Oakville Holiday Rentals

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Our top choices for Oakville holiday rentals

3.0 star property
The price is AU$714
includes taxes & fees
14 Mar - 15 Mar
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
9.8 out of 10, Exceptional, (40 reviews)
"Very comfortable property. The host had thought of everything!"
United States
Jennifer Y.
Cozy & Serene Cabin with Fireplace, Ski Nearby!
9.0 out of 10, Wonderful, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is AU$428
includes taxes & fees
14 Mar - 15 Mar
Once the old Schools house now a newly furnished Apartment

Apartment in Wallingford Center

All New 1BR with tons of Charm
9.8 out of 10, Exceptional, (8 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is AU$428
includes taxes & fees
16 Mar - 17 Mar
All New 1BR with tons of Charm
10.0 out of 10, Exceptional, (17 reviews)
"Everything about our stay was great - Corin and Jen were wonderful hosts. The place is spotless, cozy, comfy. Love that they were right next to the Green Way Trail along the river. Will absolutely stay there again! "
United States
Kate B.
The price is AU$372
includes taxes & fees
15 Mar - 16 Mar
Pristine, Walkable downtown, Entire 2 Bedroom apartment
10.0 out of 10, Exceptional, (23 reviews)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is AU$178
includes taxes & fees
18 Mar - 19 Mar
Cozy One Bedroom Apartment Centrally Located in Southbury
10.0 out of 10, Exceptional, (8 reviews)
"The place was absolutely spotless and magnificent in every way. Highly recommended."
United States
Robert A.
The price is AU$517
includes taxes & fees
18 Mar - 19 Mar
The Jefferson Guest House, Spacious, Special Views
3.0 star property
The price is AU$724
includes taxes & fees
10 Apr - 11 Apr
Dainty New Preston Cottage w/ Dock & Lake Views!
7.6 out of 10, Good, (7 reviews)
" Not bad for the price "
United States
Audrey L.
The price is AU$519
includes taxes & fees
14 Mar - 15 Mar
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
The price is AU$551
includes taxes & fees
14 Mar - 15 Mar
Litchfield Retreat, Wineries, Foliage & Skiing
10.0 out of 10, Exceptional, (1 review)
"Without a doubt, we will be back! Your home was so beautiful, warm and comfortable. Our host was so helpful and friendly. We can't thank you enough for providing such a wonderful experience to our trip. "
United States
Linda D.
The price is AU$836
includes taxes & fees
16 Mar - 17 Mar
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
10.0 out of 10, Exceptional, (1 review)
"Host was kind and attentive. Location was convenient and the home was clean and spacious. "
United States
Renee H.
The price is AU$587
includes taxes & fees
16 Mar - 17 Mar
Welcoming 4-bedroom house in charming Hamden
10.0 out of 10, Exceptional, (2 reviews)
"Property management team was very quick to respond to any question or issue I had. Excellent location around eateries and activities "
United States
Dominick S.
The price is AU$310
includes taxes & fees
14 Mar - 15 Mar
Private Apartment in Southbury 103
10.0 out of 10, Exceptional, (9 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
The price is AU$419
includes taxes & fees
1 Apr - 2 Apr
Newly Remodeled 1-BR Close to Everything yet Very Private
10.0 out of 10, Exceptional, (23 reviews)
"The place was perfect for the two of us. It was close to both our kids homes."
United States
Tomas M.
The price is AU$369
includes taxes & fees
30 Mar - 31 Mar
River Overlook - Check the view from your deck!

Holiday Home in Southington

#27- Luxury Collection
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home, well designed and spacious rooms. Host was fantastic and communication was great! Thank you"
United States
C B.
The price is AU$589
includes taxes & fees
19 Mar - 20 Mar
#27- Luxury Collection
9.4 out of 10, Exceptional, (16 reviews)
"Great Location - all the amenities you need for a nice restful stay. Did not have to reach-out to the host at all during our stay. "
United States
Robert S.
The price is AU$282
includes taxes & fees
24 Mar - 25 Mar
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.0 out of 10, Wonderful, (7 reviews)
"We enjoyed our stay! And happy with most!!!!"
United States
Dawn H.
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
8.4 out of 10, Very good, (12 reviews)
"Great place ! Quiet and safe place! We will be back! "
United States
Aubrey C.
The price is AU$454
includes taxes & fees
15 Mar - 16 Mar
#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!
10.0 out of 10, Exceptional, (1 review)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is AU$301
includes taxes & fees
22 Mar - 23 Mar
The Perch in the Purchase -- Cozy, unique, and private
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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Find out more about Oakville

Everything you need to know about Oakville 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 Oakville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 Oakville holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Oakville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakville. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakville 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 Oakville holiday rentals we have selected for you start as low as AU$178 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Oakville rentals

At Expedia, we put the best Oakville 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 Oakville 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 Oakville 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 Oakville. 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 holiday rentals in Oakville?

Yes, there are holiday rentals close to the most popular sights in Oakville, 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 Oakville has to offer?

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Fireplace: This holiday home rental outside of Oakville is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with an arcade/games room and 1 hot tub.

What can I see and do in Oakville?

Explore the area and family-friendly sights such as Quassy Amusement Park, or get out into nature at a spot like Bellamy-Ferriday House and Garden. In the wider area, you’ll find Mattatuck Museum Arts and History Center and Palace Theatre.

What’s a holiday rental in Oakville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakville. Holiday rentals offer extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for small groups.