Photo by Heather Beaudry

Oakville Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Tonight
Jan 7 - Jan 8
Tomorrow
Jan 8 - Jan 9
This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

Our top choices for Oakville vacation rentals

House (3 Bedrooms) | Interior
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Cottage in Oakville

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
$443 nightly
The price is $510
Jan 9 - Jan 10
Total with taxes and fees
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
1 bedroom, free WiFi, bed sheets
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

Camping in New Milford

Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
1.0 star property
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
$170 nightly
The price is $193
Jan 9 - Jan 10
Total with taxes and fees
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
Interior
Westville Stay • 2BR • Near Yale • Free Parking

Apartment in West New Haven

Westville Stay • 2BR • Near Yale • Free Parking
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.
$237 nightly
The price is $237
Jan 12 - Jan 13
Total with taxes and fees
Westville Stay • 2BR • Near Yale • Free Parking
Interior
Private Apartment in Berlin

Vacation 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.
$266 nightly
The price is $301
Jan 11 - Jan 12
Total with taxes and fees
Private Apartment in Berlin
Exterior
Cozy One Bedroom Apartment Centrally Located in Southbury

Apartment in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
10.0 out of 10, Exceptional, (21)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
$112 nightly
The price is $126
Jan 11 - Jan 12
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
Interior
The Historic Hideaway

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.
$233 nightly
The price is $245
Jan 9 - Jan 10
Total with taxes and fees
The Historic Hideaway
Fridge, microwave, oven, stovetop
#26 Beautifully Renovated 2 BR Home

Vacation 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.
$217 nightly
The price is $234
Jan 25 - Jan 26
Total with taxes and fees
#26 Beautifully Renovated 2 BR Home
Fridge, microwave, oven, stovetop
Private Apartment in Southbury 103

Apartment in Southbury

Private Apartment in Southbury 103
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.
$208 nightly
The price is $236
Jan 9 - Jan 10
Total with taxes and fees
Private Apartment in Southbury 103
Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Apartment in Torrington

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
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.
$303 nightly
The price is $347
Jan 11 - Jan 12
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Interior
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Apartment in Watertown

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
8.6 out of 10, Excellent, (10)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
$109 nightly
The price is $122
Jan 9 - Jan 10
Total with taxes and fees
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Exterior
All New 1BR with tons of Charm

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.
$271 nightly
The price is $288
Jan 11 - Jan 12
Total with taxes and fees
All New 1BR with tons of Charm
Interior
All New Studio apartment in center of town

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.
$273 nightly
The price is $290
Jan 9 - Jan 10
Total with taxes and fees
All New Studio apartment in center of town
Smart TV
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Apartment in Cheshire

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
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.
$145 nightly
The price is $163
Jan 14 - Jan 15
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
1 bedroom, iron/ironing board, WiFi, bed sheets
Once the old Schools house now a newly furnished Apartment

Vacation Home in Wallingford Center

Once the old Schools house now a newly furnished Apartment
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.
$266 nightly
The price is $283
Jan 31 - Feb 1
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
TV
Newly Remodeled with deck. Close to town center

Apartment in Wallingford

Newly Remodeled with deck. Close to town center
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.
$273 nightly
The price is $290
Jan 9 - Jan 10
Total with taxes and fees
Newly Remodeled with deck. Close to town center
TV
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Vacation Home in New Britain

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
10.0 out of 10, Exceptional, (9)
" Heck-on was smooth and the kitchen and facilities were great. "
United States
Elizabeth P.
$220 nightly
The price is $248
Jan 12 - Jan 13
Total with taxes and fees
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
Terrace/patio
Soothing 2-bedroom lower-level apartment in Berlin

Apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin
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.
$283 nightly
The price is $321
Jan 12 - Jan 13
Total with taxes and fees
Soothing 2-bedroom lower-level apartment in Berlin
Interior
Private Apartment in Southbury 101

Apartment in Southbury

Private Apartment in Southbury 101
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.
$244 nightly
The price is $276
Jan 14 - Jan 15
Total with taxes and fees
Private Apartment in Southbury 101
Fridge, microwave, oven, stovetop
Private Apartment in Southbury 102

Apartment in Southbury

Private Apartment in Southbury 102
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.
$243 nightly
The price is $275
Jan 11 - Jan 12
Total with taxes and fees
Private Apartment in Southbury 102
Property grounds
River Overlook - Check the view from your deck!

Apartment in Collinsville

River Overlook - Check the view from your deck!
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.
$236 nightly
The price is $267
Jan 25 - Jan 26
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 $126 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?

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage: This vacation home rental near 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 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 larger area, you’ll find Mattatuck Museum Arts and History Center and Waterbury City Hall.

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.