A rustic barn surrounded by autumn foliage and a field.

Book Windsor Bed & Breakfast

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Our top choices for Windsor bed & breakfast

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.4 out of 10, Exceptional, (1,005 reviews)
"I loved the staff! So friendly and helpful! The coffee was great, the location was perfect!"
United States
Nazli
$204 nightly
The price is $235
Jul 29 - Jul 30
Total with taxes and fees
Simsbury 1820 House

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (115 reviews)
"Cute place. Antiquey Excellent breakfast!"
United States
Valerie
$140 nightly
The price is $155
Aug 1 - Aug 2
Total with taxes and fees
Truman Gillet House Bed & Breakfast

The Connecticut River Valley Inn

The Connecticut River Valley Inn
3.5 star property
Glastonbury
9.4 out of 10, Exceptional, (27 reviews)
"This is an exceptionally nice place to stay. The hosts are warm and attentive and the property is first class in every way."
United States
Robert
$313 nightly
The price is $360
Aug 15 - Aug 16
Total with taxes and fees
The Connecticut River Valley Inn

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (449 reviews)
"Good stay"
United States
Susan
$118 nightly
The price is $134
Jul 29 - Jul 30
Total with taxes and fees
Naomi's Inn Bed & Breakfast

Silas W Robbins House

Silas W Robbins House
2.0 star property
Old Wethersfield Historic District
10.0 out of 10, Exceptional, (43 reviews)
"Beautiful place with a comfortable and relaxing atmosphere. Dimitri was gracious and knowledgeable about the house and town history. Loved it!!!"
United States
Cynthia
$449 nightly
The price is $516
Jul 29 - Jul 30
Total with taxes and fees
Silas W Robbins House

Sunny Peace Homestay

Sunny Peace Homestay
3.0 star property
Harwinton
9.4 out of 10, Exceptional, (9 reviews)
"Angela is very respectful and generous to her guests."
United States
Jean
$192 nightly
The price is $221
Aug 12 - Aug 13
Total with taxes and fees
Sunny Peace Homestay

The Bevin House Bed & Breakfast

The Bevin House Bed & Breakfast
3.5 star property
East Hampton
9.6 out of 10, Exceptional, (86 reviews)
"Wonderful stay. Excellent staff that treats the guest like family and friends. "
United States
Liliana
$242 nightly
The price is $269
Jul 30 - Jul 31
Total with taxes and fees
The Bevin House Bed & Breakfast

Peaceful Modern Private Room with Comfort & Charm

Peaceful Modern Private Room with Comfort & Charm
Harwinton
9.4 out of 10, Exceptional, (3 reviews)
"We had a very comfortable stay . Communication with our host was easy & prompt. We would stay again “"
United States
Laurel B.
$158 nightly
The price is $179
Aug 2 - Aug 3
Total with taxes and fees
Peaceful Modern Private Room with Comfort & Charm
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 Windsor Hotel Reviews

Find out more about Windsor

Windsor B&B information

Number of reviews
729
Accommodation
11 B&B
Lowest Price
$134
Highest Price
$516

Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Windsor?
Prices for B&Bs in Windsor often vary, but you can find a great deal from $134 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Windsor 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 Windsor?
The best time to book a B&B in Windsor is during the late spring to early fall, particularly from May to September. This vibrant period attracts travelers who appreciate the area's stunning landscapes, lush gardens, and outdoor festivals. As the days warm up, visitors can enjoy leisurely strolls along the scenic waterfront, explore charming local boutiques, or indulge in the culinary delights of nearby wineries.

June stands out as a particularly popular month, as it marks the beginning of summer. With temperatures typically ranging from the mid-50s to the high 80s Fahrenheit, the climate is great for outdoor activities like cycling, hiking, and attending local events. The atmosphere is lively, and the community buzzes with festivals and celebrations, making it an excellent time for social travelers seeking a vibrant experience.

For those looking for a more budget-friendly option, consider visiting in December. While the winter months may be quieter, Windsor transforms into a cozy retreat, offering a unique charm during the holiday season. You can enjoy festive decorations, local holiday markets, and a more relaxed pace, great for enjoying the area's hospitality.
What is the difference between a Windsor Bed & Breakfast and a hotel?
Every Windsor 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 Windsor B&Bs.

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