Book Windsor Bed & Breakfast

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 3 B&B in Windsor with updated reviews, rates, and availability.

Ye Olde Walkerville Bed & Breakfast

3.5 star property
9.6 out of 10, Exceptional, (355)
"Wonderful historic property, warm welcome, comfortable stay, generous breakfasts. Definitely recommended!"
$86 nightly
The price is $103
Jul 23 - Jul 24
Total includes taxes and fees
Ye Olde Walkerville Bed & Breakfast

Sandwich Boutique Hotel

3.0 star property
9.2 out of 10, Wonderful, (16)
"Well set up with a common kitchen area, basic room and bathroom. Everything one needs. Location was very convenient. Host was very approachable, even though not on site, and responded very quickly to questions. "
$118 nightly
The price is $141
Jul 13 - Jul 14
Total includes taxes and fees
Sandwich Boutique Hotel

Iron Kettle Bed and Breakfast

3.5 star property
9.8 out of 10, Exceptional, (26)
"This little B&B is a gem! What a beautiful little spot to stay, I would recommend it to anyone."
Iron Kettle Bed and Breakfast
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.
Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

What are the most popular Windsor B&Bs?
Ye Olde Walkerville Bed & Breakfast is a great choice for travelers seeking a warm, friendly space in Windsor, boasting an impressive 9.6 rating. Guests rave about the cozy bedrooms and pristine bathrooms, while the delightful breakfast and attentive service ensure a memorable start to each day. With a lovely garden to explore and options for rollaway beds and sofa beds, this B&B is superb for couples and solo adventurers alike who appreciate thoughtful touches and a homey feel.

For those wanting a unique stay, the Sandwich Boutique Hotel offers a delightful experience with a solid 9.2 rating. This property exudes character and charm, making it ideal for couples looking for a romantic getaway or friends seeking a fun escape. The nearby casino and shopping outlets provide plenty of entertainment options, while the warm hospitality from the owner and staff adds a personal touch to your stay.

Families will find a comfortable retreat at the Riverview, Waterfront, Homestay, BnB, which has a rating of 7.4. With spacious rooms featuring kitchenettes, microwaves, and dining tables, this property makes it easy to prepare family meals and enjoy quality time together. The balcony offers stunning views, making it a great spot for relaxation after a day of exploring Windsor.
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 $103 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.
Are there any family-friendly Bed & Breakfasts in Windsor?
Ye Olde Walkerville Bed & Breakfast is an excellent choice for families visiting Windsor. This charming property features spacious rooms with rollaway beds and sofa beds, ensuring that everyone has a cozy spot to unwind after a busy day. The inviting garden provides a superb space for children to play and families to relax together, making it a delightful home base as you explore the area.

Another fantastic option is the Riverview, waterfront, homestay, B&B. This property is particularly family-friendly, boasting a kitchenette equipped with a microwave and dishwasher, allowing for convenient meal prep, especially for those traveling with young children. The secured yard offers a safe environment for kids to play while parents enjoy the beautiful waterfront views. Additionally, the availability of highchairs adds to its family-centric appeal, ensuring that dining is comfortable for guests of all ages.

Whether you're looking for a serene garden getaway or a riverside retreat, these B&Bs in Windsor provide attentive service and thoughtful amenities that cater to family needs, ensuring a stress-free and enjoyable stay for all.
Do any Windsor B&Bs allow dogs?
Ye Olde Walkerville Bed & Breakfast in Windsor is an excellent choice for travelers with dogs, welcoming service animals and offering a homely atmosphere. This charming property features a shared kitchen, great for families looking to prepare meals together or enjoy a midnight snack.
Are there any romantic Bed and Breakfasts in Windsor for couples?
For couples seeking a romantic retreat in Windsor, the Riverview, Waterfront Homestay BnB offers a serene atmosphere and stunning views that make it a great getaway. Nestled along the water, this charming property features a historic theme that adds a unique touch to your stay. Couples will appreciate the delightful balconies, where they can enjoy morning coffee or evening sunsets together, all while taking in the soothing sounds of the water.

The BnB is well-equipped with kitchenettes and full kitchens, allowing guests the convenience of preparing intimate meals at their leisure. The secured yard provides a sense of privacy, creating an ideal environment for relaxation. Additionally, the nearby beach offers the great setting for a romantic stroll or a day of sunbathing, further ideal for couples looking to reconnect in a beautiful setting.
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 summer months of June through August, when the area comes alive with vibrant festivals and outdoor events. This peak season attracts travelers looking to indulge in the sunny weather while enjoying picturesque views of the surrounding vineyards and gardens. The warm temperatures, typically ranging from the mid-70s to low 90s Fahrenheit, create a great backdrop for leisurely strolls through the charming downtown area and wine tastings at local wineries.

July stands out as the most popular month to visit Windsor, drawing in both families and couples eager to experience the delightful atmosphere of summer. Visitors can expect a bustling scene with plenty of opportunities for outdoor activities, including hiking, biking, and enjoying the scenic beauty of nearby parks.

For those seeking a more budget-friendly experience, consider visiting in October. This month offers the stunning backdrop of fall foliage and the chance to participate in harvest festivals, allowing travelers to immerse themselves in the local culture without the crowds. The crisp autumn air provides a refreshing contrast to the summer heat, making it an excellent time for hiking and exploring the area's natural beauty.
What is the difference between a Windsor B&B 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.