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Oakville Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Oakville holiday rentals

A spacious living room with large windows, a fireplace, and a view of the outdoors.

1. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Watertown
9.0 out of 10, Wonderful, (6 reviews)
"In town to visit our new grandchild. It was just my husband and me. It had more then enough room and was very comfortable."
United States
Elizabeth H.
The price is HK$1,719
HK$4,238 total
includes taxes & fees
16 Oct - 17 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A spacious living room with large windows, a fireplace, and a view of the outdoors.

2. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
Oakville
The price is HK$2,142
HK$4,230 total
includes taxes & fees
16 Oct - 17 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A two-story house with a porch, a front door with a wreath, and a small garden area.

3. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (11 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is HK$911
HK$2,668 total
includes taxes & fees
18 Oct - 19 Oct
Bear Retreat - 2-bedroom house in Waterbury
A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

4. Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Watertown
8.4 out of 10, Very good, (12 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is HK$753
HK$1,023 total
includes taxes & fees
9 Nov - 10 Nov
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
A staircase with a handrail, a potted plant with yellow flowers, and a sign above the stairs.

5. Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Waterbury
8.0 out of 10, Very good, (1 review)
"I had an emergency and was only able to stay one night, but enjoyed my stay "
United States
Dirk N.
The price is HK$863
HK$1,150 total
includes taxes & fees
25 Oct - 26 Oct
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A compact kitchen with wooden cabinets, a microwave, a sink, and a chair.

6. Cozy Studio apartment in delightful Waterbury with Central Air

Cozy Studio apartment in delightful Waterbury with Central Air
Waterbury
2.0 out of 10, (1 review)
"The place wasn’t how the pictures were on the app. It was hard to find the room. The keys for the room are very hard to open the room door . It’s like you have to struggle just to get inside . The room is inside of an abandoned building… some staff in the building was telling me that I shouldn’t be staying there or they wouldn’t stay there so it made me feel unsafe… the bed doesn’t match the head board. Everything just doesn’t match the images the host posted.."
United States
zynaisha
The price is HK$530
HK$766 total
includes taxes & fees
2 Nov - 3 Nov
Cozy Studio apartment in delightful Waterbury with Central Air
A white house with a wooden staircase leading to a porch.

7. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (37 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
The price is HK$692
HK$953 total
includes taxes & fees
18 Oct - 19 Oct
Cozy One Bedroom Apartment Centrally Located in Southbury
A living room with a sectional sofa, a small side table, and a floor lamp.

8. Lakehaven • Hot Tub, Decks, Fires & More

Lakehaven • Hot Tub, Decks, Fires & More
Plymouth
10.0 out of 10, Exceptional, (1 review)
"Great find!! Amazing views, house was superb!"
United States
Iva B.
The price is HK$2,197
HK$6,090 total
includes taxes & fees
18 Oct - 19 Oct
Lakehaven • Hot Tub, Decks, Fires & More
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

9. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris
9.8 out of 10, Exceptional, (19 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is HK$1,687
HK$2,160 total
includes taxes & fees
18 Oct - 19 Oct
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A deck with a white chair and a table, a sliding glass door, and a potted plant.

10. Bristol Condo Near Espn HQ & Lake Compounce!

Bristol Condo Near Espn HQ & Lake Compounce!
3.5 star property
Bristol
The price is HK$1,373
HK$2,463 total
includes taxes & fees
18 Oct - 19 Oct
Bristol Condo Near Espn HQ & Lake Compounce!
A modern kitchen with stainless steel appliances, a central island, and a dining area with a sofa.

11. #27- Luxury Collection

#27- Luxury Collection
Southington
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home, well designed and spacious rooms. Host was fantastic and communication was great! Thank you"
United States
C B.
The price is HK$1,632
HK$3,658 total
includes taxes & fees
20 Oct - 21 Oct
#27- Luxury Collection
A modern interior with a central light fixture, seating arrangement, and large windows.

12. Coming Soon! #32- Sleeps 10!

Coming Soon! #32- Sleeps 10!
Plymouth
8.0 out of 10, Very good, (1 review)
"Everything was great, just 2 things… Is only 1 tv for the whole apartment, and there is another apartment upstairs and you can hear everything….other than that everything was great."
United States
Humberto H.
The price is HK$1,528
HK$3,727 total
includes taxes & fees
19 Oct - 20 Oct
Coming Soon! #32- Sleeps 10!
A view through a window with a clear sky and lush greenery outside.

