Oakville Holiday Rentals

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Our top choices for Oakville holiday rentals

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
Oakville
The price is NZ$917
includes taxes & fees
8 June - 9 June
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Watertown
10.0 out of 10, Exceptional, (3 reviews)
"Everything was good just needed to have a tV in each room trash cans also"
United States
Deborah B.
The price is NZ$898
includes taxes & fees
11 June - 12 June
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (30 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
The price is NZ$215
includes taxes & fees
22 June - 23 June
Cozy One Bedroom Apartment Centrally Located in Southbury

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
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$492
includes taxes & fees
14 June - 15 June
Once the old Schools house now a newly furnished Apartment

The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
9.0 out of 10, Wonderful, (26 reviews)
"Host had great communication. The unit was clean, cozy and comfortable. Will book again when in the area."
United States
Tod B.
The price is NZ$425
includes taxes & fees
7 June - 8 June
The Sun Filled Cozy Creamery

Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfectly located for where we needed to be. The host was amazing, would stay again. Unit was comfy and cozy with perfect little homey touches. "
United States
Brittany M.
The price is NZ$649
includes taxes & fees
8 June - 9 June
Art House 3 Beds Close to Warner Theater

Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
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$460
includes taxes & fees
8 June - 9 June
Cozy Attic 10 min to Llitchfield

All new 1BR apartment with all the features you are looking for

All new 1BR apartment with all the features you are looking for
Wallingford Center
The price is NZ$497
includes taxes & fees
7 June - 8 June
All new 1BR apartment with all the features you are looking for

Tiny, Budget Friendly 1 Bedroom Central CT

Tiny, Budget Friendly 1 Bedroom Central CT
Southington
The price is NZ$328
includes taxes & fees
1 July - 2 July
Tiny, Budget Friendly 1 Bedroom Central CT

1 Min to I-91 - Newly Renovated Modern 2 BR Home

1 Min to I-91 - Newly Renovated Modern 2 BR Home
Berlin
The price is NZ$537
includes taxes & fees
7 June - 8 June
1 Min to I-91 - Newly Renovated Modern 2 BR Home

New Railside Residents

New Railside Residents
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"Clean & comfortable, in an architecturally unique setting. Great proximity to a variety of downtown shops & restaurants - check out Center Street Brewing Co. for some excellent beer."
United States
Thomas S.
New Railside Residents

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
9.8 out of 10, Exceptional, (10 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is NZ$497
includes taxes & fees
7 June - 8 June
All New 1BR with tons of Charm

The Historic Hideaway

The Historic Hideaway
Avon
6.0 out of 10, (4 reviews)
"Once we found the house it was very warm & cozy. The mini- muffins on the counter was a bonus. House mailbox was 87 but address was 89 that you only see if door is closed which it wasn't on 1st 2 passes. Limited exterior lights made coming back at night a challenge. "
United States
Kim C.
The price is NZ$454
includes taxes & fees
7 June - 8 June
The Historic Hideaway

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Waterbury
8.0 out of 10, Very good, (1 review)
"I had an emergency and was only able to stay one night, but enjoyed my stay "
United States
Dirk N.
The price is NZ$250
includes taxes & fees
23 June - 24 June
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.2 out of 10, Wonderful, (20 reviews)
"Easy check in Rooms were comfortably spacious "
United States
Benjamin W.
The price is NZ$361
includes taxes & fees
7 June - 8 June
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Private Apartment in Southbury 104

Private Apartment in Southbury 104
Southbury
The price is NZ$508
includes taxes & fees
30 June - 1 July
Private Apartment in Southbury 104

Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
The price is NZ$497
includes taxes & fees
7 June - 8 June
Newly Remodeled with deck. Close to town center

beautiful Cozy 1BR Apt near New Haven

beautiful Cozy 1BR Apt near New Haven
Seymour
The price is NZ$482
includes taxes & fees
7 June - 8 June
beautiful Cozy 1BR Apt near New Haven

Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.0 out of 10, Wonderful, (7 reviews)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
The price is NZ$490
includes taxes & fees
9 June - 10 June
Private Apartment in Berlin

#31 - Downtown Terryville- 1 Br

#31 - Downtown Terryville- 1 Br
Plymouth
10.0 out of 10, Exceptional, (1 review)
"In convenient safe area. Os is easy to contact"
United States
Gina P.
#31 - Downtown Terryville- 1 Br
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 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?

Amazing Lakefront Property: 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 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

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 Waterbury Green. In the wider area, you’ll find Waterbury City Hall 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.