Oakville Vacation Rentals from $486: Search Short-Term Rentals

Q: What's the top vacation rental in Oakville?

Amazing Lakefront Property : This vacation home near Oakville is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

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In two weeks

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Our top choices for Oakville vacation rentals

Cozy One Bedroom Apartment Centrally Located in Southbury

Southbury

Bob

$115 nightly

Jun 29 - Jun 30

Total with taxes and fees

River Overlook - What a view from your deck!

Collinsville

Mary S.

$264 nightly

Jun 30 - Jul 1

Total with taxes and fees

Private Apartment in Southbury 104

Southbury

$194 nightly

Jun 30 - Jul 1

Total with taxes and fees

Tiny, Budget Friendly 1 Bedroom Central CT

Southington

$194 nightly

Jun 29 - Jun 30

Total with taxes and fees

Art House 3 Beds Close to Warner Theater

Torrington

Brittany M.

$363 nightly

Jun 29 - Jun 30

Total with taxes and fees

1 bedroom, iron/ironing board, WiFi, bed sheets

Once the old Schools house now a newly furnished Apartment

Wallingford Center

Jeanette W.

$274 nightly

Jul 5 - Jul 6

Total with taxes and fees

All New 1BR with tons of Charm

Wallingford Center

David S.

$274 nightly

Jun 29 - Jun 30

Total with taxes and fees

Cozy Attic 10 min to Llitchfield

Torrington

Rhonda H.

$232 nightly

Jun 29 - Jun 30

Total with taxes and fees

Newly Remodeled with deck. Close to town center

Wallingford

Karen F.

$271 nightly

Jul 28 - Jul 29

Total with taxes and fees

Modern Westville Home Near Yale University

West New Haven

$229 nightly

Jun 29 - Jun 30

Total with taxes and fees

Newly Remodeled 1-BR Close to Everything yet Very Private

Wallingford

David M.

$277 nightly

Jul 11 - Jul 12

Total with taxes and fees

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Watertown

Laurie P.

$130 nightly

Jul 2 - Jul 3

Total with taxes and fees

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

Cheshire

Benjamin W.

$185 nightly

Jun 29 - Jun 30

Total with taxes and fees

1 bedroom, iron/ironing board, free WiFi, bed sheets

#2 Beautiful 1 BR Apartment - Central CT

Plainville

Rodney L.

$181 nightly

Jun 29 - Jun 30

Total with taxes and fees

Private Apartment in Southbury 103

Southbury

Dominick S.

$241 nightly

Jul 2 - Jul 3

Total with taxes and fees

Private Apartment in Berlin

Berlin

Daniel L.

$222 nightly

Jul 1 - Jul 2

Total with taxes and fees

Cozy Modern Farmhouse Private Apt - 3 Beds

Torrington

Louisa A.

$351 nightly

Jun 29 - Jun 30

Total with taxes and fees

Private Apartment in Southbury 102

Southbury

Debbie P.

$203 nightly

Jul 2 - Jul 3

Total with taxes and fees

All new 1BR apartment with all the features you are looking for

Wallingford Center

Thomas S.

$274 nightly

Jun 29 - Jun 30

Total with taxes and fees

Fully Furnished 1BR Apartment

Wallingford

Jennifer L.

