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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Winchester vacation rentals

A swimming pool with a covered patio area, lounge chairs, and a slide.

1. Doran Bay Resort

Doran Bay Resort
2.5 star property
South Dundas
8.0 out of 10, Very good, (31 reviews)
"2 night, beautiful pool, clean cottage, excellent view, the beach nearby was perfect. We enjoyed it !"
Canada
Oussama
$120 nightly
The price is $136
Oct 3 - Oct 4
Total with taxes and fees
Doran Bay Resort
An outdoor patio with wicker furniture, a lantern, and a wooden deck.

2. Cozy Country Bungalow

Cozy Country Bungalow
Mountain
9.0 out of 10, Wonderful, (2 reviews)
"Nice"
Canada
Marko I.
$154 nightly
The price is $174
Oct 4 - Oct 5
Total with taxes and fees
Cozy Country Bungalow
A spacious living area with a dining table, chairs, a sofa, a TV, and a potted plant.

3. Cozy 2-bedroom Basement Unit Near Calypso Water Park Embrun

Cozy 2-bedroom Basement Unit Near Calypso Water Park Embrun
Embrun
$199 nightly
The price is $225
Sep 30 - Oct 1
Total with taxes and fees
Cozy 2-bedroom Basement Unit Near Calypso Water Park Embrun
A modern living room with two sofas, a coffee table, and a dining area with chairs and a glass table.

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

The Beautiful Nubia - 5 Mins Drive to the Calypso Waterpark.
Limoges
8.8 out of 10, Excellent, (5 reviews)
"Very nice place for work trip or for Calypso trip."
United States
Mayssoun A.
$162 nightly
The price is $183
Sep 30 - Oct 1
Total with taxes and fees
The Beautiful Nubia - 5 Mins Drive to the Calypso Waterpark.
A hammock suspended between a wooden frame, set on a concrete floor with a patterned rug.

5. Beautifully appointed Island Chalet close to multiple attractions and activities

Beautifully appointed Island Chalet close to multiple attractions and activities
South Stormont
$355 nightly
The price is $401
Sep 24 - Sep 25
Total with taxes and fees
Beautifully appointed Island Chalet close to multiple attractions and activities
A stone building with a sign for Linden Leaf Restaurant and Gasthaus Inn.

6. 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
$108 nightly
The price is $122
Oct 6 - Oct 7
Total with taxes and fees
Linden Leaf Gasthaus Inn Apartment Pet friendly Country walks, just off hwy 416
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

Arrow Properties

Arrow Properties

10/10 Excellent
"What a beautiful place. It was a little challenging to find in the dark but with Brandy's help we got there. The parking lot was well lit and the entrance was easy to find from there. We were very impressed from the time we arrived. The room was beautiful and well layed out. Very comfortable bed and couch! The bedding was perfect and the little snacks were a wonderful added touch. My 6'6" husband enjoyed the luxurious shower which is an underrated amenity for those who are of average height. We would highly recommend the Kemptville Suites to anyone staying in the area and we are definitely going to stay again for future trips to the area. Thank you for an easy reservation, confirmation and payment process."
Kary-Ann 1-night trip
Posted 3 days ago
Arrow Properties

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $122 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 free WiFi 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, Rideau River Provincial Park and Ferguson Forest Dog Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Township of Russell 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.