Oakville Vacation Rentals

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Oct 24 - Oct 25
Tomorrow
Oct 25 - Oct 26
This weekend
Oct 24 - Oct 26
Next weekend
Oct 31 - Nov 2

Vacation Rentals in Oakville

Dining
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
10.0 out of 10, Exceptional, (2)
"This is a property that is very good for large family gatherings, which is how we gathered for a birthday celebration. This area of CT. is great and has lots to do.The house is in the perfect location to do all of it.Again, suits large groups well. Room for everyone."
United States
Paula R.
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Outdoor dining
The Goshen Glass Chalet
The Goshen Glass Chalet
9.6 out of 10, Exceptional, (41)
"The chalet was great. Plenty of room, very cozy and in a very quiet neighborhood community. "
United States
Tracy F.
The Goshen Glass Chalet
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.
$281 nightly
The price is $318
Oct 28 - Oct 29
Total with taxes and fees
Private Apartment in Berlin
Dining
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
8.6 out of 10, Excellent, (26)
"The cabin was great! Exactly as described and pictured. The kitchen was well stocked with all the basic cooking instruments and utensils. We had a blast and would absolutely come back."
United States
Angela C.
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
TV
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
10.0 out of 10, Exceptional, (5)
"The space was clean and light, great finishes. The home felt comfortable and was easy to find. Thank you for a wonderful weekend. "
United States
Lara S.
$217 nightly
The price is $245
Oct 27 - Oct 28
Total with taxes and fees
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
Property grounds
Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area
Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area
9.8 out of 10, Exceptional, (6)
"Everything was amazing "
United States
MELISSA G.
Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area
Exterior detail
Private Annex/Former Artist Studio
Private Annex/Former Artist Studio
10.0 out of 10, Exceptional, (52)
"It has stairs to climb up to apartment. Everything was lovely.And the owners go out of their way to make you feel welcome."
United States
Liz G.
Private Annex/Former Artist Studio
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
Outdoor dining
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
10.0 out of 10, Exceptional, (11)
"I stayed with my mom and the 2 bedroom 1 bath was perfect for our stay. The house way cozy and in a quiet area. Would absolutely stay again; my mom is already talking about coming back to explore more of the surrounding areas!"
United States
Tyler A.
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Outdoor dining
Fun Downtown Location 2nd flr
Fun Downtown Location 2nd flr
9.8 out of 10, Exceptional, (77)
"Wonderful stay. Cute, clean, well organized, stocked and the owner was very responsive when we had a power issue that was 100% out of their control. He even shared some local recommendations including an oddities museum across the street! "
United States
Tiana C.
Fun Downtown Location 2nd flr
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
Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi
Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi
10.0 out of 10, Exceptional, (1)
"Clean and quiet location, great place for a relaxing stay."
United States
robert p.
Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi
Microwave, oven, stovetop, dishwasher
Spacious 3-Bedroom Home Awaits - Designed for Comfort & Relaxation!!!
Spacious 3-Bedroom Home Awaits - Designed for Comfort & Relaxation!!!
Spacious 3-Bedroom Home Awaits - Designed for Comfort & Relaxation!!!
Exterior
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
9.6 out of 10, Exceptional, (14)
"It was a great time. Loved it hear would come back again. Owner was very helpful."
United States
Nosa I.
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Fridge, microwave, oven, stovetop
Cozy Safe Home
Cozy Safe Home
$357 nightly
The price is $404
Oct 26 - Oct 27
Total with taxes and fees
Cozy Safe Home
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.
$263 nightly
The price is $298
Nov 17 - Nov 18
Total with taxes and fees
Private Apartment in Southbury 103
Interior
Amazing Lakefront Property
Amazing Lakefront Property
9.6 out of 10, Exceptional, (28)
"Great views and a good central location for day trips 👌. "
United States
Paul B.
Amazing Lakefront Property
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
Fridge, microwave, oven, stovetop
KING BED, Affordable Classic Bristol Home Sleep 8+
KING BED, Affordable Classic Bristol Home Sleep 8+
$270 nightly
The price is $306
Nov 11 - Nov 12
Total with taxes and fees
KING BED, Affordable Classic Bristol Home Sleep 8+
Fridge, microwave, oven, stovetop
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
10.0 out of 10, Exceptional, (61)
"There is a lot of fun things to do close by. The house was spotless and it was nice to relax on the sofa or outside patio and look at the river. "
United States
Amanda W.
$401 nightly
The price is $454
Oct 26 - Oct 27
Total with taxes and fees
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
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

Days Inn by Wyndham Southington

Days Inn by Wyndham Southington

10/10 Excellent
"Room was clean and spacious. The 1 sitting chair was a little uncomfortable. Pillows were not comfortable either but sheets were clean and bedding was perfect. I have been to other places were the air conditioning kicking on sounded like a plane taking off, the rooms air conditioning unit was so quiet. Helped us sleep better. Bathroom amenities were awesome!!"
Sherry 1-night trip
Posted 4 days ago
Days Inn by Wyndham Southington

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.