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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Winchester vacation rentals

Seasonal outdoor pool

1. Doran Bay Resort

Doran Bay Resort
2.5 star property
South Dundas
8.0 out of 10, Very Good, (28 reviews)
"2 night, beautiful pool, clean cottage, excellent view, the beach nearby was perfect. We enjoyed it !"
Canada
Oussama
The price is ￥12,489
￥19,949 total
includes taxes & fees
Aug 30 - Aug 31
Doran Bay Resort
Outdoor dining

2. Cozy Country Bungalow

Cozy Country Bungalow
Mountain
9.0 out of 10, Wonderful, (2 reviews)
"Nice"
Canada
Marko I.
The price is ￥21,694
￥28,146 total
includes taxes & fees
Sep 13 - Sep 14
Cozy Country Bungalow
Smart TV

3. 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
Entire Suite in Kemptville, Ontario, Canada
Exterior

4. 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 ￥13,326
￥18,690 total
includes taxes & fees
Sep 22 - Sep 23
Linden Leaf Gasthaus Inn Apartment Pet friendly Country walks, just off hwy 416
Interior

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

Cozy 2-bedroom Basement Unit Near Calypso Water Park Embrun
Embrun
The price is ￥21,334
￥27,748 total
includes taxes & fees
Aug 30 - Aug 31
Cozy 2-bedroom Basement Unit Near Calypso Water Park Embrun
Smart TV

6. 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.
The price is ￥22,956
￥29,702 total
includes taxes & fees
Sep 3 - Sep 4
The Beautiful Nubia - 5 Mins Drive to the Calypso Waterpark.
Smart TV

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

Beautifully appointed Island Chalet close to multiple attractions and activities
South Stormont
The price is ￥41,321
￥66,408 total
includes taxes & fees
Aug 31 - Sep 1
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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Top Winchester Hotel Reviews

Hard Rock Hotel & Casino Ottawa

Hard Rock Hotel & Casino Ottawa

10/10 Excellent
"Check in rapide et courtois!"
Alain 2-night trip
Posted 22 hours ago
Hard Rock Hotel & Casino Ottawa

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
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  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

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 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 Mountain Memorial Community 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 Baxter Conservation Area.

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.