Oakville Holiday Rentals

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Holiday Rentals in Oakville

Beautiful cozy rooms near hospital and down town area
8.4 out of 10, Very good, (9)
"My friends and I had a great time. Nice and spacious. Thanks for quick reaponces."
The price is AU$374
per night
7 May - 8 May
Beautiful cozy rooms near hospital and down town area
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
10.0 out of 10, Exceptional, (9)
"The house had everything we needed and was the perfect winter getaway for our group to celebrate a birthday! Would rent again and again! Amazing property manager who was communicative and gave us all the information we needed. Amazing amenities better than a hotel stay! They have thought of everything - stocked with games and everything you should need for a great vacation! Comfortable and fabulous!"
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Guest Cottage on Country Estate
9.2 out of 10, Wonderful, (33)
"My husband and son stayed here for 5 days. They had a fabulous time hiking in the state park nearby. Thanks for a great stay!"
Guest Cottage on Country Estate
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Peaceful apartment on 3.5 acres w/ artist studio.
10.0 out of 10, Exceptional, (11)
"The place was cozy quiet and clean. Exactly what I was looking for."
The price is AU$325
per night
7 May - 8 May
Peaceful apartment on 3.5 acres w/ artist studio.
lakefront estate
3.8 out of 10, (8)
"Overall do not stay in this house! They are scamming people! They say they are military family yet took advantage of one!! Still owe me my refund and refuse to answer VRBO to give the okay to refund my money! This place was not clean it was very unsanitary and there were drug paraphernalia in the backyard! Towels wet and dirty on the bathroom floor and one of the bedrooms the sheets were dirty in the floor claimed that the house keeper cleaned it! The pool was disgusting!! I have videos pictures...
lakefront estate
Cozy & Chic Cabin by the Lake, with access to private Beach!
10.0 out of 10, Exceptional, (6)
"Marianna was super responsive and the house was adorable!"
The price is AU$651
per night
7 May - 8 May
Cozy & Chic Cabin by the Lake, with access to private Beach!
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.
Candlewood Lake Retreat with year round views
10.0 out of 10, Exceptional, (6)
"This house was exactly as advertised and very charming. The owners were very easy to work with. We had a beautiful view of the lake from the porch. We would stay here again."
Candlewood Lake Retreat with year round views
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
10.0 out of 10, Exceptional, (5)
"From the very beginning the hosts were fantastic. There was great communication and offered support. The property was super clean , well organized, and perfect for what we needed. I will be staying here again and truly recommend it !"
The price is AU$362
per night
7 May - 8 May
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
10.0 out of 10, Exceptional, (17)
"Well appointed and modern. A great quiet spot for the family."
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
10.0 out of 10, Exceptional, (15)
"From the moment we came we felt right at home! Such a comfortable place to stay! Every morning we were greeted by a beautiful bald eagle on the lake as well as the chitter chatter of birds. For those who have a hard time climbing stairs, this is NOT the place for you. Bedrooms as well as bathrooms are not on the main level. No matter we would definitely want to stay again!"
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
The Long View of Candlewood Lake
10.0 out of 10, Exceptional, (5)
"Patricia is an outstanding host with great communication and always pleasantly and quickly responding! The house is just beautiful - clean, comfortable and has clear 'welcome guide'. The location is amazing. We had a great, relaxing time and appreciate it so very much. Everything was perfect! Really want to book again! Thank you!"
The Long View of Candlewood Lake
Fun Downtown Location
9.8 out of 10, Exceptional, (47)
"Host was amazing 5 star all the way ... we walked right down the street and had some pizza everything we needed was just around the corner."
Fun Downtown Location
The Goshen Glass Chalet
9.4 out of 10, Exceptional, (21)
"We came up to celebrate a family Birthday, great place to stay, The host has tons of little extras that are really great. Thank you for a great stay."
The Goshen Glass Chalet
Amazing Lakefront Property
10.0 out of 10, Exceptional, (15)
"This was my second go round staying at this property. My family and I enjoyed it the first time. More so the second time with the upgrades. Being familiar with the area was a great help. This time we went in the lake and enjoyed ourselves. We are looking forward to returning back again. Thank you Raymond for letting us stay at your property. Richard and Joanne"
Amazing Lakefront Property
Cozy Lakefront Bungalow w firepit/dock/kayaks
9.8 out of 10, Exceptional, (19)
"Words cannot describe how beautiful and peaceful this place was I did not wanna leave and I’m already looking forward to my next stay! Owners were wonderful to communicate, and exceeded my expectations. Thank you for giving me blissful place to spend my birthday."
Cozy Lakefront Bungalow w firepit/dock/kayaks
Personal Lounge Experience
6.0 out of 10, (2)
"Good spot for hosting a get together"
The price is AU$921
per night
7 May - 8 May
Personal Lounge Experience
Historic Whitneyville Cottage
9.6 out of 10, Exceptional, (10)
"We have stayed in this little cottage several times now. Convenient location for visiting downtown New Haven. Bed is comfortable - kitchen small but it has what you need. Nice walking neighborhood if you have dogs. We will be back."
Historic Whitneyville Cottage
Lovely Family sized 3 bedroom Colonial home, close to restaurant.
8.6 out of 10, Excellent, (10)
"Nice house..Good area.."
Lovely Family sized 3 bedroom Colonial home, close to restaurant.
Amazing GParadise with King Bed, Private Pool and BBQ
Amazing GParadise with King Bed, Private Pool and BBQ
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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.

Other types of properties in Oakville you may be interested in

Courtyard by Marriott Waterbury Downtown
3.0 star property
8.2 out of 10, Very good, (1009)
"gOOD SPOT, CLEAN AND EVERYTHING. AC MADE A HELL OF A NOISE. ROOM 210 I THINK OTHER THAN THAT. A+"
The price is AU$155
per night
8 May - 9 May
Courtyard by Marriott Waterbury Downtown
Holiday Inn Express Southington, an IHG Hotel
2.5 star property
8.4 out of 10, Very good, (1007)
"Overall my stay was nice breakfast options could be much better I will definitely still be back. "
The price is AU$242
per night
27 May - 28 May
Holiday Inn Express Southington, an IHG Hotel
Red Roof Inn Meriden
2.0 star property
7.6 out of 10, Good, (1001)
"Staff was friendly, room was clean and had Roku TV. Parking was ample and location was excellent as it was next to the highways. Very good value, would stay there again!"
The price is AU$171
per night
12 May - 13 May
Red Roof Inn Meriden
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.

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$325 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.

How many holiday rentals are there in Oakville?

Choose from 5 Expedia holiday rentals in Oakville for a memorable holiday.

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 Hop Brook Lake. In the wider area, you’ll find Union Station Clocktower and Waterbury City Hall.

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.

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