Oakville Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Oakville vacation rentals

House (3 Bedrooms) | Interior

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
Oakville
$468 nightly
The price is $538
Jun 8 - Jun 9
Total with taxes and fees
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Interior

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Watertown
10.0 out of 10, Exceptional, (3 reviews)
"Everything was good just needed to have a tV in each room trash cans also"
United States
Deborah B.
$473 nightly
The price is $532
Jun 8 - Jun 9
Total with taxes and fees
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Exterior

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (30 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
$111 nightly
The price is $125
Jun 22 - Jun 23
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
1 bedroom, iron/ironing board, WiFi, bed sheets

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
Jun 6 - Jun 7
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
Interior

The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
9.0 out of 10, Wonderful, (26 reviews)
"Host had great communication. The unit was clean, cozy and comfortable. Will book again when in the area."
United States
Tod B.
$236 nightly
The price is $251
Jun 7 - Jun 8
Total with taxes and fees
The Sun Filled Cozy Creamery
Hair dryer, towels

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.
$333 nightly
The price is $383
Jun 7 - Jun 8
Total with taxes and fees
Art House 3 Beds Close to Warner Theater
Exterior

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.
$224 nightly
The price is $266
Jun 7 - Jun 8
Total with taxes and fees
Cozy Attic 10 min to Llitchfield
TV

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
$274 nightly
The price is $292
Jun 6 - Jun 7
Total with taxes and fees
All new 1BR apartment with all the features you are looking for
Bathroom

Tiny, Budget Friendly 1 Bedroom Central CT

Tiny, Budget Friendly 1 Bedroom Central CT
Southington
$180 nightly
The price is $193
Jul 1 - Jul 2
Total with taxes and fees
Tiny, Budget Friendly 1 Bedroom Central CT
Terrace/patio

1 Min to I-91 - Newly Renovated Modern 2 BR Home

1 Min to I-91 - Newly Renovated Modern 2 BR Home
Berlin
$295 nightly
The price is $319
Jun 7 - Jun 8
Total with taxes and fees
1 Min to I-91 - Newly Renovated Modern 2 BR Home
Interior

New Railside Residents

New Railside Residents
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"Clean & comfortable, in an architecturally unique setting. Great proximity to a variety of downtown shops & restaurants - check out Center Street Brewing Co. for some excellent beer."
United States
Thomas S.
New Railside Residents
Exterior

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
9.8 out of 10, Exceptional, (10 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
$274 nightly
The price is $292
Jun 6 - Jun 7
Total with taxes and fees
All New 1BR with tons of Charm
Interior

The Historic Hideaway

The Historic Hideaway
Avon
6.0 out of 10, (4 reviews)
"Once we found the house it was very warm & cozy. The mini- muffins on the counter was a bonus. House mailbox was 87 but address was 89 that you only see if door is closed which it wasn't on 1st 2 passes. Limited exterior lights made coming back at night a challenge. "
United States
Kim C.
$252 nightly
The price is $268
Jun 7 - Jun 8
Total with taxes and fees
The Historic Hideaway
Interior

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Waterbury
8.0 out of 10, Very Good, (1 review)
"I had an emergency and was only able to stay one night, but enjoyed my stay "
United States
Dirk N.
$130 nightly
The price is $147
Jun 8 - Jun 9
Total with taxes and fees
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Smart TV

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.
$187 nightly
The price is $212
Jun 7 - Jun 8
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Fridge, microwave, oven, stovetop

Private Apartment in Southbury 104

Private Apartment in Southbury 104
Southbury
$258 nightly
The price is $293
Jun 30 - Jul 1
Total with taxes and fees
Private Apartment in Southbury 104
TV

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.
$274 nightly
The price is $292
Jun 6 - Jun 7
Total with taxes and fees
Newly Remodeled with deck. Close to town center
Bathroom

beautiful Cozy 1BR Apt near New Haven

beautiful Cozy 1BR Apt near New Haven
Seymour
$289 nightly
The price is $289
Jun 6 - Jun 7
Total with taxes and fees
beautiful Cozy 1BR Apt near New Haven
Shower, towels

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.
$250 nightly
The price is $284
Jun 9 - Jun 10
Total with taxes and fees
Private Apartment in Berlin
Interior

#31 - Downtown Terryville- 1 Br

#31 - Downtown Terryville- 1 Br
Plymouth
10.0 out of 10, Exceptional, (1 review)
"In convenient safe area. Os is easy to contact"
United States
Gina P.
#31 - Downtown Terryville- 1 Br
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

Hamden Hotel and Suites – Hamden New Haven

Hamden Hotel and Suites – Hamden New Haven

8/10 Good
"Staff was great"
lisandro 3-night trip
Posted 1 hour ago
Hamden Hotel and Suites – Hamden New Haven

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 $125 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.

Explore a world of travel with Expedia

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.