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Oakville Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Oakville holiday rentals

A spacious living room with large windows, a fireplace, and a view of the outdoors.

1. 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 AU$779
includes taxes & fees
11 Nov - 12 Nov
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A spacious living room with large windows, a fireplace, and a view of the outdoors.

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

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Watertown
9.0 out of 10, Wonderful, (6 reviews)
"In town to visit our new grandchild. It was just my husband and me. It had more then enough room and was very comfortable."
United States
Elizabeth H.
The price is AU$738
includes taxes & fees
11 Nov - 12 Nov
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A two-story house with a porch, a front door with a wreath, and a small garden area.

3. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (13 reviews)
"Very clean, all you need away from home, super !!!"
United States
Igor L.
The price is AU$468
includes taxes & fees
22 Nov - 23 Nov
Bear Retreat - 2-bedroom house in Waterbury
A building entrance with a brick facade, a green awning, and a glass door.

4. Cozy Studio apartment in delightful Waterbury with Central Air

Cozy Studio apartment in delightful Waterbury with Central Air
Waterbury
2.0 out of 10, (1 review)
"The place wasn’t how the pictures were on the app. It was hard to find the room. The keys for the room are very hard to open the room door . It’s like you have to struggle just to get inside . The room is inside of an abandoned building… some staff in the building was telling me that I shouldn’t be staying there or they wouldn’t stay there so it made me feel unsafe… the bed doesn’t match the head board. Everything just doesn’t match the images the host posted.."
United States
zynaisha
The price is AU$150
includes taxes & fees
8 Dec - 9 Dec
Cozy Studio apartment in delightful Waterbury with Central Air
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

5. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris
9.8 out of 10, Exceptional, (21 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is AU$380
includes taxes & fees
11 Nov - 12 Nov
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A front view of a house with a wooden staircase leading to a front door, a small porch area, and a garage door.

6. 1-bedroom vacation home 22 minutes from Quinnipiac University

1-bedroom vacation home 22 minutes from Quinnipiac University
Wolcott
9.6 out of 10, Exceptional, (4 reviews)
"Very clean and the host was great "
United States
David G.
The price is AU$547
includes taxes & fees
30 Nov - 1 Dec
1-bedroom vacation home 22 minutes from Quinnipiac University
A white house with a wooden staircase leading to a porch.

7. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (39 reviews)
"Charles was super responsive and the bed was amazingly comfortable. Also the shower head great water pressure :-)"
United States
Lisbeth
The price is AU$191
includes taxes & fees
1 Dec - 2 Dec
Cozy One Bedroom Apartment Centrally Located in Southbury
A modern kitchen with stainless steel appliances, a central island, and a built-in oven.

8. #27- Luxury Collection

#27- Luxury Collection
Southington
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$713
includes taxes & fees
22 Nov - 23 Nov
#27- Luxury Collection
A modern living room with a fireplace, leather sofas, a flat-screen TV, and large windows.

9. #30 - Spacious & Cozy!

#30 - Spacious & Cozy!
Southington
7.4 out of 10, Good, (6 reviews)
"the house was great for our needs - it was nicely furnished fully stocked with the essentials in the kitchen. the host checked in when it was especially cold to ensure the heat and water were working correctly. the living room was very comfortable with leather reclining chairs and a gas fireplace that heated the room very well. We enjoyed how easy our stay was and recommend this location "
United States
Kaity B.
The price is AU$591
includes taxes & fees
11 Nov - 12 Nov
#30 - Spacious & Cozy!
A kitchen with a marble island, wooden cabinets, a clock, and a window with a view of trees.

10. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (9 reviews)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
United States
Jennifer A.
The price is AU$534
includes taxes & fees
15 Nov - 16 Nov
The Jefferson Guest House, Spacious, Special Views
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

11. Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (3 reviews)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
The price is AU$668
includes taxes & fees
20 Nov - 21 Nov
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
A modern kitchen with white cabinets, a dining area with a black table and chairs, and a large window with curtains.

