Oakville Vacation Rentals

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Check prices for these dates

Tonight
Feb 21 - Feb 22
Tomorrow
Feb 22 - Feb 23
This weekend
Feb 21 - Feb 23
Next weekend
Feb 28 - Mar 2

Vacation Rentals in Oakville

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, (22)
"Mariana is a wonderful host. She communicates well and is very efficient in responding to any questions or inquiries you may have.The cabin is very clean, and has just about everything you would need. We really enjoyed using the fireplace! 10/10 recommend. "
Cozy & Chic Cabin by the Lake, with access to private Beach!
NEW! LAKE FRONT, Private Dock, Fire Pit, Paddle Boards, Kayaks & Rec Room!
Property grounds

NEW! LAKE FRONT, Private Dock, Fire Pit, Paddle Boards, Kayaks & Rec Room!

10.0 out of 10, Exceptional, (3)
"First time booking and the place was perfect, beautiful views, real cozy vibes, and the host did a great job to attend at anything we needed "
NEW! LAKE FRONT, Private Dock, Fire Pit, Paddle Boards, Kayaks & Rec Room!
Litchfield Hills Hideaway
Fridge, microwave, oven, stovetop

Litchfield Hills Hideaway

10.0 out of 10, Exceptional, (55)
"Great place to end our Gilmore Girls adventure!!! The Hideaway was clean and cozy, and the hosts are very professional! We would stay here again!!!!"
The price is ￥22,430
￥38,579 total
includes taxes & fees
Feb 26 - Feb 27
Litchfield Hills Hideaway
The Connecticut Chalet - On 5 Acres!
Interior

The Connecticut Chalet - On 5 Acres!

10.0 out of 10, Exceptional, (2)
"If you’re looking for a relaxing, unique/fun home this is it!! The host was amazing & left no questions to ask. The home is fully stocked with all your needs from cooking utensils, wood to start a warm fire & even games for in between time. The bedrooms are cozy and the beds are super soft. The deck & sun room/dining room was a fav, the views are amazing. I would certainly recommend and even stay here again. Thank you "
The Connecticut Chalet - On 5 Acres!
Amazing Lakefront Property
Dining

Amazing Lakefront Property

9.8 out of 10, Exceptional, (24)
"Absolutely beautiful house! Super clean! Superb setting! Very comfortable! Amazing view! Many amenities! Host very responsive and kind! The property manager quickly responded to our needs. My family and friends loved the spectacular experience and would definitely comeback! "
Amazing Lakefront Property
New One Bedroom Apartment Centrally Located in Southbury
Exterior

New One Bedroom Apartment Centrally Located in Southbury

10.0 out of 10, Exceptional, (1)
"Excellent place in an excellent location. Charles is a wonderful host. Will be staying there again. "
The price is ￥11,962
￥16,747 total
includes taxes & fees
Feb 23 - Feb 24
New One Bedroom Apartment Centrally Located in Southbury
Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!
Interior

Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!

10.0 out of 10, Exceptional, (11)
"This was just what we were looking for. The house was roomy, open and charming. It was also relaxing to sit on the back deck surrounded by trees and listening to the calming sound of the brook. It felt like you out in the countryside yet the cute village of Sandy Hook along with Newtown restaurants and shopping were less than 10 minutes away."
Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!
NEW-Another Fun Downtown Location 1st floor
Interior

NEW-Another Fun Downtown Location 1st floor

2.0 star property
10.0 out of 10, Exceptional, (9)
"It was a nice quiet valuable time spent together .just what we needed for that very special memorable time. Thanks."
NEW-Another Fun Downtown Location 1st floor
The Long View of Candlewood Lake
Smart TV, fireplace

The Long View of Candlewood Lake

10.0 out of 10, Exceptional, (20)
"A great place to stay with the family! "
The Long View of Candlewood Lake
Quiet 2bd Townhome apt in the heart of Cheshire. Cleaning Fee Waived
Fridge, microwave, oven, stovetop

Quiet 2bd Townhome apt in the heart of Cheshire. Cleaning Fee Waived

10.0 out of 10, Exceptional, (1)
"Overall a positive experience. Property was clean and worked out really well for us as location was close to family we were visiting. We are from Florida, and it was cold in CT and the heat worked great so that was really good. Andrew was responsive to requests. Only criticism was in some of the set up. There are no dressers, so you need to stack your clothes on shelves in closet, which was not terrible. Also, the only mirror in the entire place was in the bathroom downstairs (bedrooms...
The price is ￥17,794
￥23,454 total
includes taxes & fees
Feb 24 - Feb 25
Quiet 2bd Townhome apt in the heart of Cheshire. Cleaning Fee Waived
River Overlook - Check the view from your deck!
Fridge, microwave, oven, stovetop

River Overlook - Check the view from your deck!

