Oakville Vacation Rentals

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Check prices for these dates

Tonight
Oct 25 - Oct 26
Tomorrow
Oct 26 - Oct 27
Next weekend
Oct 31 - Nov 2
In two weeks
Nov 7 - Nov 9

Vacation Rentals in Oakville

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
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.
$264 nightly
The price is $281
Oct 31 - Nov 1
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
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.
9.8 out of 10, Exceptional, (7)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
$109 nightly
The price is $122
Oct 26 - Oct 27
Total with taxes and fees
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Fridge, microwave, oven, stovetop
Private Apartment in Berlin
Private Apartment in Berlin
2.0 star property
9.2 out of 10, Wonderful, (5)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
United States
Stacy B.
$279 nightly
The price is $316
Oct 26 - Oct 27
Total with taxes and fees
Private Apartment in Berlin
Exterior detail
New One Bedroom Apartment Centrally Located in Southbury
New One Bedroom Apartment Centrally Located in Southbury
9.8 out of 10, Exceptional, (14)
"Excellent place in an excellent location. Charles is a wonderful host. Will be staying there again. "
United States
Robert
$110 nightly
The price is $124
Nov 3 - Nov 4
Total with taxes and fees
New One Bedroom Apartment Centrally Located in Southbury
TV
All New Private and Cozy in great location
All New Private and Cozy in great location
8.8 out of 10, Excellent, (6)
"The pictures must have been old. Very deceiving. Expected it to be more spacious. Hard to get in and out because of the busy road"
United States
ROBERT P.
$271 nightly
The price is $288
Oct 26 - Oct 27
Total with taxes and fees
All New Private and Cozy in great location
Outdoor dining
Soothing 2-bedroom lower-level 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.
$235 nightly
The price is $266
Oct 28 - Oct 29
Total with taxes and fees
Soothing 2-bedroom lower-level apartment in Berlin
Outdoor dining
The Sun Filled Cozy Creamery
The Sun Filled Cozy Creamery
8.8 out of 10, Excellent, (22)
"Nice,cozy and a reasonable rate."
United States
Rachelle B.
$257 nightly
The price is $275
Oct 29 - Oct 30
Total with taxes and fees
The Sun Filled Cozy Creamery
Fridge, microwave, oven, stovetop
All New 1BR with tons of Charm
All New 1BR with tons of Charm
9.6 out of 10, Exceptional, (4)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
$271 nightly
The price is $288
Oct 26 - Oct 27
Total with taxes and fees
All New 1BR with tons of Charm
Fridge, microwave, oven, stovetop
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.4 out of 10, Exceptional, (9)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
$155 nightly
The price is $175
Oct 27 - Oct 28
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Fridge, microwave, oven, stovetop
New 1BR Great Location Center of Town
New 1BR Great Location Center of Town
10.0 out of 10, Exceptional, (2)
"Perfect spot for Oakdale Theater. Everything was as described and we were very comfortable. "
United States
Sarah W.
$271 nightly
The price is $288
Oct 27 - Oct 28
Total with taxes and fees
New 1BR Great Location Center of Town
Fridge, microwave, oven, stovetop
Westville Stay • 2BR • Near Yale • Free Parking
Westville Stay • 2BR • Near Yale • Free Parking
$239 nightly
The price is $239
Oct 29 - Oct 30
Total with taxes and fees
Westville Stay • 2BR • Near Yale • Free Parking
Interior
Newly Remodeled 1-BR Close to Everything yet Very Private
Newly Remodeled 1-BR Close to Everything yet Very Private
10.0 out of 10, Exceptional, (9)
"I was very pleased with the accomodations. I had everything I needed and it was comfortable and quiet. I was able to get my research done and enjoyed the peaceful setting, and it was convenient to the friends and family I visited during my stay. I will definitely stay here again. "
United States
Paula S.
$271 nightly
The price is $288
Oct 26 - Oct 27
Total with taxes and fees
Newly Remodeled 1-BR Close to Everything yet Very Private
Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
9.6 out of 10, Exceptional, (4)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
$230 nightly
The price is $274
Oct 26 - Oct 27
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
1 bedroom, iron/ironing board, WiFi, bed sheets
All New Studio apartment in center of town
All New Studio apartment in center of town
10.0 out of 10, Exceptional, (1)
"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.
$271 nightly
The price is $288
Oct 27 - Oct 28
Total with taxes and fees
All New Studio apartment in center of town
Fridge, microwave, oven, stovetop
Private Apartment in Southbury 103
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.
$266 nightly
The price is $301
Nov 17 - Nov 18
Total with taxes and fees
Private Apartment in Southbury 103
Fridge, microwave, oven, stovetop
Charming apartment 7 minute walk to downtown
Charming apartment 7 minute walk to downtown
10.0 out of 10, Exceptional, (15)
"Everything about our stay was great - Corin and Jen were wonderful hosts. The place is spotless, cozy, comfy. Love that they were right next to the Green Way Trail along the river. Will absolutely stay there again! "
United States
Kate B.
$216 nightly
The price is $245
Nov 6 - Nov 7
Total with taxes and fees
Charming apartment 7 minute walk to downtown
Fridge, microwave, oven, stovetop
River Overlook - Check the view from your deck!
River Overlook - Check the view from your deck!
10.0 out of 10, Exceptional, (23)
"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.
$253 nightly
The price is $286
Oct 27 - Oct 28
Total with taxes and fees
River Overlook - Check the view from your deck!
Interior
Private Apartment in Southbury 101
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.
$295 nightly
The price is $334
Nov 5 - Nov 6
Total with taxes and fees
Private Apartment in Southbury 101
Game room
Peaceful apartment on 3.5 acres w/ artist studio.
Peaceful apartment on 3.5 acres w/ artist studio.
9.6 out of 10, Exceptional, (19)
"This was a nice get away for us that was not too far away from home."
United States
Isabella M.
$171 nightly
The price is $194
Oct 26 - Oct 27
Total with taxes and fees
Peaceful apartment on 3.5 acres w/ artist studio.
Fridge, microwave, oven, stovetop
New Railside Residents
New Railside Residents
$290 nightly
The price is $310
Oct 28 - Oct 29
Total with taxes and fees
New Railside Residents
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

Wyndham Southbury

Wyndham Southbury

10/10 Excellent
"Room & Building were very clean. Staff was friendly. "
Thomas 1-night trip
Posted 2 days ago
Wyndham Southbury

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 $194 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?

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit: This vacation home rental near Oakville is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, an arcade game room, 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 Holy Land USA. In the larger area, you’ll find Palace Theatre and Brass Mill Center.

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.