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Oakville Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Oakville holiday rentals

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

Cottage in Oakville

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
The price is HK$1,711
HK$3,964 total
includes taxes & fees
2 Jan - 3 Jan 2026
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
1 bedroom, free WiFi, bed sheets
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

Camping in New Milford

Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
1.0 star property
8.0 out of 10, Very good, (1)
"We camped at Freedom Farm and enjoyed the secluded woods setting for our tent. Everything was clean and well prepared for our stay, and the hosts were friendly and helpful. It is beautifully situated and is a short drive from some excellent hiking and biking in nearby state parks. I think a couple of things, though, could be improved. The tent was set up on an incline, which made sleeping a bit less comfortable than it might have been. I would recommend that the hosts build a level platform...
United States
Eric
The price is HK$1,167
HK$1,505 total
includes taxes & fees
25 Dec - 26 Dec
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
Interior
Westville Stay • 2BR • Near Yale • Free Parking

Apartment in West New Haven

Westville Stay • 2BR • Near Yale • Free Parking
10.0 out of 10, Exceptional, (3)
"We were only here for a short stay, but everything was smooth and comfortable for us! Hotel-like linens and blackout curtains made for a very cozy sleeping experience."
United States
ross f.
The price is HK$622
HK$1,821 total
includes taxes & fees
8 Jan - 9 Jan 2026
Westville Stay • 2BR • Near Yale • Free Parking
Interior
The Historic Hideaway

Apartment in Avon

The Historic Hideaway
2.0 star property
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 HK$436
HK$1,906 total
includes taxes & fees
9 Jan - 10 Jan 2026
The Historic Hideaway
Interior
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Apartment in Watertown

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
9.0 out of 10, Wonderful, (8)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is HK$692
HK$952 total
includes taxes & fees
5 Jan - 6 Jan 2026
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Fridge, microwave, oven, stovetop
#26 Beautifully Renovated 2 BR Home

Holiday Home in Plainville

#26 Beautifully Renovated 2 BR Home
10.0 out of 10, Exceptional, (4)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
The price is HK$907
HK$1,821 total
includes taxes & fees
5 Jan - 6 Jan 2026
#26 Beautifully Renovated 2 BR Home
Exterior
New One Bedroom Apartment Centrally Located in Southbury

Apartment in Southbury

New One Bedroom Apartment Centrally Located in Southbury
9.8 out of 10, Exceptional, (20)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is HK$700
HK$961 total
includes taxes & fees
29 Dec - 30 Dec
New One Bedroom Apartment Centrally Located in Southbury
Smart TV
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Apartment in Cheshire

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.4 out of 10, Exceptional, (13)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is HK$665
HK$1,278 total
includes taxes & fees
26 Dec - 27 Dec
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Exterior
All New 1BR with tons of Charm

Apartment in Wallingford Center

All New 1BR with tons of Charm
9.8 out of 10, Exceptional, (7)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is HK$894
HK$2,242 total
includes taxes & fees
30 Dec - 31 Dec
All New 1BR with tons of Charm
Interior
Private Apartment in Berlin

Holiday Home in Berlin

Private Apartment in Berlin
2.0 star property
9.2 out of 10, Wonderful, (5)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
The price is HK$824
HK$2,344 total
includes taxes & fees
11 Jan - 12 Jan 2026
Private Apartment in Berlin
Dining
Once the old Schools house now a newly furnished Apartment

Holiday Home in Wallingford Center

Once the old Schools house now a newly furnished Apartment
9.0 out of 10, Wonderful, (13)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is HK$894
HK$2,242 total
includes taxes & fees
2 Jan - 3 Jan 2026
Once the old Schools house now a newly furnished Apartment
Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Apartment in Torrington

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
9.6 out of 10, Exceptional, (4)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
The price is HK$692
HK$2,656 total
includes taxes & fees
30 Dec - 31 Dec
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Interior
Private Apartment in Southbury 101

Apartment in Southbury

Private Apartment in Southbury 101
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 HK$824
HK$2,095 total
includes taxes & fees
20 Jan - 21 Jan 2026
Private Apartment in Southbury 101
Fridge, microwave, oven, stovetop
Private Apartment in Southbury 103

Apartment in Southbury

Private Apartment in Southbury 103
10.0 out of 10, Exceptional, (2)
"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 HK$824
HK$2,095 total
includes taxes & fees
20 Jan - 21 Jan 2026
Private Apartment in Southbury 103
Interior
All New Studio apartment in center of town

Apartment in Wallingford Center

All New Studio apartment in center of town
10.0 out of 10, Exceptional, (2)
"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 HK$894
HK$2,242 total
includes taxes & fees
4 Jan - 5 Jan 2026
All New Studio apartment in center of town
Outdoor dining
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.

Apartment in Southbury

Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
2.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is HK$884
HK$1,486 total
includes taxes & fees
29 Dec - 30 Dec
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
Interior
New Railside Residents

Apartment in Wallingford Center

New Railside Residents
10.0 out of 10, Exceptional, (1)
"This apartment was the perfect base for visiting family in Wallingford. It had everything we needed, was very clean, and super convenient to downtown cafes and restaurants. The train is a bit loud but to be expected! Will definitely stay again. "
United States
Kelsey S.
The price is HK$894
HK$2,242 total
includes taxes & fees
30 Dec - 31 Dec
New Railside Residents
TV
Newly Remodeled with deck. Close to town center

Apartment in Wallingford

Newly Remodeled with deck. Close to town center
10.0 out of 10, Exceptional, (2)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
The price is HK$894
HK$2,242 total
includes taxes & fees
3 Jan - 4 Jan 2026
Newly Remodeled with deck. Close to town center
Fridge, microwave, oven, stovetop
Private Apartment in Southbury 102

Apartment in Southbury

Private Apartment in Southbury 102
9.6 out of 10, Exceptional, (4)
"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$825
HK$2,096 total
includes taxes & fees
20 Jan - 21 Jan 2026
Private Apartment in Southbury 102
TV
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Holiday Home in New Britain

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
10.0 out of 10, Exceptional, (8)
" Heck-on was smooth and the kitchen and facilities were great. "
United States
Elizabeth P.
The price is HK$875
HK$1,916 total
includes taxes & fees
5 Jan - 6 Jan 2026
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

Homewood Suites by Hilton Southington, CT

Homewood Suites by Hilton Southington, CT

10/10 Excellent
"Staff was Amazing 👏 👏 My family had a great time and we have all intentions of returning very soon 😀 "
Liza Marie 2-night trip
Posted 1 day ago
Homewood Suites by Hilton Southington, CT

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
  • Use the map to find apartments and other holiday homes in the Oakville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakville while they last

Look no further and take a look at our great range of rental properties in Oakville!

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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?

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage: This holiday home rental outside of Oakville offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

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 Holy Land USA. In the wider area, you’ll find Mattatuck Museum Arts and History Center 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.