Oakville Holiday Rentals

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Check prices for these dates

Tonight
17 July - 18 July
Tomorrow
18 July - 19 July
This weekend
18 July - 20 July
Next weekend
25 July - 27 July

Holiday Rentals in Oakville

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Enjoy a formal dining experience with a view of the surrounding forest from the large windows.

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Enjoy a serene lakeside view from this outdoor space with a wooden deck and glass door.

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

8.8 out of 10, Excellent, (20)
"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!
Cozy Lakefront Bungalow w firepit/dock/kayaks
Enjoy the view from the upper balcony, which offers a fire pit and Adirondack chairs in the yard.

Cozy Lakefront Bungalow w firepit/dock/kayaks

10.0 out of 10, Exceptional, (29)
"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
Tranquil Litchfield Connecticut Retreat".
Relax by the fire pit in a serene outdoor seating area surrounded by Adirondack chairs.

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (14)
"My friends and stayed for a night. The house is nice and the owners is very communicative. "
The price is AU$498
includes taxes & fees
24 July - 25 July
Tranquil Litchfield Connecticut Retreat".
Modern 3BR ★ Fast Wi-Fi + Free Parking ★ Flexible Cancel Anytime! - 10 Mins WeHa
Enjoy meals in this kitchen with a microwave, stainless steel range hood, and dining area with a table and chairs.

Modern 3BR ★ Fast Wi-Fi + Free Parking ★ Flexible Cancel Anytime! - 10 Mins WeHa

2.0 star property
6.6 out of 10, (4)
"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!"
Modern 3BR ★ Fast Wi-Fi + Free Parking ★ Flexible Cancel Anytime! - 10 Mins WeHa
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Enjoy a peaceful lakeside retreat with a dock, table, and chairs, surrounded by lush grass and a shaded tree.

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (33)
"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
Spacious Woodbury Home w/ Pool + Hot Tub!
Relax in a warm and inviting space with a hot tub, wicker furniture, and large windows.

Spacious Woodbury Home w/ Pool + Hot Tub!

8.0 out of 10, Very good, (2)
"The host was very kind and responsive, which we truly appreciated. However, the house was not properly cleaned. There were a lot of flies inside, the basement had a strong musty smell, and the hot tub water was untreated and had a bad odor, With better cleaning, maintenance, and care for the house the stay could have been much more pleasant."
Spacious Woodbury Home w/ Pool + Hot Tub!
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Enjoy cooking in this well-equipped kitchen with a large window offering a view of the surrounding landscape.

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

10.0 out of 10, Exceptional, (57)
"We had a great time and I would highly recommend for your next stay. Very clean and had everything to make your vacation enjoyable."
The price is AU$709
includes taxes & fees
20 July - 21 July
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Spectacular Lake front house
Stunning waterfront property with a charming detached house and beautifully maintained garden.

Spectacular Lake front house

9.6 out of 10, Exceptional, (4)
"This beautiful home offered plenty of space for our family of 6 adults and 2 children to enjoy a week together. "
Spectacular Lake front house
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Outdoor dining

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

10.0 out of 10, Exceptional, (3)
"I stayed with my mom and the 2 bedroom 1 bath was perfect for our stay. The house way cozy and in a quiet area. Would absolutely stay again; my mom is already talking about coming back to explore more of the surrounding areas!"
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
New One Bedroom Apartment Centrally Located in Southbury
Enjoy a meal or relax with friends on the deck, surrounded by a lush yard and trees.

New One Bedroom Apartment Centrally Located in Southbury

9.8 out of 10, Exceptional, (6)
"Excellent place in an excellent location. Charles is a wonderful host. Will be staying there again. "
The price is AU$272
includes taxes & fees
28 July - 29 July
New One Bedroom Apartment Centrally Located in Southbury
Cozy 2 bedroom home located minutes from downtown
Kitchen features a central island, microwave, coffee maker, and dining table with four chairs.

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (26)
"Perfect stay for the Yale-Harvard game. "
Cozy 2 bedroom home located minutes from downtown
Private Apartment in Berlin
Fridge, microwave, oven, stovetop

Private Apartment in Berlin

2.0 star property
10.0 out of 10, Exceptional, (4)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
The price is AU$668
includes taxes & fees
22 July - 23 July
Private Apartment in Berlin
Cozy 2-bedroom Cottage with Access to Bantam Lake
Stroll through the lush garden, surrounded by vibrant greenery and colorful flowers, to a serene outdoor space with a wooden fence and inviting bench.

Cozy 2-bedroom Cottage with Access to Bantam Lake

9.6 out of 10, Exceptional, (17)
"Even with horrible weather, we had a wonderful stay!"
Cozy 2-bedroom Cottage with Access to Bantam Lake
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
Compact kitchen with modern cabinetry, oven, and stovetop, offering versatile cooking options.

Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment

7.6 out of 10, Good, (7)
"Overall, this property is honestly one of the nicest homes I’ve stayed at. The kitchen was nice and big and the bathroom was so pretty. I enjoyed my stay it was very nice and would love to come and stay again. I recommend this home !! The neighbor is also very nice ! they helped me find my parking spot! ❤️"
The price is AU$507
includes taxes & fees
20 July - 21 July
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and oven, complemented by white cabinetry and a skylight above the island.

Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi

Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Escape to a serene garden oasis with a traditional lantern and a charming wooden house in the background.

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

9.6 out of 10, Exceptional, (14)
"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
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Fully equipped kitchen with double sink, coffee maker, microwave, and oven.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

9.6 out of 10, Exceptional, (7)
"Overall a positive experience. Property was clean and worked out really well for us as location was close to family we were visiting. We are from Florida, and it was cold in CT and the heat worked great so that was really good. Andrew was responsive to requests. Only criticism was in some of the set up. There are no dressers, so you need to stack your clothes on shelves in closet, which was not terrible. Also, the only mirror in the entire place was in the bathroom downstairs (bedrooms...
The price is AU$247
includes taxes & fees
21 July - 22 July
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Fun Downtown Location 2nd flr
Enjoy al fresco dining with a view of the street from our outdoor seating area.

Fun Downtown Location 2nd flr

9.8 out of 10, Exceptional, (73)
"Nice place, comfy beds, good amenities, clean. Good restaurants."
Fun Downtown Location 2nd flr
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds
Relax in this stylish living room with a sofa, coffee table, and television, surrounded by a globe and a hanging plant.

Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds

10.0 out of 10, Exceptional, (1)
"The space was clean and light, great finishes. The home felt comfortable and was easy to find. Thank you for a wonderful weekend. "
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds
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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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?

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit: 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 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

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.