Oakville Holiday Rentals

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Holiday Rentals in Oakville

󰀄 Modern Boho Dream Home 󰀄 Completely Renovated

󰀄 Modern Boho Dream Home 󰀄 Completely Renovated

Amazing Lakefront Property

9.8 out of 10, Exceptional, (24)
"Absolutely beautiful house! Super clean! Superb setting! Very comfortable! Amazing view! Many amenities! Host very responsive and kind! The property manager quickly responded to our needs. My family and friends loved the spectacular experience and would definitely comeback! "
Amazing Lakefront Property

Stylish & Luxurious 3 BDR Home with Play Station

9.4 out of 10, Exceptional, (9)
"We needed a place for our family of 6 to stay while visiting family in the area. This place was exactly what we needed, as advertised, and the owner was quick with communications. We would definitely stay here again!"
Stylish & Luxurious 3 BDR Home with Play Station

Cozy quite private location that makes you feel like home

10.0 out of 10, Exceptional, (3)
"The apartment had everything we needed for our short trip. Bedrooms were cozy and had soft beds, big closets, and their own TVs. The bathroom was amazing!! Double sinks and included rain-like shower head. The kitchen, living room, and large patio were bonuses for this place. I will definitely book again."
The price is AU$338
includes taxes & fees
16 Mar - 17 Mar
Cozy quite private location that makes you feel like home

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (32)
"Went there for a weekend with a friend to hole up and relax in February and it was lovely. Listing is accurate and Cindy was very easy to communicate with. Hot tub was great!"
The Goshen Glass Chalet

Cozy & Chic Cabin by the Lake, with access to private Beach!

10.0 out of 10, Exceptional, (23)
"Very cute , well supplied, clean, nice property. Wed definitely stay again. 1"
Cozy & Chic Cabin by the Lake, with access to private Beach!

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

10.0 out of 10, Exceptional, (6)
"It was a great house to host our family for Thanksgiving dinner! "
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Litchfield County Four Season Country Paradise

9.6 out of 10, Exceptional, (40)
"Considering that area does not have convenient hotels, this location was perfect for the event we attended. It was nice of them to vacate their home so we could stay - though we wish that would have been communicated. There is no extra room with twin beds - at least not functional. The property is nice. Whomever took the pictures did a great job. It worked for us for the short time we were in the area."
Litchfield County Four Season Country Paradise

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

8.0 out of 10, Very good, (1)
"Solo New England trip for a 3 nights. "
The price is AU$165
includes taxes & fees
17 Mar - 18 Mar
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Tranquil Litchfield Connecticut Retreat".

9.4 out of 10, Exceptional, (9)
"This is a neat, clean and lovely little place that perfectly suited our needs. It had all the amenities we needed for our short stay. Jose was a gracious host, answering all of my questions promptly - even the one about the mattresses which were incredibly comfortable! "
The price is AU$504
includes taxes & fees
21 Mar - 22 Mar
Tranquil Litchfield Connecticut Retreat".

Sunny Day Lakefront Cottage - Private Dock, Kayaks, Stunning Lake Views, Family Fun

9.8 out of 10, Exceptional, (33)
"I spent a week at the Cottage at Sunny Day in mid January and it was just what I was looking for. I wanted a quiet, relaxing retreat in a beautiful location. The house was immaculate and very comfortable. Everything was provided, and there was a great fireplace and a beautiful view of Lake Taunton. Jenna and Tony were very nice and easy to deal with and made sure that everything was perfect. It would be a great stay at any time, but would be especially nice in the warm weather with direct access...
Sunny Day Lakefront Cottage - Private Dock, Kayaks, Stunning Lake Views, Family Fun

lakefront estate

3.8 out of 10, (8)
"Overall do not stay in this house! They are scamming people! They say they are military family yet took advantage of one!! Still owe me my refund and refuse to answer VRBO to give the okay to refund my money! This place was not clean it was very unsanitary and there were drug paraphernalia in the backyard! Towels wet and dirty on the bathroom floor and one of the bedrooms the sheets were dirty in the floor claimed that the house keeper cleaned it! The pool was disgusting!! I have videos pictures...
lakefront estate

NEW! LAKE FRONT, Private Dock, Fire Pit, Paddle Boards, Kayaks & Rec Room!

10.0 out of 10, Exceptional, (3)
"First time booking and the place was perfect, beautiful views, real cozy vibes, and the host did a great job to attend at anything we needed "
NEW! LAKE FRONT, Private Dock, Fire Pit, Paddle Boards, Kayaks & Rec Room!

