Winchester Holiday Rentals from €89: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Winchester has to offer?

RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa : This highly rated holiday home rental in Winchester 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.

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Holiday Rentals in Winchester

Enjoy cooking in this well-equipped kitchen with a central island, stainless steel range hood, and ample natural light.

"How is very well designed and equipped, full of nice details. Location cannot be better. Communication has been great and listing accurate. Highly recommended!"

includes taxes & fees

4 Aug - 5 Aug

Kitchen features a granite countertop, stainless steel appliances, and a small island with a railing.

"Was attending an event in the area; this property was well situated for our needs with shops and amenities nearby. Property was clean and well kept. "

includes taxes & fees

12 Aug - 13 Aug

Enjoy cooking in this well-equipped kitchen with a central island, appliances, and ample counter space.

"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"

includes taxes & fees

12 Aug - 13 Aug

Experience navigation and scenic views from the comfort of this cabin, featuring a central control station and large windows overlooking the water.

"This property is in a lovely location with some marvellous outdoor options. It is close enough to Ottawa to be able to experience all the area has to offer yet far enough out to find peaceful relaxation if you prefer. The houseboat is such a unique experience. The host is very helpful and personable. "

Two single beds, a flat-screen TV, and a dresser are featured in this stylish room.

includes taxes & fees

12 Aug - 13 Aug

Relax on the floating dock with a serene view of the surrounding forest.

"Nice and secluded. The dock has incredible views. Sandy bottom, clear water, we really enjoyed our stay."

Relax by the pool surrounded by lush greenery and a tranquil atmosphere.

"Clean and comfortable, with all your necessities, great host, friendly and full of information."

includes taxes & fees

31 Jul - 1 Aug

Relax in Adirondack chairs at the end of a serene pier, surrounded by calm water and lush trees.

"Loved my stay! It’s a beautiful property and the host is great! Definitely would recommend!"

Enjoy cooking in this well-equipped kitchen with a gas stove, wine cooler, and ample counter space.

"Beautiful accommodation, very modernized, the house was very climate controlled for our comfort, it was awesome to wake up and enjoy a coffee on the back deck overlooking the water. Everything a family needs to have foe a comfortable stay. Thanks so much Chris"

Relax in this stylish living room with a large window, flat-screen TV, and comfortable sofa.

"The place was clean and communication with owner great! A few things missing in the place but I’m sure they will be fixed. Thank you"

includes taxes & fees

11 Aug - 12 Aug

Enjoy cooking in this well-equipped kitchen with a central island, sink, and stainless steel appliances.

"The suite was beautifully decorated and spotlessly cleaned. There were nice personal touches, easy check-in and check-out. The host were very nice to deal with and I couldn't be happier with our stay. I would highly recommend them and their suite and would stay again."

includes taxes & fees

12 Aug - 13 Aug

Enjoy a kitchen with a large window offering a view of the outdoors, featuring a double sink, microwave, and stove.

includes taxes & fees

7 Aug - 8 Aug

includes taxes & fees

6 Aug - 7 Aug

Enjoy meals in the kitchen with an oven and large island, or dine at the table with a view.

"The place was perfect for 6 people. We spent 1 night and the rooms were spacious. The neighbourhood was really calm."

Relax in a spacious room with a large bed, flat-screen TV, and a dresser.

"Food and fuel close by."

includes taxes & fees

31 Jul - 1 Aug

"The property was absolutely amazing and my family loved every day we were there! Chantelle and Gary were very nice and checked in on us. We would love to go back again soon"

Enjoy meals in this stylish dining area with a long table, comfortable seating, and a unique ceiling design.

"It worked out great for our family and was very nice!"

Enjoy meals in the kitchen with a double sink, oven, and stainless steel range hood, adjacent to a dining area with a table and chairs.

"A great place to stay to visit Ottawa and surrounding area. Very close to Parc Calypso (the waterpark), 30 minutes to Ottawa. Very bucolic and peaceful surroundings."

includes taxes & fees

31 Jul - 1 Aug

Enjoy al fresco dining in this outdoor kitchen with a countertop, sink, grill, and dining table for four.

"Lots to do in the area and great place"

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Top Winchester Hotel Reviews

SureStay Hotel by Best Western Kemptville

10/10 Excellent

"Our room was very clean and the bathroom was also clean. Most most important to us. We had a fridge which was a nice option. Coffee was in the room but the hotel had a nice breakfast including boiled eggs, cereal, yogurt, breads, muffins, juice and a nice coffee machine that offers a variety of hot beverages. Would stay here again without hesitation "

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

2/10 Terrible

"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"

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as €89 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday 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 holiday.

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.

Frequently asked questions

Can I find a holiday rental in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winchester has to offer?

RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa: This highly rated holiday home rental in Winchester 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 exploring the area, visit family-friendly sights like Calypso Water Park, or get outside and enjoy nature at Russell Township Dog Park. In the wider area, you’ll find Place D'Embrun and Osgoode Village Community Centre.

What are holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals offer extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for a small group gathering.

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Holiday Rentals in Winchester

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Check prices for these dates

Holiday Rentals in Winchester

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

Beautiful Home with castor river view

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

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

Restauparc Motel - 2 Double Bed & Kitchenette & Private Washroom

Hot Tub | Dock | Swimming | Close To Ottawa

Doran Bay Resort

Rideau River Retreat - Waterfront Home

Waterfront Retreat - South Nation River

Entire Suite in Kemptville, Ontario, Canada

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

Cozy Country Bungalow

The “Old School” • Historic Town • Free Parking

Quiet Riverfront , Pet friendly

Restauparc Motel - Double Bed Size with Kitchenette & Desk & Private

Pet friendly Cottage on World Heritage Rideau River

The Wabi Sabi: 4-bedrooms designer home

Inviting 1 Bedroom Fully Furnished smoke-free Guest House

The “Old School” • Historic Town • Free Parking

Rideau River Getaway

Top Winchester Hotel Reviews

SureStay Hotel by Best Western Kemptville

McIntosh Country Inn & Conference Centre in Canada

Waterfront Retreat - South Nation River

Microtel by Wyndham Casselman

Hot Tub | Dock | Swimming | Close To Ottawa

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

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

Kemptville Suites

Terrace Green Bed & Breakfast

Find out more about Winchester

Frequently asked questions