Winchester Hotels

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 4 - Aug 5
Tomorrow
Aug 5 - Aug 6
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Winchester hotels

Terrace Green Bed & Breakfast
Premium bedding, blackout drapes, iron/ironing board, cribs/infant beds

Terrace Green Bed & Breakfast

3.0 star property
9.6 out of 10, Exceptional, (105)
"Well done property - clean and pleasant place"
The price is P4,852
P5,483 total
includes taxes & fees
Aug 8 - Aug 9
Terrace Green Bed & Breakfast
Microtel by Wyndham Casselman
Front of property

Microtel by Wyndham Casselman

3.0 star property
9.0 out of 10, Wonderful, (937)
"It was nice and quiet and a good breakfast and was close to where we needed to be "
The price is P6,379
P7,209 total
includes taxes & fees
Aug 10 - Aug 11
Microtel by Wyndham Casselman
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, (396)
"Nice clean place to stay. Staff was very friendly and helpful. Great restaurant on the property."
McIntosh Country Inn & Conference Centre in Canada
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, (479)
"Good place to stay for a night or 2"
The price is P5,992
P6,771 total
includes taxes & fees
Aug 10 - Aug 11
SureStay Hotel by Best Western Kemptville
Kemptville Suites
Living area

Kemptville Suites

4.0 star property
9.6 out of 10, Exceptional, (255)
"Everything was amazing!"
The price is P9,835
P11,113 total
includes taxes & fees
Aug 5 - Aug 6
Kemptville Suites
Cedar Drive Inn
Laptop workspace, free WiFi, bed sheets

Cedar Drive Inn

3.0 star property
9.2 out of 10, Wonderful, (89)
"Only thing we felt would be nice is a personal bar fridge in the rooms. "
The price is P5,750
P6,497 total
includes taxes & fees
Aug 5 - Aug 6
Cedar Drive Inn
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."
The price is P5,696
P8,582 total
includes taxes & fees
Aug 5 - Aug 6
Doran Bay Resort
KC's Country Inn
Terrace/patio

KC's Country Inn

2.5 star property
7.6 out of 10, Good, (314)
"I liked the old country feel of the Inn and the attached restaurant. Good service and good food. 1/2 price breakfast when you stay at the Inn. Great stay for a cheap price. Not too far away from Ottawa."
The price is P4,599
P5,197 total
includes taxes & fees
Aug 6 - Aug 7
KC's Country Inn
Enduring Heart Bed and Breakfast Inc.
Front of property

Enduring Heart Bed and Breakfast Inc.

3.5 star property
10.0 out of 10, Exceptional, (23)
"Wonderful experience, great hosts, amazing food!"
The price is P10,126
P11,442 total
includes taxes & fees
Aug 7 - Aug 8
Enduring Heart Bed and Breakfast Inc.
Hard Rock Hotel & Casino Ottawa
In-room safe, laptop workspace, blackout drapes, free WiFi

Hard Rock Hotel & Casino Ottawa

4.5 star property
8.0 out of 10, Very Good, (3)
"The king suit was very modern and luxurious. Overall very well designed and has great potential to be even better. Also, this is a great addition to Ottawa. It will only get better! "
The price is P7,130
P8,460 total
includes taxes & fees
Aug 5 - Aug 6
Hard Rock Hotel & Casino Ottawa
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
Sign in
Sign up, it's free

Learn more about Winchester

Check out Place D'Embrun and Osgoode Village Community Centre—just a couple of the sights around Winchester.

See all hotels in Winchester

Top Winchester Hotel Reviews

Microtel by Wyndham Casselman

Microtel by Wyndham Casselman

10/10 Excellent
"All good"
Alex 1-night trip
Posted 3 days ago
Microtel by Wyndham Casselman

Frequently asked questions

What's the best place for a stay in Winchester?

Based on our traveler data, Terrace Green Bed & Breakfast is one of the top choices for your stay. This B&B offers free breakfast and free parking. Other good options for your stay in the area are Microtel by Wyndham Casselman and SureStay Hotel by Best Western Kemptville. See all available top hotels, or vacation rentals in Winchester.

If I need to cancel my hotel reservation in Winchester, will I receive a refund?

Yes, most hotel room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If your reservation is non-refundable, you may still be able to cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

Where can I learn more about changing or cancelling my trip to Winchester?

To access more information about rescheduling or cancelling your trip to Winchester, head over to our customer service page.

What are some accommodations with pools in Winchester?

McIntosh Country Inn & Conference Centre in Canada: Features 2 restaurants, a seasonal outdoor pool, and a sauna.

What is the best spa hotel in Winchester?

Terrace Green Bed & Breakfast is a top spa hotel with 5 rooms, free WiFi, and barbecue grills. Enjoy a facial, reflexology, or massage at the onsite spa.

What's the best place to stay near Ogdensburg International Airport (OGS)?

The Stonefence Resort is one of the top choices for your stay and is a popular property, featuring free breakfast and an outdoor pool. It's located 2.4 mi (3.9 km) from Ogdensburg Intl. Airport. Other good choices close to the airport include The Inn at Gran View, an Ascend Hotel Collection Member and Windjammer Lodge.

What is staying in Winchester like?

Visitors are sure to enjoy all that Winchester has to offer. In Winchester, there are 2 hotels and other accommodations to choose from. Find out more about Winchester.

What should I do while I'm visiting Winchester?

Places to visit in the wider area include Place D'Embrun, Osgoode Village Community Centre, and Dupont Provincial Park. You'll also find Ferguson Forest and Upper Canada Playhouse in the area. Check out what more to see and do in Expedia's Winchester guide.

What's the seasonal weather like in Winchester?

The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 21°F. The snowiest months in Winchester are January, February, December, and November, with each month seeing an average of 18 inches of snowfall.