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Book Cheshire Bed & Breakfast

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Aug 22 - Aug 24
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Aug 29 - Aug 31
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Sep 12 - Sep 14
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Oct 10 - Oct 12

B&B in Cheshire

The Homestead
Room, 1 King Bed, Patio, Ground Floor (7) | 1 bedroom, Egyptian cotton sheets, premium bedding, down comforters

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (83)
"Best breakfast. The little things that were provided (warm bathroom towels, comfortable bed, patio outside our room just for us to enjoy) added to our wonderful 3 day get away in Madison. Don't want to forget the freshly made popcorn in the evening we so enjoyed. "
$375 nightly
The price is $416
Aug 17 - Aug 18
Total includes taxes and fees
The Homestead
The Bevin House Bed & Breakfast
Seasonal outdoor pool, pool umbrellas, sun loungers

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. "
$265 nightly
The price is $295
Aug 13 - Aug 14
Total includes taxes and fees
The Bevin House Bed & Breakfast
Jay's Ranch
Exterior

Jay's Ranch

4.0 star property
7.6 out of 10, Good, (44)
"This was an amazing stay. Renee is a great host. She is clean, personable, and professional. The home is very cozy, and while still a work in progress, the outdoor area is beautiful and teeming with potential. This is not a hotel or a motel, understanding this, do not expect the starchy atmosphere of those places, but instead appreciate the friendly, homely vibe. If you’re looking for somewhere reasonably priced, clean, and cozy, this is a great spot."
$109 nightly
The price is $125
Aug 18 - Aug 19
Total includes taxes and fees
Jay's Ranch
Higganum House B&B
Exterior

Higganum House B&B

3.0 star property
Higganum House B&B
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Property grounds

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

$863 nightly
The price is $976
Aug 12 - Aug 13
Total includes taxes and fees
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Thimble Islands Bed & Breakfast
Porch

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
Sunny Peace Homestay
Exterior

Sunny Peace Homestay

2.0 star property
9.0 out of 10, Wonderful, (6)
"Stayed there for business. Cute bed and breakfast! She made me tea when I got there late. Angie was a sweetheart Will def stay every time I have a shift at the hospital! "
Sunny Peace Homestay
The Connecticut River Valley Inn
Deluxe Room, 1 King Bed, Fireplace, Garden Area | Desk, blackout drapes, soundproofing, iron/ironing board

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
Seasonal outdoor pool

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

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

10/10 Excellent
"Love it room and be the service was great "
Antonio 1-night trip
Posted 21 hours ago
Hyatt Place Milford / New Haven

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 $125 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.