Oakville Vacation Rentals

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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Oakville vacation rentals

House (3 Bedrooms) | Interior

Cottage in Oakville

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
The price is ￥34,973
￥81,033 total
includes taxes & fees
Mar 14 - Mar 15
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Interior

Cabin in Bethlehem

Cozy & Serene Cabin with Fireplace, Ski Nearby!
9.8 out of 10, Exceptional, (40 reviews)
"Very comfortable property. The host had thought of everything!"
United States
Jennifer Y.
Cozy & Serene Cabin with Fireplace, Ski Nearby!
TV

Vacation Home in Wallingford Center

Once the old Schools house now a newly furnished Apartment
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 ￥20,110
￥46,337 total
includes taxes & fees
Mar 14 - Mar 15
Once the old Schools house now a newly furnished Apartment
Exterior

Apartment in Wallingford Center

All New 1BR with tons of Charm
9.8 out of 10, Exceptional, (8 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is ￥20,110
￥48,086 total
includes taxes & fees
Mar 15 - Mar 16
All New 1BR with tons of Charm
Interior

Apartment in Torrington

Pristine, Walkable downtown, Entire 2 Bedroom apartment
10.0 out of 10, Exceptional, (17 reviews)
"Everything about our stay was great - Corin and Jen were wonderful hosts. The place is spotless, cozy, comfy. Love that they were right next to the Green Way Trail along the river. Will absolutely stay there again! "
United States
Kate B.
The price is ￥25,435
￥44,670 total
includes taxes & fees
Mar 15 - Mar 16
Pristine, Walkable downtown, Entire 2 Bedroom apartment
Exterior

Apartment in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
10.0 out of 10, Exceptional, (23 reviews)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is ￥14,519
￥19,883 total
includes taxes & fees
Mar 16 - Mar 17
Cozy One Bedroom Apartment Centrally Located in Southbury
Fridge, microwave, oven, stovetop

Apartment in Litchfield

The Jefferson Guest House, Spacious, Special Views
10.0 out of 10, Exceptional, (8 reviews)
"The place was absolutely spotless and magnificent in every way. Highly recommended."
United States
Robert A.
The price is ￥46,356
￥59,551 total
includes taxes & fees
Mar 15 - Mar 16
The Jefferson Guest House, Spacious, Special Views
Cottage (3 Bedrooms) | Interior

Cottage in New Preston

Dainty New Preston Cottage w/ Dock & Lake Views!
3.0 star property
The price is ￥34,020
￥82,172 total
includes taxes & fees
Apr 10 - Apr 11
Dainty New Preston Cottage w/ Dock & Lake Views!
Dining

Apartment in New Britain

Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
7.6 out of 10, Good, (7 reviews)
" Not bad for the price "
United States
Audrey L.
The price is ￥21,898
￥59,122 total
includes taxes & fees
Mar 14 - Mar 15
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
Private kitchen

Vacation Home in Torrington

Litchfield Retreat, Wineries, Foliage & Skiing
The price is ￥41,491
￥63,214 total
includes taxes & fees
Mar 14 - Mar 15
Litchfield Retreat, Wineries, Foliage & Skiing
Exterior

Vacation Home in Goshen

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
10.0 out of 10, Exceptional, (1 review)
"Without a doubt, we will be back! Your home was so beautiful, warm and comfortable. Our host was so helpful and friendly. We can't thank you enough for providing such a wonderful experience to our trip. "
United States
Linda D.
The price is ￥42,127
￥94,388 total
includes taxes & fees
Mar 14 - Mar 15
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Private kitchen

Vacation Home in Hamden

Welcoming 4-bedroom house in charming Hamden
10.0 out of 10, Exceptional, (1 review)
"Host was kind and attentive. Location was convenient and the home was clean and spacious. "
United States
Renee H.
The price is ￥36,372
￥66,786 total
includes taxes & fees
Mar 15 - Mar 16
Welcoming 4-bedroom house in charming Hamden
Fridge, microwave, oven, stovetop

Apartment in Southbury

Private Apartment in Southbury 103
10.0 out of 10, Exceptional, (2 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 ￥13,735
￥34,514 total
includes taxes & fees
Mar 14 - Mar 15
Private Apartment in Southbury 103
TV

Vacation Home in Wallingford

Newly Remodeled 1-BR Close to Everything yet Very Private
10.0 out of 10, Exceptional, (9 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
The price is ￥20,110
￥47,291 total
includes taxes & fees
Apr 1 - Apr 2
Newly Remodeled 1-BR Close to Everything yet Very Private
Property grounds

Apartment in Collinsville

River Overlook - Check the view from your deck!
10.0 out of 10, Exceptional, (23 reviews)
"The place was perfect for the two of us. It was close to both our kids homes."
United States
Tomas M.
The price is ￥23,687
￥45,879 total
includes taxes & fees
Mar 29 - Mar 30
River Overlook - Check the view from your deck!
Fridge, microwave, oven, stovetop

Vacation Home in Southington

#27- Luxury Collection
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home, well designed and spacious rooms. Host was fantastic and communication was great! Thank you"
United States
C B.
The price is ￥28,456
￥67,698 total
includes taxes & fees
Mar 19 - Mar 20
#27- Luxury Collection
Smart TV

Apartment in Cheshire

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.4 out of 10, Exceptional, (16 reviews)
"Great Location - all the amenities you need for a nice restful stay. Did not have to reach-out to the host at all during our stay. "
United States
Robert S.
The price is ￥18,456
￥31,717 total
includes taxes & fees
Mar 24 - Mar 25
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Property grounds

Vacation Home in Southington

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
9.0 out of 10, Wonderful, (7 reviews)
"We enjoyed our stay! And happy with most!!!!"
United States
Dawn H.
The price is ￥63,429
￥112,368 total
includes taxes & fees
Mar 28 - Mar 29
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Interior

Apartment in Plainville

#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!
8.4 out of 10, Very Good, (12 reviews)
"Great place ! Quiet and safe place! We will be back! "
United States
Aubrey C.
The price is ￥22,097
￥50,688 total
includes taxes & fees
Mar 15 - Mar 16
#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!
Outdoor dining

Apartment in Southbury

The Perch in the Purchase -- Cozy, unique, and private
10.0 out of 10, Exceptional, (1 review)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is ￥20,946
￥33,665 total
includes taxes & fees
Mar 22 - Mar 23
The Perch in the Purchase -- Cozy, unique, and 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

Hamden Hotel and Suites – Hamden New Haven

Hamden Hotel and Suites – Hamden New Haven

4/10 Poor
"The heat did not work in the room the breakfast staff were very nice and the breakfast was great"
tomorrow 1-night trip
Posted 2 hours ago
Hamden Hotel and Suites – Hamden New Haven

Find out more about Oakville

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

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: This vacation home near Oakville 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. You can relax into your vacation with an arcade game room and a hot tub.

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 Bellamy-Ferriday House and Garden. In the larger area, you’ll find Mattatuck Museum Arts and History Center 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.