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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Winchester vacation rentals

Seasonal outdoor pool

Doran Bay Resort

Doran Bay Resort
2.5 star property
South Dundas
7.8 out of 10, Good, (26 reviews)
"Clean and comfortable, with all your necessities, great host, friendly and full of information."
Canada
Peg
The price is CA $144
CA $214 total
includes taxes & fees
Aug 1 - Aug 2
Doran Bay Resort
Smart TV, computer monitors, printers

The Beautiful Nubia - 5 Mins Drive to the Calypso Waterpark.

The Beautiful Nubia - 5 Mins Drive to the Calypso Waterpark.
Limoges
9.6 out of 10, Exceptional, (4 reviews)
"Very nice place for work trip or for Calypso trip."
United States
Mayssoun A.
The price is CA $200
CA $258 total
includes taxes & fees
Jul 20 - Jul 21
The Beautiful Nubia - 5 Mins Drive to the Calypso Waterpark.
Outdoor dining

Cozy Country Bungalow

Cozy Country Bungalow
Mountain
9.0 out of 10, Wonderful, (2 reviews)
"Nice"
Canada
Marko I.
The price is CA $189
CA $245 total
includes taxes & fees
Jul 18 - Jul 19
Cozy Country Bungalow
Exterior

Linden Leaf Gasthaus Inn, 2 minutes from 416 close to 401. Restaurant on site

Linden Leaf Gasthaus Inn, 2 minutes from 416 close to 401. Restaurant on site
Oxford Station
The price is CA $140
CA $189 total
includes taxes & fees
Jul 16 - Jul 17
Linden Leaf Gasthaus Inn, 2 minutes from 416 close to 401. Restaurant on site
Exterior

Linden Leaf Gasthaus Inn Apartment Pet friendly Country walks, just off hwy 416

Linden Leaf Gasthaus Inn Apartment Pet friendly Country walks, just off hwy 416
Oxford Station
The price is CA $121
CA $168 total
includes taxes & fees
Jul 21 - Jul 22
Linden Leaf Gasthaus Inn Apartment Pet friendly Country walks, just off hwy 416
Interior

Cozy 2-bedroom Basement Unit Near Calypso Water Park Embrun

Cozy 2-bedroom Basement Unit Near Calypso Water Park Embrun
Embrun
The price is CA $185
CA $241 total
includes taxes & fees
Jul 30 - Jul 31
Cozy 2-bedroom Basement Unit Near Calypso Water Park Embrun
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

KC's Country Inn

KC's Country Inn

10/10 Excellent
"If you want an experience ….. pay 2 to 3 times the cost and stay in Ottawa. If you want a basic, clean, quiet, safe covenantally located place to stay over this works. First of all cost Really cheap… about as low as you will find. Cleanliness…. Top notch. Not fancy at all but functional. The whole room very clean and the bed itself was exceptionally clean. The bathroom - though basic - was one of the cleanest ones I have seen. Looked like new tile on walls. Looks like some workers stay here. Very quiet. No noise. Right on Hwy 17 … quick 15 minute rip to Ottawa. From Toronto you can go cross country on country roads just before you cross the Rideau River to have a wide open no traffic approach. The staff is very friendly. The restaurant looks closed for renovations. There is a gas station with store right beside it and a country style donuts and looks like small store like a variety other side of gas station. No when I go to Ottawa I look for a comfortable place to sleep and shower. This more than fits the bill perfectly. I’ll be back."
George 1-night trip
Posted 1 hour ago
KC's Country Inn

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester vacation rentals we have selected for you start as low as CA $168 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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Frequently asked questions

Can I find a vacation rental in Winchester?

Yes, we offer vacation rentals near popular points of interest in Winchester, or you can go with a more remote option if you're looking for relaxation.

What are some of the best vacation rentals in Winchester?

RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa: Visitors give good reviews to this Winchester vacation home rental, which is equipped with a fireplace, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in Winchester?

While you're exploring the area, Russell Township Dog Park and Rideau River Provincial Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Domaine du Cervin and Osgoode Village Community Centre.

What are vacation rentals like in Winchester?

Vacation rentals are privately owned accommodations you can book for a short or long stay in Winchester. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll feel just like you're at home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.