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Oakville Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Oakville vacation rentals

Interior

1. 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
8.6 out of 10, Excellent, (10 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is ￥17,344
￥23,099 total
includes taxes & fees
Aug 19 - Aug 20
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Interior

2. 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 ￥19,709
￥25,819 total
includes taxes & fees
Sep 6 - Sep 7
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
House (3 Bedrooms) | Interior

3. Lakefront Home, Close to Mt Southington!

Lakefront Home, Close to Mt Southington!
3.0 star property
Wolcott
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful house with great views of the lake. "
United States
Darrell
Lakefront Home, Close to Mt Southington!
Exterior

4. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (35 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
The price is ￥17,454
￥23,226 total
includes taxes & fees
Sep 2 - Sep 3
Cozy One Bedroom Apartment Centrally Located in Southbury
Property grounds

5. Lakefront Home, Close to Mt Southington!

Lakefront Home, Close to Mt Southington!
Wolcott
10.0 out of 10, Exceptional, (33 reviews)
"This was such a beautiful house, my family enjoyed it all, the view, the lake and the kayaking. House was clean, host was amazing, made our stay one for the books, will definitely book again."
United States
Yogesh R.
Lakefront Home, Close to Mt Southington!
Interior

6. 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 ￥22,399
￥45,752 total
includes taxes & fees
Aug 8 - Aug 9
Private Apartment in Southbury 101
Coffee/tea maker, fridge, microwave, oven

7. 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 ￥23,188
￥46,817 total
includes taxes & fees
Aug 26 - Aug 27
Private Apartment in Southbury 104
Interior

8. 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, (11 reviews)
"The property was very clean and inviting and the owner was very welcoming and helpful!"
United States
Sarah
The price is ￥33,899
￥42,926 total
includes taxes & fees
Aug 19 - Aug 20
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Coffee/tea maker, fridge, microwave, oven

9. Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
10.0 out of 10, Exceptional, (4 reviews)
"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.
The price is ￥23,976
￥48,197 total
includes taxes & fees
Aug 31 - Sep 1
Private Apartment in Southbury 103
Interior

10. The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
9.0 out of 10, Wonderful, (26 reviews)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
The price is ￥10,879
￥39,532 total
includes taxes & fees
Aug 12 - Aug 13
The Sun Filled Cozy Creamery
TV

11. #43- Modern Luxury Log Cabin Retreat | Fire Pit

#43- Modern Luxury Log Cabin Retreat | Fire Pit
Prospect
9.0 out of 10, Wonderful, (2 reviews)
"3.5 rounding up to 4. We had a good stay overall. I travel fairly often and tend to reserve 5 stars for places where every detail of the guest experience feels really thoughtfully considered. This home was comfortable and worked fine for our trip, but it felt a bit more basic compared to some other rentals I’ve stayed in."
United States
Lauren P.
#43- Modern Luxury Log Cabin Retreat | Fire Pit
1 bedroom, iron/ironing board, WiFi, bed sheets

12. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (14 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is ￥18,605
￥45,992 total
includes taxes & fees
Aug 13 - Aug 14
Once the old Schools house now a newly furnished Apartment
Smart TV

13. #23 *COMFORT & LUXURY* 3 BR/2 BA House

#23 *COMFORT & LUXURY* 3 BR/2 BA House
Southington
9.8 out of 10, Exceptional, (9 reviews)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
The price is ￥50,466
￥88,480 total
includes taxes & fees
Aug 29 - Aug 30
#23 *COMFORT & LUXURY* 3 BR/2 BA House
TV

14. Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
Newly Remodeled with deck. Close to town center
Coffee/tea maker, fridge, microwave, oven

15. #16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Southington
9.0 out of 10, Wonderful, (8 reviews)
"We enjoyed our stay! And happy with most!!!!"
United States
Dawn H.
The price is ￥38,634
￥81,008 total
includes taxes & fees
Aug 10 - Aug 11
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Interior

16. 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 ￥22,241
￥45,571 total
includes taxes & fees
Aug 26 - Aug 27
Private Apartment in Southbury 102
Exterior

17. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."
United States
Nadine C.
The price is ￥18,605
￥45,519 total
includes taxes & fees
Aug 31 - Sep 1
All New Studio apartment in center of town
Smart TV

18. 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, (22 reviews)
"Great place clean and quiet "
United States
James P.
The price is ￥20,664
￥34,332 total
includes taxes & fees
Sep 1 - Sep 2
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
TV

19. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Best stay ever! Parking lot was easy; apartment was clean and felt like home. Bed comfortable. Would booked this apartment next trip. My only recommendation that was the kitchen did not have a toaster. "
United States
Linda v.
The price is ￥18,605
￥45,992 total
includes taxes & fees
Aug 13 - Aug 14
Newly Remodeled 1-BR Close to Everything yet Very Private
Outdoor dining

20. The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is ￥22,998
￥36,425 total
includes taxes & fees
Aug 9 - Aug 10
The Perch in the Purchase -- Cozy, unique, and private
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

Wyndham Southbury

Wyndham Southbury

8/10 Good
"Stay was last minute but worked out well. Loved how clean the entire room was."
Cynthia 2-night trip
Posted 1 hour ago
Wyndham Southbury

Find out more about Oakville

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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?

Well laid out 2-bedroom private home in Washington-close to the green and depot: This vacation home near Oakville offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave. Make the most of the 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 Lake Quassapaug. In the larger area, you’ll find Palace Theatre and Seven Angels Theater.

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.