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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Winchester vacation rentals

An outdoor patio with wicker furniture, a lantern, and a wooden deck.

1. Cozy Country Bungalow

Cozy Country Bungalow
Mountain
9.0 out of 10, Wonderful, (2 reviews)
"Nice"
Canada
Marko I.
The price is ￥20,987
￥27,354 total
includes taxes & fees
Oct 12 - Oct 13
Cozy Country Bungalow
A stone building with a sign for Linden Leaf Restaurant and Gasthaus Inn.

2. 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
The price is ￥12,492
￥17,755 total
includes taxes & fees
Oct 12 - Oct 13
Linden Leaf Gasthaus Inn Apartment Pet friendly Country walks, just off hwy 416
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
The price is ￥20,098
￥33,125 total
includes taxes & fees
Nov 2 - Nov 3
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.
The price is ￥22,208
￥28,734 total
includes taxes & fees
Oct 18 - Oct 19
The Beautiful Nubia - 5 Mins Drive to the Calypso Waterpark.
Two rocking chairs with cushioned seats and backs, positioned on a concrete patio in front of a stone wall and a glass door.

5. 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 ￥39,974
￥62,486 total
includes taxes & fees
Oct 12 - Oct 13
Beautifully appointed Island Chalet close to multiple attractions and activities
A swimming pool with a covered patio area, lounge chairs, and a slide.

6. 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
Doran Bay Resort
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

Terrace Green Bed & Breakfast

Terrace Green Bed & Breakfast

10/10 Excellent
"Had a great stay!"
Sribharathan 1-night trip
Posted 2 days ago
Terrace Green Bed & Breakfast

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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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 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.