12. Private Apartment in Southbury 105

Private Apartment in Southbury 105
Southbury
The price is AU$343
includes taxes & fees
11 Nov - 12 Nov
Private Apartment in Southbury 105
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

13. Escape to Bantam Lake- With Fireplace and Hot tub!

Escape to Bantam Lake- With Fireplace and Hot tub!
Morris
10.0 out of 10, Exceptional, (6 reviews)
"This house is a dream. First, the views are incredible. Second, it’s beautifully decorated and very cozy. Lastly, the property location is perfect. I can’t wait to stay again!"
United States
Shannon M.
The price is AU$667
includes taxes & fees
18 Nov - 19 Nov
Escape to Bantam Lake- With Fireplace and Hot tub!
A modern living room with a dark sofa, a small side table, and a kitchen area with a refrigerator and microwave.

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

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.0 out of 10, Wonderful, (26 reviews)
"Great place clean and quiet "
United States
James P.
The price is AU$288
includes taxes & fees
9 Dec - 10 Dec
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
A view through a window with a clear sky and lush greenery outside.

15. Private Apartment in Southbury 101

Private Apartment in Southbury 101
Southbury
9.6 out of 10, Exceptional, (7 reviews)
"The apartment was nice, big area, loved this rental."
United States
Marissa G.
The price is AU$383
includes taxes & fees
6 Dec - 7 Dec
Private Apartment in Southbury 101
A modern kitchen with white cabinets, stainless steel appliances, and a dining table with chairs.

16. Private Apartment in Southbury 104

Private Apartment in Southbury 104
Southbury
10.0 out of 10, Exceptional, (1 review)
"Pro Unit very clean, check in was easy and host was responsive to issues 24/7.Unit is large with new appliances in full kitchen.It is located in a beautiful rural area of CT. I highly recommend it"
United States
Daniel R.
The price is AU$366
includes taxes & fees
30 Nov - 1 Dec
Private Apartment in Southbury 104
A living room with a blue sofa, patterned armchair, wooden coffee table, and a globe on a side table.

17. Brand New Platform #1

Brand New Platform #1
Wallingford Center
9.6 out of 10, Exceptional, (4 reviews)
"This is the second time we have stayed at this location, although it was a different "platform/room." Once again, a very nice stay. Room was perfect for the 2 of us, and all the right ameneties. This is a perfect location within Wallenford, with access to everything, whether walking or driving. The property is very well maintained, and feels very secure. "
United States
Cherie G.
The price is AU$424
includes taxes & fees
11 Nov - 12 Nov
Brand New Platform #1
Stairwell

18. Private Apartment in Berlin

Private Apartment in Berlin
Berlin
8.8 out of 10, Excellent, (8 reviews)
"Clean, convenient, and great location."
United States
Shaun L.
The price is AU$349
includes taxes & fees
11 Nov - 12 Nov
Private Apartment in Berlin
A two-story house with a front porch, a small balcony, and a white picket fence.

19. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.6 out of 10, Exceptional, (7 reviews)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
The price is AU$507
includes taxes & fees
11 Nov - 12 Nov
Cozy Attic 10 min to Llitchfield
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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Top Oakville Hotel Reviews

Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center

10/10 Excellent
"Booked 1 night (Saturday) at the Heritage Hotel for a girls trip with my sister in law. It was a really nice hotel! It was centrally located - driving distance to many surrounding things. The staff was friendly. The room was clean. The tavern was awesome. I forgot my toothbrush and they had one complimentary for me at the front desk. The ONLY down side was that the smoke alarm went off at the hotel late at night. Everyone began walking outside, the fire dept had to come - it was a false alarm."
Alexis 1-night trip
Posted 6 hours ago
Heritage Hotel, Golf & Conference Center

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$288 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?

Well laid out 2-bedroom private home in Washington-close to the green and depot: This holiday home rental outside of Oakville offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave. 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 Palace Theatre and Abbey of Regina Laudis.

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.