NEW-Another Fun Downtown Location 1st floor

2.0 star property
10.0 out of 10, Exceptional, (10)
"Can’t beat proximity to downtown and other CT locations.Unfortunately we were hit with icy conditions so we could not enjoy all it has to offer. Owner checked in on us and kept driveway safe and clear. We really appreciated his hospitality.The rental was well equipped with everything you need. I LOVED the sunny kitchen to enjoy my morning coffee.We’ll definitely come back when it is warmer!"
NEW-Another Fun Downtown Location 1st floor

Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

9.8 out of 10, Exceptional, (23)
"We made happy memories over a cold January weekend. We cooked together, sat around the fire, played games and dozed in comfortable beds with high quality linens. We enjoyed the view of the water and the twinkling lights on the property at night. The steam shower was divine. If you like cooking, bring good knives, a veggie peeler and good pans. Plenty of glassware and dishes and some cookware provided. "
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

River Overlook - Check the view from your deck!

10.0 out of 10, Exceptional, (15)
"This was a great, cozy place for my wife and I to stay in Collinsville. The rooms were tastefully decorated, in great shape, updated, clean, and peppered with cute artwork based on the "when pigs can fly" theme that always brought a smile to my face when I found another one. The queen bed was very comfortable; the kitchen had all of the appliances, dishes, and cookware we needed; the HVAC system was easy to use and kept the rooms at whatever temperature we wanted; and there was a nice deck with...
The price is AU$427
includes taxes & fees
18 Mar - 19 Mar
River Overlook - Check the view from your deck!

The Jefferson House, Charming, Exceptional, Spacious Home, Estate in Litchfield

10.0 out of 10, Exceptional, (1)
"The lighting is warm and inviting as you step up the stairs into a large open concept room. Every detail is beyond modern from the giant marble counter equipped with the comfiest and largest leather barstools, to the kitchen whose colors and appliances are so beautifully designed; cabinets stocked with every item you need to cook a homemade meal.The king size bed was like a cloud, swallowing us in the fluffiest duvets and sheets, comfortable pillows, making it an easy switch to use the TV in the...
The price is AU$593
includes taxes & fees
19 Mar - 20 Mar
The Jefferson House, Charming, Exceptional, Spacious Home, Estate in Litchfield

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

The price is AU$473
includes taxes & fees
12 Mar - 13 Mar
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

Private Dock & Pool - Candlewood Lake Retreat

10.0 out of 10, Exceptional, (2)
"Incredible host - Jarrett took care of everything for us and made my Birthday weekend , one to remember. Prime location and the views are just beyond words. Pictures don’t do it justice. If you were thinking of booking this do it immediately because it is something you will never forget! "
The price is AU$1,355
includes taxes & fees
12 Mar - 13 Mar
Private Dock & Pool - Candlewood Lake Retreat

Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust

10.0 out of 10, Exceptional, (9)
"We really enjoyed being able to stay at such a beautiful home. Between the animals and the hot tub view - the serenity will be hard to match elsewhere!"
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
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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Other types of properties in Oakville you may be interested in

Courtyard by Marriott Waterbury Downtown

3.0 star property
8.6 out of 10, Excellent, (1020)
"Nice clean hotel. Friendly staff."
The price is AU$163
includes taxes & fees
12 Mar - 13 Mar
Courtyard by Marriott Waterbury Downtown

Holiday Inn Express Southington by IHG

2.5 star property
8.8 out of 10, Excellent, (1013)
"Great for the price it was "
The price is AU$167
includes taxes & fees
16 Mar - 17 Mar
Holiday Inn Express Southington by IHG

Clarion Inn

3.0 star property
7.4 out of 10, Good, (1015)
"Unfortunately we had hoped the converted Best Western plus to Clarion would have gotten even better than it was. No improvements. The room wasn’t heated when we arrived, no bath mat, no shampoo, no shower soap and this time the train outside our window was more annoying than we remembered. Probably won’t go back after many stays there. "
The price is AU$153
includes taxes & fees
17 Mar - 18 Mar
Clarion Inn
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.

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?

󰀄 Modern Boho Dream Home 󰀄 Completely Renovated: This holiday home rental outside of Oakville has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Oakville?

Choose from 5 Expedia holiday rentals in Oakville for a memorable 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 Waterbury Green. In the wider area, you’ll find Soldiers' Monument 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.