10.0 out of 10, Exceptional, (15)
"This was a great, cozy place for my wife and I to stay in Collinsville. The rooms were tastefully decorated, in great shape, updated, clean, and peppered with cute artwork based on the "when pigs can fly" theme that always brought a smile to my face when I found another one. The queen bed was very comfortable; the kitchen had all of the appliances, dishes, and cookware we needed; the HVAC system was easy to use and kept the rooms at whatever temperature we wanted; and there was a nice deck with...
The price is ￥22,430
￥42,878 total
includes taxes & fees
Feb 24 - Feb 25
River Overlook - Check the view from your deck!
Litchfield County Four Season Country Paradise
Outdoor pool, a heated pool

Litchfield County Four Season Country Paradise

9.6 out of 10, Exceptional, (40)
"Considering that area does not have convenient hotels, this location was perfect for the event we attended. It was nice of them to vacate their home so we could stay - though we wish that would have been communicated. There is no extra room with twin beds - at least not functional. The property is nice. Whomever took the pictures did a great job. It worked for us for the short time we were in the area."
Litchfield County Four Season Country Paradise
The Jefferson House, Charming, Exceptional, Spacious Home, Estate in Litchfield
1 bedroom, desk, iron/ironing board, WiFi

The Jefferson House, Charming, Exceptional, Spacious Home, Estate in Litchfield

10.0 out of 10, Exceptional, (1)
"The lighting is warm and inviting as you step up the stairs into a large open concept room. Every detail is beyond modern from the giant marble counter equipped with the comfiest and largest leather barstools, to the kitchen whose colors and appliances are so beautifully designed; cabinets stocked with every item you need to cook a homemade meal.The king size bed was like a cloud, swallowing us in the fluffiest duvets and sheets, comfortable pillows, making it an easy switch to use the TV in the...
The price is ￥37,383
￥55,850 total
includes taxes & fees
Feb 23 - Feb 24
The Jefferson House, Charming, Exceptional, Spacious Home, Estate in Litchfield
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Aerial view

Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust

10.0 out of 10, Exceptional, (9)
"We really enjoyed being able to stay at such a beautiful home. Between the animals and the hot tub view - the serenity will be hard to match elsewhere!"
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Old Avon Village
Living area

Old Avon Village

2.0 star property
6.0 out of 10, (4)
"We had a nice stay while visiting our son at AOF. There were a couple of small issues which the owner remedied IMMEDIATELY. Things happen in life which are unforeseen, we appreciated the owner jumping on the issues quickly."
The price is ￥18,691
￥53,083 total
includes taxes & fees
Mar 5 - Mar 6
Old Avon Village
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Property grounds

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (29)
"Vladimir and Cristina's Plymouth listing is such a great find! It was a great home base for visiting family in the area for the holidays. I don't think I've ever been to a rental that had everything you could possibly need. All this plus an amazing view - we'll be back!"
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.

9.8 out of 10, Exceptional, (15)
"This adorable cottage attached to the main house was fabulous for my wife and I for 4 nights! It has a little kitchen, space heaters everywhere (us southerners can’t handle the New England winters like we used to!) and was very clean! We have never stayed in an attached rental before and I would say we would be open to exploring more because of our experience! "
The price is ￥20,934
￥31,364 total
includes taxes & fees
Feb 23 - Feb 24
Peaceful apartment on 3.5 acres w/ artist studio.
󰀄 Modern Boho Dream Home 󰀄 Completely Renovated
Outdoor dining

󰀄 Modern Boho Dream Home 󰀄 Completely Renovated

󰀄 Modern Boho Dream Home 󰀄 Completely Renovated
Beautiful cozy rooms near hospital and down town area
Fridge, microwave, oven, stovetop

Beautiful cozy rooms near hospital and down town area

7.8 out of 10, Good, (18)
"I will forever love coming here. The host was great, Parking was amazing, Rooms were so cleanly. "
Beautiful cozy rooms near hospital and down town area
lakefront estate
Pool

lakefront estate

3.8 out of 10, (8)
"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
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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Other types of properties in Oakville you may be interested in

Courtyard by Marriott Waterbury Downtown
Lobby

Courtyard by Marriott Waterbury Downtown

3.0 star property
8.4 out of 10, Very Good, (1003)
"Safe clean quite"
The price is ￥13,308
￥15,304 total
includes taxes & fees
Feb 23 - Feb 24
Courtyard by Marriott Waterbury Downtown
Clarion Inn
Indoor pool

Clarion Inn

3.0 star property
7.4 out of 10, Good, (1004)
"Enjoyed my stay here "
The price is ￥16,396
￥18,855 total
includes taxes & fees
Mar 4 - Mar 5
Clarion Inn
Holiday Inn Express Southington by IHG
Exterior

Holiday Inn Express Southington by IHG

2.5 star property
8.8 out of 10, Excellent, (1000)
"Room was clean. Bed was very comfortable and sheets were clean. Breakfast was very good and had a lot of options. Overall everything was great !"
The price is ￥14,056
￥16,164 total
includes taxes & fees
Mar 9 - Mar 10
Holiday Inn Express Southington by IHG
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.

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?

Amazing Lakefront Property: 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 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

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 Black Rock State Park. In the larger area, you’ll find Waterbury City Hall and Palace Theatre.

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.