Holiday Rentals in Oakville

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Holiday Rentals in Oakville

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

3.0 star property
Oakville
The price is €367
includes taxes & fees
17 Nov - 18 Nov
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Westville Stay • 2BR • Near Yale • Free Parking

West New Haven
10.0 out of 10, Exceptional, (1)
"The unit was very clean and in a walkable neighborhood. Laundry was shared but easy to use in basement. The parking is not included. There's lots of safe street parking. "
United States
Thomas B.
The price is €220
includes taxes & fees
19 Nov - 20 Nov
Westville Stay • 2BR • Near Yale • Free Parking

All New Private and Cozy in great location

Wallingford
8.8 out of 10, Excellent, (6)
"The pictures must have been old. Very deceiving. Expected it to be more spacious. Hard to get in and out because of the busy road"
United States
ROBERT P.
The price is €228
includes taxes & fees
21 Nov - 22 Nov
All New Private and Cozy in great location

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

Watertown
9.8 out of 10, Exceptional, (7)
"Great place, friendly people as usual! Love the place! We always enjoy our stay! Thanks again Brian and Laurie "
United States
Laurie P.
The price is €109
includes taxes & fees
17 Nov - 18 Nov
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

All New Fully Furnished Cozy Studio

Wallingford Center
9.8 out of 10, Exceptional, (8)
"Clean and well designed apartment in a great location. Book here if you are interested as you won't have any regrets. Enjoy! "
United States
Rick C.
The price is €228
includes taxes & fees
17 Nov - 18 Nov
All New Fully Furnished Cozy Studio

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

Southington
9.8 out of 10, Exceptional, (8)
"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 €260
includes taxes & fees
17 Nov - 18 Nov
#23 *COMFORT & LUXURY* 3 BR/2 BA House

Private Apartment in Berlin

2.0 star property
Berlin
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.
The price is €278
includes taxes & fees
17 Nov - 18 Nov
Private Apartment in Berlin

The Sun Filled Cozy Creamery

Plainville
8.8 out of 10, Excellent, (24)
"Pleasure staying here. "
United States
Jesse H.
The price is €242
includes taxes & fees
21 Nov - 22 Nov
The Sun Filled Cozy Creamery

Once the old Schools house now a newly furnished Apartment

Wallingford Center
9.0 out of 10, Wonderful, (13)
"The fact that it was listed with a hot tub and there wasn't one was very disappointing! Clean and cute. Location was convenient. Could use a better bed and pillows. It was a good place to stay,"
United States
Robert K.
The price is €228
includes taxes & fees
26 Nov - 27 Nov
Once the old Schools house now a newly furnished Apartment

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

Cheshire
9.2 out of 10, Wonderful, (11)
"Very nice location in a country setting. Saw deer in the backyard every morning. Very clean and accurate description of the property. Friendly hosts who supplied everything we needed. Would stay here again. Highly recommend."
United States
Eileen A.
The price is €144
includes taxes & fees
17 Nov - 18 Nov
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Soothing 2-bedroom lower-level apartment in Berlin

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.
The price is €246
includes taxes & fees
17 Nov - 18 Nov
Soothing 2-bedroom lower-level apartment in Berlin

ENTIRE APARTMENT RECENTLY RENOVATED 2BR

Ansonia
8.0 out of 10, Very good, (3)
"Home was great, Will definitely be returning "
United States
Daniel M.
ENTIRE APARTMENT RECENTLY RENOVATED 2BR

Newly Remodeled with deck. Close to town center

Wallingford
10.0 out of 10, Exceptional, (2)
"Felt like coming home. Moved out of state 20 yrs ago. "
United States
Beth C.
The price is €228
includes taxes & fees
13 Dec - 14 Dec
Newly Remodeled with deck. Close to town center

Private Apartment in Southbury 101

Southbury
9.4 out of 10, Exceptional, (6)
"Great stay. Clean, open space, easy access, and a nice pond in back to bring the dog. Would come back again."
United States
Rooster D.
The price is €255
includes taxes & fees
19 Nov - 20 Nov
Private Apartment in Southbury 101

#31 - Downtown Terryville- 1 Br

Plymouth
10.0 out of 10, Exceptional, (1)
"In convenient safe area. Os is easy to contact"
United States
Gina P.
The price is €206
includes taxes & fees
22 Nov - 23 Nov
#31 - Downtown Terryville- 1 Br

New One Bedroom Apartment Centrally Located in Southbury

Southbury
9.8 out of 10, Exceptional, (16)
"Excellent stay !!!! Everything was perfect. Communication was phenomenal.!!!!"
United States
daniellle
The price is €115
includes taxes & fees
23 Nov - 24 Nov
New One Bedroom Apartment Centrally Located in Southbury

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Torrington
9.6 out of 10, Exceptional, (4)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
The price is €241
includes taxes & fees
17 Nov - 18 Nov
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Private Apartment in Southbury 103

Southbury
10.0 out of 10, Exceptional, (2)
"The host was amazing! We had no problems at all whatsoever. "
United States
Manduella F.
The price is €256
includes taxes & fees
1 Dec - 2 Dec
Private Apartment in Southbury 103

The Historic Hideaway

2.0 star property
Avon
7.0 out of 10, Good, (2)
"House exactly as listed. We had a question and the property owner replied instantly - great communication. Close to Talcott Mountain which was an amazing hike with beautiful views. "
United States
Nicole M.
The price is €248
includes taxes & fees
18 Nov - 19 Nov
The Historic Hideaway

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

New Britain
10.0 out of 10, Exceptional, (7)
"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.
The price is €219
includes taxes & fees
18 Nov - 19 Nov
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
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

Find out more about Oakville

Everything you need to know about Oakville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oakville holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakville holiday rentals we have selected for you start as low as €115 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oakville rentals

At Expedia, we put the best Oakville holiday 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 holiday.

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. 

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?

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit: This holiday home rental outside of Oakville is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. It offers a garden, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

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 Hollow Park. In the wider area, you’ll find Union Station Clocktower and Waterbury City Hall.

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.