossils.

See all hotels in Winchester
A large industrial facility with multiple warehouses and storage tanks in a mountainous region.

Top reviews in Winchester

A residential property with a well-maintained garden, a stone staircase leading to the entrance, and string lights overhead.
Inn at Churon Winery

Inn at Churon Winery

Inn at Churon Winery
Valle De Los Caballos

10/10 Excellent

This place is amazing. The staff even better, especially the front desk staff like Julie who truly made us feel welcomed and was super helpful.
United States
Rafael
Reviewed March 23, 2025
Inn at Churon Winery

Frequently Asked Questions

What is the nightly rate for a B&B in Winchester?

Prices for B&Bs in Winchester often vary, but you can find a great deal from $89 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winchester B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.

When is the best time to book a B&B in Winchester?

The best time to book a B&B in Winchester is during the peak season from April to June, when the weather is pleasantly warm and outdoor activities flourish. This time frame is particularly popular among visitors who appreciate the area's rich history and vibrant arts scene, making it an ideal backdrop for sightseeing and leisurely exploration.

With temperatures typically ranging from the upper 50s to mid-80s Fahrenheit, visitors can comfortably stroll through the scenic historic downtown, visit local wineries, or enjoy the beauty of the surrounding countryside. The stunning blooms of spring add an extra layer of charm, making it a great time for outdoor festivities and events.

May stands out as the most popular month to visit Winchester, as it often features a variety of local events and festivals that showcase the community's culture. This month is bustling with energy, attracting both adventure seekers and those looking to unwind in a picturesque setting.

For travelers seeking a more budget-friendly experience, November offers a quieter alternative. While the weather is cooler, with temperatures dropping to the 30s and 40s Fahrenheit, this month allows for peaceful explorations of the area's historical sites and cozy indoor activities, all while enjoying the tranquility of the off-peak season.

What is the difference between a Winchester Bed and Breakfast and a hotel?

Every Winchester B&B has its own unique feel. Whether it’s a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Winchester B&Bs.

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