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Book Windsor Bed & Breakfast

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Our top choices for Windsor bed & breakfast

1. Clary Lake Bed and Breakfast

Clary Lake Bed and Breakfast
3.0 star property
Jefferson
9.8 out of 10, Exceptional, (118 reviews)
"Beautiful property and Linda was friendly and helpful. Lovely breakfast each day."
United States
Elisabeth
$120 nightly
The price is $131
Sep 27 - Sep 28
Total with taxes and fees
Clary Lake Bed and Breakfast

2. Blueberry Fields B&B

Blueberry Fields B&B
3.0 star property
Washington
10.0 out of 10, Exceptional, (103 reviews)
"We highly recommend this place. It was a wonderful experience."
United States
ailinel
$199 nightly
The price is $217
Sep 13 - Sep 14
Total with taxes and fees
Blueberry Fields B&B

3. Pressey House Lakeside Bed & Breakfast

Pressey House Lakeside Bed & Breakfast
3.0 star property
Oakland
$241 nightly
The price is $263
Oct 13 - Oct 14
Total with taxes and fees
Pressey House Lakeside Bed & Breakfast

4. Experience comfort and elegance in The Nobel Estate Suite,

Experience comfort and elegance in The Nobel Estate Suite,
Newcastle
$312 nightly
The price is $315
Sep 13 - Sep 14
Total with taxes and fees
Experience comfort and elegance in The Nobel Estate Suite,

5. The Waldoboro Inn Room 1

The Waldoboro Inn Room 1
Waldoboro
10.0 out of 10, Exceptional, (1 review)
"You can certainly tell the property was very, very old....tons of character for sure! A total step back in time, but there were some great modern conveniences; heat pumps, electronic locks for check in and for the rooms, wifi. The host was very accomodating. The room and common areas were clean and inviting."
United States
Kenneth A.
$295 nightly
The price is $322
Sep 14 - Sep 15
Total with taxes and fees
The Waldoboro Inn Room 1

6. The Waldoboro Inn Room 3

The Waldoboro Inn Room 3
Waldoboro
$296 nightly
The price is $323
Sep 15 - Sep 16
Total with taxes and fees
The Waldoboro Inn Room 3

7. Graceful and inviting, The Serenity Garden Suite No Cleaning Fee

Graceful and inviting, The Serenity Garden Suite No Cleaning Fee
Newcastle
10.0 out of 10, Exceptional, (1 review)
"Very nice facility. Clean, and wee decorated. Great outside deckls and garden."
United States
Alan
$312 nightly
The price is $315
Sep 13 - Sep 14
Total with taxes and fees
Graceful and inviting, The Serenity Garden Suite No Cleaning Fee

8. The Waldoboro Inn Room 5

The Waldoboro Inn Room 5
Waldoboro
$295 nightly
The price is $322
Sep 13 - Sep 14
Total with taxes and fees
The Waldoboro Inn Room 5
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
223
Accommodation
11 B&B
Lowest Price
$131
Highest Price
$323

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 $131 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 Bed & Breakfast in Windsor?
The best time to book a B&B in Windsor is during the vibrant summer months, particularly from July to September. This peak season draws visitors eager to experience the area's beautiful parks, picturesque riverfront, and a range of outdoor activities under the warm sun. July, in particular, is popular for its lively atmosphere, offering a variety of local festivals and events that showcase Windsor's rich culture and community spirit.

Temperatures during this time typically range from the mid-60s to the low 80s Fahrenheit, creating a comfortable setting for sightseeing and leisurely strolls along the waterfront. You can explore charming neighborhoods, visit gardens in full bloom, or relax at cafes that spill out onto the streets, creating a friendly and inviting ambiance.

For those seeking a more budget-friendly option, October presents a wonderful opportunity to enjoy the beauty of Windsor in a quieter setting. The fall foliage is stunning during this time, and the cooler temperatures—often in the 50s to low 60s Fahrenheit—make for great walking weather without the summer crowds. Visitors can enjoy scenic drives, local harvest festivals, and the peaceful ambiance that autumn brings.
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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