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Oakville Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

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
8.8 out of 10, Excellent, (11 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is AED 404
AED 538 total
includes taxes & fees
19 Aug - 20 Aug
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 AED 404
AED 538 total
includes taxes & fees
8 Sep - 9 Sep
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Interior

3. 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, (13 reviews)
"The property was very clean and inviting and the owner was very welcoming and helpful!"
United States
Sarah
The price is AED 790
AED 1,022 total
includes taxes & fees
16 Aug - 17 Aug
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Coffee/tea maker, fridge, microwave, oven

4. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (8 reviews)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
United States
Jennifer A.
The price is AED 1,131
AED 1,461 total
includes taxes & fees
18 Aug - 19 Aug
The Jefferson Guest House, Spacious, Special Views
Exterior

5. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (36 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 AED 364
AED 492 total
includes taxes & fees
10 Sep - 11 Sep
Cozy One Bedroom Apartment Centrally Located in Southbury
TV

6. 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 AED 433
AED 1,086 total
includes taxes & fees
15 Aug - 16 Aug
Newly Remodeled 1-BR Close to Everything yet Very Private
Coffee/tea maker, fridge, microwave, oven

7. 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 AED 514
AED 1,068 total
includes taxes & fees
9 Sep - 10 Sep
Private Apartment in Southbury 103
Interior

8. #3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!

#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!
Plainville
8.8 out of 10, Excellent, (15 reviews)
"Great place and good location."
United States
MARC S.
#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!
Coffee/tea maker, fridge, microwave, oven

9. 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 AED 400
AED 919 total
includes taxes & fees
18 Aug - 19 Aug
Private Apartment in Southbury 104
TV, fireplace

10. #41- Available 12/8! - sleeps 14

#41- Available 12/8! - sleeps 14
Southington
The price is AED 1,293
AED 2,512 total
includes taxes & fees
26 Aug - 27 Aug
#41- Available 12/8! - sleeps 14
Smart TV, fireplace

11. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (19 reviews)
"Wow what an enjoyable stay! Clean, fresh, relaxing, and wonderful to meet owners Corin and Jen… gracious and hospitable hosts. Very comfortable, great location, well appointed… everything we were looking for!"
United States
James M.
The price is AED 624
AED 1,068 total
includes taxes & fees
1 Sep - 2 Sep
Pristine Cozy Walkable Downtown 2BR Getaway
Exterior

12. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is AED 433
AED 1,086 total
includes taxes & fees
3 Sep - 4 Sep
All New 1BR with tons of Charm
Interior

13. 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 AED 253
AED 932 total
includes taxes & fees
19 Aug - 20 Aug
The Sun Filled Cozy Creamery
TV

14. Tiny, Budget Friendly 1 Bedroom Central CT

Tiny, Budget Friendly 1 Bedroom Central CT
Southington
8.0 out of 10, Very Good, (1 review)
"There were minor cleaning issues in the bathroom, and my only/biggest complaint is the listing is misleading as it says you have no neighbors but the space is physically attached to a larger house and the driveway and entry/exit doors for both units open into the same small space. Additionally the front door has a large glass window with no curtains so you have absolutely no privacy. This is a direct conflict with the listing and I did bring this up to the landlord. That being said the location...
United States
Zackary G.
The price is AED 330
AED 765 total
includes taxes & fees
16 Aug - 17 Aug
Tiny, Budget Friendly 1 Bedroom Central CT
Outdoor dining

15. 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
Collinsville
10.0 out of 10, Exceptional, (68 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is AED 1,146
AED 1,953 total
includes taxes & fees
17 Aug - 18 Aug
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
1 bedroom, iron/ironing board, WiFi, bed sheets

16. 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 AED 433
AED 1,082 total
includes taxes & fees
6 Sep - 7 Sep
Once the old Schools house now a newly furnished Apartment
Dining

17. Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Torrington
10.0 out of 10, Exceptional, (1 review)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
The price is AED 859
AED 1,914 total
includes taxes & fees
16 Aug - 17 Aug
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Interior

18. 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 AED 415
AED 939 total
includes taxes & fees
18 Aug - 19 Aug
Private Apartment in Southbury 101
Smart TV

19. 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 AED 476
AED 808 total
includes taxes & fees
26 Aug - 27 Aug
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Interior

20. New Railside Residents

New Railside Residents
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"Clean & comfortable, in an architecturally unique setting. Great proximity to a variety of downtown shops & restaurants - check out Center Street Brewing Co. for some excellent beer."
United States
Thomas S.
New Railside Residents
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

The Farmington Inn & Suites

The Farmington Inn & Suites

10/10 Excellent
"Great service! Very friendly and helpful staff. "
Nicole 1-night trip
Posted 1 hour ago
The Farmington Inn & Suites

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.