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Holiday Rentals in Oakville

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Our top choices for Oakville holiday rentals

3.0 star property
The price is €435
includes taxes & fees
19 Jan - 20 Jan
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
8.0 out of 10, Very good, (1)
"We camped at Freedom Farm and enjoyed the secluded woods setting for our tent. Everything was clean and well prepared for our stay, and the hosts were friendly and helpful. It is beautifully situated and is a short drive from some excellent hiking and biking in nearby state parks. I think a couple of things, though, could be improved. The tent was set up on an incline, which made sleeping a bit less comfortable than it might have been. I would recommend that the hosts build a level platform...
United States
Eric
The price is €168
includes taxes & fees
8 Jan - 9 Jan
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
10.0 out of 10, Exceptional, (3)
"We were only here for a short stay, but everything was smooth and comfortable for us! Hotel-like linens and blackout curtains made for a very cozy sleeping experience."
United States
ross f.
The price is €208
includes taxes & fees
8 Jan - 9 Jan
Westville Stay • 2BR • Near Yale • Free Parking

Holiday Home in Berlin

Private Apartment in Berlin
2.0 star property
9.2 out of 10, Wonderful, (5)
"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 €263
includes taxes & fees
11 Jan - 12 Jan
Private Apartment in Berlin
9.8 out of 10, Exceptional, (20)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is €112
includes taxes & fees
8 Jan - 9 Jan
Cozy One Bedroom Apartment Centrally Located in Southbury

Apartment in Avon

The Historic Hideaway
2.0 star property
7.0 out of 10, Good, (2)
"House exactly as listed. We had a question and the property owner replied instantly - great communication. Close to Talcott Mountain which was an amazing hike with beautiful views. "
United States
Nicole M.
The price is €213
includes taxes & fees
9 Jan - 10 Jan
The Historic Hideaway

Holiday Home in Plainville

#26 Beautifully Renovated 2 BR Home
10.0 out of 10, Exceptional, (4)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
The price is €204
includes taxes & fees
25 Jan - 26 Jan
#26 Beautifully Renovated 2 BR Home
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 €235
includes taxes & fees
11 Jan - 12 Jan
Private Apartment in Southbury 103
9.6 out of 10, Exceptional, (4)
"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 €302
includes taxes & fees
20 Jan - 21 Jan
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
8.6 out of 10, Excellent, (10)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is €108
includes taxes & fees
8 Jan - 9 Jan
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Apartment in Wallingford Center

All New 1BR with tons of Charm
9.8 out of 10, Exceptional, (7)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is €254
includes taxes & fees
2 Feb - 3 Feb
All New 1BR with tons of Charm

Apartment in Wallingford Center

All New Studio apartment in center of town
10.0 out of 10, Exceptional, (2)
"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."
United States
Nadine C.
All New Studio apartment in center of town
9.4 out of 10, Exceptional, (14)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is €144
includes taxes & fees
14 Jan - 15 Jan
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.0 out of 10, Wonderful, (13)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is €247
includes taxes & fees
31 Jan - 1 Feb
Once the old Schools house now a newly furnished Apartment
10.0 out of 10, Exceptional, (2)
"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 €253
includes taxes & fees
8 Jan - 9 Jan
Newly Remodeled with deck. Close to town center
10.0 out of 10, Exceptional, (9)
" Heck-on was smooth and the kitchen and facilities were great. "
United States
Elizabeth P.
The price is €218
includes taxes & fees
12 Jan - 13 Jan
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
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 €281
includes taxes & fees
12 Jan - 13 Jan
Soothing 2-bedroom lower-level apartment in Berlin
9.4 out of 10, Exceptional, (6)
"Great stay. Clean, open space, easy access, and a nice pond in back to bring the dog. Would come back again."
United States
Rooster D.
The price is €241
includes taxes & fees
14 Jan - 15 Jan
Private Apartment in Southbury 101
9.6 out of 10, Exceptional, (4)
"Over all a great place. Nice to have everything on one floor. Dogs loved it. Some businesses in the building and everyone is friendly!"
United States
Debbie P.
The price is €241
includes taxes & fees
11 Jan - 12 Jan
Private Apartment in Southbury 102
10.0 out of 10, Exceptional, (23)
"The place was perfect for the two of us. It was close to both our kids homes."
United States
Tomas M.
The price is €234
includes taxes & fees
20 Jan - 21 Jan
River Overlook - Check the view from your deck!
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, apart-hotels, 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 €112 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?

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage: This holiday home rental outside of Oakville offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

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 Mattatuck Museum Arts and History Center 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.