Oakville Holiday Rentals

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Holiday Rentals in Oakville

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
10.0 out of 10, Exceptional, (2)
"This is a property that is very good for large family gatherings, which is how we gathered for a birthday celebration. This area of CT. is great and has lots to do.The house is in the perfect location to do all of it.Again, suits large groups well. Room for everyone."
United States
Paula R.
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
The Goshen Glass Chalet
9.6 out of 10, Exceptional, (41)
"The chalet was great. Plenty of room, very cozy and in a very quiet neighborhood community. "
United States
Tracy F.
The Goshen Glass Chalet
Private Apartment in Berlin
2.0 star property
9.2 out of 10, Wonderful, (5)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
United States
Stacy B.
The price is AU$495
includes taxes & fees
17 Nov - 18 Nov
Private Apartment in Berlin
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
8.6 out of 10, Excellent, (26)
"The cabin was great! Exactly as described and pictured. The kitchen was well stocked with all the basic cooking instruments and utensils. We had a blast and would absolutely come back."
United States
Angela C.
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
10.0 out of 10, Exceptional, (5)
"The space was clean and light, great finishes. The home felt comfortable and was easy to find. Thank you for a wonderful weekend. "
United States
Lara S.
The price is AU$380
includes taxes & fees
29 Oct - 30 Oct
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area
9.8 out of 10, Exceptional, (6)
"Everything was amazing "
United States
MELISSA G.
Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area
Private Annex/Former Artist Studio
10.0 out of 10, Exceptional, (52)
"It has stairs to climb up to apartment. Everything was lovely.And the owners go out of their way to make you feel welcome."
United States
Liz G.
Private Annex/Former Artist Studio
The Sun Filled Cozy Creamery
8.8 out of 10, Excellent, (22)
"Nice,cozy and a reasonable rate."
United States
Rachelle B.
The price is AU$426
includes taxes & fees
29 Oct - 30 Oct
The Sun Filled Cozy Creamery
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
10.0 out of 10, Exceptional, (11)
"I stayed with my mom and the 2 bedroom 1 bath was perfect for our stay. The house way cozy and in a quiet area. Would absolutely stay again; my mom is already talking about coming back to explore more of the surrounding areas!"
United States
Tyler A.
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Fun Downtown Location 2nd flr
9.8 out of 10, Exceptional, (77)
"Wonderful stay. Cute, clean, well organized, stocked and the owner was very responsive when we had a power issue that was 100% out of their control. He even shared some local recommendations including an oddities museum across the street! "
United States
Tiana C.
Fun Downtown Location 2nd flr
Peaceful apartment on 3.5 acres w/ artist studio.
9.6 out of 10, Exceptional, (19)
"This was a nice get away for us that was not too far away from home."
United States
Isabella M.
The price is AU$300
includes taxes & fees
5 Nov - 6 Nov
Peaceful apartment on 3.5 acres w/ artist studio.
Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi
10.0 out of 10, Exceptional, (1)
"Clean and quiet location, great place for a relaxing stay."
United States
robert p.
Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi
Spacious 3-Bedroom Home Awaits - Designed for Comfort & Relaxation!!!
Spacious 3-Bedroom Home Awaits - Designed for Comfort & Relaxation!!!
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
9.6 out of 10, Exceptional, (14)
"It was a great time. Loved it hear would come back again. Owner was very helpful."
United States
Nosa I.
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Cozy Safe Home
The price is AU$630
includes taxes & fees
27 Oct - 28 Oct
Cozy Safe Home
Private Apartment in Southbury 103
10.0 out of 10, Exceptional, (2)
"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$465
includes taxes & fees
16 Nov - 17 Nov
Private Apartment in Southbury 103
Amazing Lakefront Property
9.6 out of 10, Exceptional, (28)
"Great views and a good central location for day trips 👌. "
United States
Paul B.
Amazing Lakefront Property
Soothing 2-bedroom lower-level apartment in Berlin
10.0 out of 10, Exceptional, (1)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
The price is AU$413
includes taxes & fees
3 Nov - 4 Nov
Soothing 2-bedroom lower-level apartment in Berlin
KING BED, Affordable Classic Bristol Home Sleep 8+
The price is AU$476
includes taxes & fees
10 Nov - 11 Nov
KING BED, Affordable Classic Bristol Home Sleep 8+
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
10.0 out of 10, Exceptional, (61)
"There is a lot of fun things to do close by. The house was spotless and it was nice to relax on the sofa or outside patio and look at the river. "
United States
Amanda W.
The price is AU$707
includes taxes & fees
26 Oct - 27 Oct
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
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

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$300 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/Firepit: 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. It offers a garden, an arcade/games room and 1 hot tub so that you can immerse yourself in your 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 Holy Land USA. In the wider area, you’ll find Palace Theatre and Brass Mill Center.

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.