Oakville Vacation Rentals

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Vacation Rentals in Oakville

Fun Downtown Location 2nd flr
Dining
Fun Downtown Location 2nd flr
9.8 out of 10, Exceptional, 51 reviews
"Great property for our family trip. We had lots of fun. Owner was responsive and communicative. Hope to be back some day!"
Fun Downtown Location 2nd flr
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
Property grounds
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
9.8 out of 10, Exceptional, 19 reviews
"Our family enjoyed our stay at the Cottage during our recent visit to CT for our son's college graduation. The views of the lake from the living room, the deck and the patio with fire pit are great and very peaceful. The kitchen was nicely outfitted with everything needed to cook and prepare meals. The only drawback was that there were no closets or chest of drawers in the (2) basement bedrooms. There was no place to unpack and hang our clothes for the 4 days we were there; the only closet was...
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
Beautiful cozy rooms near hospital and down town area
Private kitchen | Fridge, microwave, oven, stovetop
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 $109
$246 total
includes taxes & fees
Jun 18 - Jun 19
Beautiful cozy rooms near hospital and down town area
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Cozy & Chic Cabin by the Lake, with access to private Beach!
Exterior
Cozy & Chic Cabin by the Lake, with access to private Beach!
10.0 out of 10, Exceptional, 8 reviews
"We’d go back."
The price is $250
$489 total
includes taxes & fees
Jul 1 - Jul 2
Cozy & Chic Cabin by the Lake, with access to private Beach!
Guest Cottage on Country Estate
Property grounds
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
lakefront estate
Pool
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
Amazing Lakefront Property
Smart TV, fireplace, offices
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
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.
1 bedroom, iron/ironing board, WiFi, bed sheets
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.
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
9.8 out of 10, Exceptional, 8 reviews
"This is an immaculate guest suite with incredible views in a gorgeous setting. The owners were extremely responsive and communicative, enhancing our stay. The bed is very comfortable and the appliances and just about everything looks brand new. The grounds, pool area and views are amazing. If you’re looking for a comfortable and peaceful stay in a relaxing setting, this is the place! Your hosts will make sure you are well taken care of."
The price is $220
$296 total
includes taxes & fees
Jul 8 - Jul 9
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Smart TV, fireplace, table tennis, stereo
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...
Candlewood Lake Retreat with year round views
Property grounds
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
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Property grounds
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
Peaceful apartment on 3.5 acres w/ artist studio.
Game room
Peaceful apartment on 3.5 acres w/ artist studio.
10.0 out of 10, Exceptional, 11 reviews
"Cute."
The price is $140
$213 total
includes taxes & fees
Jun 18 - Jun 19
Peaceful apartment on 3.5 acres w/ artist studio.
Lakefront Home, Close to Mt Southington!
Fridge, microwave, stovetop, dishwasher
Lakefront Home, Close to Mt Southington!
10.0 out of 10, Exceptional, 7 reviews
"This is a charming house that actually is even better than the photos! Spotless and organized. Kitchen is perfectly stocked. Came with a bag of nice Italian coffee, Kurig and teas with refrigerated creamer. Bed was terrific and large. AC and Heat easy to use. Easy to find and surrounded by everything you need, like food, coffee, bagels, restaurants."
Lakefront Home, Close to Mt Southington!
The Long View of Candlewood Lake
Smart TV, fireplace
The Long View of Candlewood Lake
9.8 out of 10, Exceptional, 9 reviews
"We were In the area for Kent Graduation . Wish we had more time to spend at the house . Perfect area by lake. Nice setup . Great neighbors . The host was very responsive and so accommodating with our busy schedule and short stay. We’ll be back for a longer stay to enjoy the property, house and lake."
The Long View of Candlewood Lake
Historic Whitneyville Cottage
Fridge, microwave, oven, stovetop
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
Cozy newly remodeled home close to major amenities in Connecticut a
Private kitchen
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
#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 13!*
Fridge, microwave, stovetop, coffee/tea maker
#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 13!*
#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 13!*
Tranquil Litchfield Connecticut Retreat".
Property grounds
Tranquil Litchfield Connecticut Retreat".
9.6 out of 10, Exceptional, 5 reviews
"Great property close to all kinds of places to visit and scenic nature!"
The price is $207
$294 total
includes taxes & fees
Jul 4 - Jul 5
Tranquil Litchfield Connecticut Retreat".
Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!
Interior
Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!
9.8 out of 10, Exceptional, 10 reviews
"It was a beautiful place to be with family and relax"
Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!
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

Courtyard by Marriott Waterbury Downtown
Lobby lounge
Courtyard by Marriott Waterbury Downtown
3.0 star property
8.2 out of 10, Very Good, 1,003 reviews
"Wish they had a pool .otherwise everythi g was fine.."
The price is $109
$125 total
includes taxes & fees
Jun 16 - Jun 17
Courtyard by Marriott Waterbury Downtown
Holiday Inn Express Southington, an IHG Hotel
Exterior
Holiday Inn Express Southington, an IHG Hotel
2.5 star property
8.4 out of 10, Very Good, 1,005 reviews
"Was set off the Maine road and close access to highway 84"
The price is $138
$159 total
includes taxes & fees
Jun 17 - Jun 18
Holiday Inn Express Southington, an IHG Hotel
Wyndham Southbury
Lobby
Wyndham Southbury
3.0 star property
8.0 out of 10, Very Good, 1,005 reviews
"Clean and accessible "
The price is $110
$126 total
includes taxes & fees
Jun 23 - Jun 24
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.

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 $109 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.

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 Holy Land USA. 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

Holiday Inn Express Southington, an IHG Hotel

Holiday Inn Express Southington, an IHG Hotel

5/5 Excellent
"A nice hotel!"
A verified traveler stayed at Holiday Inn Express Southington, an IHG Hotel
Posted 2 days ago
Holiday Inn Express Southington, an IHG Hotel