Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 17 - Oct 19
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28
In four months
Jan 23 - Jan 25

Vacation Rentals in Winchester

RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa
Fridge, microwave, oven, stovetop

RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa

10.0 out of 10, Exceptional, (5)
"How is very well designed and equipped, full of nice details. Location cannot be better. Communication has been great and listing accurate. Highly recommended!"
RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa
Entire Suite in Kemptville, Ontario, Canada
Smart TV

Entire Suite in Kemptville, Ontario, Canada

7.0 out of 10, Good, (4)
"Everything was fine for our overnight stay. Was not expecting an apartment but other than that the stay was comfortable."
Entire Suite in Kemptville, Ontario, Canada
Elegance and serenity on Parkview Terrace/Élégance et sérénité sur Parkview Terr
Private kitchen

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

2.0 out of 10, (1)
"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"
The price is ￥8,984
￥15,885 total
includes taxes & fees
Oct 6 - Oct 7
Elegance and serenity on Parkview Terrace/Élégance et sérénité sur Parkview Terr
Rideau River Retreat - Waterfront Home
Property grounds

Rideau River Retreat - Waterfront Home

10.0 out of 10, Exceptional, (13)
"Loved my stay! It’s a beautiful property and the host is great! Definitely would recommend!"
Rideau River Retreat - Waterfront Home
Doran Bay Resort
Seasonal outdoor pool

Doran Bay Resort

2.5 star property
7.8 out of 10, Good, (21)
"Clean and comfortable, with all your necessities, great host, friendly and full of information."
The price is ￥14,270
￥21,499 total
includes taxes & fees
Oct 13 - Oct 14
Doran Bay Resort
Beautiful Home with castor river view
Fridge, microwave, oven, stovetop

Beautiful Home with castor river view

7.0 out of 10, Good, (18)
"Very basic. Light in bedroom windows and noisy street, but met our needs for one night. "
The price is ￥14,269
￥24,246 total
includes taxes & fees
Oct 6 - Oct 7
Beautiful Home with castor river view
Hot Tub | Dock | Swimming | Close To Ottawa
Property grounds

Hot Tub | Dock | Swimming | Close To Ottawa

10.0 out of 10, Exceptional, (6)
"Nice and secluded. The dock has incredible views. Sandy bottom, clear water, we really enjoyed our stay."
Hot Tub | Dock | Swimming | Close To Ottawa
Unique houseboat rental with private dock and land on the historic Rideau River.
Dining

Unique houseboat rental with private dock and land on the historic Rideau River.

9.8 out of 10, Exceptional, (12)
"Trevor was a great host and was accommodating"
Unique houseboat rental with private dock and land on the historic Rideau River.
M’s Studio - Private Modern Luxury Apartment (close to Calypso Waterpark)
Interior

M’s Studio - Private Modern Luxury Apartment (close to Calypso Waterpark)

10.0 out of 10, Exceptional, (5)
"We enjoyed our stay here. Propert was clean and quiet. Found no priblems when staying here. Would highly recommend. "
The price is ￥14,269
￥19,468 total
includes taxes & fees
Oct 21 - Oct 22
M’s Studio - Private Modern Luxury Apartment (close to Calypso Waterpark)
Waterfront Retreat - South Nation River
Fridge, microwave, oven, stovetop

Waterfront Retreat - South Nation River

10.0 out of 10, Exceptional, (23)
"Stayed here as a family travelling gurba local wedding. Perfect for groups! Don't hesitate to book if you are considering it, you won't regret it!"
Waterfront Retreat - South Nation River
Modern Comfort + Private View. 30 mins to Ottawa downtown and Airport.
Fridge, microwave, oven, stovetop

Modern Comfort + Private View. 30 mins to Ottawa downtown and Airport.

10.0 out of 10, Exceptional, (1)
"Absolute amazing experience. We were seeking quietness and relaxation which we found"
Modern Comfort + Private View. 30 mins to Ottawa downtown and Airport.
Cozy Country Bungalow
Fridge, microwave, oven, stovetop

Cozy Country Bungalow

The price is ￥19,977
￥25,918 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Country Bungalow
Rideau River Getaway
Interior

Rideau River Getaway

10.0 out of 10, Exceptional, (2)
"Lots to do in the area and great place"
Rideau River Getaway
The “Old School” • Historic Town • Free Parking
Property grounds

The “Old School” • Historic Town • Free Parking

The “Old School” • Historic Town • Free Parking
Stunning Home close to Ottawa
Interior

Stunning Home close to Ottawa

Stunning Home close to Ottawa
Inviting 1 Bedroom Fully Furnished smoke-free Guest House
Fridge, microwave, oven, stovetop

Inviting 1 Bedroom Fully Furnished smoke-free Guest House

10.0 out of 10, Exceptional, (5)
"Quiet, clean, great location and most of all very personable hosts!"
Inviting 1 Bedroom Fully Furnished smoke-free Guest House
The Meadow House, Country Retreat
TV, fireplace

The Meadow House, Country Retreat

The Meadow House, Country Retreat
The Wabi Sabi: 5-bedrooms luxury golf course home
Dining

The Wabi Sabi: 5-bedrooms luxury golf course home

The Wabi Sabi: 5-bedrooms luxury golf course home
Quiet Riverfront , Pet friendly
Dining

Quiet Riverfront , Pet friendly

10.0 out of 10, Exceptional, (4)
"House is beautiful and very clean. Owner’s were quick to answer questions. I highly recommend this place. "
Quiet Riverfront , Pet friendly
Newly Renovated Private 2 bed with 1 bath Getaway
Fridge, microwave, oven, stovetop

Newly Renovated Private 2 bed with 1 bath Getaway

8.8 out of 10, Excellent, (5)
"Exactly where you’d want to stay, close to everything, secure location. Excellent communication, thank you again!"
Newly Renovated Private 2 bed with 1 bath Getaway
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
"The hotel was clean and beautiful. The staff were so friendly and helpful. The food was delicious with a few different restaurants to choose from. We will definitely be back. "
Tracy 1-night trip
Posted 5 days ago
Hard Rock Hotel & Casino Ottawa

Find out more about Winchester

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:

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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 exploring the area, visit family-friendly sights like Calypso Water Park, or get outside and enjoy nature at Rideau River Provincial Park. In the larger area, you’ll find Smokie Ridge Vineyard 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.