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Oakville Vacation Rentals

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

Our top choices for Oakville vacation rentals

House (3 Bedrooms) | 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
$443 nightly
The price is $510
Jan 2 - Jan 3, 2026
Total with taxes and fees
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Exterior
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
$170 nightly
The price is $193
Dec 28 - Dec 29
Total with taxes and fees
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
Private kitchen
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.
$239 nightly
The price is $239
Jan 8 - Jan 9, 2026
Total with taxes and fees
Westville Stay • 2BR • Near Yale • Free Parking
1 bedroom, iron/ironing board, WiFi, bed sheets
Once the old Schools house now a newly furnished Apartment

Vacation 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.
$271 nightly
The price is $288
Jan 2 - Jan 3, 2026
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
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.
8.6 out of 10, Excellent, (10)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
$109 nightly
The price is $122
Jan 3 - Jan 4, 2026
Total with taxes and fees
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Fridge, microwave, oven, stovetop
Private Apartment in Berlin

Vacation 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.
$266 nightly
The price is $301
Dec 28 - Dec 29
Total with taxes and fees
Private Apartment in Berlin
Fridge, microwave, oven, stovetop
#26 Beautifully Renovated 2 BR Home

Vacation 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.
$217 nightly
The price is $234
Jan 5 - Jan 6, 2026
Total with taxes and fees
#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
$106 nightly
The price is $118
Dec 29 - Dec 30
Total with taxes and fees
New One Bedroom Apartment Centrally Located in Southbury
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.
$246 nightly
The price is $279
Dec 29 - Dec 30
Total with taxes and fees
Private Apartment in Southbury 103
Fridge, microwave, oven, stovetop
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.
New Railside Residents
Fridge, microwave, oven, stovetop
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.
$271 nightly
The price is $288
Jan 1 - Jan 2, 2026
Total with taxes and fees
All New 1BR with tons of Charm
1 bedroom, iron/ironing board, WiFi, bed sheets
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.
$271 nightly
The price is $288
Jan 12 - Jan 13, 2026
Total with taxes and fees
All New Studio apartment in center of town
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.
$238 nightly
The price is $270
Dec 28 - Dec 29
Total with taxes and fees
Private Apartment in Southbury 101
Exterior
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.
$271 nightly
The price is $288
Jan 3 - Jan 4, 2026
Total with taxes and fees
Newly Remodeled with deck. Close to town center
Fridge, microwave, oven, stovetop
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.
$145 nightly
The price is $163
Jan 14 - Jan 15, 2026
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Microwave, oven, stovetop, dishwasher
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
$169 nightly
The price is $191
Dec 29 - Dec 30
Total with taxes and fees
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
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.
$298 nightly
The price is $342
Dec 30 - Dec 31
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Property grounds
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.
$242 nightly
The price is $275
Jan 20 - Jan 21, 2026
Total with taxes and fees
Private Apartment in Southbury 102
Outdoor dining
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.
$233 nightly
The price is $245
Jan 9 - Jan 10, 2026
Total with taxes and fees
The Historic Hideaway
TV
Newly Remodeled 1-BR Close to Everything yet Very Private

Vacation Home in Wallingford

Newly Remodeled 1-BR Close to Everything yet Very Private
10.0 out of 10, Exceptional, (9)
"The flat has a nice layout and was very comfortable. We enjoyed our stay."
United States
Mary R.
$271 nightly
The price is $288
Jan 1 - Jan 2, 2026
Total with taxes and fees
Newly Remodeled 1-BR Close to Everything yet Very 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

Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

10/10 Excellent
"The employees are wonderful and front desk me, I was very ill and immediately offered a water. Rooms were clean. The had hot cocoa and marshmallows and cookies felt so welcoming. Great place to stay if your traveling for work "
Kimberly 1-night trip
Posted 2 days ago
Courtyard by Marriott Waterbury Downtown

Find out more about Oakville

Everything you need to know about Oakville vacation rentals

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

Oakville vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oakville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $118 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oakville rentals

At Expedia, we put the best Oakville vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Private Apartment in Berlin: This vacation home rental near Oakville is equipped with a balcony, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 larger area, you’ll find Union Station Clocktower and Mattatuck Museum Arts and History Center.

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.