Default HTG hotel image

Winchester Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winchester vacation rentals

A swimming pool with a covered patio area, lounge chairs, and a slide.

1. 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
The price is AED 372
AED 551 total
includes taxes & fees
2 Oct - 3 Oct
Doran Bay Resort
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.
The price is AED 488
AED 633 total
includes taxes & fees
4 Oct - 5 Oct
Cozy Country Bungalow
A modern living room with two sofas, a coffee table, and a dining area with chairs and a glass table.

3. 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 AED 516
AED 665 total
includes taxes & fees
11 Oct - 12 Oct
The Beautiful Nubia - 5 Mins Drive to the Calypso Waterpark.
A spacious living area with a dining table, chairs, a sofa, a TV, and a potted plant.

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

Cozy 2-bedroom Basement Unit Near Calypso Water Park Embrun
Embrun
The price is AED 485
AED 793 total
includes taxes & fees
1 Nov - 2 Nov
Cozy 2-bedroom Basement Unit Near Calypso Water Park Embrun
A stone building with a sign for Linden Leaf Restaurant and Gasthaus Inn.

5. 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
10.0 out of 10, Exceptional, (1 review)
"As an added bonus, we had a great dinner at the restaurant on this property."
Canada
Cathy
The price is AED 300
AED 420 total
includes taxes & fees
21 Oct - 22 Oct
Linden Leaf Gasthaus Inn Apartment Pet friendly Country walks, just off hwy 416
Two rocking chairs with cushioned seats and backs, positioned on a concrete patio in front of a stone wall and a glass door.

6. 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 AED 929
AED 1,452 total
includes taxes & fees
9 Oct - 10 Oct
Beautifully appointed Island Chalet close to multiple attractions and activities
Living area

7. 3 Bedroom water Oasis with Hottub on the banks of the Rideau river.

3 Bedroom water Oasis with Hottub on the banks of the Rideau river.
Ottawa
The price is AED 987
AED 1,471 total
includes taxes & fees
15 Oct - 16 Oct
3 Bedroom water Oasis with Hottub on the banks of the Rideau river.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Hard Rock Hotel & Casino Ottawa

Hard Rock Hotel & Casino Ottawa

10/10 Excellent
"really good"
Mathieu 4-night trip
Posted less than an hour ago
Hard Rock Hotel & Casino Ottawa

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.