Oakville Holiday Rentals

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Holiday Rentals in Oakville

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, (17)
"great chic house, very clean"
Cozy & Chic Cabin by the Lake, with access to private Beach!
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Property grounds

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (27)
"We stayed at the property for 2 nights and it was just what we had hoped. We enjoyed the lake, the fall colors and the house thoroughly. Would love to come back someday. "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
TWO BEDROOM APARTMENT ON FIRST FLOOR ON A DUPLEX
Fridge, microwave, stovetop, dishwasher

TWO BEDROOM APARTMENT ON FIRST FLOOR ON A DUPLEX

9.8 out of 10, Exceptional, (18)
"My stay here was amazing.Very clean.Very welcoming with a forever homely feel.The communication with the property owner/manager was great and very helpful with everything.When i return to Connecticut,I will be looking forward to returning to this rental and also recommending to family and friends if traveling to the area.5*"
TWO BEDROOM APARTMENT ON FIRST FLOOR ON A DUPLEX
Historic Whitneyville Cottage
Fridge, microwave, oven, stovetop

Historic Whitneyville Cottage

9.4 out of 10, Exceptional, (13)
"Road noise was annoying. Otherwise as advertised."
Historic Whitneyville Cottage
Charming 1870 cape cottage in Litchfield
Outdoor dining

Charming 1870 cape cottage in Litchfield

10.0 out of 10, Exceptional, (40)
"Beautiful property. Super clean. Wish we could have stayed longer."
Charming 1870 cape cottage in Litchfield
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, (29)
"The place has stunning views from just about every window. Taunton Lake is so serene and the surrounding area has so much local charm. The beds were comfy and the amenities were abundant. I hope to be back again someday."
Stay 3 Nights or Longer Until January 31 and Get 15% Off
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$637
HK$888 total
includes taxes & fees
20 Dec - 21 Dec
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.
Fun Downtown Location 2nd flr
Outdoor dining

Fun Downtown Location 2nd flr

9.8 out of 10, Exceptional, (66)
"This place is amazing. It has just such a homey feel to it. My 2 year son and I stayed here and he absolutely loved it and to me it just felt like a nice comfort, home environment and when you’re traveling that’s all you really want is a place that makes you feel at home and that’s what you get when you stay here. "
Fun Downtown Location 2nd flr
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, (21)
"Gorgeous home and property, loved being on the lake with the game room cabana, the outdoor areas are so relaxing, and the home is so tastefully decorated. We enjoyed it so much!"
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
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, (16)
"I love staying here. Each visit I bring something new from Louisiana and leave it for the next guest. The cooking supplies are admirable for a home, and especially so for a home away-from-home. We couldn't find a better place to stay. The beds are super comfy, though the furniture requires extra padding. Fortunately there are lots of blankets to use as cishioning."
Cozy newly remodeled home close to major amenities in Connecticut a
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!
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
Candlewood Lake Retreat with year round views
Property grounds

Candlewood Lake Retreat with year round views

10.0 out of 10, Exceptional, (10)
"Liked outdoor area and fire place "
Candlewood Lake Retreat with year round views
Peaceful farm area, on the reservoir, near vineyards
Smart TV

Peaceful farm area, on the reservoir, near vineyards

10.0 out of 10, Exceptional, (27)
"Everything about this property makes me smile!!! From the location to the hosts and everything in between, it is just PERFECT!!! This will be the first property I check availability on when we visit the area. It is quaint, clean, nicely appointed and the hosts are wonderful people!"
Peaceful farm area, on the reservoir, near vineyards
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$1,166
HK$2,251 total
includes taxes & fees
1 Jan - 2 Jan 2025
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
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
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
Tranquil Litchfield Connecticut Retreat".
Property grounds

Tranquil Litchfield Connecticut Retreat".

9.4 out of 10, Exceptional, (8)
"Perfect location for visiting family in the area. Close to restaurants, grocery stores and other amenties. Simple place with everything you need to make visiting family plessurable. The washer and dryer will remind me to pack much less next time. Jose was a grear jost. On top of any questions and responded within the hour. Thank you for allowing us into your property. Shane share "
The price is HK$1,709
HK$2,453 total
includes taxes & fees
29 Dec - 30 Dec
Tranquil Litchfield Connecticut Retreat".
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

Courtyard by Marriott Waterbury Downtown
Lobby

Courtyard by Marriott Waterbury Downtown

3.0 star property
8.4 out of 10, Very good, (1002)
"I recomended"
The price is HK$769
HK$885 total
includes taxes & fees
24 Dec - 25 Dec
Courtyard by Marriott Waterbury Downtown
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)
"Clean, good shower, decent breakfast. We ‘ve stayed here before and find it a fine place for a quick stay while traveling. "
The price is HK$855
HK$983 total
includes taxes & fees
5 Jan - 6 Jan 2025
Holiday Inn Express Southington, an IHG Hotel
Red Roof Inn Meriden
Exterior

Red Roof Inn Meriden

2.0 star property
7.6 out of 10, Good, (1001)
"Room was ok clean, but needs some work. Is outdated. "
The price is HK$700
HK$805 total
includes taxes & fees
19 Dec - 20 Dec
Red Roof Inn Meriden
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?

Stay 3 Nights or Longer Until January 31 and Get 15% Off: This holiday home rental outside of Oakville is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 Lake Quassapaug. 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.