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Check prices for these dates

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Sep 5 - Sep 7
In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26

Browse Select Winchester Guest Houses

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Recommended hotels in Winchester

Hard Rock Hotel & Casino Ottawa
In-room safe, laptop workspace, blackout drapes, free WiFi

Hard Rock Hotel & Casino Ottawa

4.5 star property
8.8 out of 10, Excellent, (46)
"It was a great stay"
The price is CA $165
CA $196 total
includes taxes & fees
Sep 15 - Sep 16
Hard Rock Hotel & Casino Ottawa
Terrace Green Bed & Breakfast
Deluxe Room, 1 King Bed, Ensuite

Terrace Green Bed & Breakfast

3.0 star property
9.6 out of 10, Exceptional, (108)
"Friendly and helpful owner"
The price is CA $115
CA $130 total
includes taxes & fees
Aug 26 - Aug 27
Terrace Green Bed & Breakfast
SureStay Hotel by Best Western Kemptville
Property amenity

SureStay Hotel by Best Western Kemptville

2.5 star property
8.2 out of 10, Very good, (495)
"Very quiet, clean and friendly place"
The price is CA $142
CA $160 total
includes taxes & fees
Aug 31 - Sep 1
SureStay Hotel by Best Western Kemptville
McIntosh Country Inn & Conference Centre in Canada
Daily cooked-to-order breakfast (CAD 11.99 per person)

McIntosh Country Inn & Conference Centre in Canada

3.5 star property
8.2 out of 10, Very good, (420)
"Had a great stay on our trip home for a rest."
The price is CA $178
CA $202 total
includes taxes & fees
Aug 30 - Aug 31
McIntosh Country Inn & Conference Centre in Canada
RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa
Fridge, microwave, oven, stovetop

RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa

10.0 out of 10, Exceptional, (5)
"How is very well designed and equipped, full of nice details. Location cannot be better. Communication has been great and listing accurate. Highly recommended!"
The price is CA $142
CA $248 total
includes taxes & fees
Aug 27 - Aug 28
RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa
Doran Bay Resort
Seasonal outdoor pool

Doran Bay Resort

2.5 star property
7.8 out of 10, Good, (21)
"Clean and comfortable, with all your necessities, great host, friendly and full of information."
Doran Bay Resort
Cedar Drive Inn
Family Quadruple Room, Ensuite, Ground Floor (Cardinal)

Cedar Drive Inn

3.0 star property
9.2 out of 10, Wonderful, (91)
"Only thing we felt would be nice is a personal bar fridge in the rooms. "
The price is CA $136
CA $154 total
includes taxes & fees
Aug 26 - Aug 27
Cedar Drive Inn
Restauparc Motel - 2 Double Bed & Kitchenette & Private Washroom
8 bedrooms, internet, bed sheets

Restauparc Motel - 2 Double Bed & Kitchenette & Private Washroom

10.0 out of 10, Exceptional, (1)
"Everything is great gor the price"
The price is CA $98
CA $148 total
includes taxes & fees
Aug 26 - Aug 27
Restauparc Motel - 2 Double Bed & Kitchenette & Private Washroom
Microtel by Wyndham Casselman
Front of property

Microtel by Wyndham Casselman

3.0 star property
8.8 out of 10, Excellent, (966)
"Clean hotel."
The price is CA $131
CA $148 total
includes taxes & fees
Sep 14 - Sep 15
Microtel by Wyndham Casselman
KC's Country Inn
Terrace/patio

KC's Country Inn

2.5 star property
7.6 out of 10, Good, (318)
"Staff were amazing and the breakfast was the absolute best !!! "
The price is CA $109
CA $123 total
includes taxes & fees
Aug 26 - Aug 27
KC's Country Inn
Kemptville Suites
Honeymoon Suite, 1 King Bed | Living area

Kemptville Suites

4.0 star property
9.6 out of 10, Exceptional, (259)
"The property was small but very spacious and very nice clean room, the room was beautiful and the place was quiet and comfortable. Will definitely stay here again."
The price is CA $233
CA $263 total
includes taxes & fees
Sep 4 - Sep 5
Kemptville Suites
Beautiful Home with castor river view
Fridge, microwave, oven, stovetop

Beautiful Home with castor river view

7.2 out of 10, Good, (16)
"Was attending an event in the area; this property was well situated for our needs with shops and amenities nearby. Property was clean and well kept. "
The price is CA $135
CA $229 total
includes taxes & fees
Aug 26 - Aug 27
Beautiful Home with castor river view
M’s Studio - Private Modern Luxury Apartment (close to Calypso Waterpark)
Interior

M’s Studio - Private Modern Luxury Apartment (close to Calypso Waterpark)

10.0 out of 10, Exceptional, (5)
"We enjoyed our stay here. Propert was clean and quiet. Found no priblems when staying here. Would highly recommend. "
The price is CA $135
CA $184 total
includes taxes & fees
Sep 1 - Sep 2
M’s Studio - Private Modern Luxury Apartment (close to Calypso Waterpark)
Stay Above The Village Pantry- Suite 1
1 bedroom, iron/ironing board, WiFi, bed sheets

Stay Above The Village Pantry- Suite 1

2.0 star property
The price is CA $179
CA $296 total
includes taxes & fees
Sep 2 - Sep 3
Stay Above The Village Pantry- Suite 1
Cozy Country Bungalow
Fridge, microwave, oven, stovetop

Cozy Country Bungalow

The price is CA $189
CA $245 total
includes taxes & fees
Aug 26 - Aug 27
Cozy Country Bungalow
The “Old School” • Historic Town • Free Parking
Property grounds

The “Old School” • Historic Town • Free Parking

The price is CA $177
CA $358 total
includes taxes & fees
Sep 2 - Sep 3
The “Old School” • Historic Town • Free Parking
Restauparc Motel - Double Bed Size with Kitchenette & Desk & Private
8 bedrooms, internet, bed sheets

Restauparc Motel - Double Bed Size with Kitchenette & Desk & Private

5.4 out of 10, (3)
"Food and fuel close by."
The price is CA $89
CA $137 total
includes taxes & fees
Aug 26 - Aug 27
Restauparc Motel - Double Bed Size with Kitchenette & Desk & Private
The “Old School” • Historic Town • Free Parking
Property grounds

The “Old School” • Historic Town • Free Parking

The price is CA $177
CA $357 total
includes taxes & fees
Sep 1 - Sep 2
The “Old School” • Historic Town • Free Parking
Entire Suite in Kemptville, Ontario, Canada
Smart TV

Entire Suite in Kemptville, Ontario, Canada

6.0 out of 10, (3)
"Everything was fine for our overnight stay. Was not expecting an apartment but other than that the stay was comfortable."
The price is CA $117
CA $243 total
includes taxes & fees
Sep 1 - Sep 2
Entire Suite in Kemptville, Ontario, Canada
Stay Above The Village Pantry - Suite 2
Iron/ironing board, WiFi, bed sheets

Stay Above The Village Pantry - Suite 2

The price is CA $179
CA $294 total
includes taxes & fees
Sep 1 - Sep 2
Stay Above The Village Pantry - Suite 2
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 Winchester Hotel Reviews

SureStay Hotel by Best Western Kemptville

SureStay Hotel by Best Western Kemptville

10/10 Excellent
"Great, friendly, professional service! Clean and spacious rooms. Wonderful stay."
Kathryn 1-night trip
Posted 22 hours ago
SureStay Hotel by Best Western Kemptville

Frequently asked questions

What is the nightly rate for a guest house in Winchester?
Rates for Winchester 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 Winchester 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 Winchester guest house and a B&B?
A guest house in Winchester 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.