Oakville Holiday Rentals

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Check prices for these dates

Tonight
18 Jan - 19 Jan
Tomorrow
19 Jan - 20 Jan
Next weekend
24 Jan - 26 Jan
In two weeks
31 Jan - 2 Feb

Holiday Rentals in Oakville

Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Smart TV, fireplace, ping pong, stereo

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

9.8 out of 10, Exceptional, (22)
"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...
Cozy & Chic Cabin by the Lake, with access to private Beach!
Exterior

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

10.0 out of 10, Exceptional, (20)
"My partner and I stayed here for three days over the new year. Lovely location with very comfortable amenities. Perfect to just settle in and stay cozy in the winter. I will certainly be back during the warm weather to explore the nearby beach"
Cozy & Chic Cabin by the Lake, with access to private Beach!
Historic Whitneyville Cottage
Fridge, microwave, oven, stovetop

Historic Whitneyville Cottage

9.6 out of 10, Exceptional, (14)
"Road noise was annoying. Otherwise as advertised."
Historic Whitneyville Cottage
Amazing Lakefront Property
Dining

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
The Goshen Glass Chalet
Outdoor dining

The Goshen Glass Chalet

9.4 out of 10, Exceptional, (29)
"Nice and cozy property. The host has been very responsive. "
The Goshen Glass Chalet
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Property grounds

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (29)
"Vladimir and Cristina's Plymouth listing is such a great find! It was a great home base for visiting family in the area for the holidays. I don't think I've ever been to a rental that had everything you could possibly need. All this plus an amazing view - we'll be back!"
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Stay 3 Nights or Longer Until January 31 and Get 15% Off
Miscellaneous

Stay 3 Nights or Longer Until January 31 and Get 15% Off

9.8 out of 10, Exceptional, (30)
"A lovely place but a lot of stairs - there is a broken stair lift for the upstairs bedroom - no bathroom on the main floor so for anyone with knee etc issues, this is not the place to stay- beautiful home and location - fully equipped kitchen and comfortable stay otherwise - perfect for warmer months with lake activities"
Stay 3 Nights or Longer Until January 31 and Get 15% Off
Peaceful apartment on 3.5 acres w/ artist studio.
Games room

Peaceful apartment on 3.5 acres w/ artist studio.

9.8 out of 10, Exceptional, (15)
"This adorable cottage attached to the main house was fabulous for my wife and I for 4 nights! It has a little kitchen, space heaters everywhere (us southerners can’t handle the New England winters like we used to!) and was very clean! We have never stayed in an attached rental before and I would say we would be open to exploring more because of our experience! "
The price is HK$1,090
HK$1,641 total
includes taxes & fees
20 Jan - 21 Jan
Peaceful apartment on 3.5 acres w/ artist studio.
River Overlook - Check the view from your deck!
Fridge, microwave, oven, stovetop

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 HK$1,168
HK$2,240 total
includes taxes & fees
20 Jan - 21 Jan
River Overlook - Check the view from your deck!
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Interior

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (18)
"So glad we found this property to accommodate our family of six for the weekend. It was cozy, updated and immaculately clean. The owners seem to have thought of everything and clearly care about providing an exceptional experience. Highly recommend!"
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Cozy Lakefront Bungalow w firepit/dock/kayaks
Terrace/patio

Cozy Lakefront Bungalow w firepit/dock/kayaks

10.0 out of 10, Exceptional, (25)
"This is our second time visiting the area and staying at this beautiful home. It's close to many activities for children and adults, easy to access food and services and a beautiful overall area and home. We truly enjoy visiting!"
Cozy Lakefront Bungalow w firepit/dock/kayaks
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.
1 bedroom, iron/ironing board, WiFi, bed sheets

cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.

