A wooden covered bridge over a river surrounded by lush greenery.

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Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1

Our top choices for Windsor guest houses

Interior

1. Bonnie's Guesthouse @ Peridot Equine Sanctuary

Bonnie's Guesthouse @ Peridot Equine Sanctuary
Chardon
9.6 out of 10, Exceptional, (86 reviews)
"It is a beautiful, peaceful property. "
United States
Roselle E.
The price is CA $208
CA $235 total
includes taxes & fees
Sep 7 - Sep 8
Bonnie's Guesthouse @ Peridot Equine Sanctuary
Interior

2. Cozy two bedroom house close to Middlefield, and not far from Route 80 and 422

Cozy two bedroom house close to Middlefield, and not far from Route 80 and 422
West Farmington
10.0 out of 10, Exceptional, (14 reviews)
"Everything in this stay was great. My family and I enjoyed our stay & felt welcomed "
United States
ana V.
The price is CA $133
CA $189 total
includes taxes & fees
Sep 7 - Sep 8
Cozy two bedroom house close to Middlefield, and not far from Route 80 and 422
Front of property

3. Steele Mansion

Steele Mansion
3.5 star property
Painesville
10.0 out of 10, Exceptional, (469 reviews)
"Beautiful place to stay with such unique rooms. The owner was there and so helpful for any of our needs. Breakfast was great. Will stay there again when back in the area."
United States
James
The price is CA $269
CA $310 total
includes taxes & fees
Sep 8 - Sep 9
Steele Mansion
Front of property

4. Tall Oaks Resort

Tall Oaks Resort
4.0 star property
Willoughby
9.4 out of 10, Exceptional, (37 reviews)
"The facility was extremely clean & well maintained. We were the only people staying on the property (no staff) so that was different. Instructions were clear for accessing our room, etc."
United States
Gina
The price is CA $206
CA $280 total
includes taxes & fees
Sep 13 - Sep 14
Tall Oaks Resort
Outdoor spa tub

5. Geneva Loft, Hot Tub + Arcade *Mins to Spire, Wineries and I-90* Great Location

Geneva Loft, Hot Tub + Arcade *Mins to Spire, Wineries and I-90* Great Location
Geneva
10.0 out of 10, Exceptional, (75 reviews)
"This place was amazing the host was very welcoming and the house was incredible would recommend to anyone that wanted to get away I will definitely be staying again "
United States
Corbin W.
The price is CA $280
CA $442 total
includes taxes & fees
Sep 9 - Sep 10
Geneva Loft, Hot Tub + Arcade *Mins to Spire, Wineries and I-90* Great Location
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

Holiday Inn Express & Suites Madison by IHG

Holiday Inn Express & Suites Madison by IHG

10/10 Excellent
"Clean room, loved the standard size bed pillows & bed was comfy."
Paula S 1-night trip
Posted less than an hour ago
Holiday Inn Express & Suites Madison by IHG

Find out more about Windsor

Windsor Guest Houses information

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 Guest Houses
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Frequently asked questions

What is the nightly rate for a guest house in Windsor?
Rates for Windsor guest houses vary, but travelers can find great-value prices with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Windsor guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
What's the difference between a Windsor guest house and a B&B?
A guest house in Windsor is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.

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