Oakville Vacation Rentals

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Vacation Rentals in Oakville

Fun Downtown Location
9.8 out of 10, Exceptional, 48 reviews
"Nice space with 3 roomy bedrooms. Plenty of storage for clothes. Bathroom is small but not untypical of this era home. Steps to second floor are steep, so consider this. Kitchen has what you need for a short stay."
Fun Downtown Location
Beautiful cozy rooms near hospital and down town area
8.4 out of 10, Very good, 10 reviews
"People were very nice and welcoming. Area looks questionable but the place itself is very comfortable, clean and enjoyable."
The price is CA $149
CA $339 total
includes taxes & fees
Jun 3 - Jun 4
Beautiful cozy rooms near hospital and down town area
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
9.8 out of 10, Exceptional, 8 reviews
"Beautiful, quiet, private yet convenient setting, perfect room setup and accommodations/amenities, along with a gracious and helpful host. Based on my stay experience, I would recommend this property unconditionally and look forward to a longer stay in the future. Thanks!"
The price is CA $312
CA $524 total
includes taxes & fees
Jul 1 - Jul 2
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
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Cozy & Chic Cabin by the Lake, with access to private Beach!
10.0 out of 10, Exceptional, 8 reviews
"Absolutely loved my stay. The host was incredibly accommodating and went above and beyond to make sure we had everything we needed. The space was stylish, clean, and cozy, with thoughtful touches throughout. The location was perfect, close to all the attractions yet tucked away in a quiet neighborhood. Would highly recommend to anyone looking for a comfortable and enjoyable stay!"
The price is CA $307
CA $623 total
includes taxes & fees
Jun 4 - Jun 5
Cozy & Chic Cabin by the Lake, with access to private Beach!
Peaceful apartment on 3.5 acres w/ artist studio.
10.0 out of 10, Exceptional, 11 reviews
"Cute."
The price is CA $191
CA $291 total
includes taxes & fees
Jun 3 - Jun 4
Peaceful apartment on 3.5 acres w/ artist studio.
lakefront estate
3.8 out of 10, 8 reviews
"Overall do not stay in this house! They are scamming people! They say they are military family yet took advantage of one!! Still owe me my refund and refuse to answer VRBO to give the okay to refund my money! This place was not clean it was very unsanitary and there were drug paraphernalia in the backyard! Towels wet and dirty on the bathroom floor and one of the bedrooms the sheets were dirty in the floor claimed that the house keeper cleaned it! The pool was disgusting!! I have videos pictures...
lakefront estate
Candlewood Lake Retreat with year round views
10.0 out of 10, Exceptional, 7 reviews
"We thoroughly enjoyed our time at this wonderful little home. It was pleasantly quiet and secluded, but was just minutes away from some wonderful restaurants and just a short walk to the lake. The hosts were just so responsive and accommodating. We also had one day of rainy weather, which afforded us the opportunity to simply stay in and relax. The kitchen had all of the amenities we could have asked for. The seating area on the deck was spacious and comfortable. We are certainly looking forward...
Candlewood Lake Retreat with year round views
Guest Cottage on Country Estate
9.2 out of 10, Wonderful, 33 reviews
"My husband and son stayed here for 5 days. They had a fabulous time hiking in the state park nearby. Thanks for a great stay!"
Guest Cottage on Country Estate
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
10.0 out of 10, Exceptional, 17 reviews
"The property is lovely and well prepared for guests. The location is wonderful. One of our highlights was watching a bald eagle soar over the lake."
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.
Amazing Lakefront Property
10.0 out of 10, Exceptional, 15 reviews
"This was my second go round staying at this property. My family and I enjoyed it the first time. More so the second time with the upgrades. Being familiar with the area was a great help. This time we went in the lake and enjoyed ourselves. We are looking forward to returning back again. Thank you Raymond for letting us stay at your property. Richard and Joanne"
Amazing Lakefront Property
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
10.0 out of 10, Exceptional, 11 reviews
"We absolutely loved the house! This was the perfect place to bring my adult children together for a weekend away. The rooms were beautiful, beds were super comfortable, and house nicely decorated. There were spots for smaller groups to sit together and hang out or to come together and chat. The hot tub was appealing to my 20somethings but it was rainy- next time!"
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
