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Book Cheshire Bed & Breakfast

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B&B in Cheshire

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (87)
"This is our 2nd year staying at the Homestead B & B. We absolutely love it here! Great food, amenities galore, and just an awesome getaway!"
$331 nightly
The price is $368
Oct 26 - Oct 27
Total with taxes and fees
The Homestead

The Bevin House Bed & Breakfast

3.5 star property
9.6 out of 10, Exceptional, (78)
"The staff was super friendly and welcoming. The house was beautiful and the grounds full of things to explore. The breakfast was presently with panache and tasted great. We swam in the pool, ate at local restaurants, pet a turkey, and visited the local winery. I would highly recommend this establishment. "
$257 nightly
The price is $286
Oct 27 - Oct 28
Total with taxes and fees
The Bevin House Bed & Breakfast

Jay's Ranch

4.0 star property
7.8 out of 10, Good, (46)
"Im so happy I found this place to stay. Meets all my needs and great service !!"
Jay's Ranch

Sunny Peace Homestay

2.0 star property
9.4 out of 10, Exceptional, (8)
"Angela is very respectful and generous to her guests."
Sunny Peace Homestay

Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space

$856 nightly
The price is $969
Sep 29 - Sep 30
Total with taxes and fees
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space

Higganum House B&B

3.0 star property
Higganum House B&B

Thimble Islands Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (4)
"A beautiful, quiet home in a stunning setting run by two extremely gracious hosts. Breakfast on both days was excellent."
Thimble Islands Bed & Breakfast

The Connecticut River Valley Inn

3.5 star property
9.4 out of 10, Exceptional, (24)
"Charming Inn, "
The Connecticut River Valley Inn

Green Acres B&B

3.0 star property
9.8 out of 10, Exceptional, (150)
"Gracious hosts, many amenities and the best breakfast!"
Green Acres B&B
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 Cheshire Hotel Reviews

Find out more about Cheshire

Find out more about Cheshire

Cheshire B&B information

Number of reviews
219
Accommodation
9 B&B
Lowest Price
$286
Highest Price
$969

Frequently asked questions

What is the nightly rate for a B&B in Cheshire?
Prices for B&Bs in Cheshire often vary, but you can find a great deal from $286 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Cheshire 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 Cheshire?
The best time to book a B&B in Cheshire is during the late spring to early summer months of May through July. This period showcases the region's natural beauty, with lush landscapes and vibrant flowers in full bloom, making it an ideal time for outdoor enthusiasts and nature lovers alike. Visitors can indulge in scenic hikes, explore charming villages, or take leisurely strolls along the picturesque waterways.

July stands out as the most popular month for travelers, as the warm temperatures (ranging from the mid-50s to the low 80s Fahrenheit) invite plenty of outdoor activities. The lively atmosphere is complemented by local events and festivals, offering visitors a chance to immerse themselves in the community's rich culture.

For those seeking a more budget-conscious option, consider visiting in November. While this month sees fewer crowds, it provides a unique opportunity to experience the region's tranquil beauty, with the landscape often adorned in autumn hues. This quieter time allows for peaceful explorations of the area's historic sites and scenic routes.
What is the difference between a Cheshire Bed & Breakfast and a hotel?
Every Cheshire 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 Cheshire B&Bs.

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