Oakville Holiday Rentals

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Tonight
18 Apr - 19 Apr
Tomorrow
19 Apr - 20 Apr
This weekend
18 Apr - 20 Apr
Next weekend
25 Apr - 27 Apr

Holiday Rentals in Oakville

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Dining

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

9.0 out of 10, Wonderful, (12)
"We had a wonderful time at the cabin by the lake. Beautiful views in the Morning!! Loved it."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Litchfield Hills Hideaway
Fridge, microwave, oven, stovetop

Litchfield Hills Hideaway

10.0 out of 10, Exceptional, (55)
"Great place to end our Gilmore Girls adventure!!! The Hideaway was clean and cozy, and the hosts are very professional! We would stay here again!!!!"
The price is HK$1,164
HK$1,987 total
includes taxes & fees
4 May - 5 May
Litchfield Hills Hideaway
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, (23)
"Very cute , well supplied, clean, nice property. Wed definitely stay again. 1"
Cozy & Chic Cabin by the Lake, with access to private Beach!
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Exterior

Lakeview property in private community. Lake & beach access. Swim/Kayak all day!

9.6 out of 10, Exceptional, (5)
"The house on the lake is clean and very cute. A few things to keep in mind… The stairs to the loft are VERY steep and VERY narrow. So both adults and small children may struggle to get up and down, especially with any type of luggage. There are no closets or dressers for your clothes so maybe bring hangers and a hook for behind the door. Everything else was perfect. "
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Tranquil Litchfield Connecticut Retreat".
Property grounds

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (10)
"My friends and stayed for a night. The house is nice and the owners is very communicative. "
The price is HK$1,707
HK$2,451 total
includes taxes & fees
3 May - 4 May
Tranquil Litchfield Connecticut Retreat".
The Goshen Glass Chalet
Outdoor dining

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (34)
"Great place. Really enjoyed staying there"
The Goshen Glass Chalet
Cottage at Sunny Day- Lakeside, views, kayak, dock
Miscellaneous

Cottage at Sunny Day- Lakeside, views, kayak, dock

9.8 out of 10, Exceptional, (35)
"This property was very new and clean. It had everything you needed. Every room was comfortable and had its own TV. The open layout of the main floor made for great socializing and eating, and the 180 views of the frozen lake (in February) were beautifully serene. Would definitely come again and maybe next time in the summer! Thanks you for sharing this lovely property."
Cottage at Sunny Day- Lakeside, views, kayak, dock
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$1,087
HK$1,636 total
includes taxes & fees
29 Apr - 30 Apr
Peaceful apartment on 3.5 acres w/ artist studio.
Waterfront Family Retreat on Candlewood Lake
Outdoor dining

Waterfront Family Retreat on Candlewood Lake

10.0 out of 10, Exceptional, (42)
"We had a great time staying here. This house was perfect for our group, with plenty of space for an even larger group. We had two couples and two teenagers. It was nice having two master suites, so each couple had a spacious bedroom with their own full bath. Each of the teenagers had their own bedroom upstairs, and a full bath to share. We easily could’ve had a few more people, especially if they were kids. The kitchen was set up well for cooking, we made multiple meals, and had some local...
Waterfront Family Retreat on Candlewood Lake
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...

9.6 out of 10, Exceptional, (24)
"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...
Lakefront Home, Close to Mt Southington!
Fridge, microwave, stovetop, dishwasher

Lakefront Home, Close to Mt Southington!

10.0 out of 10, Exceptional, (16)
"Beautiful lakefront home. Tastefully furnished. Spotless with all the little touches included. Loved ir"
Lakefront Home, Close to Mt Southington!
Cozy & New / 3 Bedroom Apartment / Free Cancellation / Free WIFI &Parking
Fridge, microwave, oven, stovetop

Cozy & New / 3 Bedroom Apartment / Free Cancellation / Free WIFI &Parking

2.0 star property
10.0 out of 10, Exceptional, (2)
"Communication with the host was excellent. His place was clean, bright, and very well equipped! The location makes it easy to get around the greater Hartford area. Our stay was very good!"
Cozy & New / 3 Bedroom Apartment / Free Cancellation / Free WIFI &Parking
Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants
Fridge, microwave, oven, stovetop

Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants

10.0 out of 10, Exceptional, (39)
"Excellent stay in s as wonderful house. "
Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants
Modern cozy home, pet friendly
Fridge, microwave, oven, stovetop

Modern cozy home, pet friendly

10.0 out of 10, Exceptional, (1)
"I wish every spot had a ping pong table. My son and I loved being able to play. As well, such a cool shower! Beautiful open space and just what we needed for a quick overnight. "
The price is HK$893
HK$2,291 total
includes taxes & fees
27 Apr - 28 Apr
Modern cozy home, pet friendly
Sunny Days w/ Lakeview, seasonal Pool, Hot Tub, close to dining, shopping, town
Exterior

Sunny Days w/ Lakeview, seasonal Pool, Hot Tub, close to dining, shopping, town

10.0 out of 10, Exceptional, (18)
"House is beautiful and a great layout for multiple families. We had a family reunion with kids and everyone loved the pool, all the seating options, large & well stocked kitchen for lots of cooking, and lake access with kayaks and toys to use. We had a great time and hope to be returning next year. Tony was quick to answer our questions before and during the stay and made access and communication easy. We appreciate you, Tony! Thanks again for a wonderful stay!!"
Sunny Days w/ Lakeview, seasonal Pool, Hot Tub, close to dining, shopping, town
Litchfield County Four Season Country Paradise
Outdoor pool, a heated pool

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
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
Lakefront Cottage - Hot Tub, Game Room & Scenic Views
Outdoor spa tub

Lakefront Cottage - Hot Tub, Game Room & Scenic Views

10.0 out of 10, Exceptional, (3)
"Everything was great. "
Lakefront Cottage - Hot Tub, Game Room & Scenic Views
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Property grounds

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (31)
"Stayed here for a work trip for a couple of nights. Very comfortable, quiet, and nice scenery."
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
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$1,048
HK$2,084 total
includes taxes & fees
20 Apr - 21 Apr
River Overlook - Check the view from your deck!
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.
Don't see what you're looking for?
See all available properties in Oakville
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Oakville you may be interested in

Holiday Inn Express Southington by IHG
Exterior

Holiday Inn Express Southington by IHG

2.5 star property
8.8 out of 10, Excellent, (1002)
"Hotel was clean and quiet. Beds were comfortable. "
The price is HK$644
HK$741 total
includes taxes & fees
24 Apr - 25 Apr
Holiday Inn Express Southington by IHG
Clarion Inn
Indoor pool

Clarion Inn

3.0 star property
7.4 out of 10, Good, (1004)
"Pool was too cold"
The price is HK$752
HK$865 total
includes taxes & fees
1 May - 2 May
Clarion Inn
Courtyard by Marriott Waterbury Downtown
Lobby

Courtyard by Marriott Waterbury Downtown

3.0 star property
8.6 out of 10, Excellent, (1008)
"Great stay clean and comfy"
The price is HK$613
HK$705 total
includes taxes & fees
20 Apr - 21 Apr
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?

Tranquil Litchfield Connecticut Retreat".: This holiday home rental outside of Oakville is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 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.