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Oakville holiday rentals

We found 136 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Oakville that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include a hot tub and a washer and dryer. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Oakville

Showing deals for:13 Nov - 20 Nov

Private kitchen
Gorgeous sunsets every night
Movie room with 85" 4k screen and surround sound Sonos System
Steam shower
Exceptional
(55 reviews)

Litchfield County Four Season Country Paradise

Roxbury

8% off
AU$11,620
for 7 nights, 1 home
AU$1,660 per night
includes taxes & fees
Litchfield County Four Season Country Paradise
Living Room
Sunset
Bedroom 1: King
Foyer
Exceptional
(9 reviews)

6-Acre Luxurious Country Home with Goddess Point Lookout

Woodbury

8% off
AU$17,996
for 7 nights, 1 home
AU$2,571 per night
includes taxes & fees
6-Acre Luxurious Country Home with Goddess Point Lookout
Interior
Private kitchen
Room
Private kitchen
Very good
(9 reviews)

Excellent Home Away From Home

Waterbury

15% off
AU$2,167
for 7 nights, 1 home
AU$310 per night
includes taxes & fees
Excellent Home Away From Home
Kitchen
Summer; forest view
3rd sleeping area with ground-floor walkout
Entrance
Exceptional
(8 reviews)

Peaceful Wooded Retreat – Quiet Escape, Close to Wolcott Lakes

Waterbury

8% off
AU$4,106
for 7 nights, 1 cabin
AU$587 per night
includes taxes & fees
Peaceful Wooded Retreat – Quiet Escape, Close to Wolcott Lakes
Room
Room
Private kitchen
Dining
Exceptional
(23 reviews)

TWO BEDROOM APARTMENT ON FIRST FLOOR ON A DUPLEX

Bristol

16% off
AU$2,002
for 7 nights, 1 apartment
AU$286 per night
includes taxes & fees
TWO BEDROOM APARTMENT ON FIRST FLOOR ON A DUPLEX
Entryway Stairs
View of the Pond
Entertainment Area
Dining Peninsula
Exceptional
(7 reviews)

Private Apartment in Southbury 101

Southbury

7% off
AU$2,014
for 7 nights, 1 apartment
AU$288 per night
includes taxes & fees
Private Apartment in Southbury 101
Living area
Pool
Living area
Private kitchen
Exceptional
(6 reviews)

Southbury Charming Studio Retreat on Beautiful Grounds — Sleeps 4

Southbury

8% off
AU$1,753
for 7 nights, 1 apartment
AU$250 per night
includes taxes & fees
Southbury Charming Studio Retreat on Beautiful Grounds — Sleeps 4
Outdoors
Open Concept Living Room, Dining Room, Kitchen
Dining Room
Open Concept Living Room and Kitchen
Wonderful
(6 reviews)

Private Apartment in Southbury 102

Southbury

8% off
AU$1,798
for 7 nights, 1 apartment
AU$257 per night
includes taxes & fees
Private Apartment in Southbury 102
Backyard
Porch/Foyer
Living Room
Living Room
Exceptional
(39 reviews)

Charming 3BR Hilltop House, Newly Remodeled with Arcade

Terryville

7% off
AU$2,317
for 7 nights, 1 home
AU$331 per night
includes taxes & fees
Charming 3BR Hilltop House, Newly Remodeled with Arcade
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Oakville getaway

Learn about the unique charm of Oakville with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Oakville

Are you looking for attractions to see in the city? Venture out of your holiday home and check out everything that makes Oakville a fun place to get away to. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Quassy Amusement Park (5.7 mi / 9.2 km)
  • The Christmas Shop (7.5 mi / 12 km)
  • Mount Southington Ski Area (7.9 mi / 12.8 km)
  • Lake Compounce (8.6 mi / 13.9 km)
  • Hawks Landing Country Club (12.1 mi / 19.5 km)
  • Connecticut Valley Winery (16 mi / 25.8 km)

Exploring the natural landscape of Oakville

Whether you're an adventurous traveller or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Oakville. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Lake Quassapaug (5.4 mi / 8.7 km)
  • Glebe House Museum and The Gertrude Jekyll Garden (7.7 mi / 12.3 km)
  • Bantam Lake (10.8 mi / 17.4 km)
  • White Memorial Conservation Center (11.6 mi / 18.7 km)
  • Litchfield Town Green (12.3 mi / 19.8 km)
  • Harwinton Conservation and Recreation Area (12.5 mi / 20.1 km)

Transport options to and around Oakville

The nearest airport is in Oxford, CT (OXC-Waterbury - Oxford), located 8.3 mi (13.3 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into New Haven, CT (HVN-Tweed - New Haven Regional), which is 24.2 mi (38.9 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Oakville?
The most in-demand types of holiday homes in Oakville are apartments. After something a little different? Stayz has a variety of options to match our guests' requirements, so you'll see properties in loads of sizes and shapes. The ideal fit is waiting for you — get hold of yours today.
How much does it cost to rent a holiday home in Oakville?
Length of stay, property type and time of year are some of the conditions that can affect the price of a holiday home. Simply enter your dates of travel to find your ideal escape. From comfy cottages to expansive luxury villas, all Stayz holiday homes offer amazing value.
How much does it cost to rent a beach house in Oakville?
When you travel and the style and size of the property will determine the cost of your beachside stay. Click on your Oakville travel dates to see your options on Stayz. Can't live without a hot tub? Use our filters to pick the amenities and features you want in your beach house.
What are popular home amenities in Oakville?
An oven, a balcony and a fridge head the list of most popular home amenities in Oakville. Whether you plan to go solo, with your significant other or a group of dear friends, Stayz will help you find a holiday home that suits your style with all the features you'll enjoy.
What are the top attractions for families in Oakville?
Keeping the kiddos entertained during your holiday in Oakville is easy with these leading family-friendly attractions:
  • Lake Compounce
  • Quassy Amusement Park
  • Mattatuck Beach
How old do you have to be to rent a holiday home in Oakville?
The minimum age is typically 16, 18 or 21. It can vary between properties on Stayz, so look at the rules of your chosen Oakville stay before you book.
How long can I rent a holiday home in Oakville for?
How long you can rent a holiday home in Oakville depends on the property. Just enter your chosen dates to display a list of options offering extended stays. With a range of creature comforts like kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get somewhere just right to call your home away from home in Oakville.