The price is HK$638
HK$890 total
includes taxes & fees
20 Jan - 21 Jan
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.
Beautiful cozy rooms near hospital and down town area
Fridge, microwave, oven, stovetop

Beautiful cozy rooms near hospital and down town area

7.8 out of 10, Good, (18)
"I will forever love coming here. The host was great, Parking was amazing, Rooms were so cleanly. "
The price is HK$849
HK$1,932 total
includes taxes & fees
25 Jan - 26 Jan
Beautiful cozy rooms near hospital and down town area
lakefront estate
Pool

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
Guest Cottage on Country Estate
Property grounds

Guest Cottage on Country Estate

9.2 out of 10, Wonderful, (40)
"Beautiful cottage, spectacular property, wonderful hosts. Not sure what else to say? We came up to CT with our pup to look at areas we may want to move to. The cottage was perfect for us, nice and private and lots of land for our pup to walk. Great state park a few miles away and plenty of good restaurants nearby. Very happy!"
Guest Cottage on Country Estate
Fun Downtown Location 2nd flr
Outdoor dining

Fun Downtown Location 2nd flr

9.8 out of 10, Exceptional, (68)
"Nice place, comfy beds, good amenities, clean. Good restaurants."
Fun Downtown Location 2nd flr
Cozy newly remodeled home close to major amenities in Connecticut a
Fridge, microwave, oven, dishwasher

Cozy newly remodeled home close to major amenities in Connecticut a

8.4 out of 10, Very good, (17)
"I stayed for about two days and nights and had a great experience. The house was clean, everything we needed was easy to find, the only thing was that the shower was a little clogged. Overall, it was a great experience!!"
Cozy newly remodeled home close to major amenities in Connecticut a
Tranquil Litchfield Connecticut Retreat".
Property grounds

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 HK$1,713
HK$2,435 total
includes taxes & fees
22 Jan - 23 Jan
Tranquil Litchfield Connecticut Retreat".
Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!
Interior

Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!

10.0 out of 10, Exceptional, (11)
"This was just what we were looking for. The house was roomy, open and charming. It was also relaxing to sit on the back deck surrounded by trees and listening to the calming sound of the brook. It felt like you out in the countryside yet the cute village of Sandy Hook along with Newtown restaurants and shopping were less than 10 minutes away."
Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!
Private hidden gem walking distance to town, restaurants, and shopping!
Outdoor dining

Private hidden gem walking distance to town, restaurants, and shopping!

9.8 out of 10, Exceptional, (14)
"It was very nice and relaxing . Close to everything. "
Private hidden gem walking distance to town, restaurants, and shopping!
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

Holiday Inn Express Southington, an IHG Hotel
Exterior

Holiday Inn Express Southington, an IHG Hotel

2.5 star property
8.8 out of 10, Excellent, (1002)
"Easy access from hi way "
The price is HK$856
HK$985 total
includes taxes & fees
2 Feb - 3 Feb
Holiday Inn Express Southington, an IHG Hotel
The Farmington Inn & Suites
Staircase

The Farmington Inn & Suites

3.0 star property
8.8 out of 10, Excellent, (1002)
"Great staff quaint inn"
The price is HK$771
HK$1,021 total
includes taxes & fees
20 Jan - 21 Jan
The Farmington Inn & Suites
Courtyard by Marriott Waterbury Downtown
Lobby lounge

Courtyard by Marriott Waterbury Downtown

3.0 star property
8.4 out of 10, Very good, (1006)
"Amazing stay as always. We have stayed here for three years on Christmas Eve to visit family. "
The price is HK$771
HK$886 total
includes taxes & fees
24 Jan - 25 Jan
Courtyard by Marriott Waterbury Downtown
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?

Immaculate waterfront home nestled in the Litchfield hills w/ tons of...: This holiday home rental outside of Oakville is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a stovetop, a microwave and a coffee maker, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with an arcade/games room and 1 hot tub.

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 Black Rock State Park. In the wider area, you’ll find Waterbury City Hall and Palace Theatre.

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.