Winchester Vacation Rentals

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Winchester vacation rentals

A stone building with a sign for Linden Leaf Restaurant and Gasthaus Inn, surrounded by greenery.

1. 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
9.0 out of 10, Wonderful, (2 reviews)
"As an added bonus, we had a great dinner at the restaurant on this property."
Canada
Cathy
$90 nightly
The price is $101
Nov 9 - Nov 10
Total with taxes and fees
Linden Leaf Gasthaus Inn Apartment Pet friendly Country walks, just off hwy 416
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.
$142 nightly
The price is $161
Nov 8 - Nov 9
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
$178 nightly
The price is $202
Nov 30 - Dec 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.
$150 nightly
The price is $170
Nov 14 - Nov 15
Total with taxes and fees
The Beautiful Nubia - 5 Mins Drive to the Calypso Waterpark.
A modern kitchen with stainless steel appliances, wooden cabinets, a central island with stools, and a view of greenery outside.

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

Beautifully appointed Island Chalet close to multiple attractions and activities
South Stormont
$333 nightly
The price is $376
Nov 8 - Nov 9
Total with taxes and fees
Beautifully appointed Island Chalet close to multiple attractions and activities
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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Find vacation rentals that suit your style

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Top Winchester Hotel Reviews

A spacious living room with a fireplace, leather sofas, a coffee table, and a large rug.
Terrace Green Bed & Breakfast

Terrace Green Bed & Breakfast

Terrace Green Bed & Breakfast
North Dundas

10/10 Excellent

Annette made the most wonderful breakfast and was so accommodating in every way. It was a real delight, staying at her bed and breakfast.
United States
Brian
Reviewed September 17, 2025
Terrace Green Bed & Breakfast

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 $101 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.

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 Osgoode Village Community Centre and Metcalfe Golf Club.

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.

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