Oakville Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

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
$443 nightly
The price is $510
Mar 30 - Mar 31
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, (24 reviews)
"Excellent host."
United States
David
$111 nightly
The price is $125
Mar 30 - Mar 31
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
Interior

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.
$109 nightly
The price is $122
Mar 29 - Mar 30
Total with taxes and fees
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
House (3 Bedrooms) | Interior

New Milford Home: 29 Mi to Lime Rock Park!

New Milford Home: 29 Mi to Lime Rock Park!
3.0 star property
New Milford
New Milford Home: 29 Mi to Lime Rock Park!
Fridge, microwave, oven, stovetop

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.
$200 nightly
The price is $226
Mar 30 - Mar 31
Total with taxes and fees
Private Apartment in Southbury 103
Room

Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
$323 nightly
The price is $377
Mar 30 - Mar 31
Total with taxes and fees
Art House 3 Beds Close to Warner Theater
2 bedrooms, WiFi, bed sheets

Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.0 out of 10, Wonderful, (6 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.
$211 nightly
The price is $240
Mar 29 - Mar 30
Total with taxes and fees
Private Apartment in Berlin
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
$272 nightly
The price is $290
Apr 19 - Apr 20
Total with taxes and fees
All new 1BR apartment with all the features you are looking for
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
$349 nightly
The price is $396
Mar 29 - Mar 30
Total with taxes and fees
Litchfield Retreat, Wineries, Foliage & Skiing
Property grounds

River Overlook - Check the view from your deck!

River Overlook - Check the view from your deck!
Collinsville
10.0 out of 10, Exceptional, (23 reviews)
"The place was perfect for the two of us. It was close to both our kids homes."
United States
Tomas M.
$237 nightly
The price is $268
Mar 29 - Mar 30
Total with taxes and fees
River Overlook - Check the view from your deck!
Outdoor pool

Cozy 1-bedroom apartment in lovely Oxford

Cozy 1-bedroom apartment in lovely Oxford
Oxford
10.0 out of 10, Exceptional, (3 reviews)
"This was my second time staying here. The apartment was immaculately clean and the owner was both professional and personal! The apartment had all the comforts of home, from coffee and snacks in the kitchen to self-care items (e.g., toothbrush, toothpaste, etc). Truly a hidden gem, close to shopping, restaurants, and highways! "
United States
LIsa G.
$142 nightly
The price is $160
Mar 31 - Apr 1
Total with taxes and fees
Cozy 1-bedroom apartment in lovely Oxford
Interior

Private Apartment in Southbury 101

Private Apartment in Southbury 101
Southbury
9.4 out of 10, Exceptional, (6 reviews)
"The apartment was nice, big area, loved this rental."
United States
Marissa G.
$200 nightly
The price is $227
Apr 2 - Apr 3
Total with taxes and fees
Private Apartment in Southbury 101
TV

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.
$272 nightly
The price is $290
Apr 19 - Apr 20
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
Outdoor dining

The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, Exceptional, (1 review)
"Beautiful place. Very clean & welcoming "
United States
Chris
$190 nightly
The price is $216
Mar 29 - Mar 30
Total with taxes and fees
The Perch in the Purchase -- Cozy, unique, and private
Fridge, microwave, oven, stovetop

All New Fully Furnished Cozy Studio

All New Fully Furnished Cozy Studio
Wallingford Center
9.8 out of 10, Exceptional, (8 reviews)
"Clean and well designed apartment in a great location. Book here if you are interested as you won't have any regrets. Enjoy! "
United States
Rick C.
$279 nightly
The price is $297
Apr 8 - Apr 9
Total with taxes and fees
All New Fully Furnished Cozy Studio
Exterior

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
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.
$298 nightly
The price is $342
Mar 29 - Mar 30
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
TV

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, (9 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
Newly Remodeled 1-BR Close to Everything yet Very Private
Interior

New Railside Residents

New Railside Residents
Wallingford Center
10.0 out of 10, Exceptional, (1 review)
"This apartment was the perfect base for visiting family in Wallingford. It had everything we needed, was very clean, and super convenient to downtown cafes and restaurants. The train is a bit loud but to be expected! Will definitely stay again. "
United States
Kelsey S.
$278 nightly
The price is $296
Apr 10 - Apr 11
Total with taxes and fees
New Railside Residents
Fridge, microwave, oven, stovetop

Private Apartment in Southbury 104

Private Apartment in Southbury 104
Southbury
$196 nightly
The price is $222
Apr 2 - Apr 3
Total with taxes and fees
Private Apartment in Southbury 104
1 bedroom, free WiFi, bed sheets

Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
New Milford
8.0 out of 10, Very Good, (1 review)
"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
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
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

Best Western Plus New England Inn & Suites

Best Western Plus New England Inn & Suites

4/10 Poor
"Overall what one would expect but issues with no hot water for a day and there were 2 remotes needed for even basic TV viewing in the room. Hard to figure out so just turned it off and watched my phone"
Joseph 2-night trip
Posted 23 hours ago
Best Western Plus New England Inn & Suites

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?

Lakefront Cottage in CT with Hot Tub Pet Friendly: This vacation home near Oakville is located on a lake and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 Mattatuck Museum Arts and History Center 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.