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Oakville Vacation Rentals

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Our top choices for Oakville vacation rentals

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (33 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
$115 nightly
The price is $129
Jun 29 - Jun 30
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury

River Overlook - What a view from your deck!

River Overlook - What a view from your deck!
Collinsville
10.0 out of 10, Exceptional, (25 reviews)
"I only did a short stay (2 nights) but it was super adorable! I will definitely stay again when I'm back in the area."
United States
Mary S.
$264 nightly
The price is $299
Jun 30 - Jul 1
Total with taxes and fees
River Overlook - What a view from your deck!

Private Apartment in Southbury 104

Private Apartment in Southbury 104
Southbury
$194 nightly
The price is $220
Jun 30 - Jul 1
Total with taxes and fees
Private Apartment in Southbury 104

Tiny, Budget Friendly 1 Bedroom Central CT

Tiny, Budget Friendly 1 Bedroom Central CT
Southington
$194 nightly
The price is $208
Jun 29 - Jun 30
Total with taxes and fees
Tiny, Budget Friendly 1 Bedroom Central CT

Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfectly located for where we needed to be. The host was amazing, would stay again. Unit was comfy and cozy with perfect little homey touches. "
United States
Brittany M.
$363 nightly
The price is $418
Jun 29 - Jun 30
Total with taxes and fees
Art House 3 Beds Close to Warner Theater

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
$274 nightly
The price is $292
Jul 5 - Jul 6
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
$274 nightly
The price is $292
Jun 29 - Jun 30
Total with taxes and fees
All New 1BR with tons of Charm

Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.2 out of 10, Wonderful, (5 reviews)
"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.
$232 nightly
The price is $276
Jun 29 - Jun 30
Total with taxes and fees
Cozy Attic 10 min to Llitchfield

Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
$271 nightly
The price is $289
Jul 28 - Jul 29
Total with taxes and fees
Newly Remodeled with deck. Close to town center

Modern Westville Home Near Yale University

Modern Westville Home Near Yale University
West New Haven
$229 nightly
The price is $259
Jun 29 - Jun 30
Total with taxes and fees
Modern Westville Home Near Yale University

Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
$277 nightly
The price is $295
Jul 11 - Jul 12
Total with taxes and fees
Newly Remodeled 1-BR Close to Everything yet Very Private

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

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Watertown
8.6 out of 10, Excellent, (10 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
$130 nightly
The price is $147
Jul 2 - Jul 3
Total with taxes and fees
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

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

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.2 out of 10, Wonderful, (20 reviews)
"Easy check in Rooms were comfortably spacious "
United States
Benjamin W.
$185 nightly
The price is $210
Jun 29 - Jun 30
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

#2 *Beautiful 1 BR Apartment - Central CT*

#2 *Beautiful 1 BR Apartment - Central CT*
Plainville
9.0 out of 10, Wonderful, (2 reviews)
"I try to come up to Connecticut at least once a year if possible and this really worked out perfect for me first floor no steps easy to bring luggage in very comfortable. Would definitely come back and stay there again."
United States
Rodney L.
$181 nightly
The price is $193
Jun 29 - Jun 30
Total with taxes and fees
#2 *Beautiful 1 BR Apartment - Central CT*

Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
10.0 out of 10, Exceptional, (3 reviews)
"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.
$241 nightly
The price is $273
Jul 2 - Jul 3
Total with taxes and fees
Private Apartment in Southbury 103

Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.0 out of 10, Wonderful, (7 reviews)
"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.
$222 nightly
The price is $251
Jul 1 - Jul 2
Total with taxes and fees
Private Apartment in Berlin

Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
$351 nightly
The price is $404
Jun 29 - Jun 30
Total with taxes and fees
Cozy Modern Farmhouse Private Apt - 3 Beds

Private Apartment in Southbury 102

Private Apartment in Southbury 102
Southbury
9.2 out of 10, Wonderful, (5 reviews)
"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.
$203 nightly
The price is $229
Jul 2 - Jul 3
Total with taxes and fees
Private Apartment in Southbury 102

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

All new 1BR apartment with all the features you are looking for
Wallingford Center
10.0 out of 10, Exceptional, (1 review)
"Clean & Comfortable, excellent accessibility to area restaurants & shopping.There was a hitch with my payment before check-in, the owner was helpful & communicative in resolving the issue.Overall, a great place to stay."
United States
Thomas S.
$274 nightly
The price is $292
Jun 29 - Jun 30
Total with taxes and fees
All new 1BR apartment with all the features you are looking for

Fully Furnished 1BR Apartment

Fully Furnished 1BR Apartment
Wallingford
10.0 out of 10, Exceptional, (3 reviews)
"This was a great place to stay in town when visiting family! Kitchen was well stocked, location was convenient, & it had everything we needed!"
United States
Jennifer L.
$274 nightly
The price is $292
Jul 18 - Jul 19
Total with taxes and fees
Fully Furnished 1BR Apartment
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 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.