$274 nightly

Jul 18 - Jul 19

Total with taxes and fees

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Top Oakville Hotel Reviews

Days Inn by Wyndham Berlin Meriden

8/10 Good

"Stayed here for 2 nights for the Travelers Chamionship in Cromwell (bout an 18 minute drive from the hotel). When researching for this trip there were some mixed reviews about this place... I have come to set the record straight! 1st off, we're talking about a hotel for $125 a night, not the Ritz. That being said- this place was a bargain for the price. Sketchy area? Ehhh.... I get where you're coming from but I think that's just kinda CT in general. 2 queen sized beds were nice and comfy. Sheets were clean (no visible dirt or holes). The tv hooked up to my firestick nice and easily, wifi password was right on the room key card. Electric room key worked fine everytime! The shower had nice hot water. The AC unit was great, got super cold for sleeping at night. We set it to 65 but im pretty sure you could set it to 60. Mini fridge was set to off when we got there but got down to temperature quickly after it was turned on (good enough size for some leftovers and a few beverages). The in-ground pool was nice- my son had a good time popping in there each night for a little bit. Breakfast was 7a-10a which included coffee, juice, cereal, bagels, apples/oranges. Staff was helpful and always looked like they were in a good mood. For $125 a night, would stay again! Side note- the New Mill Restaurant was fantastic! Great service, great food!"

Red Roof Inn Meriden

8/10 Good

"This place was ok for one night the only. The one issue that I had was there other people next to us. I had someone banging on the wall cause I was getting freaking with the wife. 1. It was early. 2 isn’t these places are what they’re for? Yes people travel and want to rest etc. I paid money for the room so I can have some privacy with my wife. Some people clearly don’t understand or don’t get it."

Wyndham Southbury

10/10 Excellent

"I was pleasantly surprised with this property. I arrived and first thing I noticed was a huge parking lot. Even more pleasing are the parking spaces, which had ample room to park my mid size car. It is an actual pet peeve when a property provides very little space to park, to where cars are parked so closely together, there's a good chance that some other guests will wildly open their car doors and chip the paint from your vehicle.. This was a sign of good things to come. The lobby area and overall property was just as big. It was much bigger than I anticipated. The staff was super friendly and accommodating to my needs and answered my questions upon check in. They key cards worked (last property I stayed had terrible key cards, preventing entry to room). The room was clean, spacious, and in excellent condition. All of the necessities were there to use. The bed was comfortable. There was a bar across the front desk but I did not use it. A quick glance of their menu and business hours were available to see in the elevator and other areas. It seemed well kept. There's a buffet breakfast which was reasonably priced. The food was actually decent in comparison to other properties that offer breakfast. I did not use any other their other on site serviess such as laundry or fitness room. I enjoyed my time at this property, which I never have known about prior to my stay. This is in fact the longest, detailed review I've written, which means I'd gladly return here again!"

Find out more about Oakville

Everything you need to know about Oakville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oakville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oakville vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oakville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $486 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oakville rentals

At Expedia, we put the best Oakville vacation 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 vacation.

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.

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Frequently asked questions

Can I find vacation rentals in Oakville?

Yes, you can find vacation rentals close to popular attractions in Oakville, or you can choose a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental in Oakville?

Amazing Lakefront Property: This vacation home near Oakville is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the 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 larger area, you’ll find Waterbury City Hall and Palace Theatre.

What’s a vacation rental in Oakville like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Oakville. Vacation rentals offer amenities like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a small group gathering.

Oakville Vacation Rentals

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Check prices for these dates

Our top choices for Oakville vacation rentals

Cozy One Bedroom Apartment Centrally Located in Southbury

River Overlook - What a view from your deck!

Private Apartment in Southbury 104

Tiny, Budget Friendly 1 Bedroom Central CT

Art House 3 Beds Close to Warner Theater

Once the old Schools house now a newly furnished Apartment

All New 1BR with tons of Charm

Cozy Attic 10 min to Llitchfield

Newly Remodeled with deck. Close to town center

Modern Westville Home Near Yale University

Newly Remodeled 1-BR Close to Everything yet Very Private

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

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

#2 *Beautiful 1 BR Apartment - Central CT*

Private Apartment in Southbury 103

Private Apartment in Berlin

Cozy Modern Farmhouse Private Apt - 3 Beds

Private Apartment in Southbury 102

All new 1BR apartment with all the features you are looking for

Fully Furnished 1BR Apartment

Find vacation rentals that suit your style

Top Oakville Hotel Reviews

Days Inn by Wyndham Berlin Meriden

Find out more about Oakville

Explore a world of travel with Expedia

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#2 Beautiful 1 BR Apartment - Central CT