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Oakville Vacation Rentals

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Oakville vacation rentals

1 bedroom, iron/ironing board, WiFi, bed sheets

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, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is ￥19,033
￥47,535 total
includes taxes & fees
Jun 22 - Jun 23
Once the old Schools house now a newly furnished Apartment
Dining

1 Min to I-91 - Newly Renovated Modern 2 BR Home

1 Min to I-91 - Newly Renovated Modern 2 BR Home
Berlin
The price is ￥24,508
￥49,637 total
includes taxes & fees
Jun 23 - Jun 24
1 Min to I-91 - Newly Renovated Modern 2 BR Home
Fridge, microwave, oven, stovetop

Private Apartment in Southbury 104

Private Apartment in Southbury 104
Southbury
The price is ￥13,936
￥35,181 total
includes taxes & fees
Jun 23 - Jun 24
Private Apartment in Southbury 104
TV

Modern Westville Home Near Yale University

Modern Westville Home Near Yale University
West New Haven
The price is ￥17,420
￥42,010 total
includes taxes & fees
Jun 23 - Jun 24
Modern Westville Home Near Yale University
Exterior

Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.2 out of 10, Wonderful, (5 reviews)
"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 ￥13,888
￥43,558 total
includes taxes & fees
Jun 29 - Jun 30
Cozy Attic 10 min to Llitchfield
Interior

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 ￥17,743
￥23,630 total
includes taxes & fees
Jun 22 - Jun 23
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
TV

Tiny, Budget Friendly 1 Bedroom Central CT

Tiny, Budget Friendly 1 Bedroom Central CT
Southington
The price is ￥16,224
￥35,272 total
includes taxes & fees
Jul 2 - Jul 3
Tiny, Budget Friendly 1 Bedroom Central CT
Exterior

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 ￥19,033
￥46,728 total
includes taxes & fees
Jun 23 - Jun 24
All New 1BR with tons of Charm
TV

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.
The price is ￥19,033
￥47,535 total
includes taxes & fees
Jun 22 - Jun 23
Newly Remodeled with deck. Close to town center
TV

All New Private and Cozy in great location

All New Private and Cozy in great location
Wallingford
8.8 out of 10, Excellent, (6 reviews)
"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 ￥19,033
￥47,535 total
includes taxes & fees
Jun 22 - Jun 23
All New Private and Cozy in great location
Interior

Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.0 out of 10, Wonderful, (7 reviews)
"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 ￥18,582
￥44,596 total
includes taxes & fees
Jun 22 - Jun 23
Private Apartment in Berlin
Interior

The Historic Hideaway

The Historic Hideaway
Avon
6.0 out of 10, (4 reviews)
"Once we found the house it was very warm & cozy. The mini- muffins on the counter was a bonus. House mailbox was 87 but address was 89 that you only see if door is closed which it wasn't on 1st 2 passes. Limited exterior lights made coming back at night a challenge. "
United States
Kim C.
The price is ￥11,775
￥42,678 total
includes taxes & fees
Jun 22 - Jun 23
The Historic Hideaway
Outdoor dining

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 ￥23,518
￥37,087 total
includes taxes & fees
Jun 22 - Jun 23
The Perch in the Purchase -- Cozy, unique, and private
Interior

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 ￥15,969
￥21,590 total
includes taxes & fees
Jul 5 - Jul 6
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Fridge, microwave, oven, stovetop

Entire Private Apartment w/Patio and Big Driveway.

Entire Private Apartment w/Patio and Big Driveway.
West New Haven
10.0 out of 10, Exceptional, (1 review)
"This place was very clean and Michael was great, answering all my questions quickly. check in was simple just a code to get in it was very updated and the beds were very comfortable. It was close to Yale and to some great pizza places"
United States
Sabrina P.
The price is ￥27,582
￥64,947 total
includes taxes & fees
Jun 22 - Jun 23
Entire Private Apartment w/Patio and Big Driveway.
Exterior

The Old Avon Village

The Old Avon Village
Avon
6.2 out of 10, (10 reviews)
"Great location. Alexander was very responsive to any requests. Met our needs. "
United States
Deborah S.
The price is ￥11,775
￥43,646 total
includes taxes & fees
Jun 24 - Jun 25
The Old Avon Village
TV, books

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Shelton
The price is ￥30,558
￥84,077 total
includes taxes & fees
Jun 23 - Jun 24
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Smart TV

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

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.2 out of 10, Wonderful, (20 reviews)
"Easy check in Rooms were comfortably spacious "
United States
Benjamin W.
The price is ￥20,033
￥33,684 total
includes taxes & fees
Jun 29 - Jun 30
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
TV, fireplace

#30 - Spacious & Cozy!

#30 - Spacious & Cozy!
Southington
6.8 out of 10, (5 reviews)
"the house was great for our needs - it was nicely furnished fully stocked with the essentials in the kitchen. the host checked in when it was especially cold to ensure the heat and water were working correctly. the living room was very comfortable with leather reclining chairs and a gas fireplace that heated the room very well. We enjoyed how easy our stay was and recommend this location "
United States
Kaity B.
The price is ￥31,757
￥77,006 total
includes taxes & fees
Jun 22 - Jun 23
#30 - Spacious & Cozy!
Exterior

Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
The price is ￥25,574
￥69,973 total
includes taxes & fees
Jul 8 - Jul 9
Cozy Modern Farmhouse Private Apt - 3 Beds
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

Red Roof Inn Meriden

Red Roof Inn Meriden

10/10 Excellent
"Everything was amazing. I had a smoke-free room, and it was very clean and well maintained. The only two issues I noticed were minor. First, the blanket had a small burn hole that appeared to be from a cigarette, but it wasn't a major concern. Second, on the night before checkout, I returned to my room around 1:45 AM and found that my key card had been deactivated even though my checkout time wasn't until 12:00 PM. The staff corrected the issue immediately, and I appreciated their quick response. Overall, I had a great stay and would return."
Angela 3-night trip
Posted less than an hour ago
Red Roof Inn Meriden

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?

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Fireplace: You might like this vacation home rental near Oakville. It is located on a lake and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 Waterbury Green. In the larger area, you’ll find Waterbury City Hall and Palace Theatre.

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.