An aerial view of a densely populated urban area with a river, surrounding mountains, and a clear sky.

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Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1

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
9.6 out of 10, Exceptional, (1,001 reviews)
"Lovely views, tasty breakfast, very clean and comfortable rooms."
United States
Jennifer
$166 nightly
The price is $186
Sep 7 - Sep 8
Total with taxes and fees
Inn at Churon Winery
A bedroom with a large bed, a freestanding bathtub, a fireplace, and a TV mounted on the wall.

2. Domaine Chardonnay

Domaine Chardonnay
5.0 star property
Valle De Los Caballos
10.0 out of 10, Exceptional, (38 reviews)
"The owner came out to greet us and check us in. The room was thoughtfully designed with a grand yet comfortable feel. Will plan to come back again."
United States
Emilie
$480 nightly
The price is $537
Sep 13 - Sep 14
Total with taxes and fees
Domaine Chardonnay
A motel with a red exterior, multiple rooms, and a parking lot.

3. Idyllwild Bunkhouse

Idyllwild Bunkhouse
3.0 star property
Idyllwild
8.6 out of 10, Excellent, (1,000 reviews)
"Had a lovely stay at Idyllwild Bunkhouse! Was the perfect spot - could walk to town and walk easily to the amazing hikes. A beautiful view, and very peaceful! Grateful for this place and would definitely come again. Easy parking too!"
United States
Samantha E
$86 nightly
The price is $95
Sep 3 - Sep 4
Total with taxes and fees
Idyllwild Bunkhouse
A large stone building with a symmetrical facade, multiple chimneys, 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, (4 reviews)
"We stayed here for a wedding/boyfriend’s birthday and it was amazing. Very private and beautiful view. Would recommend!"
United States
Diana H.
$545 nightly
The price is $602
Sep 13 - Sep 14
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 stately house with a prominent black front door, a stone facade, 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, (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
$623 nightly
The price is $688
Sep 8 - Sep 9
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.

6. 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.
$708 nightly
The price is $782
Sep 3 - Sep 4
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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Top Winchester Hotel Reviews

Carter Estate Winery and Resort

Carter Estate Winery and Resort

10/10 Excellent
"Quiet and secluded with great atmosphere and beautiful accommodations."
Jennifer 1-night trip
Posted 4 hours ago
Carter Estate Winery and Resort

Find out more about Winchester

Winchester B&B information

Number of reviews
1,057
Accommodation
8 B&B
Lowest Price
$95
Highest Price
$782

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 $95 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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