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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Winchester vacation rentals

Seasonal outdoor pool

Doran Bay Resort

Doran Bay Resort
2.5 star property
South Dundas
7.6 out of 10, Good, (22 reviews)
"Clean and comfortable, with all your necessities, great host, friendly and full of information."
Canada
Peg
$160 nightly
The price is $181
Jun 22 - Jun 23
Total with taxes and fees
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.
$154 nightly
The price is $174
Jun 29 - Jun 30
Total with taxes and fees
The Beautiful Nubia - 5 Mins Drive to the Calypso Waterpark.
Interior

Elegance and serenity on Parkview Terrace/Élégance et sérénité sur Parkview Terr

Elegance and serenity on Parkview Terrace/Élégance et sérénité sur Parkview Terr
Russell
2.0 out of 10, (1 review)
"This property was listed as 3 Bedrooms / 1 Bath BUT, after reserving, I was told it was a Single Room with a SHARED Bath!! The listing explicitly says, per the VRBO guidelines, that you have the whole house and only share with your family. I cancelled immediately BUT have not heard from either the Property Owner or VRBO about a REFUND. NOT ACCEPTAB:E"
Canada
Mike
$94 nightly
The price is $106
Jun 22 - Jun 23
Total with taxes and fees
Elegance and serenity on Parkview Terrace/Élégance et sérénité sur Parkview Terr
Smart TV

Entire Suite in Kemptville, Ontario, Canada

Entire Suite in Kemptville, Ontario, Canada
Kemptville
7.8 out of 10, Good, (7 reviews)
"Wonderful 2 nights stay. Clean, friendly, safe and very spacious. "
Canada
Natasha
$152 nightly
The price is $172
Jul 4 - Jul 5
Total with taxes and fees
Entire Suite in Kemptville, Ontario, Canada
Outdoor dining

Cozy Country Bungalow

Cozy Country Bungalow
Mountain
9.0 out of 10, Wonderful, (2 reviews)
"Nice"
Canada
Marko I.
$153 nightly
The price is $173
Jul 6 - Jul 7
Total with taxes and fees
Cozy Country Bungalow
Interior

Cozy 2-bedroom Basement Unit Near Calypso Water Park Embrun

Cozy 2-bedroom Basement Unit Near Calypso Water Park Embrun
Embrun
$151 nightly
The price is $170
Jun 22 - Jun 23
Total with taxes and fees
Cozy 2-bedroom Basement Unit Near Calypso Water Park Embrun
Dining

Escape to Country Comfort Perfect for a romantic escape, or family retreat.

Escape to Country Comfort Perfect for a romantic escape, or family retreat.
Iroquois
Escape to Country Comfort Perfect for a romantic escape, or family retreat.
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

Hard Rock Hotel & Casino Ottawa

Hard Rock Hotel & Casino Ottawa

8/10 Good
"Little Vegas in Ottawa. Great restaurants and entertainment. Room was comfortable except the pillows were too thick, I like thinner pillows. Duvet cover had a rip, dirty glass in the bathroom and the light switch was dirty. Loved the vanity in the bathroom. The mattress was comfortable. Tv didn't have any Hard Rock stations that worked. Safe was in the night stand. Ice machine down the hall. One shower head worked, couldn't figure out how to get the second one on. We enjoyed our stay in and out of the room. Rock of Ages was funny and completely entertaining."
Stephen 1-night trip
Posted 4 hours ago
Hard Rock Hotel & Casino Ottawa

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 $106 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.

Explore a world of travel with Expedia

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, Rideau River Provincial Park and Russell Township Dog Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Domaine du Cervin and Place D'Embrun.

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.