The Long View of Candlewood Lake
9.8 out of 10, Exceptional, 7 reviews
"Great location! Never found the beach passes, but it wasn't an issue. Enjoyed using the kayaks. Loved the house. Wish the primary bed was more comfortable. Could not find a toilet plunger. Enjoyed meeting Mark who briefed us on the community policies."
The Long View of Candlewood Lake
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
10.0 out of 10, Exceptional, 20 reviews
"We were in area from Uk visiting friends who live not far away. So this little home was just ideal for us. Weather improved on the day we left so we didnt sit outside by the lake but we did enjoy watching the birds and fish."
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
The Nest at The Granary
10.0 out of 10, Exceptional, 23 reviews
"The Nest is so close to everything. Walked in and the place is so clean. Like no one has ever stayed there before. Cass was super responsive (within minutes of messaging him I had a response). Checked in with us to ensure we were enjoying our stay. Our next visit to the area, we will be staying there again. Best place in town for sure. Tip: Enter the front door code to the lobby super fast. That thing is a little temperamental. Side note: Check out Theo’s restaurant for breakfast."
The Nest at The Granary
Historic Whitneyville Cottage
9.6 out of 10, Exceptional, 10 reviews
"We have stayed in this little cottage several times now. Convenient location for visiting downtown New Haven. Bed is comfortable - kitchen small but it has what you need. Nice walking neighborhood if you have dogs. We will be back."
Historic Whitneyville Cottage
River Overlook - Check the view from your deck!
10.0 out of 10, Exceptional, 8 reviews
"The location was just as promised. The view on the deck is beautiful and the apartment was clean and well stocked with anything you might need. The location is also walking distance to various shops, pizza, restaurants and bars. The river walk across the street is also great if you want to take a stroll. Carol was also great to work with. We’ll be back."
River Overlook - Check the view from your deck!
Cozy newly remodeled home close to major amenities in Connecticut a
8.4 out of 10, Very good, 10 reviews
"We stayed here while visiting our family. The property was clean, quiet and exactly as described. The kitchen seemed well stocked. The huge washing machine/dryer was great after our cross country drive. There are just a few things to be aware of: the bathroom is on the second floor. The bed we slept on was not too too comfortable (a little firm for our tastes). The single bed was very firm. Other than that it was a nice place to stay."
Cozy newly remodeled home close to major amenities in Connecticut a
Cozy Lakefront Bungalow w firepit/dock/kayaks
9.8 out of 10, Exceptional, 19 reviews
"Words cannot describe how beautiful and peaceful this place was I did not wanna leave and I’m already looking forward to my next stay! Owners were wonderful to communicate, and exceeded my expectations. Thank you for giving me blissful place to spend my birthday."
Cozy Lakefront Bungalow w firepit/dock/kayaks
Stunning Warren Lakefront Home: Deck, Grill, Sauna
10.0 out of 10, Exceptional, 5 reviews
"The house worked perfectly for our large group. Spacious and clean, Sean was a pleasure to deal with!"
Stunning Warren Lakefront Home: Deck, Grill, Sauna
Don't see what you're looking for?
See all available properties in Oakville
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.

Other types of properties in Oakville you may be interested in

Holiday Inn Express Southington, an IHG Hotel
2.5 star property
8.4 out of 10, Very good, 1,005 reviews
"The property was well kept and clean"
The price is CA $196
CA $226 total
includes taxes & fees
Jun 2 - Jun 3
Holiday Inn Express Southington, an IHG Hotel
Courtyard by Marriott Waterbury Downtown
3.0 star property
8.2 out of 10, Very good, 1,005 reviews
"Just love the stay "
The price is CA $121
CA $139 total
includes taxes & fees
Jun 3 - Jun 4
Courtyard by Marriott Waterbury Downtown
Wyndham Southbury
3.0 star property
8.0 out of 10, Very good, 1,003 reviews
"Very convenient!"
The price is CA $149
CA $172 total
includes taxes & fees
Jun 17 - Jun 18
Wyndham Southbury
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Oakville. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly: This vacation home rental 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 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Oakville?

Choose from 5 Expedia vacation rentals in Oakville for a memorable 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 Hop Brook Lake. In the larger area, you’ll find Union Station Clocktower 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.

Recent reviews of Oakville properties
Expedia verified reviews