13. Private Apartment in Southbury 101

Private Apartment in Southbury 101
Southbury
9.6 out of 10, Exceptional, (7 reviews)
"The apartment was nice, big area, loved this rental."
United States
Marissa G.
The price is HK$1,017
HK$2,172 total
includes taxes & fees
16 Oct - 17 Oct
Private Apartment in Southbury 101
A living room with a sectional sofa, a wooden coffee table, a lamp, and a ceiling fan.

14. #25 Massive 5 BR in Downtown Southington

#25 Massive 5 BR in Downtown Southington
Southington
9.0 out of 10, Wonderful, (4 reviews)
"The house was perfect. We came in for my son’s wedding and had family staying from all over- Canada, Arkansas and Florida. The house worked out perfect. All the rooms are large and the beds are very comfortable. Kitchen is well stocked. There is a bit of a steep staircase to enter the house which can be tricky for the elderly but completely doable. I would definitely rent this property again if needed."
United States
michelle d.
The price is HK$1,545
HK$3,551 total
includes taxes & fees
19 Oct - 20 Oct
#25 Massive 5 BR in Downtown Southington
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

15. Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (3 reviews)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
The price is HK$1,956
HK$5,702 total
includes taxes & fees
29 Oct - 30 Oct
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

16. Escape to Bantam Lake- With Fireplace and Hot tub!

Escape to Bantam Lake- With Fireplace and Hot tub!
Morris
10.0 out of 10, Exceptional, (5 reviews)
"This house is a dream. First, the views are incredible. Second, it’s beautifully decorated and very cozy. Lastly, the property location is perfect. I can’t wait to stay again!"
United States
Shannon M.
The price is HK$2,119
HK$4,199 total
includes taxes & fees
9 Nov - 10 Nov
Escape to Bantam Lake- With Fireplace and Hot tub!
A modern living room with a dark sofa, a small side table, and a kitchen area with a refrigerator and microwave.

17. Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.0 out of 10, Wonderful, (24 reviews)
"Great place clean and quiet "
United States
James P.
The price is HK$973
HK$1,645 total
includes taxes & fees
3 Nov - 4 Nov
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
A modern kitchen with white cabinets, stainless steel appliances, and a dining table with chairs.

18. Private Apartment in Southbury 104

Private Apartment in Southbury 104
Southbury
10.0 out of 10, Exceptional, (1 review)
"Pro Unit very clean, check in was easy and host was responsive to issues 24/7.Unit is large with new appliances in full kitchen.It is located in a beautiful rural area of CT. I highly recommend it"
United States
Daniel R.
The price is HK$1,028
HK$2,169 total
includes taxes & fees
15 Nov - 16 Nov
Private Apartment in Southbury 104
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

19. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and comfortable with easy communication with host I recommend this unit to all who want to visit Wallingford or who desire to take the train to ny or Boston etc"
United States
DAVID B.
The price is HK$926
HK$2,289 total
includes taxes & fees
20 Oct - 21 Oct
All New Studio apartment in center of town
A modern kitchen with white cabinets, a black countertop, and a dining area with a table and chairs.

20. Private Apartment in Southbury 102

Private Apartment in Southbury 102
Southbury
9.0 out of 10, Wonderful, (6 reviews)
"Over all a great place. Nice to have everything on one floor. Dogs loved it. Some businesses in the building and everyone is friendly!"
United States
Debbie P.
The price is HK$926
HK$2,036 total
includes taxes & fees
10 Nov - 11 Nov
Private Apartment in Southbury 102
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

Red Roof Inn Meriden

Red Roof Inn Meriden

10/10 Excellent
"Amazing and clean looking"
Erica 1-night trip
Posted 2 hours ago
Red Roof Inn Meriden

Find out more about Oakville

Search for holiday rentals in Oakville on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakville using one of the methods below:

  • View our selection of featured holiday rentals in Oakville
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Look no further and take a look at our great range of rental properties in Oakville!

Frequently asked questions

Can I find holiday rentals in Oakville?

Yes, there are holiday rentals close to the most popular sights in Oakville, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Oakville has to offer?

Well laid out 2-bedroom private home in Washington-close to the green and depot: This holiday home rental outside of Oakville offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave. Make the most of garden in this rental home to help you unwind.

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 Waterbury Green. In the wider area, you’ll find Palace Theatre and Abbey of Regina Laudis.

What’s a holiday rental in Oakville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakville. Holiday rentals offer extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for small groups.