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Oakville Holiday Rentals

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Holiday Rentals in Oakville

Cottage in Oakville

3.0 star property
The price is NZ$883
includes taxes & fees
7 Dec - 8 Dec
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Holiday Home in Brookfield

9.6 out of 10, Exceptional, (4)
"The host was very kind and welcoming. The home was spacious and the perfect setting for our celebration weekend. Everyone had their own space and we had multiple spaces for group activities. We enjoyed our time and appreciate the hospitality. "
United States
Valerie V.
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Holiday Home in Plymouth

9.8 out of 10, Exceptional, (40)
"Our stay was so peaceful and relaxing. The property was beautiful and exactly as described in the listing. We loved having a fire outside, sitting in the screened-in porch. Will absolutely be coming back!"
United States
Jean R.
Cozy Lakefront Bungalow w firepit/dock/kayaks

Apartment in Cheshire

9.2 out of 10, Wonderful, (12)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Cabin in Northwest Harwinton

8.6 out of 10, Excellent, (27)
"Love the place.. very clean ..loved the neighbors.. got to catch up on well needed rest.. the neighbors on the right were wonderful than the owners came and they were also wonderful also"
United States
Andrea m.
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Holiday Home 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 NZ$547
includes taxes & fees
7 Dec - 8 Dec
Private Apartment in Berlin

Holiday Home in New Britain

10.0 out of 10, Exceptional, (7)
" Heck-on was smooth and the kitchen and facilities were great. "
United States
Elizabeth P.
The price is NZ$427
includes taxes & fees
8 Dec - 9 Dec
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Holiday Home in Goshen

9.6 out of 10, Exceptional, (42)
"The place was very nice met all of our expectations. "
United States
Marie G.
The Goshen Glass Chalet

Apartment in Southbury

9.8 out of 10, Exceptional, (19)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is NZ$214
includes taxes & fees
8 Dec - 9 Dec
New One Bedroom Apartment Centrally Located in Southbury

Holiday Home in Cornwall

9.6 out of 10, Exceptional, (53)
"Great house and great stay!"
United States
Timothy P.
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent

Apartment in Wallingford Center

9.8 out of 10, Exceptional, (6)
"I highly recommend this property!! We were in town for a wedding celebration, and it proved perfect. The property is completely updated, well-appointed and clean. The property is centrally located and close to restaurants, shops and grocery markets. Karl was a great host and communicated with us throughout our stay. I highly recommend!!"
United States
Francis S.
The price is NZ$499
includes taxes & fees
8 Dec - 9 Dec
All New 1BR with tons of Charm

Holiday Home in Watertown

9.6 out of 10, Exceptional, (16)
"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

Cabin in Bethlehem

10.0 out of 10, Exceptional, (35)
"Awesome location and cottage. So peaceful and easy. Would 100% book again "
United States
Leah G.
Cozy & Serene Cabin with Fireplace, Ski Nearby!

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 NZ$482
includes taxes & fees
10 Dec - 11 Dec
Soothing 2-bedroom lower-level apartment in Berlin

Holiday Home in Bethlehem

2.0 star property
10.0 out of 10, Exceptional, (14)
"3 lied the fire pit and the kitchen was well equipped"
United States
WINNIE M.
Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook

Holiday Home in Collinsville

10.0 out of 10, Exceptional, (61)
"A very nice period home in a beautiful setting. The home is immaculate with all of the necessary essentials for an extended stay. The host is very responsive and keeps in touch to ensure that your stay is as enjoyable and comfortable as possible. "
United States
Virginia M.
The price is NZ$787
includes taxes & fees
7 Dec - 8 Dec
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Apartment in New Britain

7.6 out of 10, Good, (7)
" Not bad for the price "
United States
Audrey L.
The price is NZ$644
includes taxes & fees
7 Dec - 8 Dec
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment

Holiday Home in New Milford

10.0 out of 10, Exceptional, (49)
"The house and property were beautiful! It was well appointed and supplied all necessities plus. The cabana and the extras like floating devices were great to have. We swam in the water and used the canoes. The basement was LOADED with fun games that everyone participated in. They even had a kids area, including toys for infants!! Communications with the host were very responsive. We had zero issues and enjoyed our stay here. We highly recommend this property!!!"
United States
Suzy B.
Candlewood Lake Retreat; Dock, Game Room & Firepit

Holiday Home in Roxbury

9.6 out of 10, Exceptional, (50)
"Great time for all. Hosts were great."
United States
Ray S.
Litchfield County Four Season Country Paradise

Apartment in New Britain

2.0 star property
7.2 out of 10, Good, (7)
"Communication with the host was excellent. His place was clean, bright, and very well equipped! The location makes it easy to get around the greater Hartford area. Our stay was very good!"
United States
Julie M.
Stylish 3BR ★ Super Fast Wi-Fi + Free Parking ★ Cancel Anytime! 10 Mins to WeHa
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 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$214 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?

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 Hollow Park. 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.