Oakville Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Oakville holiday rentals

3.0 star property
The price is NZ$864
includes taxes & fees
9 Mar - 10 Mar
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
8.0 out of 10, Very good, (1 review)
"We camped at Freedom Farm and enjoyed the secluded woods setting for our tent. Everything was clean and well prepared for our stay, and the hosts were friendly and helpful. It is beautifully situated and is a short drive from some excellent hiking and biking in nearby state parks. I think a couple of things, though, could be improved. The tent was set up on an incline, which made sleeping a bit less comfortable than it might have been. I would recommend that the hosts build a level platform...
United States
Eric
The price is NZ$326
includes taxes & fees
9 Mar - 10 Mar
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

Camping in New Milford

Creekside Retreat Tent
10.0 out of 10, Exceptional, (4 reviews)
"Absolutely beautiful location and wonderful hosts very romantic spot lots of hiking trails near and on premises me and my husband loved the fact we slept by the water and can hear the water running all night very peaceful and beautiful site ."
United States
yarelis t.
The price is NZ$326
includes taxes & fees
9 Mar - 10 Mar
Creekside Retreat Tent
9.8 out of 10, Exceptional, (8 reviews)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
The price is NZ$570
includes taxes & fees
9 Mar - 10 Mar
#23 *COMFORT & LUXURY* 3 BR/2 BA House
9.8 out of 10, Exceptional, (40 reviews)
"Very comfortable property. The host had thought of everything!"
United States
Jennifer Y.
The price is NZ$710
includes taxes & fees
8 Mar - 9 Mar
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 NZ$504
includes taxes & fees
8 Mar - 9 Mar
Once the old Schools house now a newly furnished 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 NZ$215
includes taxes & fees
8 Mar - 9 Mar
Cozy One Bedroom Apartment Centrally Located in Southbury

Apartment in Wallingford Center

All New Studio apartment in center of town
10.0 out of 10, Exceptional, (2 reviews)
"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."
United States
Nadine C.
All New Studio apartment in center of town

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 NZ$504
includes taxes & fees
9 Mar - 10 Mar
All New 1BR with tons of Charm
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 NZ$390
includes taxes & fees
16 Mar - 17 Mar
Private Apartment in Southbury 103
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 NZ$452
includes taxes & fees
8 Mar - 9 Mar
River Overlook - Check the view from your deck!
The price is NZ$667
includes taxes & fees
9 Mar - 10 Mar
Litchfield Retreat, Wineries, Foliage & Skiing
10.0 out of 10, Exceptional, (1 review)
"I made a late reservation, and my host, Jackie, was always accommodating, welcoming, and in regular communication with me. The amenities were just what I needed, right down to the coffee pod and snack selection! The apartment is well laid out, as if I were walking into my own home, convenient to shopping and friends.Thank you, Jackie!"
United States
LIsa G.
The price is NZ$272
includes taxes & fees
10 Mar - 11 Mar
Cozy 1-bedroom apartment in lovely Oxford
8.6 out of 10, Excellent, (10 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is NZ$207
includes taxes & fees
1 Apr - 2 Apr
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
10.0 out of 10, Exceptional, (16 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 NZ$473
includes taxes & fees
12 Mar - 13 Mar
Pristine, Walkable downtown, Entire 2 Bedroom apartment
10.0 out of 10, Exceptional, (1 review)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is NZ$361
includes taxes & fees
11 Mar - 12 Mar
The Perch in the Purchase -- Cozy, unique, and private

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 NZ$828
includes taxes & fees
18 Mar - 19 Mar
#27- Luxury Collection
The price is NZ$513
includes taxes & fees
24 Mar - 25 Mar
1 Min to I-91 - Newly Renovated Modern 2 BR Home
9.4 out of 10, Exceptional, (6 reviews)
"The apartment was nice, big area, loved this rental."
United States
Marissa G.
The price is NZ$411
includes taxes & fees
16 Mar - 17 Mar
Private Apartment in Southbury 101
9.2 out of 10, Wonderful, (5 reviews)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
The price is NZ$578
includes taxes & fees
25 Mar - 26 Mar
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Oakville Hotel Reviews

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 favorite 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 depends 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 NZ$215 per night. Entering your travel dates in the search wizard you might find 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?

Candlewood Lake Retreat; Dock, Game Room & Firepit: This holiday home rental outside of Oakville is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Beacon Falls Town Recreation Field. In the wider area, you’ll find Palace Theatre and Black Rock State Park.

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.